NPASS Compound

Structure

NPC475434 OpenBabel07101718242D 85 90 0 0 1 0 0 0 0 0999 V2000 -4.3301 4.5000 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 6.9282 1.0000 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 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 6.0000 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 -7.7942 5.5000 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 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 -0.8660 -0.5000 0.0000 C 0 0 2 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 1 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 -0.8660 -1.5000 0.0000 C 0 0 1 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 -6.9282 4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 4.0000 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 -6.0622 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 28 1 0 0 0 0 9 29 1 0 0 0 0 10 30 1 0 0 0 0 11 31 1 0 0 0 0 12 32 1 0 0 0 0 13 67 1 0 0 0 0 14 68 1 0 0 0 0 15 16 2 0 0 0 0 15 33 1 0 0 0 0 16 35 1 0 0 0 0 17 33 2 0 0 0 0 17 36 1 0 0 0 0 18 34 2 0 0 0 0 18 37 1 0 0 0 0 19 34 1 0 0 0 0 19 38 2 0 0 0 0 20 69 1 0 0 0 0 21 1 1 6 0 0 0 21 42 1 0 0 0 0 21 71 1 0 0 0 0 22 2 1 6 0 0 0 22 43 1 0 0 0 0 22 70 1 0 0 0 0 23 56 2 0 0 0 0 23 72 1 0 0 0 0 24 57 2 0 0 0 0 24 73 1 0 0 0 0 25 58 2 0 0 0 0 25 74 1 0 0 0 0 26 59 2 0 0 0 0 26 75 1 0 0 0 0 27 60 2 0 0 0 0 27 76 1 0 0 0 0 28 61 2 0 0 0 0 28 77 1 0 0 0 0 29 62 2 0 0 0 0 29 78 1 0 0 0 0 30 63 2 0 0 0 0 30 79 1 0 0 0 0 31 64 2 0 0 0 0 31 80 1 0 0 0 0 32 65 2 0 0 0 0 32 81 1 0 0 0 0 33 44 1 0 0 0 0 34 67 1 0 0 0 0 35 36 2 0 0 0 0 35 72 1 0 0 0 0 36 68 1 0 0 0 0 37 40 2 0 0 0 0 37 73 1 0 0 0 0 38 40 1 0 0 0 0 38 82 1 0 0 0 0 39 20 1 1 0 0 0 39 45 1 0 0 0 0 39 83 1 0 0 0 0 40 41 1 0 0 0 0 41 46 1 0 0 0 0 41 66 2 0 0 0 0 42 47 1 0 0 0 0 42 74 1 1 0 0 0 43 48 1 0 0 0 0 43 84 1 1 0 0 0 44 46 2 0 0 0 0 44 82 1 0 0 0 0 45 49 1 0 0 0 0 45 75 1 1 0 0 0 46 85 1 0 0 0 0 47 51 1 0 0 0 0 47 76 1 6 0 0 0 48 50 1 0 0 0 0 48 77 1 6 0 0 0 49 52 1 0 0 0 0 49 78 1 1 0 0 0 50 53 1 0 0 0 0 50 79 1 6 0 0 0 51 54 1 0 0 0 0 51 80 1 6 0 0 0 52 55 1 0 0 0 0 52 81 1 6 0 0 0 53 69 1 1 0 0 0 53 70 1 0 0 0 0 54 71 1 0 0 0 0 54 84 1 1 0 0 0 55 83 1 0 0 0 0 55 85 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1204.35
Volume:	1124.747
LogP:	3.07
LogD:	1.66
LogS:	-5.115
# Rotatable Bonds:	30
TPSA:	367.05
# H-Bond Aceptor:	30
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	30

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	6.274
Fsp3:	0.545
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:	-5.121
MDCK Permeability:	0.0005681577022187412
Pgp-inhibitor:	0.999
Pgp-substrate:	0.529
Human Intestinal Absorption (HIA):	0.92
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	41.479774475097656%
Volume Distribution (VD):	0.954
Pgp-substrate:	18.12044906616211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.991
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.414
CYP3A4-substrate:	0.149

ADMET: Excretion

Clearance (CL):	1.962
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.994
AMES Toxicity:	0.134
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.744
Carcinogencity:	0.01
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC475434

Natural Product ID:	NPC475434
*Common Name:**	[(2S,3S,4R,5R,6S)-4,5-Diacetyloxy-6-[(2S,3S,4R,5R,6R)-4,5-Diacetyloxy-2-Methyl-6-[[(2R,3S,4S,5R,6S)-3,4,5-Triacetyloxy-6-[5-Acetyloxy-2-(4-Acetyloxy-3-Methoxyphenyl)-7-Methoxy-4-Oxochromen-3-Yl]Oxyoxan-2-Yl]Methoxy]Oxan-3-Yl]Oxy-2-Methyloxan-3-Yl] Acetate
IUPAC Name:	[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-[(2S,3S,4R,5R,6R)-4,5-diacetyloxy-2-methyl-6-[[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[5-acetyloxy-2-(4-acetyloxy-3-methoxyphenyl)-7-methoxy-4-oxochromen-3-yl]oxyoxan-2-yl]methoxy]oxan-3-yl]oxy-2-methyloxan-3-yl] acetate
Synonyms:
Standard InCHIKey:	RMJWWUJWFIGESI-GSAJJTMASA-N
Standard InCHI:	InChI=1S/C55H64O30/c1-21-42(74-25(5)58)47(76-27(7)60)51(80-31(11)64)54(71-21)84-43-22(2)70-53(50(79-30(10)63)48(43)77-28(8)61)69-20-39-45(75-26(6)59)49(78-29(9)62)52(81-32(12)65)55(83-39)85-46-41(66)40-37(73-24(4)57)18-34(67-13)19-38(40)82-44(46)33-15-16-35(72-23(3)56)36(17-33)68-14/h15-19,21-22,39,42-43,45,47-55H,20H2,1-14H3/t21-,22-,39+,42-,43-,45-,47+,48+,49-,50+,51+,52+,53+,54-,55-/m0/s1
SMILES:	COc1cc(OC(=O)C)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2OC(=O)C)OC(=O)C)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2OC(=O)C)OC(=O)C)OC(=O)C)[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)c1ccc(c(c1)OC)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505646
PubChem CID:	21676310
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*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
NPO33118	Rhamnus	Genus	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350094]

☑ 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	3

Activity Type	# Activity
CELL-LINE	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	88.8	%	PMID[574112]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	87.8	%	PMID[574112]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	90.8	%	PMID[574112]

☑ 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 NPC475434 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	528
0.1-0.2	1967
0.2-0.3	4597
0.3-0.4	9666
0.4-0.5	8395
0.5-0.6	5197
0.6-0.7	6095
0.7-0.8	5075
0.8-0.85	648
0.85-0.9	444
0.9-0.95	81
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC476180
0.9811	High Similarity	NPC475214
0.9623	High Similarity	NPC414831
0.9568	High Similarity	NPC477165
0.956	High Similarity	NPC473516
0.9497	High Similarity	NPC321478
0.9398	High Similarity	NPC48984
0.9398	High Similarity	NPC473862
0.9371	High Similarity	NPC117478
0.9341	High Similarity	NPC89052
0.9341	High Similarity	NPC251417
0.9341	High Similarity	NPC173837
0.9294	High Similarity	NPC295625
0.9294	High Similarity	NPC473554
0.9294	High Similarity	NPC470719
0.9286	High Similarity	NPC192539
0.9281	High Similarity	NPC219043
0.9281	High Similarity	NPC471669
0.9281	High Similarity	NPC14187
0.9281	High Similarity	NPC122467
0.9281	High Similarity	NPC292019
0.9281	High Similarity	NPC202908
0.9281	High Similarity	NPC89127
0.9235	High Similarity	NPC460984
0.9235	High Similarity	NPC223860
0.9235	High Similarity	NPC470717
0.9235	High Similarity	NPC25946
0.9235	High Similarity	NPC470720
0.9235	High Similarity	NPC21359
0.9235	High Similarity	NPC249560
0.9235	High Similarity	NPC470451
0.9235	High Similarity	NPC470455
0.9235	High Similarity	NPC470713
0.9235	High Similarity	NPC275977
0.9226	High Similarity	NPC120952
0.9222	High Similarity	NPC19108
0.9222	High Similarity	NPC473327
0.9222	High Similarity	NPC294815
0.9222	High Similarity	NPC476472
0.9222	High Similarity	NPC16194
0.9222	High Similarity	NPC220173
0.9181	High Similarity	NPC33083
0.9176	High Similarity	NPC470446
0.9176	High Similarity	NPC162394
0.9176	High Similarity	NPC156785
0.9176	High Similarity	NPC470447
0.9176	High Similarity	NPC470445
0.9176	High Similarity	NPC241781
0.9176	High Similarity	NPC470449
0.9176	High Similarity	NPC470718
0.9146	High Similarity	NPC475366
0.9146	High Similarity	NPC284277
0.9146	High Similarity	NPC15358
0.9146	High Similarity	NPC475497
0.9136	High Similarity	NPC477164
0.9128	High Similarity	NPC97817
0.9128	High Similarity	NPC72554
0.9128	High Similarity	NPC30011
0.9125	High Similarity	NPC471746
0.9112	High Similarity	NPC477895
0.9107	High Similarity	NPC253685
0.9107	High Similarity	NPC198199
0.9102	High Similarity	NPC176740
0.9102	High Similarity	NPC180918
0.9102	High Similarity	NPC155877
0.9102	High Similarity	NPC471725
0.9102	High Similarity	NPC153755
0.9102	High Similarity	NPC60735
0.9102	High Similarity	NPC26230
0.9102	High Similarity	NPC203259
0.9102	High Similarity	NPC471748
0.9102	High Similarity	NPC134532
0.9102	High Similarity	NPC33054
0.907	High Similarity	NPC104910
0.907	High Similarity	NPC474093
0.9059	High Similarity	NPC126784
0.9059	High Similarity	NPC473682
0.9059	High Similarity	NPC110941
0.9059	High Similarity	NPC470443
0.9059	High Similarity	NPC473571
0.9059	High Similarity	NPC470444
0.9059	High Similarity	NPC241423
0.9057	High Similarity	NPC472535
0.9057	High Similarity	NPC474388
0.9057	High Similarity	NPC474170
0.9048	High Similarity	NPC4390
0.9042	High Similarity	NPC255157
0.9042	High Similarity	NPC244776
0.9042	High Similarity	NPC136042
0.9042	High Similarity	NPC29958
0.9042	High Similarity	NPC67326
0.9042	High Similarity	NPC95866
0.9042	High Similarity	NPC67105
0.9042	High Similarity	NPC156869
0.9042	High Similarity	NPC259896
0.9042	High Similarity	NPC285197
0.9042	High Similarity	NPC254855
0.9042	High Similarity	NPC116864
0.9024	High Similarity	NPC244875
0.9017	High Similarity	NPC475179
0.9	High Similarity	NPC475261
0.9	High Similarity	NPC139571
0.9	High Similarity	NPC217520
0.8994	High Similarity	NPC264735
0.8994	High Similarity	NPC177839
0.8988	High Similarity	NPC175107
0.8988	High Similarity	NPC190003
0.8982	High Similarity	NPC61791
0.8982	High Similarity	NPC120099
0.8982	High Similarity	NPC209296
0.8982	High Similarity	NPC225434
0.8982	High Similarity	NPC203050
0.8982	High Similarity	NPC223747
0.8982	High Similarity	NPC227508
0.8982	High Similarity	NPC293629
0.8982	High Similarity	NPC219904
0.8982	High Similarity	NPC195257
0.8982	High Similarity	NPC86008
0.8976	High Similarity	NPC186816
0.8976	High Similarity	NPC203145
0.8976	High Similarity	NPC256188
0.8976	High Similarity	NPC189564
0.8976	High Similarity	NPC11432
0.8976	High Similarity	NPC12013
0.8976	High Similarity	NPC221342
0.8976	High Similarity	NPC142142
0.8976	High Similarity	NPC477613
0.8976	High Similarity	NPC476470
0.8976	High Similarity	NPC32641
0.8976	High Similarity	NPC64425
0.8963	High Similarity	NPC182045
0.8953	High Similarity	NPC473072
0.8951	High Similarity	NPC257277
0.8947	High Similarity	NPC473895
0.8941	High Similarity	NPC255799
0.8941	High Similarity	NPC169733
0.8941	High Similarity	NPC472384
0.8941	High Similarity	NPC472385
0.8941	High Similarity	NPC470949
0.8941	High Similarity	NPC472382
0.8941	High Similarity	NPC198324
0.8941	High Similarity	NPC65563
0.8941	High Similarity	NPC472380
0.8941	High Similarity	NPC8573
0.8929	High Similarity	NPC177731
0.8929	High Similarity	NPC20505
0.8929	High Similarity	NPC206123
0.8929	High Similarity	NPC138990
0.8929	High Similarity	NPC105095
0.8929	High Similarity	NPC209550
0.8929	High Similarity	NPC277532
0.8929	High Similarity	NPC155763
0.8929	High Similarity	NPC194483
0.8929	High Similarity	NPC52353
0.8929	High Similarity	NPC79056
0.8929	High Similarity	NPC293004
0.8929	High Similarity	NPC175429
0.8929	High Similarity	NPC235260
0.8929	High Similarity	NPC44328
0.8922	High Similarity	NPC52550
0.8922	High Similarity	NPC275454
0.8922	High Similarity	NPC226304
0.8922	High Similarity	NPC325555
0.8922	High Similarity	NPC317489
0.8922	High Similarity	NPC223424
0.8922	High Similarity	NPC265530
0.8922	High Similarity	NPC84362
0.8922	High Similarity	NPC173637
0.8922	High Similarity	NPC127546
0.8916	High Similarity	NPC76831
0.8916	High Similarity	NPC287889
0.8916	High Similarity	NPC289667
0.8916	High Similarity	NPC135358
0.8916	High Similarity	NPC292929
0.8902	High Similarity	NPC110349
0.8902	High Similarity	NPC148710
0.8902	High Similarity	NPC470416
0.8895	High Similarity	NPC473073
0.8895	High Similarity	NPC473071
0.8889	High Similarity	NPC34725
0.8889	High Similarity	NPC253521
0.8889	High Similarity	NPC122623
0.8889	High Similarity	NPC113836
0.8889	High Similarity	NPC258044
0.8889	High Similarity	NPC196127
0.8889	High Similarity	NPC293626
0.8889	High Similarity	NPC217387
0.8889	High Similarity	NPC276059
0.8889	High Similarity	NPC35167
0.8889	High Similarity	NPC267680
0.8889	High Similarity	NPC37668
0.8889	High Similarity	NPC284353
0.8889	High Similarity	NPC241774
0.8882	High Similarity	NPC214621
0.8882	High Similarity	NPC43211
0.8882	High Similarity	NPC210094
0.8882	High Similarity	NPC223426
0.8882	High Similarity	NPC102028
0.8882	High Similarity	NPC34267
0.8882	High Similarity	NPC49344

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 NPC475434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	438
0.1-0.2	1011
0.2-0.3	2126
0.3-0.4	2701
0.4-0.5	1772
0.5-0.6	744
0.6-0.7	241
0.7-0.8	105
0.8-0.85	4
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9337	High Similarity	NPD7808	Phase 3
0.9162	High Similarity	NPD7251	Discontinued
0.9102	High Similarity	NPD6797	Phase 2
0.9042	High Similarity	NPD7472	Approved
0.8982	High Similarity	NPD7054	Approved
0.8929	High Similarity	NPD7074	Phase 3
0.8889	High Similarity	NPD3817	Phase 2
0.8882	High Similarity	NPD4338	Clinical (unspecified phase)
0.8757	High Similarity	NPD7804	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6166	Phase 2
0.8471	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD5494	Approved
0.8225	Intermediate Similarity	NPD7075	Discontinued
0.8204	Intermediate Similarity	NPD1934	Approved
0.8176	Intermediate Similarity	NPD919	Approved
0.816	Intermediate Similarity	NPD6799	Approved
0.8125	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD5402	Approved
0.8095	Intermediate Similarity	NPD6801	Discontinued
0.8059	Intermediate Similarity	NPD3882	Suspended
0.8047	Intermediate Similarity	NPD7819	Suspended
0.8047	Intermediate Similarity	NPD2801	Approved
0.8047	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD5401	Approved
0.7953	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD1512	Approved
0.795	Intermediate Similarity	NPD2796	Approved
0.788	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6599	Discontinued
0.7831	Intermediate Similarity	NPD1511	Approved
0.7812	Intermediate Similarity	NPD1933	Approved
0.7809	Intermediate Similarity	NPD5844	Phase 1
0.7784	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7771	Intermediate Similarity	NPD1247	Approved
0.7765	Intermediate Similarity	NPD4380	Phase 2
0.7719	Intermediate Similarity	NPD7411	Suspended
0.7697	Intermediate Similarity	NPD7473	Discontinued
0.7692	Intermediate Similarity	NPD8312	Approved
0.7692	Intermediate Similarity	NPD8313	Approved
0.7688	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD3926	Phase 2
0.7647	Intermediate Similarity	NPD1653	Approved
0.764	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1465	Phase 2
0.763	Intermediate Similarity	NPD8455	Phase 2
0.7627	Intermediate Similarity	NPD3787	Discontinued
0.7627	Intermediate Similarity	NPD6232	Discontinued
0.7582	Intermediate Similarity	NPD7685	Pre-registration
0.7581	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6959	Discontinued
0.7571	Intermediate Similarity	NPD7199	Phase 2
0.7556	Intermediate Similarity	NPD7228	Approved
0.7556	Intermediate Similarity	NPD3751	Discontinued
0.7542	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD1549	Phase 2
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7486	Intermediate Similarity	NPD7240	Approved
0.7485	Intermediate Similarity	NPD920	Approved
0.7462	Intermediate Similarity	NPD8151	Discontinued
0.7455	Intermediate Similarity	NPD3748	Approved
0.7412	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7783	Phase 2
0.7387	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7435	Discontinued
0.7381	Intermediate Similarity	NPD1243	Approved
0.7371	Intermediate Similarity	NPD37	Approved
0.7368	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1510	Phase 2
0.7345	Intermediate Similarity	NPD4967	Phase 2
0.7345	Intermediate Similarity	NPD7768	Phase 2
0.7345	Intermediate Similarity	NPD4965	Approved
0.7345	Intermediate Similarity	NPD4966	Approved
0.7321	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7696	Phase 3
0.7296	Intermediate Similarity	NPD7697	Approved
0.7296	Intermediate Similarity	NPD7698	Approved
0.7288	Intermediate Similarity	NPD5353	Approved
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD447	Suspended
0.7263	Intermediate Similarity	NPD6234	Discontinued
0.7262	Intermediate Similarity	NPD7266	Discontinued
0.7259	Intermediate Similarity	NPD8319	Approved
0.7259	Intermediate Similarity	NPD8320	Phase 1
0.7254	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7874	Approved
0.725	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3750	Approved
0.7235	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD3749	Approved
0.7172	Intermediate Similarity	NPD7871	Phase 2
0.7172	Intermediate Similarity	NPD7870	Phase 2
0.715	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD6782	Approved
0.7143	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD6779	Approved
0.7143	Intermediate Similarity	NPD6778	Approved
0.7143	Intermediate Similarity	NPD6781	Approved
0.7143	Intermediate Similarity	NPD6777	Approved
0.7119	Intermediate Similarity	NPD6386	Approved
0.7119	Intermediate Similarity	NPD6385	Approved
0.7108	Intermediate Similarity	NPD1240	Approved
0.7105	Intermediate Similarity	NPD8434	Phase 2
0.7104	Intermediate Similarity	NPD5242	Approved
0.7102	Intermediate Similarity	NPD7458	Discontinued
0.7101	Intermediate Similarity	NPD1551	Phase 2
0.71	Intermediate Similarity	NPD7584	Approved
0.7093	Intermediate Similarity	NPD6190	Approved
0.7076	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5005	Approved
0.7071	Intermediate Similarity	NPD5006	Approved
0.7041	Intermediate Similarity	NPD7699	Phase 2
0.7041	Intermediate Similarity	NPD7700	Phase 2
0.7035	Intermediate Similarity	NPD4628	Phase 3
0.7024	Intermediate Similarity	NPD1607	Approved
0.7016	Intermediate Similarity	NPD8150	Discontinued
0.7015	Intermediate Similarity	NPD7583	Approved
0.7006	Intermediate Similarity	NPD3226	Approved
0.7005	Intermediate Similarity	NPD8285	Discontinued
0.7	Intermediate Similarity	NPD2935	Discontinued
0.6995	Remote Similarity	NPD8127	Discontinued
0.6994	Remote Similarity	NPD3887	Approved
0.6988	Remote Similarity	NPD6798	Discontinued
0.698	Remote Similarity	NPD7585	Approved
0.6971	Remote Similarity	NPD2532	Approved
0.6971	Remote Similarity	NPD2534	Approved
0.6971	Remote Similarity	NPD2533	Approved
0.6971	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3146	Approved
0.6964	Remote Similarity	NPD6355	Discontinued
0.6964	Remote Similarity	NPD230	Phase 1
0.6961	Remote Similarity	NPD7801	Approved
0.6957	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4420	Approved
0.6946	Remote Similarity	NPD6233	Phase 2
0.6905	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1613	Approved
0.689	Remote Similarity	NPD3266	Approved
0.689	Remote Similarity	NPD3267	Approved
0.6888	Remote Similarity	NPD6535	Approved
0.6888	Remote Similarity	NPD6534	Approved
0.6886	Remote Similarity	NPD2313	Discontinued
0.6884	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2403	Approved
0.6879	Remote Similarity	NPD1652	Phase 2
0.6878	Remote Similarity	NPD5953	Discontinued
0.6875	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7680	Approved
0.6862	Remote Similarity	NPD7286	Phase 2
0.686	Remote Similarity	NPD2346	Discontinued
0.6848	Remote Similarity	NPD2798	Approved
0.6848	Remote Similarity	NPD1019	Discontinued
0.6842	Remote Similarity	NPD7033	Discontinued
0.6842	Remote Similarity	NPD2799	Discontinued
0.6834	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6823	Phase 2
0.6816	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7549	Discontinued
0.6805	Remote Similarity	NPD943	Approved
0.6805	Remote Similarity	NPD4307	Phase 2
0.6796	Remote Similarity	NPD6844	Discontinued
0.6793	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1203	Approved
0.6786	Remote Similarity	NPD3268	Approved
0.6786	Remote Similarity	NPD1296	Phase 2
0.6784	Remote Similarity	NPD7097	Phase 1
0.6782	Remote Similarity	NPD6674	Discontinued
0.6766	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5124	Phase 1
0.6763	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2353	Approved
0.6761	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5890	Approved
0.674	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5889	Approved
0.6728	Remote Similarity	NPD17	Approved
0.6727	Remote Similarity	NPD3225	Approved
0.6726	Remote Similarity	NPD3027	Phase 3
0.672	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3018	Phase 2
0.6707	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD9717	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