NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.13
Volume:	211.303
LogP:	4.1
LogD:	3.59
LogS:	-3.978
# Rotatable Bonds:	3
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.646
Synthetic Accessibility Score:	3.615
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.628
MDCK Permeability:	3.685604679048993e-05
Pgp-inhibitor:	0.401
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.267
Plasma Protein Binding (PPB):	92.22991180419922%
Volume Distribution (VD):	1.146
Pgp-substrate:	4.413082122802734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.512
CYP1A2-substrate:	0.581
CYP2C19-inhibitor:	0.406
CYP2C19-substrate:	0.507
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.426
CYP2D6-inhibitor:	0.263
CYP2D6-substrate:	0.266
CYP3A4-inhibitor:	0.577
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	10.159
Half-life (T1/2):	0.227

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.313
Drug-inuced Liver Injury (DILI):	0.24
AMES Toxicity:	0.475
Rat Oral Acute Toxicity:	0.833
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.96
Carcinogencity:	0.826
Eye Corrosion:	0.916
Eye Irritation:	0.983
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC199557

Natural Product ID:	NPC199557
*Common Name:**	Cnidilide
IUPAC Name:	(3S,3aS,7aR)-3-butyl-3a,4,5,7a-tetrahydro-3H-2-benzofuran-1-one
Synonyms:
Standard InCHIKey:	UXDIXFDKSPCUIX-AXFHLTTASA-N
Standard InCHI:	InChI=1S/C12H18O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7,9-11H,2-4,6,8H2,1H3/t9-,10+,11-/m0/s1
SMILES:	CCCC[C@@H]1OC(=O)[C@H]2[C@@H]1CCC=C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252753
PubChem CID:	160710
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003408] Isobenzofurans

*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
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10785419]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19778086]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	sclerotium	n.a.	PMID[21250700]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22932311]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23721280]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26521454]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf Wax	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Pt	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	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
LD50	1
Others	3

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	Ratio	=	0.4	n.a.	PMID[505416]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	LD50	=	9.17	ug	PMID[505416]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	RatioLC50	<	0.001	n.a.	PMID[505416]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	LC50	>	16000000.0	nM	PMID[505416]

☑ 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 NPC199557 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	163
0.1-0.2	1081
0.2-0.3	6840
0.3-0.4	16436
0.4-0.5	8354
0.5-0.6	6836
0.6-0.7	2582
0.7-0.8	366
0.8-0.85	29
0.85-0.9	9
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8971	High Similarity	NPC472955
0.8824	High Similarity	NPC296522
0.8824	High Similarity	NPC144511
0.8714	High Similarity	NPC472956
0.863	High Similarity	NPC35574
0.8611	High Similarity	NPC41017
0.8493	Intermediate Similarity	NPC41780
0.8493	Intermediate Similarity	NPC187568
0.8472	Intermediate Similarity	NPC324762
0.8356	Intermediate Similarity	NPC266159
0.8356	Intermediate Similarity	NPC472967
0.8333	Intermediate Similarity	NPC472966
0.831	Intermediate Similarity	NPC129665
0.8243	Intermediate Similarity	NPC195785
0.8243	Intermediate Similarity	NPC15975
0.8219	Intermediate Similarity	NPC193351
0.8219	Intermediate Similarity	NPC138408
0.8219	Intermediate Similarity	NPC155587
0.8219	Intermediate Similarity	NPC226669
0.8108	Intermediate Similarity	NPC235906
0.8108	Intermediate Similarity	NPC472959
0.8077	Intermediate Similarity	NPC470948
0.8056	Intermediate Similarity	NPC163003
0.8052	Intermediate Similarity	NPC475665
0.8028	Intermediate Similarity	NPC5714
0.8026	Intermediate Similarity	NPC182550
0.8026	Intermediate Similarity	NPC264227
0.8026	Intermediate Similarity	NPC63649
0.8026	Intermediate Similarity	NPC472965
0.8	Intermediate Similarity	NPC470240
0.8	Intermediate Similarity	NPC65603
0.8	Intermediate Similarity	NPC476794
0.7975	Intermediate Similarity	NPC139566
0.7975	Intermediate Similarity	NPC295799
0.7973	Intermediate Similarity	NPC475861
0.7949	Intermediate Similarity	NPC178676
0.7945	Intermediate Similarity	NPC269206
0.7945	Intermediate Similarity	NPC295633
0.7945	Intermediate Similarity	NPC58956
0.7922	Intermediate Similarity	NPC195424
0.7922	Intermediate Similarity	NPC276356
0.7917	Intermediate Similarity	NPC475310
0.7895	Intermediate Similarity	NPC11796
0.7895	Intermediate Similarity	NPC218817
0.7857	Intermediate Similarity	NPC304665
0.7857	Intermediate Similarity	NPC154728
0.7857	Intermediate Similarity	NPC126899
0.7848	Intermediate Similarity	NPC39588
0.7838	Intermediate Similarity	NPC140287
0.7838	Intermediate Similarity	NPC469643
0.7838	Intermediate Similarity	NPC469641
0.7838	Intermediate Similarity	NPC476355
0.7821	Intermediate Similarity	NPC39411
0.7821	Intermediate Similarity	NPC255580
0.7805	Intermediate Similarity	NPC477128
0.7805	Intermediate Similarity	NPC215831
0.7792	Intermediate Similarity	NPC470244
0.7792	Intermediate Similarity	NPC617
0.7792	Intermediate Similarity	NPC470239
0.7792	Intermediate Similarity	NPC89128
0.7778	Intermediate Similarity	NPC6979
0.7763	Intermediate Similarity	NPC107668
0.7763	Intermediate Similarity	NPC474760
0.775	Intermediate Similarity	NPC100391
0.7722	Intermediate Similarity	NPC89555
0.7711	Intermediate Similarity	NPC73995
0.7703	Intermediate Similarity	NPC167145
0.7703	Intermediate Similarity	NPC470237
0.7703	Intermediate Similarity	NPC135703
0.7692	Intermediate Similarity	NPC469920
0.7692	Intermediate Similarity	NPC200446
0.7692	Intermediate Similarity	NPC302426
0.7692	Intermediate Similarity	NPC46151
0.7692	Intermediate Similarity	NPC69271
0.7692	Intermediate Similarity	NPC74673
0.7662	Intermediate Similarity	NPC472960
0.7662	Intermediate Similarity	NPC469495
0.7662	Intermediate Similarity	NPC128276
0.7662	Intermediate Similarity	NPC267231
0.7662	Intermediate Similarity	NPC474341
0.7654	Intermediate Similarity	NPC21471
0.7654	Intermediate Similarity	NPC161957
0.7654	Intermediate Similarity	NPC177932
0.7654	Intermediate Similarity	NPC52628
0.7654	Intermediate Similarity	NPC110405
0.7654	Intermediate Similarity	NPC33570
0.7632	Intermediate Similarity	NPC110461
0.7632	Intermediate Similarity	NPC123360
0.7632	Intermediate Similarity	NPC474527
0.7632	Intermediate Similarity	NPC12740
0.7632	Intermediate Similarity	NPC471726
0.7625	Intermediate Similarity	NPC193198
0.7625	Intermediate Similarity	NPC22611
0.7619	Intermediate Similarity	NPC469372
0.76	Intermediate Similarity	NPC330016
0.7595	Intermediate Similarity	NPC471325
0.7595	Intermediate Similarity	NPC281949
0.7595	Intermediate Similarity	NPC141810
0.7595	Intermediate Similarity	NPC207188
0.7595	Intermediate Similarity	NPC52861
0.7595	Intermediate Similarity	NPC301477
0.7595	Intermediate Similarity	NPC470241
0.7595	Intermediate Similarity	NPC38642
0.7595	Intermediate Similarity	NPC25684
0.7564	Intermediate Similarity	NPC178277
0.7564	Intermediate Similarity	NPC158565
0.7564	Intermediate Similarity	NPC209995
0.7561	Intermediate Similarity	NPC264127
0.7532	Intermediate Similarity	NPC97516
0.7532	Intermediate Similarity	NPC476028
0.7532	Intermediate Similarity	NPC7563
0.7532	Intermediate Similarity	NPC171204
0.7532	Intermediate Similarity	NPC116177
0.7532	Intermediate Similarity	NPC57744
0.7532	Intermediate Similarity	NPC320630
0.7532	Intermediate Similarity	NPC141789
0.7531	Intermediate Similarity	NPC165287
0.7531	Intermediate Similarity	NPC159635
0.75	Intermediate Similarity	NPC471491
0.75	Intermediate Similarity	NPC469868
0.75	Intermediate Similarity	NPC475690
0.75	Intermediate Similarity	NPC474252
0.75	Intermediate Similarity	NPC255060
0.75	Intermediate Similarity	NPC173609
0.747	Intermediate Similarity	NPC167877
0.7468	Intermediate Similarity	NPC223904
0.7463	Intermediate Similarity	NPC165808
0.7439	Intermediate Similarity	NPC78089
0.7439	Intermediate Similarity	NPC28887
0.7439	Intermediate Similarity	NPC329738
0.7439	Intermediate Similarity	NPC470223
0.7439	Intermediate Similarity	NPC147921
0.7439	Intermediate Similarity	NPC125290
0.7436	Intermediate Similarity	NPC108816
0.7436	Intermediate Similarity	NPC471465
0.7436	Intermediate Similarity	NPC196653
0.7436	Intermediate Similarity	NPC299235
0.7436	Intermediate Similarity	NPC93763
0.7436	Intermediate Similarity	NPC471220
0.7424	Intermediate Similarity	NPC128061
0.7424	Intermediate Similarity	NPC223677
0.7424	Intermediate Similarity	NPC200845
0.7424	Intermediate Similarity	NPC28779
0.7424	Intermediate Similarity	NPC10316
0.7412	Intermediate Similarity	NPC15059
0.7412	Intermediate Similarity	NPC212679
0.7412	Intermediate Similarity	NPC469595
0.7412	Intermediate Similarity	NPC220454
0.7412	Intermediate Similarity	NPC152467
0.7407	Intermediate Similarity	NPC318468
0.7407	Intermediate Similarity	NPC250315
0.7407	Intermediate Similarity	NPC215294
0.7407	Intermediate Similarity	NPC272814
0.7403	Intermediate Similarity	NPC474447
0.7403	Intermediate Similarity	NPC266119
0.7403	Intermediate Similarity	NPC473223
0.7403	Intermediate Similarity	NPC92489
0.7403	Intermediate Similarity	NPC279537
0.7403	Intermediate Similarity	NPC61863
0.7403	Intermediate Similarity	NPC239127
0.7397	Intermediate Similarity	NPC476614
0.7385	Intermediate Similarity	NPC71761
0.7381	Intermediate Similarity	NPC226863
0.7381	Intermediate Similarity	NPC472220
0.7381	Intermediate Similarity	NPC474845
0.7381	Intermediate Similarity	NPC97884
0.7381	Intermediate Similarity	NPC190718
0.7381	Intermediate Similarity	NPC28227
0.7375	Intermediate Similarity	NPC325031
0.7375	Intermediate Similarity	NPC191711
0.7375	Intermediate Similarity	NPC35089
0.7375	Intermediate Similarity	NPC10276
0.7375	Intermediate Similarity	NPC42470
0.7375	Intermediate Similarity	NPC474955
0.7368	Intermediate Similarity	NPC474551
0.7368	Intermediate Similarity	NPC143979
0.7368	Intermediate Similarity	NPC55527
0.7368	Intermediate Similarity	NPC320537
0.7368	Intermediate Similarity	NPC166797
0.7361	Intermediate Similarity	NPC18252
0.7356	Intermediate Similarity	NPC477129
0.7356	Intermediate Similarity	NPC477130
0.7349	Intermediate Similarity	NPC104961
0.7349	Intermediate Similarity	NPC70422
0.7349	Intermediate Similarity	NPC70555
0.7349	Intermediate Similarity	NPC107787
0.7342	Intermediate Similarity	NPC473981
0.7342	Intermediate Similarity	NPC469690
0.7342	Intermediate Similarity	NPC270126
0.7342	Intermediate Similarity	NPC475210
0.7342	Intermediate Similarity	NPC473980
0.7342	Intermediate Similarity	NPC98557
0.7342	Intermediate Similarity	NPC167881
0.7326	Intermediate Similarity	NPC233345
0.7326	Intermediate Similarity	NPC49420
0.7326	Intermediate Similarity	NPC186363
0.7324	Intermediate Similarity	NPC328089
0.7324	Intermediate Similarity	NPC469723
0.7324	Intermediate Similarity	NPC68343
0.7317	Intermediate Similarity	NPC96259

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 NPC199557 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1674
0.2-0.3	4156
0.3-0.4	2171
0.4-0.5	566
0.5-0.6	327
0.6-0.7	75
0.7-0.8	25
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
0.7654	Intermediate Similarity	NPD1694	Approved
0.7595	Intermediate Similarity	NPD5369	Approved
0.7284	Intermediate Similarity	NPD4270	Approved
0.7284	Intermediate Similarity	NPD4269	Approved
0.7284	Intermediate Similarity	NPD6435	Approved
0.7273	Intermediate Similarity	NPD8039	Approved
0.7229	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7154	Phase 3
0.7195	Intermediate Similarity	NPD5362	Discontinued
0.7143	Intermediate Similarity	NPD5786	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7093	Intermediate Similarity	NPD1695	Approved
0.7093	Intermediate Similarity	NPD6101	Approved
0.7093	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6399	Phase 3
0.7037	Intermediate Similarity	NPD5368	Approved
0.7037	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4252	Approved
0.7024	Intermediate Similarity	NPD5363	Approved
0.7	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6903	Approved
0.6977	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6411	Approved
0.6889	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5778	Approved
0.6854	Remote Similarity	NPD5779	Approved
0.6829	Remote Similarity	NPD4821	Approved
0.6829	Remote Similarity	NPD4820	Approved
0.6829	Remote Similarity	NPD4822	Approved
0.6829	Remote Similarity	NPD4819	Approved
0.6818	Remote Similarity	NPD28	Approved
0.6818	Remote Similarity	NPD5207	Approved
0.6818	Remote Similarity	NPD29	Approved
0.6818	Remote Similarity	NPD5785	Approved
0.6813	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4268	Approved
0.679	Remote Similarity	NPD4271	Approved
0.6782	Remote Similarity	NPD5737	Approved
0.6782	Remote Similarity	NPD6672	Approved
0.6744	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD4250	Approved
0.6622	Remote Similarity	NPD3197	Phase 1
0.6618	Remote Similarity	NPD3172	Approved
0.6593	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7900	Approved
0.6593	Remote Similarity	NPD5282	Discontinued
0.6588	Remote Similarity	NPD5331	Approved
0.6588	Remote Similarity	NPD5332	Approved
0.6552	Remote Similarity	NPD6098	Approved
0.6552	Remote Similarity	NPD6422	Discontinued
0.6548	Remote Similarity	NPD4790	Discontinued
0.6533	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4266	Approved
0.6522	Remote Similarity	NPD3194	Approved
0.6522	Remote Similarity	NPD3195	Phase 2
0.6522	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3196	Approved
0.6512	Remote Similarity	NPD3668	Phase 3
0.6512	Remote Similarity	NPD4786	Approved
0.6477	Remote Similarity	NPD3573	Approved
0.6471	Remote Similarity	NPD5209	Approved
0.6447	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7331	Phase 2
0.6444	Remote Similarity	NPD46	Approved
0.6444	Remote Similarity	NPD6698	Approved
0.6437	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6008	Approved
0.6413	Remote Similarity	NPD6001	Approved
0.6413	Remote Similarity	NPD7748	Approved
0.6404	Remote Similarity	NPD5208	Approved
0.6383	Remote Similarity	NPD7902	Approved
0.6374	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7983	Approved
0.6374	Remote Similarity	NPD5694	Approved
0.6364	Remote Similarity	NPD5343	Approved
0.6364	Remote Similarity	NPD3618	Phase 1
0.6344	Remote Similarity	NPD5695	Phase 3
0.6333	Remote Similarity	NPD6904	Approved
0.6333	Remote Similarity	NPD6673	Approved
0.6333	Remote Similarity	NPD6080	Approved
0.6333	Remote Similarity	NPD5370	Suspended
0.6322	Remote Similarity	NPD3665	Phase 1
0.6322	Remote Similarity	NPD3133	Approved
0.6322	Remote Similarity	NPD3666	Approved
0.6316	Remote Similarity	NPD5696	Approved
0.6308	Remote Similarity	NPD3174	Discontinued
0.6277	Remote Similarity	NPD7839	Suspended
0.6264	Remote Similarity	NPD5692	Phase 3
0.6264	Remote Similarity	NPD3672	Approved
0.6264	Remote Similarity	NPD3673	Approved
0.6211	Remote Similarity	NPD6083	Phase 2
0.6211	Remote Similarity	NPD6084	Phase 2
0.6196	Remote Similarity	NPD5281	Approved
0.6196	Remote Similarity	NPD6050	Approved
0.6196	Remote Similarity	NPD7637	Suspended
0.6196	Remote Similarity	NPD5284	Approved
0.6196	Remote Similarity	NPD5693	Phase 1
0.6196	Remote Similarity	NPD7515	Phase 2
0.6184	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5279	Phase 3
0.6146	Remote Similarity	NPD4225	Approved
0.6129	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD622	Approved
0.6104	Remote Similarity	NPD7341	Phase 2
0.6081	Remote Similarity	NPD3198	Approved
0.6071	Remote Similarity	NPD4756	Discovery
0.6047	Remote Similarity	NPD4695	Discontinued
0.604	Remote Similarity	NPD5697	Approved
0.604	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD3173	Approved
0.6022	Remote Similarity	NPD8035	Phase 2
0.6022	Remote Similarity	NPD8034	Phase 2
0.6022	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD3732	Approved
0.6	Remote Similarity	NPD4137	Phase 3
0.6	Remote Similarity	NPD1145	Discontinued
0.6	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6011	Approved
0.598	Remote Similarity	NPD6881	Approved
0.598	Remote Similarity	NPD6899	Approved
0.5978	Remote Similarity	NPD6051	Approved
0.5978	Remote Similarity	NPD5328	Approved
0.5977	Remote Similarity	NPD857	Phase 3
0.5962	Remote Similarity	NPD6650	Approved
0.5962	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD1719	Phase 1
0.5962	Remote Similarity	NPD6649	Approved
0.5962	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6402	Approved
0.5941	Remote Similarity	NPD5739	Approved
0.5941	Remote Similarity	NPD6675	Approved
0.5941	Remote Similarity	NPD7128	Approved
0.5938	Remote Similarity	NPD1989	Approved
0.5934	Remote Similarity	NPD1087	Approved
0.5926	Remote Similarity	NPD4747	Approved
0.5926	Remote Similarity	NPD4691	Approved
0.5922	Remote Similarity	NPD6372	Approved
0.5922	Remote Similarity	NPD6014	Approved
0.5922	Remote Similarity	NPD6012	Approved
0.5922	Remote Similarity	NPD6013	Approved
0.5922	Remote Similarity	NPD6373	Approved
0.5921	Remote Similarity	NPD368	Approved
0.5909	Remote Similarity	NPD6096	Approved
0.5909	Remote Similarity	NPD6097	Approved
0.5909	Remote Similarity	NPD4221	Approved
0.5909	Remote Similarity	NPD2699	Approved
0.5909	Remote Similarity	NPD4223	Phase 3
0.5904	Remote Similarity	NPD4687	Approved
0.5904	Remote Similarity	NPD4058	Approved
0.59	Remote Similarity	NPD6052	Approved
0.5897	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5701	Approved
0.5875	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD229	Approved
0.587	Remote Similarity	NPD4518	Approved
0.5865	Remote Similarity	NPD6883	Approved
0.5865	Remote Similarity	NPD7290	Approved
0.5865	Remote Similarity	NPD7102	Approved
0.5862	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD5276	Approved
0.5854	Remote Similarity	NPD5777	Approved
0.5844	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5654	Approved
0.5833	Remote Similarity	NPD7115	Discovery
0.5833	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4629	Approved
0.5833	Remote Similarity	NPD5210	Approved
0.5833	Remote Similarity	NPD1693	Approved
0.5825	Remote Similarity	NPD7320	Approved
0.5824	Remote Similarity	NPD4519	Discontinued
0.5824	Remote Similarity	NPD5690	Phase 2
0.5824	Remote Similarity	NPD4623	Approved
0.5823	Remote Similarity	NPD3704	Approved
0.5821	Remote Similarity	NPD634	Phase 3
0.5816	Remote Similarity	NPD7638	Approved
0.5816	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6847	Approved
0.581	Remote Similarity	NPD8130	Phase 1
0.581	Remote Similarity	NPD6617	Approved
0.581	Remote Similarity	NPD6869	Approved
0.5806	Remote Similarity	NPD4753	Phase 2
0.5806	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4202	Approved
0.5778	Remote Similarity	NPD4197	Approved
0.5778	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD5221	Approved
0.5773	Remote Similarity	NPD4697	Phase 3
0.5773	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD5222	Approved
0.5766	Remote Similarity	NPD8513	Phase 3

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