NPASS Compound

Structure

CID192539 OpenBabel06191715582D 63 69 0 0 1 0 0 0 0 0999 V2000 -3.4641 4.0000 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 7.7942 -1.5000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 1 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 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 2 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 2 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 -4.3301 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 1 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 2.5981 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 1.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 2 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 8.6603 -2.0000 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 -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 1.7321 -6.0000 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 3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 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 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 0.8660 -3.5000 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 -2.5981 2.5000 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 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 1.7321 -0.0000 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 3 2 0 0 0 0 2 11 1 0 0 0 0 3 13 1 0 0 0 0 4 11 2 0 0 0 0 4 16 1 0 0 0 0 5 12 2 0 0 0 0 5 14 1 0 0 0 0 6 12 1 0 0 0 0 6 17 2 0 0 0 0 7 39 1 0 0 0 0 8 15 1 0 0 0 0 8 55 1 0 0 0 0 9 56 1 0 0 0 0 10 1 1 6 0 0 0 10 21 1 0 0 0 0 10 57 1 0 0 0 0 11 32 1 0 0 0 0 12 40 1 0 0 0 0 13 16 2 0 0 0 0 13 41 1 0 0 0 0 14 20 2 0 0 0 0 14 42 1 0 0 0 0 15 22 1 0 0 0 0 15 43 1 6 0 0 0 16 59 1 0 0 0 0 17 20 1 0 0 0 0 17 58 1 0 0 0 0 18 7 1 1 0 0 0 18 23 1 0 0 0 0 18 60 1 0 0 0 0 19 9 1 1 0 0 0 19 24 1 0 0 0 0 19 61 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 21 44 1 1 0 0 0 22 29 1 0 0 0 0 22 45 1 1 0 0 0 23 27 1 0 0 0 0 23 46 1 6 0 0 0 24 28 1 0 0 0 0 24 47 1 6 0 0 0 25 33 1 0 0 0 0 25 48 2 0 0 0 0 26 30 1 0 0 0 0 26 49 1 6 0 0 0 27 31 1 0 0 0 0 27 50 1 1 0 0 0 28 34 1 0 0 0 0 28 51 1 1 0 0 0 29 36 1 0 0 0 0 29 52 1 6 0 0 0 30 35 1 0 0 0 0 30 53 1 6 0 0 0 31 37 1 0 0 0 0 31 54 1 6 0 0 0 32 33 2 0 0 0 0 32 58 1 0 0 0 0 33 62 1 0 0 0 0 34 38 1 0 0 0 0 34 63 1 6 0 0 0 35 56 1 1 0 0 0 35 57 1 0 0 0 0 36 55 1 0 0 0 0 36 63 1 1 0 0 0 37 59 1 1 0 0 0 37 60 1 0 0 0 0 38 61 1 0 0 0 0 38 62 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	904.25
Volume:	804.573
LogP:	-1.433
LogD:	-0.813
LogS:	-3.208
# Rotatable Bonds:	11
TPSA:	407.5
# H-Bond Aceptor:	25
# H-Bond Donor:	15
# Rings:	7
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.085
Synthetic Accessibility Score:	5.922
Fsp3:	0.605
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:	-6.623
MDCK Permeability:	9.564806532580405e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.991
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.356
Plasma Protein Binding (PPB):	67.36290740966797%
Volume Distribution (VD):	0.476
Pgp-substrate:	21.38810157775879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	0.57
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.518
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.436
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.876
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.048
Respiratory Toxicity:	0.005

Download Data

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

Natural Product: NPC192539

Natural Product ID:	NPC192539
*Common Name:**	Aescuflavoside
IUPAC Name:	3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-[4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
Synonyms:	Aescuflavoside
Standard InCHIKey:	PSMWEUGAGOGDBM-GARDDLFLSA-N
Standard InCHI:	InChI=1S/C38H48O25/c1-10-21(44)26(49)30(53)35(57-10)56-9-19-24(47)28(51)34(63-36-29(52)22(45)15(43)8-55-36)38(61-19)62-33-25(48)20-14(42)5-12(40)6-17(20)58-32(33)11-2-3-13(41)16(4-11)59-37-31(54)27(50)23(46)18(7-39)60-37/h2-6,10,15,18-19,21-24,26-31,34-47,49-54H,7-9H2,1H3/t10-,15+,18+,19+,21-,22-,23+,24+,26+,27-,28-,29+,30+,31+,34+,35+,36-,37+,38-/m0/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(ccc2O)c2oc3cc(O)cc(c3c(=O)c2O[C@@H]2O[C@H](CO[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)[C@H]([C@@H]([C@H]2O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL474659
PubChem CID:	11400338
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
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10579862]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15104496]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	seeds	n.a.	n.a.	PMID[25442304]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29234	Aesculus chinensis	Species	Sapindaceae	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	4
Others	5

Activity Type	# Activity
Cell Line	1
Organism	5
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell Line	MDCK	Canis lupus familiaris	IC50	=	71.3	ug.mL-1	PMID[493719]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	IC50	=	4.5	ug.mL-1	PMID[493719]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	15.8	n.a.	PMID[493719]
NPT336	Organism	Human parainfluenza virus 3	Human parainfluenza virus 3	IC50	=	35.6	ug.mL-1	PMID[493719]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	2.0	n.a.	PMID[493719]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	>	100.0	ug.mL-1	PMID[493719]
NPT2	Others	Unspecified		Ratio CC50/IC50	<	1.1	n.a.	PMID[493719]
NPT336	Organism	Human parainfluenza virus 3	Human parainfluenza virus 3	CC50	=	71.3	ug.mL-1	PMID[493719]
NPT742	Organism	Influenza A virus	Influenza A virus	CC50	=	107.5	ug.mL-1	PMID[493719]

☑ 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 NPC192539 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	487
0.1-0.2	1865
0.2-0.3	4255
0.3-0.4	9617
0.4-0.5	8104
0.5-0.6	5425
0.6-0.7	5912
0.7-0.8	4927
0.8-0.85	1227
0.85-0.9	446
0.9-0.95	380
0.95-1	52

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC89052
0.9939	High Similarity	NPC251417
0.9879	High Similarity	NPC219043
0.9879	High Similarity	NPC48984
0.9879	High Similarity	NPC14187
0.9879	High Similarity	NPC292019
0.9879	High Similarity	NPC122467
0.9879	High Similarity	NPC202908
0.9818	High Similarity	NPC473327
0.9818	High Similarity	NPC476472
0.9818	High Similarity	NPC220173
0.9818	High Similarity	NPC294815
0.9818	High Similarity	NPC198199
0.9818	High Similarity	NPC19108
0.9818	High Similarity	NPC16194
0.9701	High Similarity	NPC173837
0.9701	High Similarity	NPC120952
0.9697	High Similarity	NPC33054
0.9697	High Similarity	NPC60735
0.9697	High Similarity	NPC203259
0.9697	High Similarity	NPC471748
0.9697	High Similarity	NPC180918
0.9697	High Similarity	NPC26230
0.9697	High Similarity	NPC471725
0.9697	High Similarity	NPC155877
0.9697	High Similarity	NPC134532
0.9697	High Similarity	NPC176740
0.9647	High Similarity	NPC295625
0.9647	High Similarity	NPC473554
0.9647	High Similarity	NPC470719
0.9647	High Similarity	NPC33083
0.9643	High Similarity	NPC110941
0.9643	High Similarity	NPC470443
0.9643	High Similarity	NPC126784
0.9643	High Similarity	NPC473682
0.9643	High Similarity	NPC473571
0.9643	High Similarity	NPC241423
0.9643	High Similarity	NPC470444
0.9641	High Similarity	NPC473862
0.9641	High Similarity	NPC89127
0.9641	High Similarity	NPC471669
0.9636	High Similarity	NPC254855
0.9636	High Similarity	NPC285197
0.9636	High Similarity	NPC255157
0.9636	High Similarity	NPC29958
0.9636	High Similarity	NPC67105
0.9636	High Similarity	NPC136042
0.9636	High Similarity	NPC67326
0.9636	High Similarity	NPC156869
0.9636	High Similarity	NPC95866
0.9636	High Similarity	NPC259896
0.9588	High Similarity	NPC470720
0.9588	High Similarity	NPC223860
0.9588	High Similarity	NPC470451
0.9588	High Similarity	NPC470713
0.9588	High Similarity	NPC470717
0.9588	High Similarity	NPC460984
0.9588	High Similarity	NPC249560
0.9588	High Similarity	NPC25946
0.9588	High Similarity	NPC275977
0.9588	High Similarity	NPC470455
0.9588	High Similarity	NPC21359
0.9576	High Similarity	NPC120099
0.9576	High Similarity	NPC195257
0.9576	High Similarity	NPC227508
0.9576	High Similarity	NPC219904
0.9576	High Similarity	NPC86008
0.9576	High Similarity	NPC209296
0.9576	High Similarity	NPC225434
0.9576	High Similarity	NPC203050
0.9576	High Similarity	NPC223747
0.9529	High Similarity	NPC470446
0.9529	High Similarity	NPC162394
0.9529	High Similarity	NPC470449
0.9529	High Similarity	NPC470447
0.9529	High Similarity	NPC470718
0.9529	High Similarity	NPC241781
0.9529	High Similarity	NPC156785
0.9529	High Similarity	NPC473072
0.9529	High Similarity	NPC470445
0.9524	High Similarity	NPC8573
0.9524	High Similarity	NPC470949
0.9524	High Similarity	NPC169733
0.9524	High Similarity	NPC65563
0.9524	High Similarity	NPC255799
0.9518	High Similarity	NPC79056
0.9518	High Similarity	NPC44328
0.9518	High Similarity	NPC206123
0.9518	High Similarity	NPC177731
0.9518	High Similarity	NPC105095
0.9515	High Similarity	NPC127546
0.9515	High Similarity	NPC173637
0.9515	High Similarity	NPC265530
0.9515	High Similarity	NPC325555
0.9515	High Similarity	NPC84362
0.9515	High Similarity	NPC52550
0.9515	High Similarity	NPC223424
0.9515	High Similarity	NPC226304
0.9515	High Similarity	NPC275454
0.9515	High Similarity	NPC317489
0.9477	High Similarity	NPC30011
0.9477	High Similarity	NPC97817
0.9477	High Similarity	NPC72554
0.9474	High Similarity	NPC148710
0.9471	High Similarity	NPC473073
0.9471	High Similarity	NPC473071
0.9464	High Similarity	NPC294629
0.9464	High Similarity	NPC253685
0.9461	High Similarity	NPC153755
0.9458	High Similarity	NPC270578
0.9458	High Similarity	NPC105283
0.9458	High Similarity	NPC52382
0.9458	High Similarity	NPC43587
0.9458	High Similarity	NPC293629
0.9455	High Similarity	NPC274618
0.9455	High Similarity	NPC203145
0.9455	High Similarity	NPC197285
0.9455	High Similarity	NPC32641
0.9455	High Similarity	NPC12013
0.9455	High Similarity	NPC476470
0.9455	High Similarity	NPC113968
0.9455	High Similarity	NPC221342
0.9455	High Similarity	NPC142142
0.9455	High Similarity	NPC277174
0.9455	High Similarity	NPC256188
0.9455	High Similarity	NPC281131
0.9455	High Similarity	NPC73855
0.9455	High Similarity	NPC88789
0.9455	High Similarity	NPC135599
0.9455	High Similarity	NPC115674
0.9455	High Similarity	NPC210073
0.9455	High Similarity	NPC11432
0.9455	High Similarity	NPC118284
0.9455	High Similarity	NPC145038
0.9455	High Similarity	NPC179950
0.9455	High Similarity	NPC8856
0.9455	High Similarity	NPC21100
0.9455	High Similarity	NPC253662
0.9455	High Similarity	NPC328940
0.9455	High Similarity	NPC56077
0.9455	High Similarity	NPC477613
0.9455	High Similarity	NPC308404
0.9455	High Similarity	NPC186816
0.9455	High Similarity	NPC189564
0.9455	High Similarity	NPC276222
0.9419	High Similarity	NPC104910
0.9419	High Similarity	NPC474093
0.9405	High Similarity	NPC21666
0.9405	High Similarity	NPC24043
0.9405	High Similarity	NPC208668
0.9405	High Similarity	NPC204693
0.9405	High Similarity	NPC42773
0.9405	High Similarity	NPC169977
0.9405	High Similarity	NPC4390
0.9405	High Similarity	NPC45522
0.9405	High Similarity	NPC101026
0.9405	High Similarity	NPC25724
0.9401	High Similarity	NPC231194
0.9401	High Similarity	NPC244776
0.9401	High Similarity	NPC116864
0.9401	High Similarity	NPC51326
0.9398	High Similarity	NPC92565
0.9398	High Similarity	NPC160156
0.9394	High Similarity	NPC76831
0.9394	High Similarity	NPC135358
0.9394	High Similarity	NPC287889
0.9394	High Similarity	NPC55786
0.9394	High Similarity	NPC19388
0.9394	High Similarity	NPC15358
0.9394	High Similarity	NPC240431
0.9394	High Similarity	NPC311830
0.9394	High Similarity	NPC22832
0.9394	High Similarity	NPC289667
0.9394	High Similarity	NPC475366
0.9394	High Similarity	NPC277205
0.9394	High Similarity	NPC284277
0.9394	High Similarity	NPC292929
0.9394	High Similarity	NPC475497
0.9364	High Similarity	NPC475179
0.9364	High Similarity	NPC64755
0.9353	High Similarity	NPC139571
0.9353	High Similarity	NPC477895
0.9353	High Similarity	NPC475261
0.9353	High Similarity	NPC217520
0.9349	High Similarity	NPC142996
0.9349	High Similarity	NPC102028
0.9345	High Similarity	NPC175107
0.9345	High Similarity	NPC245452
0.9345	High Similarity	NPC476405
0.9345	High Similarity	NPC117260
0.9345	High Similarity	NPC256760
0.9345	High Similarity	NPC3583
0.9345	High Similarity	NPC190003
0.9345	High Similarity	NPC259152
0.9337	High Similarity	NPC5778
0.9337	High Similarity	NPC236934
0.9333	High Similarity	NPC222936
0.9333	High Similarity	NPC309025
0.9333	High Similarity	NPC243930
0.9333	High Similarity	NPC311850

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 NPC192539 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	977
0.2-0.3	2122
0.3-0.4	2714
0.4-0.5	1790
0.5-0.6	755
0.6-0.7	247
0.7-0.8	90
0.8-0.85	16
0.85-0.9	4
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9818	High Similarity	NPD7808	Phase 3
0.9758	High Similarity	NPD7251	Discontinued
0.9697	High Similarity	NPD6797	Phase 2
0.9636	High Similarity	NPD7472	Approved
0.9576	High Similarity	NPD7054	Approved
0.9518	High Similarity	NPD7074	Phase 3
0.9235	High Similarity	NPD4338	Clinical (unspecified phase)
0.9226	High Similarity	NPD7804	Clinical (unspecified phase)
0.9048	High Similarity	NPD6167	Clinical (unspecified phase)
0.9048	High Similarity	NPD6168	Clinical (unspecified phase)
0.9048	High Similarity	NPD6166	Phase 2
0.8941	High Similarity	NPD3818	Discontinued
0.8802	High Similarity	NPD4381	Clinical (unspecified phase)
0.8683	High Similarity	NPD3817	Phase 2
0.8675	High Similarity	NPD1934	Approved
0.8521	High Similarity	NPD3882	Suspended
0.8512	High Similarity	NPD2393	Clinical (unspecified phase)
0.8512	High Similarity	NPD2801	Approved
0.8466	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD1512	Approved
0.8363	Intermediate Similarity	NPD7075	Discontinued
0.8303	Intermediate Similarity	NPD1511	Approved
0.8225	Intermediate Similarity	NPD4380	Phase 2
0.8198	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD5402	Approved
0.8129	Intermediate Similarity	NPD6801	Discontinued
0.8111	Intermediate Similarity	NPD6559	Discontinued
0.8108	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD5403	Approved
0.8036	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6799	Approved
0.7955	Intermediate Similarity	NPD5494	Approved
0.7931	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD5401	Approved
0.7923	Intermediate Similarity	NPD8312	Approved
0.7923	Intermediate Similarity	NPD8313	Approved
0.7912	Intermediate Similarity	NPD7685	Pre-registration
0.7895	Intermediate Similarity	NPD1653	Approved
0.7889	Intermediate Similarity	NPD7228	Approved
0.7889	Intermediate Similarity	NPD3751	Discontinued
0.7874	Intermediate Similarity	NPD7819	Suspended
0.7865	Intermediate Similarity	NPD3787	Discontinued
0.7831	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD6959	Discontinued
0.7784	Intermediate Similarity	NPD1549	Phase 2
0.7771	Intermediate Similarity	NPD1465	Phase 2
0.7747	Intermediate Similarity	NPD5844	Phase 1
0.7742	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD7473	Discontinued
0.7722	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6599	Discontinued
0.7677	Intermediate Similarity	NPD8151	Discontinued
0.767	Intermediate Similarity	NPD8455	Phase 2
0.7667	Intermediate Similarity	NPD6232	Discontinued
0.7665	Intermediate Similarity	NPD2796	Approved
0.7657	Intermediate Similarity	NPD7411	Suspended
0.763	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7266	Discontinued
0.7616	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7199	Phase 2
0.7605	Intermediate Similarity	NPD1510	Phase 2
0.7602	Intermediate Similarity	NPD7698	Approved
0.7602	Intermediate Similarity	NPD7696	Phase 3
0.7602	Intermediate Similarity	NPD7435	Discontinued
0.7602	Intermediate Similarity	NPD7697	Approved
0.76	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7783	Phase 2
0.7598	Intermediate Similarity	NPD919	Approved
0.7582	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6780	Approved
0.7538	Intermediate Similarity	NPD6776	Approved
0.7538	Intermediate Similarity	NPD6781	Approved
0.7538	Intermediate Similarity	NPD6779	Approved
0.7538	Intermediate Similarity	NPD6782	Approved
0.7538	Intermediate Similarity	NPD6777	Approved
0.7538	Intermediate Similarity	NPD6778	Approved
0.7538	Intermediate Similarity	NPD7701	Phase 2
0.7527	Intermediate Similarity	NPD7240	Approved
0.7514	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7487	Intermediate Similarity	NPD7584	Approved
0.7475	Intermediate Similarity	NPD7871	Phase 2
0.7475	Intermediate Similarity	NPD8320	Phase 1
0.7475	Intermediate Similarity	NPD7870	Phase 2
0.7475	Intermediate Similarity	NPD8319	Approved
0.7474	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1613	Approved
0.7463	Intermediate Similarity	NPD7874	Approved
0.7463	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6190	Approved
0.7436	Intermediate Similarity	NPD7700	Phase 2
0.7436	Intermediate Similarity	NPD7699	Phase 2
0.7432	Intermediate Similarity	NPD3926	Phase 2
0.7416	Intermediate Similarity	NPD37	Approved
0.7389	Intermediate Similarity	NPD4966	Approved
0.7389	Intermediate Similarity	NPD4965	Approved
0.7389	Intermediate Similarity	NPD7768	Phase 2
0.7389	Intermediate Similarity	NPD4967	Phase 2
0.7384	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1240	Approved
0.7356	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7801	Approved
0.7321	Intermediate Similarity	NPD1933	Approved
0.7289	Intermediate Similarity	NPD3027	Phase 3
0.7283	Intermediate Similarity	NPD3750	Approved
0.7282	Intermediate Similarity	NPD6535	Approved
0.7282	Intermediate Similarity	NPD6534	Approved
0.7278	Intermediate Similarity	NPD1607	Approved
0.7262	Intermediate Similarity	NPD943	Approved
0.7246	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8150	Discontinued
0.724	Intermediate Similarity	NPD8434	Phase 2
0.7229	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD230	Phase 1
0.7204	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6823	Phase 2
0.7184	Intermediate Similarity	NPD4628	Phase 3
0.7169	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7680	Approved
0.7158	Intermediate Similarity	NPD3749	Approved
0.7151	Intermediate Similarity	NPD1551	Phase 2
0.7136	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD447	Suspended
0.7109	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7585	Approved
0.71	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7583	Approved
0.7056	Intermediate Similarity	NPD7458	Discontinued
0.7052	Intermediate Similarity	NPD2935	Discontinued
0.7042	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6674	Discontinued
0.7022	Intermediate Similarity	NPD2532	Approved
0.7022	Intermediate Similarity	NPD2533	Approved
0.7022	Intermediate Similarity	NPD2534	Approved
0.6994	Remote Similarity	NPD3748	Approved
0.6954	Remote Similarity	NPD6099	Approved
0.6954	Remote Similarity	NPD6100	Approved
0.6944	Remote Similarity	NPD920	Approved
0.6943	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6798	Discontinued
0.694	Remote Similarity	NPD6844	Discontinued
0.6935	Remote Similarity	NPD4363	Phase 3
0.6935	Remote Similarity	NPD4360	Phase 2
0.6932	Remote Similarity	NPD2800	Approved
0.6927	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5953	Discontinued
0.6923	Remote Similarity	NPD6832	Phase 2
0.6919	Remote Similarity	NPD6355	Discontinued
0.6911	Remote Similarity	NPD7286	Phase 2
0.6909	Remote Similarity	NPD1091	Approved
0.6901	Remote Similarity	NPD6233	Phase 2
0.6897	Remote Similarity	NPD7033	Discontinued
0.6884	Remote Similarity	NPD6213	Phase 3
0.6884	Remote Similarity	NPD6212	Phase 3
0.6884	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6651	Approved
0.6872	Remote Similarity	NPD7390	Discontinued
0.6868	Remote Similarity	NPD3226	Approved
0.6865	Remote Similarity	NPD5353	Approved
0.6864	Remote Similarity	NPD9494	Approved
0.6862	Remote Similarity	NPD8127	Discontinued
0.6836	Remote Similarity	NPD1243	Approved
0.6836	Remote Similarity	NPD1652	Phase 2
0.6833	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7930	Approved
0.6824	Remote Similarity	NPD4908	Phase 1
0.6816	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2798	Approved
0.6798	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7907	Approved
0.6771	Remote Similarity	NPD2163	Approved
0.6768	Remote Similarity	NPD6842	Approved
0.6768	Remote Similarity	NPD6841	Approved
0.6768	Remote Similarity	NPD6843	Phase 3
0.6763	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1203	Approved
0.6744	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2313	Discontinued
0.6724	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5124	Phase 1
0.6724	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2344	Approved
0.6723	Remote Similarity	NPD2346	Discontinued
0.6712	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD8059	Phase 3
0.6707	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2799	Discontinued
0.6703	Remote Similarity	NPD6385	Approved
0.6703	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6386	Approved
0.6702	Remote Similarity	NPD5242	Approved
0.6701	Remote Similarity	NPD7090	Clinical (unspecified phase)

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