NPASS Compound

Structure

NPC475468 OpenBabel07101718292D 65 65 0 0 0 0 0 0 0 0999 V2000 12.9904 -12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 22.0000 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 13.8564 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 21.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 -11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 20.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 19.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 19.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 18.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 17.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 16.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 16.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 14.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 4.3301 4.5000 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 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 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 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 62 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 25 27 1 0 0 0 0 26 28 1 0 0 0 0 27 29 1 0 0 0 0 28 30 1 0 0 0 0 29 31 1 0 0 0 0 30 32 1 0 0 0 0 31 33 1 0 0 0 0 32 34 1 0 0 0 0 33 35 1 0 0 0 0 34 36 1 0 0 0 0 35 37 1 0 0 0 0 36 38 1 0 0 0 0 37 39 1 0 0 0 0 38 40 1 0 0 0 0 39 41 1 0 0 0 0 40 42 1 0 0 0 0 41 43 1 0 0 0 0 42 55 1 0 0 0 0 43 56 1 0 0 0 0 44 46 2 0 0 0 0 44 51 1 0 0 0 0 45 47 2 0 0 0 0 45 51 1 0 0 0 0 46 53 1 0 0 0 0 47 57 1 0 0 0 0 48 51 2 0 0 0 0 48 54 1 0 0 0 0 49 52 1 0 0 0 0 49 63 1 0 0 0 0 50 52 1 0 0 0 0 50 64 1 0 0 0 0 52 65 1 0 0 0 0 53 54 2 0 0 0 0 53 58 1 0 0 0 0 54 62 1 0 0 0 0 55 59 2 0 0 0 0 55 63 1 0 0 0 0 56 60 2 0 0 0 0 56 64 1 0 0 0 0 57 61 2 0 0 0 0 57 65 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	912.74
Volume:	1037.738
LogP:	17.565
LogD:	5.793
LogS:	-6.861
# Rotatable Bonds:	51
TPSA:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.03
Synthetic Accessibility Score:	3.234
Fsp3:	0.807
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.46
MDCK Permeability:	4.849059109801601e-07
Pgp-inhibitor:	0.0
Pgp-substrate:	0.59
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	110.79996490478516%
Volume Distribution (VD):	5.388
Pgp-substrate:	0.17395800352096558%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.03
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.995
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.087
CYP3A4-substrate:	0.011

ADMET: Excretion

Clearance (CL):	4.373
Half-life (T1/2):	0.022

ADMET: Toxicity

hERG Blockers:	0.605
Human Hepatotoxicity (H-HT):	0.01
Drug-inuced Liver Injury (DILI):	0.282
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.996
Carcinogencity:	0.02
Eye Corrosion:	0.006
Eye Irritation:	0.795
Respiratory Toxicity:	0.197

Download Data

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

Natural Product: NPC475468

Natural Product ID:	NPC475468
*Common Name:**	1,3-Dibehenyl-2-Ferulyl Glyceride
IUPAC Name:	[3-docosanoyloxy-2-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxypropyl] docosanoate
Synonyms:	NSC-332563
Standard InCHIKey:	HQKOKDBCUSEPCE-LIIAXHHNSA-N
Standard InCHI:	InChI=1S/C57H100O8/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-55(59)63-49-52(65-57(61)47-45-51-44-46-53(58)54(48-51)62-3)50-64-56(60)43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-5-2/h44-48,52,58H,4-43,49-50H2,1-3H3/b47-45+
SMILES:	CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCCCCCC)OC(=O)C=CC1=CC(=C(C=C1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506193
PubChem CID:	5988101
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000175] Glycerolipids [CHEMONTID:0003815] Triradylcglycerols [CHEMONTID:0001135] Triacylglycerols

*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
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28445049]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Agarwood	n.a.	n.a.	PMID[29083898]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30672698]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320738]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.8	ug ml-1	PMID[538223]

☑ 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 NPC475468 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	282
0.1-0.2	1197
0.2-0.3	3415
0.3-0.4	8030
0.4-0.5	10473
0.5-0.6	4083
0.6-0.7	9624
0.7-0.8	5021
0.8-0.85	434
0.85-0.9	114
0.9-0.95	20
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9766	High Similarity	NPC471110
0.9365	High Similarity	NPC280767
0.9286	High Similarity	NPC60517
0.9286	High Similarity	NPC20443
0.9286	High Similarity	NPC146886
0.9225	High Similarity	NPC83062
0.9134	High Similarity	NPC312404
0.9134	High Similarity	NPC273686
0.9111	High Similarity	NPC289690
0.9111	High Similarity	NPC288452
0.9055	High Similarity	NPC164778
0.9055	High Similarity	NPC257976
0.9055	High Similarity	NPC242372
0.9055	High Similarity	NPC4181
0.9048	High Similarity	NPC177291
0.9048	High Similarity	NPC194416
0.903	High Similarity	NPC90431
0.8992	High Similarity	NPC120225
0.8992	High Similarity	NPC213552
0.8976	High Similarity	NPC114298
0.8968	High Similarity	NPC204466
0.8931	High Similarity	NPC241354
0.8923	High Similarity	NPC123228
0.8923	High Similarity	NPC123722
0.8923	High Similarity	NPC276466
0.8923	High Similarity	NPC5018
0.8923	High Similarity	NPC151167
0.8921	High Similarity	NPC53884
0.8921	High Similarity	NPC258671
0.8915	High Similarity	NPC289459
0.8898	High Similarity	NPC70752
0.8897	High Similarity	NPC284409
0.8889	High Similarity	NPC202474
0.8881	High Similarity	NPC135127
0.8855	High Similarity	NPC278308
0.8849	High Similarity	NPC304956
0.8849	High Similarity	NPC469615
0.8846	High Similarity	NPC179777
0.8846	High Similarity	NPC84076
0.8846	High Similarity	NPC90128
0.8846	High Similarity	NPC303680
0.8837	High Similarity	NPC246704
0.8819	High Similarity	NPC158949
0.8815	High Similarity	NPC113295
0.8794	High Similarity	NPC299090
0.8794	High Similarity	NPC143892
0.8794	High Similarity	NPC221383
0.8794	High Similarity	NPC283081
0.8788	High Similarity	NPC304622
0.8786	High Similarity	NPC469683
0.8779	High Similarity	NPC12022
0.8779	High Similarity	NPC20404
0.8779	High Similarity	NPC20287
0.8779	High Similarity	NPC293641
0.876	High Similarity	NPC163083
0.875	High Similarity	NPC201777
0.8741	High Similarity	NPC300776
0.8741	High Similarity	NPC68779
0.8741	High Similarity	NPC106406
0.8741	High Similarity	NPC176814
0.8741	High Similarity	NPC4982
0.8741	High Similarity	NPC5310
0.8732	High Similarity	NPC472969
0.873	High Similarity	NPC107588
0.873	High Similarity	NPC309434
0.873	High Similarity	NPC164706
0.873	High Similarity	NPC137537
0.873	High Similarity	NPC272471
0.873	High Similarity	NPC203124
0.873	High Similarity	NPC205502
0.873	High Similarity	NPC70744
0.8723	High Similarity	NPC98356
0.8722	High Similarity	NPC172673
0.8714	High Similarity	NPC160378
0.8676	High Similarity	NPC470990
0.8671	High Similarity	NPC478242
0.8667	High Similarity	NPC168799
0.8667	High Similarity	NPC155209
0.8661	High Similarity	NPC299406
0.8636	High Similarity	NPC281020
0.8633	High Similarity	NPC100675
0.863	High Similarity	NPC469888
0.8626	High Similarity	NPC257589
0.8626	High Similarity	NPC53305
0.8621	High Similarity	NPC473773
0.8621	High Similarity	NPC475579
0.8613	High Similarity	NPC120852
0.8601	High Similarity	NPC98009
0.8594	High Similarity	NPC2058
0.8593	High Similarity	NPC239302
0.8593	High Similarity	NPC61
0.8593	High Similarity	NPC25581
0.8593	High Similarity	NPC5419
0.8593	High Similarity	NPC111888
0.8593	High Similarity	NPC18074
0.8582	High Similarity	NPC319282
0.8582	High Similarity	NPC123196
0.8582	High Similarity	NPC244246
0.8582	High Similarity	NPC215941
0.8582	High Similarity	NPC137427
0.8582	High Similarity	NPC311419
0.8582	High Similarity	NPC275724
0.8582	High Similarity	NPC65935
0.8571	High Similarity	NPC226661
0.8571	High Similarity	NPC109275
0.8571	High Similarity	NPC110313
0.8571	High Similarity	NPC281277
0.8571	High Similarity	NPC131532
0.8561	High Similarity	NPC106055
0.8561	High Similarity	NPC127937
0.8561	High Similarity	NPC147379
0.8561	High Similarity	NPC276014
0.8561	High Similarity	NPC110699
0.8561	High Similarity	NPC92207
0.8552	High Similarity	NPC118033
0.8552	High Similarity	NPC243891
0.8552	High Similarity	NPC300329
0.8551	High Similarity	NPC126206
0.8551	High Similarity	NPC281780
0.8542	High Similarity	NPC476394
0.8542	High Similarity	NPC98809
0.8538	High Similarity	NPC286573
0.8529	High Similarity	NPC159418
0.8529	High Similarity	NPC129889
0.8529	High Similarity	NPC307006
0.8529	High Similarity	NPC327410
0.8529	High Similarity	NPC283823
0.8527	High Similarity	NPC470848
0.8527	High Similarity	NPC470849
0.8521	High Similarity	NPC274960
0.8521	High Similarity	NPC143120
0.8521	High Similarity	NPC473909
0.8519	High Similarity	NPC198388
0.8519	High Similarity	NPC469480
0.8516	High Similarity	NPC24474
0.8516	High Similarity	NPC311595
0.8516	High Similarity	NPC37858
0.8514	High Similarity	NPC473275
0.8514	High Similarity	NPC470896
0.8507	High Similarity	NPC48315
0.8496	Intermediate Similarity	NPC16651
0.8496	Intermediate Similarity	NPC32163
0.8493	Intermediate Similarity	NPC246566
0.8493	Intermediate Similarity	NPC267091
0.8493	Intermediate Similarity	NPC476434
0.8493	Intermediate Similarity	NPC95498
0.8493	Intermediate Similarity	NPC75695
0.8492	Intermediate Similarity	NPC233669
0.8483	Intermediate Similarity	NPC221091
0.8483	Intermediate Similarity	NPC259576
0.8478	Intermediate Similarity	NPC471665
0.8478	Intermediate Similarity	NPC157554
0.8478	Intermediate Similarity	NPC471664
0.8473	Intermediate Similarity	NPC106659
0.8473	Intermediate Similarity	NPC21238
0.8473	Intermediate Similarity	NPC244876
0.8473	Intermediate Similarity	NPC229084
0.8473	Intermediate Similarity	NPC160900
0.8473	Intermediate Similarity	NPC18984
0.8472	Intermediate Similarity	NPC1580
0.8456	Intermediate Similarity	NPC50763
0.8451	Intermediate Similarity	NPC473090
0.8444	Intermediate Similarity	NPC142985
0.8444	Intermediate Similarity	NPC66905
0.8444	Intermediate Similarity	NPC195292
0.844	Intermediate Similarity	NPC472410
0.844	Intermediate Similarity	NPC253481
0.844	Intermediate Similarity	NPC31751
0.844	Intermediate Similarity	NPC253722
0.844	Intermediate Similarity	NPC52664
0.844	Intermediate Similarity	NPC67467
0.844	Intermediate Similarity	NPC140502
0.8435	Intermediate Similarity	NPC105942
0.8435	Intermediate Similarity	NPC44730
0.8435	Intermediate Similarity	NPC205392
0.8435	Intermediate Similarity	NPC146277
0.8435	Intermediate Similarity	NPC19380
0.8433	Intermediate Similarity	NPC478215
0.8429	Intermediate Similarity	NPC474784
0.8429	Intermediate Similarity	NPC322021
0.8425	Intermediate Similarity	NPC475454
0.8425	Intermediate Similarity	NPC475311
0.8425	Intermediate Similarity	NPC473680
0.8425	Intermediate Similarity	NPC473579
0.8417	Intermediate Similarity	NPC67349
0.8417	Intermediate Similarity	NPC279676
0.8413	Intermediate Similarity	NPC328593
0.8413	Intermediate Similarity	NPC33749
0.8413	Intermediate Similarity	NPC294941
0.8413	Intermediate Similarity	NPC261453
0.8409	Intermediate Similarity	NPC288945
0.8406	Intermediate Similarity	NPC204592
0.8406	Intermediate Similarity	NPC477301
0.8394	Intermediate Similarity	NPC200422
0.8394	Intermediate Similarity	NPC289572
0.8394	Intermediate Similarity	NPC295406
0.8394	Intermediate Similarity	NPC157478
0.8392	Intermediate Similarity	NPC100998
0.8392	Intermediate Similarity	NPC34927
0.8392	Intermediate Similarity	NPC252292

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 NPC475468 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	798
0.2-0.3	1747
0.3-0.4	2527
0.4-0.5	1928
0.5-0.6	1104
0.6-0.7	660
0.7-0.8	126
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8473	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD9494	Approved
0.8175	Intermediate Similarity	NPD228	Approved
0.8056	Intermediate Similarity	NPD8166	Discontinued
0.8	Intermediate Similarity	NPD230	Phase 1
0.8	Intermediate Similarity	NPD447	Suspended
0.8	Intermediate Similarity	NPD6190	Approved
0.7972	Intermediate Similarity	NPD7266	Discontinued
0.7939	Intermediate Similarity	NPD5536	Phase 2
0.7931	Intermediate Similarity	NPD4110	Phase 3
0.7931	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD6355	Discontinued
0.7857	Intermediate Similarity	NPD1358	Approved
0.7857	Intermediate Similarity	NPD6233	Phase 2
0.7842	Intermediate Similarity	NPD3027	Phase 3
0.7817	Intermediate Similarity	NPD6653	Approved
0.7808	Intermediate Similarity	NPD4628	Phase 3
0.7786	Intermediate Similarity	NPD6798	Discontinued
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.7748	Intermediate Similarity	NPD3455	Phase 2
0.773	Intermediate Similarity	NPD4062	Phase 3
0.7716	Intermediate Similarity	NPD7685	Pre-registration
0.7712	Intermediate Similarity	NPD1934	Approved
0.7707	Intermediate Similarity	NPD8127	Discontinued
0.7692	Intermediate Similarity	NPD7843	Approved
0.7692	Intermediate Similarity	NPD6234	Discontinued
0.7682	Intermediate Similarity	NPD1653	Approved
0.7677	Intermediate Similarity	NPD3882	Suspended
0.7638	Intermediate Similarity	NPD3134	Approved
0.7636	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD3817	Phase 2
0.7612	Intermediate Similarity	NPD9545	Approved
0.7589	Intermediate Similarity	NPD7095	Approved
0.7574	Intermediate Similarity	NPD3496	Discontinued
0.7556	Intermediate Similarity	NPD1357	Approved
0.7552	Intermediate Similarity	NPD4060	Phase 1
0.7552	Intermediate Similarity	NPD825	Approved
0.7552	Intermediate Similarity	NPD826	Approved
0.7548	Intermediate Similarity	NPD2801	Approved
0.7548	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2438	Suspended
0.7531	Intermediate Similarity	NPD7054	Approved
0.7519	Intermediate Similarity	NPD7157	Approved
0.7518	Intermediate Similarity	NPD6832	Phase 2
0.7516	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD5283	Phase 1
0.75	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD5647	Approved
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7485	Intermediate Similarity	NPD7472	Approved
0.7484	Intermediate Similarity	NPD37	Approved
0.7481	Intermediate Similarity	NPD1894	Discontinued
0.7469	Intermediate Similarity	NPD7228	Approved
0.7469	Intermediate Similarity	NPD3818	Discontinued
0.7464	Intermediate Similarity	NPD9717	Approved
0.7453	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6166	Phase 2
0.7453	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4966	Approved
0.7452	Intermediate Similarity	NPD4965	Approved
0.7452	Intermediate Similarity	NPD4967	Phase 2
0.7439	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2797	Approved
0.7426	Intermediate Similarity	NPD5691	Approved
0.7419	Intermediate Similarity	NPD6385	Approved
0.7419	Intermediate Similarity	NPD6386	Approved
0.7396	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1535	Discovery
0.7385	Intermediate Similarity	NPD2684	Approved
0.7379	Intermediate Similarity	NPD1933	Approved
0.7379	Intermediate Similarity	NPD555	Phase 2
0.7372	Intermediate Similarity	NPD1778	Approved
0.7357	Intermediate Similarity	NPD1283	Approved
0.7349	Intermediate Similarity	NPD7808	Phase 3
0.7349	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1481	Phase 2
0.7338	Intermediate Similarity	NPD9269	Phase 2
0.7333	Intermediate Similarity	NPD9493	Approved
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6232	Discontinued
0.7325	Intermediate Similarity	NPD7819	Suspended
0.7325	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1465	Phase 2
0.7319	Intermediate Similarity	NPD3847	Discontinued
0.7317	Intermediate Similarity	NPD5844	Phase 1
0.7315	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4534	Discontinued
0.731	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1613	Approved
0.731	Intermediate Similarity	NPD3620	Phase 2
0.7305	Intermediate Similarity	NPD1203	Approved
0.7303	Intermediate Similarity	NPD6799	Approved
0.7303	Intermediate Similarity	NPD1511	Approved
0.7301	Intermediate Similarity	NPD7473	Discontinued
0.7297	Intermediate Similarity	NPD2239	Approved
0.7297	Intermediate Similarity	NPD2240	Approved
0.7292	Intermediate Similarity	NPD3268	Approved
0.7292	Intermediate Similarity	NPD411	Approved
0.7289	Intermediate Similarity	NPD7251	Discontinued
0.7279	Intermediate Similarity	NPD7097	Phase 1
0.7278	Intermediate Similarity	NPD5353	Approved
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7199	Phase 2
0.7266	Intermediate Similarity	NPD3705	Approved
0.7255	Intermediate Similarity	NPD3146	Approved
0.7255	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD258	Approved
0.7254	Intermediate Similarity	NPD257	Approved
0.7244	Intermediate Similarity	NPD4380	Phase 2
0.7241	Intermediate Similarity	NPD2674	Phase 3
0.7241	Intermediate Similarity	NPD259	Phase 1
0.723	Intermediate Similarity	NPD2799	Discontinued
0.7229	Intermediate Similarity	NPD6797	Phase 2
0.7226	Intermediate Similarity	NPD3686	Approved
0.7226	Intermediate Similarity	NPD3687	Approved
0.7214	Intermediate Similarity	NPD1608	Approved
0.7208	Intermediate Similarity	NPD1512	Approved
0.7208	Intermediate Similarity	NPD6273	Approved
0.72	Intermediate Similarity	NPD5958	Discontinued
0.7197	Intermediate Similarity	NPD3021	Approved
0.7197	Intermediate Similarity	NPD3022	Approved
0.7197	Intermediate Similarity	NPD6873	Phase 2
0.7192	Intermediate Similarity	NPD2979	Phase 3
0.7183	Intermediate Similarity	NPD6362	Approved
0.7179	Intermediate Similarity	NPD7458	Discontinued
0.7179	Intermediate Similarity	NPD824	Approved
0.7178	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD290	Approved
0.7174	Intermediate Similarity	NPD5585	Approved
0.717	Intermediate Similarity	NPD5402	Approved
0.7161	Intermediate Similarity	NPD5403	Approved
0.7153	Intermediate Similarity	NPD2614	Approved
0.7153	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6801	Discontinued
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD1281	Approved
0.7134	Intermediate Similarity	NPD7028	Phase 2
0.7125	Intermediate Similarity	NPD7768	Phase 2
0.7124	Intermediate Similarity	NPD7440	Discontinued
0.7123	Intermediate Similarity	NPD8032	Phase 2
0.7123	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6663	Approved
0.7114	Intermediate Similarity	NPD4308	Phase 3
0.7107	Intermediate Similarity	NPD8455	Phase 2
0.7105	Intermediate Similarity	NPD3750	Approved
0.7105	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2653	Approved
0.7086	Intermediate Similarity	NPD2424	Discontinued
0.7083	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7038	Approved
0.7083	Intermediate Similarity	NPD9569	Approved
0.7083	Intermediate Similarity	NPD5736	Approved
0.7083	Intermediate Similarity	NPD7039	Approved
0.7081	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4357	Discontinued
0.707	Intermediate Similarity	NPD3111	Phase 1
0.707	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD9570	Approved
0.7067	Intermediate Similarity	NPD6032	Approved
0.7067	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1551	Phase 2
0.7059	Intermediate Similarity	NPD2354	Approved
0.7059	Intermediate Similarity	NPD3887	Approved
0.7059	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2821	Approved
0.7055	Intermediate Similarity	NPD3145	Approved
0.7055	Intermediate Similarity	NPD3764	Approved
0.7055	Intermediate Similarity	NPD3144	Approved
0.7054	Intermediate Similarity	NPD291	Approved
0.705	Intermediate Similarity	NPD9268	Approved
0.705	Intermediate Similarity	NPD1651	Approved
0.7042	Intermediate Similarity	NPD2983	Phase 2
0.7042	Intermediate Similarity	NPD2982	Phase 2
0.7037	Intermediate Similarity	NPD5535	Approved
0.7032	Intermediate Similarity	NPD2533	Approved
0.7032	Intermediate Similarity	NPD5401	Approved
0.7032	Intermediate Similarity	NPD2532	Approved
0.7032	Intermediate Similarity	NPD2534	Approved
0.7027	Intermediate Similarity	NPD4340	Discontinued
0.7025	Intermediate Similarity	NPD6599	Discontinued
0.702	Intermediate Similarity	NPD5762	Approved
0.702	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6005	Phase 3
0.702	Intermediate Similarity	NPD6002	Phase 3
0.702	Intermediate Similarity	NPD6004	Phase 3
0.702	Intermediate Similarity	NPD5763	Approved
0.7014	Intermediate Similarity	NPD1019	Discontinued
0.7007	Intermediate Similarity	NPD6671	Approved
0.7	Intermediate Similarity	NPD1510	Phase 2
0.7	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD17	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