NPASS Compound

Structure

CID77922 OpenBabel06191715412D 33 36 0 0 1 0 0 0 0 0999 V2000 -7.1527 -1.3104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7926 0.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1309 -1.1025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7707 0.5917 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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 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 -3.8581 -0.2399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 -0.5672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4399 -0.1514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 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 -2.5981 -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 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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5054 -0.7752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 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 -9.4180 0.0565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -3.7601 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 3.0000 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 -5.1964 -1.7262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 -0.0320 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 3 1 0 0 0 0 1 10 2 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 12 2 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 6 30 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 9 31 1 0 0 0 0 10 20 1 0 0 0 0 12 24 1 0 0 0 0 13 5 1 1 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 25 1 6 0 0 0 15 8 1 1 0 0 0 15 17 1 0 0 0 0 15 32 1 0 0 0 0 16 11 1 1 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 6 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 22 1 0 0 0 0 19 28 1 6 0 0 0 20 29 2 0 0 0 0 20 31 1 0 0 0 0 21 30 1 0 0 0 0 21 33 1 6 0 0 0 22 32 1 0 0 0 0 22 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.15
Volume:	435.716
LogP:	0.511
LogD:	0.277
LogS:	-2.176
# Rotatable Bonds:	7
TPSA:	175.37
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.219
Synthetic Accessibility Score:	4.644
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.126
MDCK Permeability:	5.5385768064297736e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.348
Human Intestinal Absorption (HIA):	0.692
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.241
Plasma Protein Binding (PPB):	38.610923767089844%
Volume Distribution (VD):	0.379
Pgp-substrate:	38.78937530517578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.098
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.074

ADMET: Excretion

Clearance (CL):	1.825
Half-life (T1/2):	0.932

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.457
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.085
Carcinogencity:	0.943
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.522

Download Data

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

Natural Product: NPC77922

Natural Product ID:	NPC77922
*Common Name:**	Agnuside
IUPAC Name:	[(1S,4aR,5S,7aS)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate
Synonyms:	Agnuside
Standard InCHIKey:	GLACGTLACKLUJX-QNAXTHAFSA-N
Standard InCHI:	InChI=1S/C22H26O11/c23-8-15-17(26)18(27)19(28)22(32-15)33-21-16-11(7-14(25)13(16)5-6-30-21)9-31-20(29)10-1-3-12(24)4-2-10/h1-7,13-19,21-28H,8-9H2/t13-,14+,15+,16+,17+,18-,19+,21-,22-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2C(=C[C@H]3O)COC(=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483223
PubChem CID:	442416
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid 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
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10579867]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	subterranean part	n.a.	n.a.	PMID[11374949]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11536386]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11975496]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15577254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15621610]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO23142	Lamium album	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19904996]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23327905]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
NPO33328	cresentia alata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26351040]
NPO33356	vitex mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33113	castilleja tenuiflora	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28453270]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23142	Lamium album	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	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
EC50	1
Others	10

Activity Type	# Activity
Cell Line	3
Individual Protein	6
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	40.3	%	PMID[490111]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	40.8	%	PMID[490111]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	43.4	%	PMID[490111]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	<=	30.0	%	PMID[490111]
NPT737	Cell Line	HUVEC	Homo sapiens	Activity	<=	56.0	%	PMID[490112]
NPT737	Cell Line	HUVEC	Homo sapiens	Activity	=	20.0	%	PMID[490112]
NPT737	Cell Line	HUVEC	Homo sapiens	EC50	=	1.376	ug.mL-1	PMID[490112]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	12.9	%	PMID[490110]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	20.3	%	PMID[490110]

☑ 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 NPC77922 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	317
0.1-0.2	1191
0.2-0.3	2815
0.3-0.4	6467
0.4-0.5	10794
0.5-0.6	6551
0.6-0.7	9548
0.7-0.8	4652
0.8-0.85	294
0.85-0.9	47
0.9-0.95	18
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473281
0.9643	High Similarity	NPC473149
0.9507	High Similarity	NPC478234
0.9507	High Similarity	NPC478236
0.9375	High Similarity	NPC289021
0.9375	High Similarity	NPC158546
0.9348	High Similarity	NPC31745
0.9348	High Similarity	NPC220936
0.931	High Similarity	NPC194705
0.9155	High Similarity	NPC202391
0.9155	High Similarity	NPC296659
0.9124	High Similarity	NPC114116
0.9118	High Similarity	NPC254819
0.911	High Similarity	NPC474620
0.9091	High Similarity	NPC475528
0.9085	High Similarity	NPC293154
0.9085	High Similarity	NPC475213
0.9085	High Similarity	NPC152796
0.9085	High Similarity	NPC478250
0.9065	High Similarity	NPC471345
0.9048	High Similarity	NPC478235
0.9028	High Similarity	NPC119773
0.9028	High Similarity	NPC474268
0.9028	High Similarity	NPC143246
0.9028	High Similarity	NPC475539
0.8986	High Similarity	NPC229354
0.8973	High Similarity	NPC96599
0.8944	High Similarity	NPC80098
0.8926	High Similarity	NPC478232
0.8912	High Similarity	NPC240592
0.8912	High Similarity	NPC117346
0.8889	High Similarity	NPC63304
0.8882	High Similarity	NPC138993
0.8874	High Similarity	NPC187205
0.8794	High Similarity	NPC472132
0.8786	High Similarity	NPC169398
0.8776	High Similarity	NPC189631
0.8767	High Similarity	NPC473147
0.8767	High Similarity	NPC291153
0.8767	High Similarity	NPC473867
0.8766	High Similarity	NPC145847
0.8766	High Similarity	NPC476011
0.8725	High Similarity	NPC475379
0.871	High Similarity	NPC109990
0.8671	High Similarity	NPC49597
0.8667	High Similarity	NPC203664
0.8658	High Similarity	NPC182350
0.8658	High Similarity	NPC69367
0.8639	High Similarity	NPC212808
0.8636	High Similarity	NPC474936
0.863	High Similarity	NPC184464
0.863	High Similarity	NPC251062
0.8621	High Similarity	NPC65833
0.8618	High Similarity	NPC475484
0.8609	High Similarity	NPC257847
0.8601	High Similarity	NPC101686
0.8601	High Similarity	NPC469364
0.8601	High Similarity	NPC65262
0.8599	High Similarity	NPC301910
0.8599	High Similarity	NPC130730
0.8591	High Similarity	NPC161955
0.8571	High Similarity	NPC179914
0.8562	High Similarity	NPC186296
0.8562	High Similarity	NPC475378
0.8552	High Similarity	NPC159387
0.8552	High Similarity	NPC79908
0.8552	High Similarity	NPC7518
0.8552	High Similarity	NPC46644
0.8552	High Similarity	NPC154262
0.8552	High Similarity	NPC137501
0.8535	High Similarity	NPC180586
0.8526	High Similarity	NPC206815
0.8506	High Similarity	NPC475663
0.8506	High Similarity	NPC49173
0.8506	High Similarity	NPC286919
0.8503	High Similarity	NPC471028
0.8503	High Similarity	NPC194938
0.8493	Intermediate Similarity	NPC31081
0.8493	Intermediate Similarity	NPC245219
0.8491	Intermediate Similarity	NPC21956
0.8477	Intermediate Similarity	NPC140151
0.8467	Intermediate Similarity	NPC92117
0.8462	Intermediate Similarity	NPC212729
0.8456	Intermediate Similarity	NPC52097
0.8452	Intermediate Similarity	NPC469384
0.8446	Intermediate Similarity	NPC108455
0.8446	Intermediate Similarity	NPC210330
0.844	Intermediate Similarity	NPC281798
0.8435	Intermediate Similarity	NPC116104
0.8435	Intermediate Similarity	NPC237872
0.8435	Intermediate Similarity	NPC263397
0.8435	Intermediate Similarity	NPC302286
0.8435	Intermediate Similarity	NPC88754
0.8431	Intermediate Similarity	NPC327032
0.8431	Intermediate Similarity	NPC472128
0.8431	Intermediate Similarity	NPC194095
0.8431	Intermediate Similarity	NPC191046
0.8431	Intermediate Similarity	NPC472127
0.8429	Intermediate Similarity	NPC253595
0.8421	Intermediate Similarity	NPC134905
0.8421	Intermediate Similarity	NPC36130
0.8417	Intermediate Similarity	NPC288416
0.8411	Intermediate Similarity	NPC179128
0.8411	Intermediate Similarity	NPC116292
0.8411	Intermediate Similarity	NPC267469
0.8411	Intermediate Similarity	NPC87630
0.8406	Intermediate Similarity	NPC126991
0.8406	Intermediate Similarity	NPC83218
0.8403	Intermediate Similarity	NPC294470
0.84	Intermediate Similarity	NPC248257
0.84	Intermediate Similarity	NPC120728
0.84	Intermediate Similarity	NPC120621
0.8397	Intermediate Similarity	NPC130489
0.8397	Intermediate Similarity	NPC208676
0.8389	Intermediate Similarity	NPC208293
0.8387	Intermediate Similarity	NPC104275
0.8387	Intermediate Similarity	NPC4747
0.8387	Intermediate Similarity	NPC226759
0.8382	Intermediate Similarity	NPC11724
0.8378	Intermediate Similarity	NPC229036
0.8377	Intermediate Similarity	NPC156624
0.8377	Intermediate Similarity	NPC10205
0.8377	Intermediate Similarity	NPC172920
0.8369	Intermediate Similarity	NPC17567
0.8367	Intermediate Similarity	NPC296643
0.8366	Intermediate Similarity	NPC157898
0.8365	Intermediate Similarity	NPC282551
0.8357	Intermediate Similarity	NPC225307
0.8345	Intermediate Similarity	NPC252114
0.8345	Intermediate Similarity	NPC471157
0.8344	Intermediate Similarity	NPC111785
0.8344	Intermediate Similarity	NPC293568
0.8344	Intermediate Similarity	NPC117943
0.8344	Intermediate Similarity	NPC477627
0.8323	Intermediate Similarity	NPC471405
0.8311	Intermediate Similarity	NPC242756
0.831	Intermediate Similarity	NPC246869
0.831	Intermediate Similarity	NPC225384
0.831	Intermediate Similarity	NPC478255
0.831	Intermediate Similarity	NPC138777
0.8309	Intermediate Similarity	NPC476872
0.8301	Intermediate Similarity	NPC134819
0.8289	Intermediate Similarity	NPC88886
0.8289	Intermediate Similarity	NPC104172
0.8289	Intermediate Similarity	NPC162569
0.8289	Intermediate Similarity	NPC35160
0.8289	Intermediate Similarity	NPC35097
0.8286	Intermediate Similarity	NPC471882
0.8286	Intermediate Similarity	NPC106677
0.8286	Intermediate Similarity	NPC156692
0.8286	Intermediate Similarity	NPC45224
0.8286	Intermediate Similarity	NPC471881
0.8286	Intermediate Similarity	NPC173150
0.8286	Intermediate Similarity	NPC35288
0.8282	Intermediate Similarity	NPC171706
0.8278	Intermediate Similarity	NPC140722
0.8278	Intermediate Similarity	NPC92054
0.8278	Intermediate Similarity	NPC4958
0.8273	Intermediate Similarity	NPC123704
0.8269	Intermediate Similarity	NPC43638
0.8269	Intermediate Similarity	NPC133984
0.8269	Intermediate Similarity	NPC472860
0.8267	Intermediate Similarity	NPC37838
0.8267	Intermediate Similarity	NPC474044
0.8255	Intermediate Similarity	NPC478240
0.8247	Intermediate Similarity	NPC259767
0.8247	Intermediate Similarity	NPC137813
0.8247	Intermediate Similarity	NPC16024
0.8247	Intermediate Similarity	NPC88484
0.8247	Intermediate Similarity	NPC61152
0.8247	Intermediate Similarity	NPC205037
0.8247	Intermediate Similarity	NPC3746
0.8247	Intermediate Similarity	NPC44260
0.8239	Intermediate Similarity	NPC319995
0.8239	Intermediate Similarity	NPC289415
0.8235	Intermediate Similarity	NPC191154
0.8228	Intermediate Similarity	NPC477629
0.8228	Intermediate Similarity	NPC195685
0.8228	Intermediate Similarity	NPC210961
0.8228	Intermediate Similarity	NPC477628
0.8228	Intermediate Similarity	NPC270675
0.8228	Intermediate Similarity	NPC472994
0.8224	Intermediate Similarity	NPC75945
0.8219	Intermediate Similarity	NPC84789
0.8219	Intermediate Similarity	NPC302583
0.8219	Intermediate Similarity	NPC100558
0.8219	Intermediate Similarity	NPC310252
0.8217	Intermediate Similarity	NPC160780
0.8217	Intermediate Similarity	NPC74319
0.8217	Intermediate Similarity	NPC289811
0.8217	Intermediate Similarity	NPC287872
0.8214	Intermediate Similarity	NPC61181
0.8214	Intermediate Similarity	NPC114096
0.8212	Intermediate Similarity	NPC18789
0.8205	Intermediate Similarity	NPC149368
0.8205	Intermediate Similarity	NPC265480
0.8205	Intermediate Similarity	NPC127406
0.8194	Intermediate Similarity	NPC322503
0.8194	Intermediate Similarity	NPC210003
0.8194	Intermediate Similarity	NPC83283

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 NPC77922 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	743
0.2-0.3	1597
0.3-0.4	2659
0.4-0.5	2198
0.5-0.6	1189
0.6-0.7	433
0.7-0.8	66
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7685	Pre-registration
0.8153	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD9545	Approved
0.7881	Intermediate Similarity	NPD4628	Phase 3
0.78	Intermediate Similarity	NPD7266	Discontinued
0.7771	Intermediate Similarity	NPD4380	Phase 2
0.7758	Intermediate Similarity	NPD3818	Discontinued
0.7712	Intermediate Similarity	NPD6190	Approved
0.7633	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7054	Approved
0.7584	Intermediate Similarity	NPD230	Phase 1
0.756	Intermediate Similarity	NPD7472	Approved
0.7532	Intermediate Similarity	NPD1653	Approved
0.7531	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD8455	Phase 2
0.7515	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7471	Intermediate Similarity	NPD7251	Discontinued
0.7471	Intermediate Similarity	NPD6559	Discontinued
0.7456	Intermediate Similarity	NPD7074	Phase 3
0.7453	Intermediate Similarity	NPD6801	Discontinued
0.7427	Intermediate Similarity	NPD7808	Phase 3
0.7384	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7375	Intermediate Similarity	NPD7458	Discontinued
0.7361	Intermediate Similarity	NPD1091	Approved
0.7358	Intermediate Similarity	NPD5403	Approved
0.7358	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7199	Phase 2
0.7347	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1549	Phase 2
0.729	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6799	Approved
0.7239	Intermediate Similarity	NPD37	Approved
0.7235	Intermediate Similarity	NPD7228	Approved
0.7233	Intermediate Similarity	NPD5401	Approved
0.7229	Intermediate Similarity	NPD6234	Discontinued
0.7226	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4966	Approved
0.7212	Intermediate Similarity	NPD4967	Phase 2
0.7212	Intermediate Similarity	NPD4965	Approved
0.7208	Intermediate Similarity	NPD1510	Phase 2
0.7197	Intermediate Similarity	NPD3750	Approved
0.7178	Intermediate Similarity	NPD7411	Suspended
0.7171	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3817	Phase 2
0.7152	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1934	Approved
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6599	Discontinued
0.711	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7097	Intermediate Similarity	NPD7033	Discontinued
0.7093	Intermediate Similarity	NPD5844	Phase 1
0.7091	Intermediate Similarity	NPD7819	Suspended
0.7091	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9493	Approved
0.7048	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7799	Discontinued
0.7019	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6166	Phase 2
0.7013	Intermediate Similarity	NPD1933	Approved
0.7013	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD5647	Approved
0.6988	Remote Similarity	NPD2801	Approved
0.6988	Remote Similarity	NPD1465	Phase 2
0.6975	Remote Similarity	NPD6273	Approved
0.6974	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6653	Approved
0.6959	Remote Similarity	NPD9269	Phase 2
0.6957	Remote Similarity	NPD1511	Approved
0.6954	Remote Similarity	NPD9494	Approved
0.695	Remote Similarity	NPD969	Suspended
0.6948	Remote Similarity	NPD1240	Approved
0.6943	Remote Similarity	NPD2935	Discontinued
0.6943	Remote Similarity	NPD2796	Approved
0.6943	Remote Similarity	NPD1551	Phase 2
0.6941	Remote Similarity	NPD8127	Discontinued
0.6933	Remote Similarity	NPD1203	Approved
0.6933	Remote Similarity	NPD2797	Approved
0.6928	Remote Similarity	NPD6798	Discontinued
0.6928	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD7097	Phase 1
0.6919	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1652	Phase 2
0.6914	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2533	Approved
0.6914	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2532	Approved
0.6914	Remote Similarity	NPD2534	Approved
0.6905	Remote Similarity	NPD3882	Suspended
0.6901	Remote Similarity	NPD6232	Discontinued
0.6899	Remote Similarity	NPD6004	Phase 3
0.6899	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6005	Phase 3
0.6899	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6002	Phase 3
0.6898	Remote Similarity	NPD7435	Discontinued
0.6891	Remote Similarity	NPD7930	Approved
0.6889	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2798	Approved
0.6879	Remote Similarity	NPD7473	Discontinued
0.6879	Remote Similarity	NPD3748	Approved
0.6875	Remote Similarity	NPD7240	Approved
0.6872	Remote Similarity	NPD8434	Phase 2
0.6872	Remote Similarity	NPD8150	Discontinued
0.6871	Remote Similarity	NPD1512	Approved
0.6867	Remote Similarity	NPD3225	Approved
0.6864	Remote Similarity	NPD3749	Approved
0.6862	Remote Similarity	NPD8320	Phase 1
0.6862	Remote Similarity	NPD8319	Approved
0.6859	Remote Similarity	NPD1607	Approved
0.6848	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1608	Approved
0.6846	Remote Similarity	NPD9717	Approved
0.6845	Remote Similarity	NPD5353	Approved
0.6842	Remote Similarity	NPD7585	Approved
0.6839	Remote Similarity	NPD3751	Discontinued
0.6831	Remote Similarity	NPD6535	Approved
0.6831	Remote Similarity	NPD6534	Approved
0.6828	Remote Similarity	NPD6782	Approved
0.6828	Remote Similarity	NPD6778	Approved
0.6828	Remote Similarity	NPD6781	Approved
0.6828	Remote Similarity	NPD6777	Approved
0.6828	Remote Similarity	NPD6780	Approved
0.6828	Remote Similarity	NPD6779	Approved
0.6828	Remote Similarity	NPD6776	Approved
0.6825	Remote Similarity	NPD7999	Approved
0.6805	Remote Similarity	NPD7768	Phase 2
0.6803	Remote Similarity	NPD9268	Approved
0.6797	Remote Similarity	NPD6832	Phase 2
0.6795	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4340	Discontinued
0.6795	Remote Similarity	NPD5124	Phase 1
0.679	Remote Similarity	NPD7236	Approved
0.679	Remote Similarity	NPD7440	Discontinued
0.6789	Remote Similarity	NPD7583	Approved
0.6786	Remote Similarity	NPD1358	Approved
0.6784	Remote Similarity	NPD5494	Approved
0.6774	Remote Similarity	NPD4062	Phase 3
0.6772	Remote Similarity	NPD2799	Discontinued
0.677	Remote Similarity	NPD8166	Discontinued
0.677	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1876	Approved
0.6747	Remote Similarity	NPD3455	Phase 2
0.6733	Remote Similarity	NPD1481	Phase 2
0.6733	Remote Similarity	NPD3972	Approved
0.6732	Remote Similarity	NPD2861	Phase 2
0.6728	Remote Similarity	NPD2354	Approved
0.6728	Remote Similarity	NPD3887	Approved
0.672	Remote Similarity	NPD7700	Phase 2
0.672	Remote Similarity	NPD7699	Phase 2
0.6719	Remote Similarity	NPD8151	Discontinued
0.6714	Remote Similarity	NPD3134	Approved
0.6711	Remote Similarity	NPD6362	Approved
0.671	Remote Similarity	NPD2313	Discontinued
0.6705	Remote Similarity	NPD3787	Discontinued
0.6705	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7584	Approved
0.669	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD447	Suspended
0.6687	Remote Similarity	NPD7239	Suspended
0.6685	Remote Similarity	NPD6212	Phase 3
0.6685	Remote Similarity	NPD6213	Phase 3
0.6685	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7874	Approved
0.6684	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD6385	Approved
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD422	Phase 1
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1535	Discovery
0.6667	Remote Similarity	NPD6386	Approved
0.6649	Remote Similarity	NPD7783	Phase 2
0.6649	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6959	Discontinued
0.6647	Remote Similarity	NPD3226	Approved
0.6646	Remote Similarity	NPD5958	Discontinued
0.6646	Remote Similarity	NPD2424	Discontinued
0.6644	Remote Similarity	NPD5125	Phase 3
0.6644	Remote Similarity	NPD17	Approved
0.6644	Remote Similarity	NPD5126	Approved
0.6643	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7698	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