NPASS Compound

Structure

NPC475442 OpenBabel07101719142D 47 53 0 0 1 0 0 0 0 0999 V2000 -1.4114 7.6993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0092 7.2325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8544 -3.6729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9727 2.9112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1518 0.1317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8276 1.0365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5304 -0.6014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2837 4.3534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8820 1.2081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5848 -0.4298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5339 4.8586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9797 -1.4824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2444 -0.4001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6046 -2.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8693 -1.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0558 3.4197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8060 6.0822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1404 0.0855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8047 0.7775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0755 7.0047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2606 0.4749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2996 -0.5762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5494 -2.0365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5411 0.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7397 0.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2670 4.2372 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.4702 5.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3694 0.8181 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5411 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9524 1.6840 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7397 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1404 1.4696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4078 2.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1716 0.6094 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.5550 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6747 0.1540 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2007 4.4650 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9026 3.3479 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4039 5.6154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3684 2.5591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9034 -0.2246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1813 2.4988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1743 -2.7667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1404 2.4306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3979 0.2176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3979 1.3374 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 43 1 0 0 0 0 4 44 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 22 2 0 0 0 0 13 15 2 0 0 0 0 13 22 1 0 0 0 0 14 23 2 0 0 0 0 15 23 1 0 0 0 0 16 38 1 0 0 0 0 17 20 2 0 0 0 0 17 27 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 45 1 0 0 0 0 19 46 1 0 0 0 0 21 28 1 0 0 0 0 23 43 1 0 0 0 0 24 29 1 0 0 0 0 24 47 1 0 0 0 0 25 31 2 0 0 0 0 25 45 1 0 0 0 0 26 37 1 0 0 0 0 26 38 1 0 0 0 0 27 37 2 3 0 0 0 27 39 1 0 0 0 0 28 30 1 0 0 0 0 28 36 1 6 0 0 0 29 32 2 0 0 0 0 29 35 1 0 0 0 0 30 33 1 0 0 0 0 30 35 1 1 0 0 0 31 32 1 0 0 0 0 31 46 1 0 0 0 0 32 44 1 0 0 0 0 33 38 1 0 0 0 0 33 40 2 0 0 0 0 34 35 1 6 0 0 0 34 36 1 0 0 0 0 34 41 1 0 0 0 0 35 42 1 6 0 0 0 36 22 1 6 0 0 0 36 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	642.26
Volume:	640.785
LogP:	3.786
LogD:	3.659
LogS:	-4.67
# Rotatable Bonds:	9
TPSA:	136.02
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	5.442
Fsp3:	0.389
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.092
MDCK Permeability:	2.053132811852265e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.516
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.259

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173
Plasma Protein Binding (PPB):	93.6989517211914%
Volume Distribution (VD):	1.459
Pgp-substrate:	3.5042476654052734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.534
CYP2C19-inhibitor:	0.67
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.889
CYP2C9-substrate:	0.56
CYP2D6-inhibitor:	0.8
CYP2D6-substrate:	0.277
CYP3A4-inhibitor:	0.969
CYP3A4-substrate:	0.7

ADMET: Excretion

Clearance (CL):	4.89
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.747
Human Hepatotoxicity (H-HT):	0.945
Drug-inuced Liver Injury (DILI):	0.733
AMES Toxicity:	0.385
Rat Oral Acute Toxicity:	0.711
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.656
Carcinogencity:	0.144
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC475442

Natural Product ID:	NPC475442
*Common Name:**	19,20-Dehydroedulirin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IJAPXRMOHJNENE-FLKKBAACSA-N
Standard InCHI:	InChI=1S/C36H38N2O9/c1-20(2)17-27(39)37-26-11-8-16-38(26)33(40)30-28(21-9-6-5-7-10-21)36(22-12-14-23(43-3)15-13-22)34(41)35(30,42)29-24(47-36)18-25-31(32(29)44-4)46-19-45-25/h5-7,9-10,12-15,17-18,26,28,30,34,41-42H,8,11,16,19H2,1-4H3,(H,37,39)/t26?,28-,30+,34+,35+,36+/m1/s1
SMILES:	COc1c2OCOc2cc2c1[C@]1(O)[C@H](C(=O)N3CCCC3N=C(C=C(C)C)O)[C@H]([C@](O2)([C@H]1O)c1ccc(cc1)OC)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505740
PubChem CID:	16099514
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002590] 5-O-methylated flavonoids

*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
NPO3902	Aglaia edulis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190457]
NPO3902	Aglaia edulis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3902	Aglaia edulis	Species	Meliaceae	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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[493692]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[493692]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[493692]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[493692]

☑ 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 NPC475442 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	331
0.1-0.2	1573
0.2-0.3	4747
0.3-0.4	11502
0.4-0.5	8077
0.5-0.6	10299
0.6-0.7	6066
0.7-0.8	87
0.8-0.85	3
0.85-0.9	5
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9899	High Similarity	NPC475565
0.9899	High Similarity	NPC475349
0.9899	High Similarity	NPC475292
0.9751	High Similarity	NPC475624
0.9458	High Similarity	NPC470846
0.9146	High Similarity	NPC79130
0.9091	High Similarity	NPC235698
0.9055	High Similarity	NPC293347
0.905	High Similarity	NPC258128
0.895	High Similarity	NPC169605
0.8737	High Similarity	NPC308709
0.8387	Intermediate Similarity	NPC5674
0.8349	Intermediate Similarity	NPC470847
0.8283	Intermediate Similarity	NPC206061
0.815	Intermediate Similarity	NPC236089
0.81	Intermediate Similarity	NPC29587
0.805	Intermediate Similarity	NPC23593
0.8	Intermediate Similarity	NPC107739
0.796	Intermediate Similarity	NPC263955
0.7811	Intermediate Similarity	NPC271755
0.7811	Intermediate Similarity	NPC254071
0.7811	Intermediate Similarity	NPC222665
0.7811	Intermediate Similarity	NPC149502
0.7778	Intermediate Similarity	NPC14390
0.7751	Intermediate Similarity	NPC470646
0.7725	Intermediate Similarity	NPC123859
0.7696	Intermediate Similarity	NPC197125
0.763	Intermediate Similarity	NPC144314
0.7612	Intermediate Similarity	NPC475621
0.7606	Intermediate Similarity	NPC242728
0.7594	Intermediate Similarity	NPC50548
0.7588	Intermediate Similarity	NPC470936
0.7583	Intermediate Similarity	NPC149962
0.7536	Intermediate Similarity	NPC471563
0.7475	Intermediate Similarity	NPC189730
0.745	Intermediate Similarity	NPC310399
0.745	Intermediate Similarity	NPC73422
0.7431	Intermediate Similarity	NPC80472
0.7424	Intermediate Similarity	NPC164152
0.7413	Intermediate Similarity	NPC90336
0.74	Intermediate Similarity	NPC209473
0.74	Intermediate Similarity	NPC329743
0.7393	Intermediate Similarity	NPC470642
0.7361	Intermediate Similarity	NPC475654
0.7361	Intermediate Similarity	NPC476661
0.7327	Intermediate Similarity	NPC476662
0.7321	Intermediate Similarity	NPC229234
0.7269	Intermediate Similarity	NPC83019
0.7264	Intermediate Similarity	NPC29531
0.7238	Intermediate Similarity	NPC241196
0.7236	Intermediate Similarity	NPC87363
0.7222	Intermediate Similarity	NPC281629
0.7222	Intermediate Similarity	NPC204580
0.722	Intermediate Similarity	NPC222531
0.7217	Intermediate Similarity	NPC473883
0.7206	Intermediate Similarity	NPC476244
0.7196	Intermediate Similarity	NPC473716
0.7196	Intermediate Similarity	NPC319549
0.7196	Intermediate Similarity	NPC475597
0.7178	Intermediate Similarity	NPC220462
0.7177	Intermediate Similarity	NPC105137
0.7172	Intermediate Similarity	NPC474560
0.717	Intermediate Similarity	NPC6709
0.717	Intermediate Similarity	NPC18306
0.7149	Intermediate Similarity	NPC82056
0.7129	Intermediate Similarity	NPC223375
0.7129	Intermediate Similarity	NPC475825
0.7129	Intermediate Similarity	NPC261254
0.7123	Intermediate Similarity	NPC471031
0.7123	Intermediate Similarity	NPC469689
0.7123	Intermediate Similarity	NPC276120
0.7117	Intermediate Similarity	NPC475768
0.7115	Intermediate Similarity	NPC472381
0.7115	Intermediate Similarity	NPC472383
0.7109	Intermediate Similarity	NPC156635
0.7109	Intermediate Similarity	NPC257714
0.7108	Intermediate Similarity	NPC476337
0.7101	Intermediate Similarity	NPC476277
0.7101	Intermediate Similarity	NPC113093
0.71	Intermediate Similarity	NPC56184
0.7089	Intermediate Similarity	NPC34780
0.7083	Intermediate Similarity	NPC24260
0.7081	Intermediate Similarity	NPC22195
0.7081	Intermediate Similarity	NPC293004
0.7081	Intermediate Similarity	NPC183357
0.7081	Intermediate Similarity	NPC265214
0.7081	Intermediate Similarity	NPC44558
0.7081	Intermediate Similarity	NPC105511
0.7081	Intermediate Similarity	NPC21190
0.7081	Intermediate Similarity	NPC212748
0.7079	Intermediate Similarity	NPC186316
0.7075	Intermediate Similarity	NPC472387
0.7073	Intermediate Similarity	NPC115624
0.7073	Intermediate Similarity	NPC288149
0.7073	Intermediate Similarity	NPC152424
0.7073	Intermediate Similarity	NPC100465
0.7067	Intermediate Similarity	NPC135345
0.7067	Intermediate Similarity	NPC93099
0.7062	Intermediate Similarity	NPC472607
0.7062	Intermediate Similarity	NPC475244
0.7062	Intermediate Similarity	NPC102028
0.7061	Intermediate Similarity	NPC38964
0.7059	Intermediate Similarity	NPC286135
0.7056	Intermediate Similarity	NPC35924
0.7056	Intermediate Similarity	NPC199172
0.7056	Intermediate Similarity	NPC230098
0.7048	Intermediate Similarity	NPC205076
0.7048	Intermediate Similarity	NPC315253
0.7048	Intermediate Similarity	NPC235575
0.7048	Intermediate Similarity	NPC472386
0.7048	Intermediate Similarity	NPC307518
0.7048	Intermediate Similarity	NPC475155
0.7048	Intermediate Similarity	NPC48773
0.7048	Intermediate Similarity	NPC470685
0.7048	Intermediate Similarity	NPC267254
0.7044	Intermediate Similarity	NPC478055
0.704	Intermediate Similarity	NPC476500
0.7039	Intermediate Similarity	NPC90984
0.7039	Intermediate Similarity	NPC469575
0.7033	Intermediate Similarity	NPC93337
0.7033	Intermediate Similarity	NPC58053
0.7033	Intermediate Similarity	NPC170675
0.7033	Intermediate Similarity	NPC210042
0.7033	Intermediate Similarity	NPC475942
0.7033	Intermediate Similarity	NPC201292
0.7033	Intermediate Similarity	NPC105025
0.7033	Intermediate Similarity	NPC471457
0.7033	Intermediate Similarity	NPC469931
0.7033	Intermediate Similarity	NPC45638
0.7033	Intermediate Similarity	NPC67424
0.7033	Intermediate Similarity	NPC112755
0.7033	Intermediate Similarity	NPC226294
0.7033	Intermediate Similarity	NPC95855
0.7033	Intermediate Similarity	NPC186807
0.703	Intermediate Similarity	NPC136757
0.7028	Intermediate Similarity	NPC67629
0.7028	Intermediate Similarity	NPC473562
0.7028	Intermediate Similarity	NPC79736
0.7024	Intermediate Similarity	NPC96593
0.7024	Intermediate Similarity	NPC119910
0.7022	Intermediate Similarity	NPC476496
0.7019	Intermediate Similarity	NPC306475
0.7018	Intermediate Similarity	NPC33256
0.7015	Intermediate Similarity	NPC51543
0.7014	Intermediate Similarity	NPC329816
0.7014	Intermediate Similarity	NPC172033
0.7014	Intermediate Similarity	NPC239549
0.7014	Intermediate Similarity	NPC175230
0.7014	Intermediate Similarity	NPC204693
0.7014	Intermediate Similarity	NPC51774
0.7014	Intermediate Similarity	NPC88560
0.7014	Intermediate Similarity	NPC316539
0.7014	Intermediate Similarity	NPC236191
0.701	Intermediate Similarity	NPC19947
0.701	Intermediate Similarity	NPC207584
0.7009	Intermediate Similarity	NPC469371
0.7005	Intermediate Similarity	NPC116759
0.7005	Intermediate Similarity	NPC470178
0.7005	Intermediate Similarity	NPC473618
0.7005	Intermediate Similarity	NPC14294
0.7	Intermediate Similarity	NPC471416
0.7	Intermediate Similarity	NPC474434
0.7	Intermediate Similarity	NPC52353
0.7	Intermediate Similarity	NPC179240
0.7	Intermediate Similarity	NPC477883
0.7	Intermediate Similarity	NPC238140
0.7	Intermediate Similarity	NPC34287
0.7	Intermediate Similarity	NPC91043
0.7	Intermediate Similarity	NPC194483
0.7	Intermediate Similarity	NPC224462
0.6995	Remote Similarity	NPC476621
0.6995	Remote Similarity	NPC476619
0.6995	Remote Similarity	NPC67302
0.6995	Remote Similarity	NPC476618
0.6995	Remote Similarity	NPC476623
0.6995	Remote Similarity	NPC475261
0.6995	Remote Similarity	NPC267549
0.6995	Remote Similarity	NPC476620
0.6995	Remote Similarity	NPC476622
0.699	Remote Similarity	NPC155754
0.699	Remote Similarity	NPC124747
0.6986	Remote Similarity	NPC185498
0.6986	Remote Similarity	NPC208818
0.6986	Remote Similarity	NPC45618
0.6986	Remote Similarity	NPC42892
0.6986	Remote Similarity	NPC58716
0.6986	Remote Similarity	NPC146792
0.6982	Remote Similarity	NPC2173
0.6982	Remote Similarity	NPC202771
0.6982	Remote Similarity	NPC328700
0.6982	Remote Similarity	NPC119818
0.6981	Remote Similarity	NPC84482
0.6981	Remote Similarity	NPC142996
0.6981	Remote Similarity	NPC169645
0.698	Remote Similarity	NPC473236
0.6978	Remote Similarity	NPC94687
0.6978	Remote Similarity	NPC106840
0.6978	Remote Similarity	NPC476495
0.6977	Remote Similarity	NPC150977
0.6977	Remote Similarity	NPC473072

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 NPC475442 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	628
0.2-0.3	1316
0.3-0.4	2830
0.4-0.5	2573
0.5-0.6	1291
0.6-0.7	313
0.7-0.8	4
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
0.7404	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7199	Phase 2
0.7196	Intermediate Similarity	NPD7296	Approved
0.7171	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD8059	Phase 3
0.7123	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7827	Phase 1
0.7062	Intermediate Similarity	NPD7549	Discontinued
0.7009	Intermediate Similarity	NPD7584	Approved
0.6986	Remote Similarity	NPD7228	Approved
0.6982	Remote Similarity	NPD5006	Approved
0.6982	Remote Similarity	NPD5005	Approved
0.6961	Remote Similarity	NPD4967	Phase 2
0.6961	Remote Similarity	NPD4965	Approved
0.6961	Remote Similarity	NPD4966	Approved
0.696	Remote Similarity	NPD7801	Approved
0.6941	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7685	Pre-registration
0.6927	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7074	Phase 3
0.6905	Remote Similarity	NPD3818	Discontinued
0.6903	Remote Similarity	NPD7701	Phase 2
0.6898	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6234	Discontinued
0.6886	Remote Similarity	NPD7783	Phase 2
0.6886	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7497	Discontinued
0.6872	Remote Similarity	NPD7054	Approved
0.6869	Remote Similarity	NPD7281	Phase 3
0.6869	Remote Similarity	NPD7280	Phase 3
0.6861	Remote Similarity	NPD2493	Approved
0.6861	Remote Similarity	NPD2494	Approved
0.6844	Remote Similarity	NPD4583	Approved
0.6844	Remote Similarity	NPD4582	Approved
0.6842	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7472	Approved
0.6833	Remote Similarity	NPD2975	Approved
0.6833	Remote Similarity	NPD2974	Approved
0.6833	Remote Similarity	NPD2973	Approved
0.6822	Remote Similarity	NPD7808	Phase 3
0.6822	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4580	Approved
0.6814	Remote Similarity	NPD37	Approved
0.6802	Remote Similarity	NPD4420	Approved
0.68	Remote Similarity	NPD4004	Approved
0.68	Remote Similarity	NPD4002	Approved
0.6798	Remote Similarity	NPD8151	Discontinued
0.6797	Remote Similarity	NPD7930	Approved
0.6793	Remote Similarity	NPD7223	Discontinued
0.6793	Remote Similarity	NPD7224	Discontinued
0.6786	Remote Similarity	NPD3452	Approved
0.6786	Remote Similarity	NPD3450	Approved
0.6784	Remote Similarity	NPD7583	Approved
0.6776	Remote Similarity	NPD7240	Approved
0.6769	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7874	Approved
0.6767	Remote Similarity	NPD7047	Phase 3
0.6765	Remote Similarity	NPD8469	Approved
0.6759	Remote Similarity	NPD8054	Approved
0.6759	Remote Similarity	NPD8053	Approved
0.6756	Remote Similarity	NPD6823	Phase 2
0.6754	Remote Similarity	NPD7585	Approved
0.6743	Remote Similarity	NPD7906	Approved
0.674	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6997	Phase 2
0.673	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6166	Phase 2
0.673	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4210	Discontinued
0.6699	Remote Similarity	NPD5773	Approved
0.6699	Remote Similarity	NPD5494	Approved
0.6699	Remote Similarity	NPD5772	Approved
0.6698	Remote Similarity	NPD7251	Discontinued
0.6682	Remote Similarity	NPD2490	Approved
0.6682	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD2488	Approved
0.6682	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4846	Phase 2
0.668	Remote Similarity	NPD8152	Approved
0.668	Remote Similarity	NPD8153	Approved
0.6667	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6797	Phase 2
0.6641	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5844	Phase 1
0.6636	Remote Similarity	NPD8156	Discontinued
0.6636	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD3787	Discontinued
0.6635	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7907	Approved
0.6624	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7871	Phase 2
0.6623	Remote Similarity	NPD7870	Phase 2
0.6622	Remote Similarity	NPD7811	Phase 3
0.6622	Remote Similarity	NPD7810	Phase 3
0.6621	Remote Similarity	NPD4663	Approved
0.6603	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6779	Approved
0.6593	Remote Similarity	NPD6782	Approved
0.6593	Remote Similarity	NPD6780	Approved
0.6593	Remote Similarity	NPD6781	Approved
0.6593	Remote Similarity	NPD6776	Approved
0.6593	Remote Similarity	NPD6778	Approved
0.6593	Remote Similarity	NPD6777	Approved
0.6592	Remote Similarity	NPD4360	Phase 2
0.6592	Remote Similarity	NPD4363	Phase 3
0.6591	Remote Similarity	NPD6842	Approved
0.6591	Remote Similarity	NPD6841	Approved
0.6591	Remote Similarity	NPD6843	Phase 3
0.6589	Remote Similarity	NPD8252	Approved
0.6589	Remote Similarity	NPD8099	Discontinued
0.6589	Remote Similarity	NPD8251	Approved
0.6579	Remote Similarity	NPD7697	Approved
0.6579	Remote Similarity	NPD7698	Approved
0.6579	Remote Similarity	NPD7696	Phase 3
0.6579	Remote Similarity	NPD7680	Approved
0.657	Remote Similarity	NPD3384	Approved
0.657	Remote Similarity	NPD3382	Approved
0.657	Remote Similarity	NPD3383	Approved
0.657	Remote Similarity	NPD1934	Approved
0.6569	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.656	Remote Similarity	NPD2971	Approved
0.656	Remote Similarity	NPD2968	Approved
0.6558	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3051	Approved
0.655	Remote Similarity	NPD8319	Approved
0.655	Remote Similarity	NPD8320	Phase 1
0.6545	Remote Similarity	NPD7048	Phase 3
0.654	Remote Similarity	NPD4665	Approved
0.654	Remote Similarity	NPD4111	Phase 1
0.6538	Remote Similarity	NPD2801	Approved
0.6526	Remote Similarity	NPD2969	Approved
0.6526	Remote Similarity	NPD2970	Approved
0.6522	Remote Similarity	NPD7110	Phase 1
0.6522	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7466	Approved
0.6515	Remote Similarity	NPD8491	Approved
0.6514	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3751	Discontinued
0.6507	Remote Similarity	NPD7435	Discontinued
0.649	Remote Similarity	NPD6625	Approved
0.649	Remote Similarity	NPD6844	Discontinued
0.6489	Remote Similarity	NPD5582	Discontinued
0.6489	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4361	Phase 2
0.6485	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4578	Approved
0.6484	Remote Similarity	NPD7310	Approved
0.6484	Remote Similarity	NPD7312	Approved
0.6484	Remote Similarity	NPD4577	Approved
0.6484	Remote Similarity	NPD7311	Approved
0.6484	Remote Similarity	NPD7313	Approved
0.6479	Remote Similarity	NPD6071	Discontinued
0.6479	Remote Similarity	NPD7608	Discontinued
0.6479	Remote Similarity	NPD7315	Approved
0.6473	Remote Similarity	NPD4675	Approved
0.6473	Remote Similarity	NPD4678	Approved
0.6468	Remote Similarity	NPD6559	Discontinued
0.6459	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7309	Approved
0.6453	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7999	Approved
0.6445	Remote Similarity	NPD7833	Phase 2
0.6445	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD7831	Phase 2
0.6435	Remote Similarity	NPD7177	Discontinued
0.6432	Remote Similarity	NPD7700	Phase 2
0.6432	Remote Similarity	NPD7699	Phase 2
0.6429	Remote Similarity	NPD5353	Approved
0.6429	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6723	Discontinued
0.6422	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7007	Discovery
0.6419	Remote Similarity	NPD2489	Approved
0.6419	Remote Similarity	NPD27	Approved
0.6417	Remote Similarity	NPD8366	Approved
0.6413	Remote Similarity	NPD6836	Approved
0.6408	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD4040	Phase 1
0.6406	Remote Similarity	NPD5312	Approved
0.6406	Remote Similarity	NPD5313	Approved
0.6404	Remote Similarity	NPD2219	Phase 1
0.6404	Remote Similarity	NPD7565	Approved
0.6398	Remote Similarity	NPD3882	Suspended
0.6394	Remote Similarity	NPD6876	Approved
0.6394	Remote Similarity	NPD6875	Approved
0.6393	Remote Similarity	NPD7038	Approved
0.6393	Remote Similarity	NPD7039	Approved
0.6391	Remote Similarity	NPD6863	Phase 2
0.639	Remote Similarity	NPD7447	Phase 1
0.6389	Remote Similarity	NPD7473	Discontinued
0.6387	Remote Similarity	NPD8404	Phase 2
0.6385	Remote Similarity	NPD6746	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data