NPASS Compound

Structure

NPC475307 OpenBabel07101718322D 41 45 0 0 1 0 0 0 0 0999 V2000 -3.2577 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5633 -2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3671 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4105 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8255 3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0090 -0.3581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9763 -0.3581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4105 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6727 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0731 1.2806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9339 1.2806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6727 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1311 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4891 0.8472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5633 -1.4674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5199 1.4674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5633 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9783 2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0035 0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8255 -1.4674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6727 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4981 0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8255 1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5089 0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9783 -0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7161 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0035 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5199 0.4891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8255 0.4891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9783 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5633 2.4457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1311 3.4239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8255 -2.4457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7161 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4872 0.4891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7161 0.9783 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 0.9783 1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0731 -0.3023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9339 -0.3023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1311 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 7 35 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 9 23 1 0 0 0 0 11 19 1 0 0 0 0 11 24 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 13 29 1 0 0 0 0 13 36 1 0 0 0 0 14 37 1 0 0 0 0 15 2 1 6 0 0 0 15 26 1 0 0 0 0 16 28 1 1 0 0 0 17 31 2 0 0 0 0 17 36 1 0 0 0 0 18 32 2 0 0 0 0 18 38 1 0 0 0 0 19 10 1 1 0 0 0 19 27 1 0 0 0 0 20 25 1 0 0 0 0 20 33 1 1 0 0 0 21 28 1 1 0 0 0 21 29 1 0 0 0 0 22 10 1 6 0 0 0 22 28 1 0 0 0 0 22 39 1 0 0 0 0 23 29 1 1 0 0 0 23 38 1 0 0 0 0 24 35 1 1 0 0 0 24 40 1 0 0 0 0 25 30 1 6 0 0 0 25 41 1 0 0 0 0 26 34 2 0 0 0 0 26 41 1 0 0 0 0 27 39 1 1 0 0 0 27 40 1 0 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 14 1 6 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.3
Volume:	573.437
LogP:	2.688
LogD:	2.455
LogS:	-4.519
# Rotatable Bonds:	11
TPSA:	139.35
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.257
Synthetic Accessibility Score:	6.069
Fsp3:	0.9
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.137
MDCK Permeability:	0.00011358469055267051
Pgp-inhibitor:	0.992
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	40.70932388305664%
Volume Distribution (VD):	1.236
Pgp-substrate:	45.35707092285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.691
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.681
CYP3A4-substrate:	0.661

ADMET: Excretion

Clearance (CL):	3.589
Half-life (T1/2):	0.656

ADMET: Toxicity

hERG Blockers:	0.391
Human Hepatotoxicity (H-HT):	0.416
Drug-inuced Liver Injury (DILI):	0.777
AMES Toxicity:	0.197
Rat Oral Acute Toxicity:	0.163
Maximum Recommended Daily Dose:	0.456
Skin Sensitization:	0.487
Carcinogencity:	0.139
Eye Corrosion:	0.004
Eye Irritation:	0.035
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC475307

Natural Product ID:	NPC475307
*Common Name:**	Lupulin A
IUPAC Name:	[(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(2S,3aS,5S,6aR)-5-methoxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] (2R)-2-methylbutanoate
Synonyms:
Standard InCHIKey:	UEZOFWAZJUOMCN-BVDQYQNCSA-N
Standard InCHI:	InChI=1S/C30H46O11/c1-8-15(2)26(34)41-25-20(33)12-21-28(6,22-10-19-11-24(35-7)40-27(19)39-22)16(3)9-23(38-18(5)32)29(21,13-36-17(4)31)30(25)14-37-30/h15-16,19-25,27,33H,8-14H2,1-7H3/t15-,16-,19+,20-,21-,22+,23+,24+,25+,27-,28+,29+,30-/m1/s1
SMILES:	CO[C@@H]1C[C@H]2[C@@H](O1)O[C@@H](C2)[C@@]1(C)[C@H](C)C[C@@H]([C@@]2([C@@H]1C[C@@H](O)[C@@H]([C@@]12CO1)OC(=O)[C@@H](CC)C)COC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503258
PubChem CID:	44566822
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO18973	Ajuga pseudoiva	Species	Lamiaceae	Eukaryota	leaves	Tunisian	n.a.	PMID[10727804]
NPO3534	Ajuga lupulina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759163]
NPO3534	Ajuga lupulina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18973	Ajuga pseudoiva	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
Others	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	1.5	mm	PMID[546156]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	3.0	mm	PMID[546156]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	3.0	mm	PMID[546156]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	AFI	=	45.0	%	PMID[546157]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	AFI	=	74.5	%	PMID[546157]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	AFI	=	100.0	%	PMID[546157]

☑ 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 NPC475307 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	418
0.1-0.2	3496
0.2-0.3	10244
0.3-0.4	12642
0.4-0.5	6458
0.5-0.6	5333
0.6-0.7	3430
0.7-0.8	620
0.8-0.85	42
0.85-0.9	6
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC470872
0.9302	High Similarity	NPC474008
0.9195	High Similarity	NPC110365
0.9195	High Similarity	NPC45833
0.9195	High Similarity	NPC213658
0.9195	High Similarity	NPC62202
0.9186	High Similarity	NPC235402
0.907	High Similarity	NPC18953
0.8652	High Similarity	NPC471410
0.8652	High Similarity	NPC471411
0.8621	High Similarity	NPC477447
0.8621	High Similarity	NPC470155
0.8621	High Similarity	NPC477446
0.8617	High Similarity	NPC475785
0.8617	High Similarity	NPC475765
0.8605	High Similarity	NPC471217
0.8605	High Similarity	NPC472951
0.8605	High Similarity	NPC471216
0.8605	High Similarity	NPC472943
0.8605	High Similarity	NPC186588
0.8526	High Similarity	NPC266417
0.8506	High Similarity	NPC470154
0.8506	High Similarity	NPC470156
0.8506	High Similarity	NPC71541
0.8462	Intermediate Similarity	NPC476435
0.8444	Intermediate Similarity	NPC268633
0.8333	Intermediate Similarity	NPC86217
0.8315	Intermediate Similarity	NPC241959
0.8298	Intermediate Similarity	NPC122083
0.8298	Intermediate Similarity	NPC211845
0.8298	Intermediate Similarity	NPC182740
0.8298	Intermediate Similarity	NPC256104
0.8295	Intermediate Similarity	NPC211049
0.828	Intermediate Similarity	NPC470114
0.8261	Intermediate Similarity	NPC221993
0.8261	Intermediate Similarity	NPC476379
0.8247	Intermediate Similarity	NPC292775
0.8242	Intermediate Similarity	NPC107603
0.8235	Intermediate Similarity	NPC305939
0.8229	Intermediate Similarity	NPC252056
0.8229	Intermediate Similarity	NPC238796
0.8229	Intermediate Similarity	NPC203434
0.8229	Intermediate Similarity	NPC237071
0.8211	Intermediate Similarity	NPC151214
0.8211	Intermediate Similarity	NPC191915
0.8202	Intermediate Similarity	NPC216800
0.8191	Intermediate Similarity	NPC475878
0.8182	Intermediate Similarity	NPC186594
0.8163	Intermediate Similarity	NPC470030
0.814	Intermediate Similarity	NPC107963
0.8125	Intermediate Similarity	NPC57964
0.8125	Intermediate Similarity	NPC94582
0.8125	Intermediate Similarity	NPC21897
0.8111	Intermediate Similarity	NPC474253
0.8111	Intermediate Similarity	NPC475820
0.8111	Intermediate Similarity	NPC474284
0.8111	Intermediate Similarity	NPC213737
0.8111	Intermediate Similarity	NPC474346
0.81	Intermediate Similarity	NPC139181
0.81	Intermediate Similarity	NPC476837
0.81	Intermediate Similarity	NPC97260
0.809	Intermediate Similarity	NPC116320
0.809	Intermediate Similarity	NPC119922
0.8081	Intermediate Similarity	NPC108227
0.8081	Intermediate Similarity	NPC475574
0.8081	Intermediate Similarity	NPC476512
0.8081	Intermediate Similarity	NPC472081
0.8065	Intermediate Similarity	NPC471221
0.8061	Intermediate Similarity	NPC472144
0.8043	Intermediate Similarity	NPC235196
0.8043	Intermediate Similarity	NPC477283
0.8043	Intermediate Similarity	NPC155531
0.8043	Intermediate Similarity	NPC215968
0.8043	Intermediate Similarity	NPC228593
0.8023	Intermediate Similarity	NPC472950
0.8023	Intermediate Similarity	NPC472952
0.8021	Intermediate Similarity	NPC113500
0.8021	Intermediate Similarity	NPC3538
0.8021	Intermediate Similarity	NPC477224
0.8	Intermediate Similarity	NPC2096
0.8	Intermediate Similarity	NPC134967
0.8	Intermediate Similarity	NPC208912
0.8	Intermediate Similarity	NPC114700
0.8	Intermediate Similarity	NPC310138
0.8	Intermediate Similarity	NPC470029
0.798	Intermediate Similarity	NPC51579
0.7979	Intermediate Similarity	NPC82955
0.7979	Intermediate Similarity	NPC20822
0.7959	Intermediate Similarity	NPC472273
0.7959	Intermediate Similarity	NPC472145
0.7957	Intermediate Similarity	NPC472396
0.7957	Intermediate Similarity	NPC5943
0.7955	Intermediate Similarity	NPC272841
0.7955	Intermediate Similarity	NPC177343
0.7955	Intermediate Similarity	NPC252483
0.7955	Intermediate Similarity	NPC43463
0.7955	Intermediate Similarity	NPC191345
0.7941	Intermediate Similarity	NPC166079
0.7935	Intermediate Similarity	NPC478111
0.7921	Intermediate Similarity	NPC34562
0.7917	Intermediate Similarity	NPC311246
0.7917	Intermediate Similarity	NPC167644
0.7895	Intermediate Similarity	NPC50443
0.7895	Intermediate Similarity	NPC18536
0.7879	Intermediate Similarity	NPC209798
0.7879	Intermediate Similarity	NPC471374
0.7879	Intermediate Similarity	NPC471375
0.7872	Intermediate Similarity	NPC128475
0.7857	Intermediate Similarity	NPC156377
0.7857	Intermediate Similarity	NPC296936
0.7857	Intermediate Similarity	NPC235109
0.7849	Intermediate Similarity	NPC131365
0.7843	Intermediate Similarity	NPC100078
0.7835	Intermediate Similarity	NPC175
0.7835	Intermediate Similarity	NPC30687
0.783	Intermediate Similarity	NPC477489
0.7826	Intermediate Similarity	NPC79308
0.7812	Intermediate Similarity	NPC5632
0.7812	Intermediate Similarity	NPC293609
0.7812	Intermediate Similarity	NPC210759
0.7812	Intermediate Similarity	NPC59006
0.7812	Intermediate Similarity	NPC473066
0.7812	Intermediate Similarity	NPC149966
0.7812	Intermediate Similarity	NPC307167
0.7812	Intermediate Similarity	NPC229801
0.7802	Intermediate Similarity	NPC154043
0.7802	Intermediate Similarity	NPC60018
0.7802	Intermediate Similarity	NPC202688
0.78	Intermediate Similarity	NPC471426
0.78	Intermediate Similarity	NPC471428
0.78	Intermediate Similarity	NPC471427
0.7778	Intermediate Similarity	NPC477223
0.7778	Intermediate Similarity	NPC198549
0.7778	Intermediate Similarity	NPC113976
0.7778	Intermediate Similarity	NPC477222
0.7767	Intermediate Similarity	NPC291414
0.7767	Intermediate Similarity	NPC306776
0.7766	Intermediate Similarity	NPC210658
0.7766	Intermediate Similarity	NPC161928
0.7766	Intermediate Similarity	NPC140446
0.7766	Intermediate Similarity	NPC43912
0.7757	Intermediate Similarity	NPC97002
0.7755	Intermediate Similarity	NPC473067
0.7755	Intermediate Similarity	NPC473065
0.7755	Intermediate Similarity	NPC473064
0.7755	Intermediate Similarity	NPC82633
0.7755	Intermediate Similarity	NPC215570
0.7742	Intermediate Similarity	NPC266651
0.7742	Intermediate Similarity	NPC290612
0.7742	Intermediate Similarity	NPC477445
0.7732	Intermediate Similarity	NPC277774
0.7727	Intermediate Similarity	NPC136424
0.7723	Intermediate Similarity	NPC477225
0.7723	Intermediate Similarity	NPC476838
0.7723	Intermediate Similarity	NPC476839
0.7717	Intermediate Similarity	NPC477285
0.7717	Intermediate Similarity	NPC111582
0.7708	Intermediate Similarity	NPC473542
0.7708	Intermediate Similarity	NPC279329
0.7701	Intermediate Similarity	NPC166250
0.7701	Intermediate Similarity	NPC308489
0.7701	Intermediate Similarity	NPC470151
0.77	Intermediate Similarity	NPC473638
0.7692	Intermediate Similarity	NPC126753
0.7685	Intermediate Similarity	NPC79193
0.7684	Intermediate Similarity	NPC56777
0.7684	Intermediate Similarity	NPC201607
0.7677	Intermediate Similarity	NPC142264
0.7677	Intermediate Similarity	NPC163685
0.7677	Intermediate Similarity	NPC476510
0.7677	Intermediate Similarity	NPC145553
0.7677	Intermediate Similarity	NPC116683
0.7653	Intermediate Similarity	NPC305418
0.7653	Intermediate Similarity	NPC473774
0.7653	Intermediate Similarity	NPC24960
0.7653	Intermediate Similarity	NPC45959
0.7653	Intermediate Similarity	NPC252253
0.7647	Intermediate Similarity	NPC213528
0.7647	Intermediate Similarity	NPC80640
0.7647	Intermediate Similarity	NPC244969
0.7634	Intermediate Similarity	NPC474156
0.7634	Intermediate Similarity	NPC65133
0.7629	Intermediate Similarity	NPC36372
0.7624	Intermediate Similarity	NPC80417
0.7624	Intermediate Similarity	NPC41843
0.7619	Intermediate Similarity	NPC207693
0.7609	Intermediate Similarity	NPC477286
0.7609	Intermediate Similarity	NPC477284
0.7609	Intermediate Similarity	NPC286719
0.7604	Intermediate Similarity	NPC131466
0.7604	Intermediate Similarity	NPC473472
0.76	Intermediate Similarity	NPC233649
0.76	Intermediate Similarity	NPC470591
0.76	Intermediate Similarity	NPC74466
0.76	Intermediate Similarity	NPC470632
0.76	Intermediate Similarity	NPC470028
0.7582	Intermediate Similarity	NPC16449
0.7582	Intermediate Similarity	NPC475456
0.7576	Intermediate Similarity	NPC477494
0.7576	Intermediate Similarity	NPC92196

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 NPC475307 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	451
0.1-0.2	3778
0.2-0.3	3349
0.3-0.4	870
0.4-0.5	396
0.5-0.6	244
0.6-0.7	60
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7374	Intermediate Similarity	NPD8171	Discontinued
0.7356	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD3669	Approved
0.7333	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1700	Approved
0.6964	Remote Similarity	NPD8133	Approved
0.6957	Remote Similarity	NPD7516	Approved
0.6909	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7328	Approved
0.687	Remote Similarity	NPD7327	Approved
0.6842	Remote Similarity	NPD6928	Phase 2
0.6809	Remote Similarity	NPD6697	Approved
0.6809	Remote Similarity	NPD6118	Approved
0.6809	Remote Similarity	NPD6115	Approved
0.6809	Remote Similarity	NPD6114	Approved
0.6739	Remote Similarity	NPD1811	Approved
0.6739	Remote Similarity	NPD1810	Approved
0.6702	Remote Similarity	NPD6116	Phase 1
0.6696	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD8380	Approved
0.6695	Remote Similarity	NPD8296	Approved
0.6695	Remote Similarity	NPD8379	Approved
0.6695	Remote Similarity	NPD8335	Approved
0.6695	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD371	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6638	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7507	Approved
0.661	Remote Similarity	NPD8294	Approved
0.661	Remote Similarity	NPD8377	Approved
0.6598	Remote Similarity	NPD1780	Approved
0.6598	Remote Similarity	NPD1779	Approved
0.6596	Remote Similarity	NPD6117	Approved
0.6585	Remote Similarity	NPD7319	Approved
0.6555	Remote Similarity	NPD8033	Approved
0.6552	Remote Similarity	NPD6940	Discontinued
0.6484	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6412	Phase 2
0.6429	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8293	Discontinued
0.6413	Remote Similarity	NPD2686	Approved
0.6413	Remote Similarity	NPD2687	Approved
0.6413	Remote Similarity	NPD2254	Approved
0.6396	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7736	Approved
0.6364	Remote Similarity	NPD6370	Approved
0.6311	Remote Similarity	NPD8328	Phase 3
0.6281	Remote Similarity	NPD7503	Approved
0.626	Remote Similarity	NPD7492	Approved
0.621	Remote Similarity	NPD6616	Approved
0.6198	Remote Similarity	NPD6059	Approved
0.6198	Remote Similarity	NPD6054	Approved
0.616	Remote Similarity	NPD7078	Approved
0.6148	Remote Similarity	NPD6921	Approved
0.6146	Remote Similarity	NPD3703	Phase 2
0.6126	Remote Similarity	NPD5344	Discontinued
0.6091	Remote Similarity	NPD4225	Approved
0.6091	Remote Similarity	NPD7638	Approved
0.6048	Remote Similarity	NPD6067	Discontinued
0.6047	Remote Similarity	NPD2267	Suspended
0.6036	Remote Similarity	NPD7640	Approved
0.6036	Remote Similarity	NPD7639	Approved
0.6017	Remote Similarity	NPD6882	Approved
0.6016	Remote Similarity	NPD6016	Approved
0.6016	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD8034	Phase 2
0.5981	Remote Similarity	NPD8035	Phase 2
0.5979	Remote Similarity	NPD3702	Approved
0.5968	Remote Similarity	NPD5988	Approved
0.5963	Remote Similarity	NPD7991	Discontinued
0.5957	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6009	Approved
0.5935	Remote Similarity	NPD6319	Approved
0.5929	Remote Similarity	NPD8082	Approved
0.5929	Remote Similarity	NPD8139	Approved
0.5929	Remote Similarity	NPD8085	Approved
0.5929	Remote Similarity	NPD7632	Discontinued
0.5929	Remote Similarity	NPD8084	Approved
0.5929	Remote Similarity	NPD8138	Approved
0.5929	Remote Similarity	NPD8086	Approved
0.5929	Remote Similarity	NPD8083	Approved
0.5913	Remote Similarity	NPD6008	Approved
0.5887	Remote Similarity	NPD8517	Approved
0.5887	Remote Similarity	NPD8515	Approved
0.5887	Remote Similarity	NPD8516	Approved
0.5887	Remote Similarity	NPD8513	Phase 3
0.5882	Remote Similarity	NPD8297	Approved
0.5877	Remote Similarity	NPD8275	Approved
0.5877	Remote Similarity	NPD8276	Approved
0.5865	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5777	Approved
0.5833	Remote Similarity	NPD4632	Approved
0.5826	Remote Similarity	NPD8081	Approved
0.582	Remote Similarity	NPD7115	Discovery
0.5812	Remote Similarity	NPD7320	Approved
0.5776	Remote Similarity	NPD7128	Approved
0.5776	Remote Similarity	NPD6402	Approved
0.5776	Remote Similarity	NPD8393	Approved
0.5776	Remote Similarity	NPD5739	Approved
0.5776	Remote Similarity	NPD6675	Approved
0.5763	Remote Similarity	NPD6373	Approved
0.5763	Remote Similarity	NPD6372	Approved
0.5755	Remote Similarity	NPD7524	Approved
0.5752	Remote Similarity	NPD6648	Approved
0.5741	Remote Similarity	NPD3168	Discontinued
0.5736	Remote Similarity	NPD6033	Approved
0.5729	Remote Similarity	NPD4244	Approved
0.5729	Remote Similarity	NPD4245	Approved
0.5726	Remote Similarity	NPD8140	Approved
0.5726	Remote Similarity	NPD8307	Discontinued
0.5699	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD5360	Phase 3
0.5684	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD229	Approved
0.5678	Remote Similarity	NPD6881	Approved
0.5678	Remote Similarity	NPD6899	Approved
0.567	Remote Similarity	NPD6081	Approved
0.5669	Remote Similarity	NPD7604	Phase 2
0.5667	Remote Similarity	NPD6650	Approved
0.5667	Remote Similarity	NPD6649	Approved
0.5638	Remote Similarity	NPD4224	Phase 2
0.5636	Remote Similarity	NPD6399	Phase 3
0.563	Remote Similarity	NPD8306	Approved
0.563	Remote Similarity	NPD8305	Approved
0.5625	Remote Similarity	NPD3698	Phase 2
0.5614	Remote Similarity	NPD8418	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data