NPASS Compound

Structure

CID44577 OpenBabel06191715382D 26 30 0 0 1 0 0 0 0 0999 V2000 -2.7241 -0.4295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0515 1.0188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8158 2.0971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9082 -1.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4660 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9079 1.5728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -1.0484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3992 -1.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6320 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2377 0.4360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3662 0.0479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7238 1.5730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8162 -1.0483 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5399 0.5248 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8161 0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6317 2.0973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7415 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7240 0.5246 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9081 0.5244 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6316 3.0514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9974 0.9555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8566 0.4944 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8762 -0.2729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5397 1.5732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4454 -0.4061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 6 1 0 0 0 0 3 12 2 0 0 0 0 4 7 2 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 24 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 11 2 0 0 0 0 10 24 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 4 1 6 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 11 1 6 0 0 0 14 25 1 0 0 0 0 15 18 1 1 0 0 0 15 19 1 0 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 1 1 1 0 0 0 19 20 1 1 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	348.616
LogP:	2.541
LogD:	1.928
LogS:	-3.971
# Rotatable Bonds:	1
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	5.782
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.183
MDCK Permeability:	1.3640655197377782e-05
Pgp-inhibitor:	0.952
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.182
Plasma Protein Binding (PPB):	91.80001068115234%
Volume Distribution (VD):	2.542
Pgp-substrate:	10.749629020690918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.128
CYP1A2-substrate:	0.663
CYP2C19-inhibitor:	0.859
CYP2C19-substrate:	0.629
CYP2C9-inhibitor:	0.717
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.124
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.437

ADMET: Excretion

Clearance (CL):	4.645
Half-life (T1/2):	0.244

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.531
Drug-inuced Liver Injury (DILI):	0.15
AMES Toxicity:	0.435
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.114
Carcinogencity:	0.856
Eye Corrosion:	0.006
Eye Irritation:	0.053
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC44577

Natural Product ID:	NPC44577
*Common Name:**	Fibleucin
IUPAC Name:	n.a.
Synonyms:	Fibleucin
Standard InCHIKey:	KVIOMDMYQSLLQA-AAMISZCHSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-18-9-14(11-5-8-24-10-11)25-16(21)12(18)3-6-19(2)15(18)13-4-7-20(19,23)17(22)26-13/h3-5,7-8,10,13-15,23H,6,9H2,1-2H3/t13-,14-,15+,18-,19-,20+/m1/s1
SMILES:	O=C1O[C@H](C[C@@]2(C1=CC[C@@]1([C@H]2[C@H]2C=C[C@]1(O)C(=O)O2)C)C)c1cocc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519368
PubChem CID:	44589004
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[17340259]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994701]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18829331]
NPO28478	Magnolia ovata	Species	Magnoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19658431]
NPO28478	Magnolia ovata	Species	Magnoliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23157012]
NPO28194	Stevia rebaudiana	Species	Asteraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[24758242]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28836430]
NPO28243	Canarium schweinfurthii	Species	Burseraceae	Eukaryota	Fruits	Edem-ani community of Nsukka local government area (LGA), Enugu State, South-east of Nigeria	n.a.	PMID[35717414]
NPO27082	Citrus yuko	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27082	Citrus yuko	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28459	Bipolaris bicolor	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28402	Solanum tomatillo	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28140	Herrania albiflora	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23215	Ilyocoris cimicoides	Species	Naucoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27809	Stereocaulon japonicum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28068	Mostuea brunonis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27082	Citrus yuko	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28194	Stevia rebaudiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28278	Axinella verrucosa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4118	Jacobaea incana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28478	Magnolia ovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28243	Canarium schweinfurthii	Species	Burseraceae	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	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	11.8	%	PMID[507376]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	13.12	%	PMID[507376]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	17.97	%	PMID[507376]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	21.61	%	PMID[507376]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	25.29	%	PMID[507376]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	25.6	%	PMID[507376]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	14.56	%	PMID[507376]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	17.79	%	PMID[507376]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20.68	%	PMID[507376]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	24.44	%	PMID[507376]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	26.19	%	PMID[507376]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	26.02	%	PMID[507376]

☑ 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 NPC44577 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	330
0.1-0.2	1230
0.2-0.3	2971
0.3-0.4	5643
0.4-0.5	10885
0.5-0.6	9836
0.6-0.7	8941
0.7-0.8	2527
0.8-0.85	246
0.85-0.9	75
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9338	High Similarity	NPC261597
0.9333	High Similarity	NPC214541
0.9333	High Similarity	NPC44675
0.9286	High Similarity	NPC146991
0.9281	High Similarity	NPC149896
0.9216	High Similarity	NPC477402
0.9211	High Similarity	NPC45101
0.9211	High Similarity	NPC36655
0.9178	High Similarity	NPC137295
0.9161	High Similarity	NPC470940
0.9156	High Similarity	NPC82851
0.9156	High Similarity	NPC18347
0.915	High Similarity	NPC477403
0.9145	High Similarity	NPC469485
0.9122	High Similarity	NPC250228
0.9097	High Similarity	NPC292389
0.9097	High Similarity	NPC469338
0.9097	High Similarity	NPC477405
0.9085	High Similarity	NPC249021
0.9085	High Similarity	NPC187149
0.9085	High Similarity	NPC173544
0.9038	High Similarity	NPC469849
0.9038	High Similarity	NPC276551
0.9038	High Similarity	NPC470182
0.9038	High Similarity	NPC271657
0.9032	High Similarity	NPC69028
0.9032	High Similarity	NPC5079
0.9032	High Similarity	NPC200782
0.9026	High Similarity	NPC475967
0.9026	High Similarity	NPC262872
0.9013	High Similarity	NPC282445
0.8981	High Similarity	NPC470875
0.8974	High Similarity	NPC234660
0.8974	High Similarity	NPC198047
0.8974	High Similarity	NPC51568
0.8968	High Similarity	NPC335761
0.8954	High Similarity	NPC264943
0.8954	High Similarity	NPC281258
0.8926	High Similarity	NPC346
0.8924	High Similarity	NPC173516
0.8919	High Similarity	NPC86935
0.891	High Similarity	NPC329938
0.891	High Similarity	NPC263432
0.891	High Similarity	NPC211777
0.891	High Similarity	NPC193798
0.8897	High Similarity	NPC220094
0.8896	High Similarity	NPC60973
0.8896	High Similarity	NPC209364
0.8875	High Similarity	NPC169299
0.8875	High Similarity	NPC160818
0.8868	High Similarity	NPC471397
0.8854	High Similarity	NPC134254
0.8854	High Similarity	NPC39986
0.8854	High Similarity	NPC302369
0.8846	High Similarity	NPC472653
0.8846	High Similarity	NPC25255
0.8839	High Similarity	NPC286722
0.8839	High Similarity	NPC299038
0.8828	High Similarity	NPC310830
0.8824	High Similarity	NPC476201
0.8824	High Similarity	NPC469503
0.8812	High Similarity	NPC82602
0.8805	High Similarity	NPC472282
0.8792	High Similarity	NPC476944
0.879	High Similarity	NPC207978
0.879	High Similarity	NPC117986
0.8782	High Similarity	NPC475295
0.8782	High Similarity	NPC473473
0.8774	High Similarity	NPC107646
0.8766	High Similarity	NPC30222
0.8766	High Similarity	NPC57998
0.8766	High Similarity	NPC178932
0.875	High Similarity	NPC160651
0.875	High Similarity	NPC271235
0.8742	High Similarity	NPC470941
0.8726	High Similarity	NPC305016
0.8725	High Similarity	NPC470741
0.8718	High Similarity	NPC472283
0.8712	High Similarity	NPC262386
0.871	High Similarity	NPC35000
0.871	High Similarity	NPC476262
0.871	High Similarity	NPC469336
0.8693	High Similarity	NPC477404
0.8693	High Similarity	NPC196864
0.8693	High Similarity	NPC46551
0.8693	High Similarity	NPC476122
0.8688	High Similarity	NPC472775
0.8688	High Similarity	NPC100333
0.8688	High Similarity	NPC472774
0.8688	High Similarity	NPC472651
0.8679	High Similarity	NPC476856
0.8679	High Similarity	NPC476858
0.8679	High Similarity	NPC123088
0.8679	High Similarity	NPC476860
0.8679	High Similarity	NPC476857
0.8671	High Similarity	NPC96443
0.8671	High Similarity	NPC290400
0.8662	High Similarity	NPC307383
0.8654	High Similarity	NPC126723
0.8654	High Similarity	NPC263265
0.8649	High Similarity	NPC90296
0.8639	High Similarity	NPC476943
0.8634	High Similarity	NPC472652
0.8625	High Similarity	NPC23387
0.8625	High Similarity	NPC93172
0.8625	High Similarity	NPC97574
0.8616	High Similarity	NPC663
0.8616	High Similarity	NPC224394
0.8616	High Similarity	NPC472773
0.8608	High Similarity	NPC475381
0.8599	High Similarity	NPC472778
0.8599	High Similarity	NPC472777
0.8599	High Similarity	NPC472776
0.8581	High Similarity	NPC90953
0.8581	High Similarity	NPC147168
0.8571	High Similarity	NPC469335
0.8571	High Similarity	NPC159927
0.8571	High Similarity	NPC476850
0.8571	High Similarity	NPC476861
0.8571	High Similarity	NPC476853
0.8562	High Similarity	NPC476942
0.8562	High Similarity	NPC92941
0.8562	High Similarity	NPC476941
0.8553	High Similarity	NPC472771
0.8553	High Similarity	NPC470939
0.8545	High Similarity	NPC478177
0.8544	High Similarity	NPC472779
0.8544	High Similarity	NPC237155
0.8543	High Similarity	NPC142113
0.8537	High Similarity	NPC94763
0.8537	High Similarity	NPC236004
0.8537	High Similarity	NPC469576
0.8519	High Similarity	NPC296558
0.8509	High Similarity	NPC475779
0.8509	High Similarity	NPC478178
0.8506	High Similarity	NPC125182
0.8506	High Similarity	NPC69647
0.8506	High Similarity	NPC195325
0.85	High Similarity	NPC419
0.85	High Similarity	NPC469846
0.85	High Similarity	NPC288602
0.85	High Similarity	NPC88841
0.8497	Intermediate Similarity	NPC476938
0.8497	Intermediate Similarity	NPC255414
0.8497	Intermediate Similarity	NPC476937
0.8491	Intermediate Similarity	NPC470789
0.8485	Intermediate Similarity	NPC469633
0.8481	Intermediate Similarity	NPC472772
0.8477	Intermediate Similarity	NPC223415
0.8471	Intermediate Similarity	NPC469850
0.8462	Intermediate Similarity	NPC268905
0.8462	Intermediate Similarity	NPC75906
0.8457	Intermediate Similarity	NPC473753
0.8457	Intermediate Similarity	NPC473766
0.8447	Intermediate Similarity	NPC261184
0.8446	Intermediate Similarity	NPC470742
0.8446	Intermediate Similarity	NPC186626
0.8442	Intermediate Similarity	NPC7388
0.8438	Intermediate Similarity	NPC188649
0.8435	Intermediate Similarity	NPC158525
0.8434	Intermediate Similarity	NPC472665
0.8431	Intermediate Similarity	NPC262198
0.8428	Intermediate Similarity	NPC473368
0.8425	Intermediate Similarity	NPC474425
0.8425	Intermediate Similarity	NPC474426
0.8425	Intermediate Similarity	NPC474407
0.8424	Intermediate Similarity	NPC471437
0.8421	Intermediate Similarity	NPC251865
0.8415	Intermediate Similarity	NPC159232
0.8411	Intermediate Similarity	NPC121158
0.8397	Intermediate Similarity	NPC18135
0.8395	Intermediate Similarity	NPC472141
0.8387	Intermediate Similarity	NPC472654
0.8385	Intermediate Similarity	NPC472139
0.8385	Intermediate Similarity	NPC165218
0.8377	Intermediate Similarity	NPC221809
0.8375	Intermediate Similarity	NPC287559
0.8366	Intermediate Similarity	NPC41182
0.8365	Intermediate Similarity	NPC167142
0.8365	Intermediate Similarity	NPC470118
0.8355	Intermediate Similarity	NPC243577
0.8355	Intermediate Similarity	NPC267632
0.8355	Intermediate Similarity	NPC476946
0.8354	Intermediate Similarity	NPC470995
0.8354	Intermediate Similarity	NPC302392
0.8344	Intermediate Similarity	NPC33938
0.8344	Intermediate Similarity	NPC476939
0.8344	Intermediate Similarity	NPC476940
0.8344	Intermediate Similarity	NPC478179
0.8323	Intermediate Similarity	NPC18986
0.8313	Intermediate Similarity	NPC474611
0.8293	Intermediate Similarity	NPC327922
0.8289	Intermediate Similarity	NPC473152
0.8282	Intermediate Similarity	NPC121995
0.8282	Intermediate Similarity	NPC149945
0.8282	Intermediate Similarity	NPC214600
0.8272	Intermediate Similarity	NPC476197
0.8269	Intermediate Similarity	NPC211625
0.8264	Intermediate Similarity	NPC83178
0.8261	Intermediate Similarity	NPC191828

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 NPC44577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	891
0.2-0.3	2034
0.3-0.4	2637
0.4-0.5	2016
0.5-0.6	970
0.6-0.7	285
0.7-0.8	33
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
0.8239	Intermediate Similarity	NPD5761	Phase 2
0.8239	Intermediate Similarity	NPD5760	Phase 2
0.8129	Intermediate Similarity	NPD8434	Phase 2
0.8037	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD6765	Approved
0.7529	Intermediate Similarity	NPD6764	Approved
0.747	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7075	Discontinued
0.7394	Intermediate Similarity	NPD6599	Discontinued
0.736	Intermediate Similarity	NPD6784	Approved
0.736	Intermediate Similarity	NPD6785	Approved
0.7235	Intermediate Similarity	NPD3749	Approved
0.7232	Intermediate Similarity	NPD6559	Discontinued
0.7202	Intermediate Similarity	NPD6801	Discontinued
0.7195	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5494	Approved
0.7134	Intermediate Similarity	NPD6799	Approved
0.7127	Intermediate Similarity	NPD8150	Discontinued
0.7118	Intermediate Similarity	NPD5402	Approved
0.7108	Intermediate Similarity	NPD920	Approved
0.7108	Intermediate Similarity	NPD5403	Approved
0.7083	Intermediate Similarity	NPD4380	Phase 2
0.7081	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5844	Phase 1
0.7059	Intermediate Similarity	NPD7819	Suspended
0.7056	Intermediate Similarity	NPD8404	Phase 2
0.7056	Intermediate Similarity	NPD8313	Approved
0.7056	Intermediate Similarity	NPD8312	Approved
0.7041	Intermediate Similarity	NPD7411	Suspended
0.7035	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD919	Approved
0.6989	Remote Similarity	NPD6166	Phase 2
0.6989	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5401	Approved
0.6988	Remote Similarity	NPD2532	Approved
0.6988	Remote Similarity	NPD2534	Approved
0.6988	Remote Similarity	NPD2533	Approved
0.6988	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3882	Suspended
0.6959	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6273	Approved
0.6931	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3226	Approved
0.6919	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3817	Phase 2
0.6914	Remote Similarity	NPD1551	Phase 2
0.691	Remote Similarity	NPD3751	Discontinued
0.6901	Remote Similarity	NPD1934	Approved
0.689	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2800	Approved
0.6889	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2346	Discontinued
0.6867	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7033	Discontinued
0.6848	Remote Similarity	NPD3750	Approved
0.6829	Remote Similarity	NPD1549	Phase 2
0.6824	Remote Similarity	NPD7458	Discontinued
0.6818	Remote Similarity	NPD1247	Approved
0.6818	Remote Similarity	NPD6959	Discontinued
0.6816	Remote Similarity	NPD4111	Phase 1
0.6816	Remote Similarity	NPD3818	Discontinued
0.6816	Remote Similarity	NPD4665	Approved
0.6813	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6797	Phase 2
0.6795	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7768	Phase 2
0.678	Remote Similarity	NPD6232	Discontinued
0.677	Remote Similarity	NPD6355	Discontinued
0.6768	Remote Similarity	NPD1471	Phase 3
0.6768	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7236	Approved
0.6763	Remote Similarity	NPD1465	Phase 2
0.676	Remote Similarity	NPD7473	Discontinued
0.6758	Remote Similarity	NPD7251	Discontinued
0.6749	Remote Similarity	NPD7907	Approved
0.6748	Remote Similarity	NPD2799	Discontinued
0.674	Remote Similarity	NPD7074	Phase 3
0.6736	Remote Similarity	NPD3057	Approved
0.6736	Remote Similarity	NPD3533	Approved
0.6736	Remote Similarity	NPD2972	Approved
0.6727	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8127	Discontinued
0.6722	Remote Similarity	NPD7799	Discontinued
0.6721	Remote Similarity	NPD7808	Phase 3
0.6719	Remote Similarity	NPD4107	Approved
0.6708	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6100	Approved
0.6707	Remote Similarity	NPD6099	Approved
0.6707	Remote Similarity	NPD2796	Approved
0.6701	Remote Similarity	NPD7435	Discontinued
0.6687	Remote Similarity	NPD2313	Discontinued
0.6687	Remote Similarity	NPD3764	Approved
0.6687	Remote Similarity	NPD1243	Approved
0.6686	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3787	Discontinued
0.6685	Remote Similarity	NPD7054	Approved
0.6684	Remote Similarity	NPD4482	Phase 3
0.6684	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD2344	Approved
0.6667	Remote Similarity	NPD7685	Pre-registration
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD447	Suspended
0.6667	Remote Similarity	NPD6004	Phase 3
0.6649	Remote Similarity	NPD2491	Approved
0.6648	Remote Similarity	NPD7472	Approved
0.6647	Remote Similarity	NPD7003	Approved
0.6646	Remote Similarity	NPD6233	Phase 2
0.6646	Remote Similarity	NPD4308	Phase 3
0.6646	Remote Similarity	NPD3748	Approved
0.6646	Remote Similarity	NPD5647	Approved
0.6633	Remote Similarity	NPD5676	Approved
0.6632	Remote Similarity	NPD6777	Approved
0.6632	Remote Similarity	NPD6779	Approved
0.6632	Remote Similarity	NPD6778	Approved
0.6632	Remote Similarity	NPD6780	Approved
0.6632	Remote Similarity	NPD6776	Approved
0.6632	Remote Similarity	NPD6782	Approved
0.6632	Remote Similarity	NPD6781	Approved
0.663	Remote Similarity	NPD7228	Approved
0.6625	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6234	Discontinued
0.6609	Remote Similarity	NPD37	Approved
0.6606	Remote Similarity	NPD2935	Discontinued
0.6603	Remote Similarity	NPD9717	Approved
0.6603	Remote Similarity	NPD1608	Approved
0.6592	Remote Similarity	NPD5710	Approved
0.6592	Remote Similarity	NPD5711	Approved
0.6591	Remote Similarity	NPD4965	Approved
0.6591	Remote Similarity	NPD4966	Approved
0.6591	Remote Similarity	NPD4967	Phase 2
0.6584	Remote Similarity	NPD3268	Approved
0.6584	Remote Similarity	NPD6798	Discontinued
0.6582	Remote Similarity	NPD2797	Approved
0.6571	Remote Similarity	NPD8455	Phase 2
0.657	Remote Similarity	NPD7239	Suspended
0.6566	Remote Similarity	NPD5762	Approved
0.6566	Remote Similarity	NPD5763	Approved
0.6564	Remote Similarity	NPD3448	Approved
0.6562	Remote Similarity	NPD6832	Phase 2
0.6559	Remote Similarity	NPD8407	Phase 2
0.6556	Remote Similarity	NPD3926	Phase 2
0.6556	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.655	Remote Similarity	NPD1512	Approved
0.6548	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1510	Phase 2
0.6538	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7696	Phase 3
0.6531	Remote Similarity	NPD7698	Approved
0.6531	Remote Similarity	NPD7697	Approved
0.6529	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7095	Approved
0.6519	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6190	Approved
0.6509	Remote Similarity	NPD2354	Approved
0.6509	Remote Similarity	NPD2309	Approved
0.6509	Remote Similarity	NPD3887	Approved
0.65	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7874	Approved
0.6497	Remote Similarity	NPD8320	Phase 1
0.6497	Remote Similarity	NPD8319	Approved
0.6486	Remote Similarity	NPD8368	Discontinued
0.6485	Remote Similarity	NPD7097	Phase 1
0.6482	Remote Similarity	NPD7701	Phase 2
0.6481	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD1203	Approved
0.6468	Remote Similarity	NPD7783	Phase 2
0.6468	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD230	Phase 1
0.6463	Remote Similarity	NPD5124	Phase 1
0.6463	Remote Similarity	NPD1933	Approved
0.6463	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.645	Remote Similarity	NPD4110	Phase 3
0.645	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.645	Remote Similarity	NPD8166	Discontinued
0.6448	Remote Similarity	NPD7177	Discontinued
0.6447	Remote Similarity	NPD7497	Discontinued
0.6444	Remote Similarity	NPD7199	Phase 2
0.6438	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD1511	Approved
0.6429	Remote Similarity	NPD9092	Discovery
0.6429	Remote Similarity	NPD2403	Approved
0.6429	Remote Similarity	NPD4534	Discontinued
0.6429	Remote Similarity	NPD2424	Discontinued
0.6424	Remote Similarity	NPD1607	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