NPASS Compound

Structure

CID194970 OpenBabel06191715582D 29 31 0 0 1 0 0 0 0 0999 V2000 -1.1248 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 -0.8912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 23 1 0 0 0 0 2 23 1 0 0 0 0 4 8 1 0 0 0 0 4 16 2 0 0 0 0 5 9 2 0 0 0 0 5 16 1 0 0 0 0 6 11 2 0 0 0 0 6 16 1 0 0 0 0 7 10 1 0 0 0 0 7 17 2 0 0 0 0 8 18 2 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 25 2 0 0 0 0 15 19 1 0 0 0 0 15 26 2 0 0 0 0 17 19 1 0 0 0 0 18 27 1 0 0 0 0 19 24 1 6 0 0 0 20 23 1 0 0 0 0 20 24 1 6 0 0 0 21 24 1 6 0 0 0 21 29 1 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 24 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.19
Volume:	420.85
LogP:	3.955
LogD:	3.095
LogS:	-3.952
# Rotatable Bonds:	6
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	4.213
Fsp3:	0.458
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.874
MDCK Permeability:	2.1016310711274855e-05
Pgp-inhibitor:	0.882
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.191
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.158

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.925
Plasma Protein Binding (PPB):	67.99303436279297%
Volume Distribution (VD):	1.97
Pgp-substrate:	15.738587379455566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.425
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.706
CYP2C19-substrate:	0.163
CYP2C9-inhibitor:	0.591
CYP2C9-substrate:	0.878
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.672
CYP3A4-inhibitor:	0.617
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	7.986
Half-life (T1/2):	0.864

ADMET: Toxicity

hERG Blockers:	0.197
Human Hepatotoxicity (H-HT):	0.828
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.977
Carcinogencity:	0.145
Eye Corrosion:	0.803
Eye Irritation:	0.698
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC194970

Natural Product ID:	NPC194970
*Common Name:**	1Beta-P-Coumaroyloxypolygodial
IUPAC Name:	[(1R,4aS,8R,8aS)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:	1Beta-P-Coumaroyloxypolygodial
Standard InCHIKey:	OOBNDBQPMFZTTD-TWEQYNAUSA-N
Standard InCHI:	InChI=1S/C24H28O5/c1-23(2)13-12-21(24(3)19(15-26)17(14-25)7-10-20(23)24)29-22(28)11-6-16-4-8-18(27)9-5-16/h4-9,11,14-15,19-21,27H,10,12-13H2,1-3H3/b11-6+/t19-,20-,21+,24+/m0/s1
SMILES:	CC1(C)CC[C@H]([C@]2(C)[C@@H](C=O)C(=CC[C@@H]12)C=O)OC(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333577
PubChem CID:	14241022
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10993146]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	Tsukuba, Japan	1998-JUN	PMID[12381108]
NPO19593	Placida dendritica	Species	Limapontiidae	Eukaryota	n.a.	Mediterranean	n.a.	PMID[14575447]
NPO19593	Placida dendritica	Species	Limapontiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14575447]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24197199]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24254087]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17965	Helenium arizonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19593	Placida dendritica	Species	Limapontiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5929	Neoscopelus microchir	Species	Neoscopelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19652	Pittosporum phillyraeoides	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17965	Helenium arizonicum	Species	Asteraceae	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
GI50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT386	Cell Line	KM12	Homo sapiens	GI50	=	25000.0	nM	PMID[459957]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	=	29000.0	nM	PMID[459957]

☑ 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 NPC194970 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	269
0.1-0.2	1180
0.2-0.3	2231
0.3-0.4	4998
0.4-0.5	9892
0.5-0.6	8837
0.6-0.7	11581
0.7-0.8	3582
0.8-0.85	103
0.85-0.9	21
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.903	High Similarity	NPC477874
0.903	High Similarity	NPC173569
0.8992	High Similarity	NPC137416
0.8978	High Similarity	NPC172311
0.8963	High Similarity	NPC249817
0.8897	High Similarity	NPC198621
0.8897	High Similarity	NPC22676
0.8897	High Similarity	NPC475482
0.8897	High Similarity	NPC216940
0.8837	High Similarity	NPC12881
0.8837	High Similarity	NPC140118
0.8769	High Similarity	NPC265413
0.8769	High Similarity	NPC10154
0.8705	High Similarity	NPC304110
0.8705	High Similarity	NPC472801
0.8705	High Similarity	NPC27518
0.8696	High Similarity	NPC234548
0.8696	High Similarity	NPC248287
0.8652	High Similarity	NPC25491
0.8626	High Similarity	NPC474532
0.8623	High Similarity	NPC471152
0.8603	High Similarity	NPC475627
0.8603	High Similarity	NPC475457
0.8603	High Similarity	NPC475346
0.8603	High Similarity	NPC18982
0.8583	High Similarity	NPC152812
0.8582	High Similarity	NPC131684
0.8582	High Similarity	NPC86257
0.8582	High Similarity	NPC469447
0.8582	High Similarity	NPC477873
0.8542	High Similarity	NPC325032
0.8542	High Similarity	NPC477483
0.8483	Intermediate Similarity	NPC473719
0.8462	Intermediate Similarity	NPC53520
0.8444	Intermediate Similarity	NPC117899
0.8429	Intermediate Similarity	NPC477593
0.8425	Intermediate Similarity	NPC267469
0.8425	Intermediate Similarity	NPC162569
0.8425	Intermediate Similarity	NPC327962
0.8425	Intermediate Similarity	NPC87630
0.8425	Intermediate Similarity	NPC179128
0.8425	Intermediate Similarity	NPC35160
0.8425	Intermediate Similarity	NPC116292
0.8403	Intermediate Similarity	NPC208293
0.8394	Intermediate Similarity	NPC165612
0.837	Intermediate Similarity	NPC3009
0.837	Intermediate Similarity	NPC193203
0.8356	Intermediate Similarity	NPC279442
0.8345	Intermediate Similarity	NPC472804
0.8333	Intermediate Similarity	NPC121168
0.8321	Intermediate Similarity	NPC18798
0.8321	Intermediate Similarity	NPC164852
0.8309	Intermediate Similarity	NPC288290
0.8308	Intermediate Similarity	NPC42657
0.8284	Intermediate Similarity	NPC137750
0.8276	Intermediate Similarity	NPC8102
0.8276	Intermediate Similarity	NPC66894
0.8276	Intermediate Similarity	NPC258856
0.8273	Intermediate Similarity	NPC11266
0.8258	Intermediate Similarity	NPC253627
0.8243	Intermediate Similarity	NPC140133
0.8239	Intermediate Similarity	NPC295339
0.8235	Intermediate Similarity	NPC229894
0.8227	Intermediate Similarity	NPC119542
0.8227	Intermediate Similarity	NPC477592
0.8222	Intermediate Similarity	NPC71610
0.8222	Intermediate Similarity	NPC169913
0.8222	Intermediate Similarity	NPC110211
0.8222	Intermediate Similarity	NPC471930
0.8222	Intermediate Similarity	NPC471929
0.8222	Intermediate Similarity	NPC204579
0.8222	Intermediate Similarity	NPC471935
0.8201	Intermediate Similarity	NPC477139
0.8201	Intermediate Similarity	NPC49742
0.8195	Intermediate Similarity	NPC11250
0.8195	Intermediate Similarity	NPC478058
0.8194	Intermediate Similarity	NPC474300
0.8182	Intermediate Similarity	NPC220496
0.8182	Intermediate Similarity	NPC32749
0.8182	Intermediate Similarity	NPC147542
0.8182	Intermediate Similarity	NPC42262
0.8182	Intermediate Similarity	NPC241001
0.8182	Intermediate Similarity	NPC327916
0.8182	Intermediate Similarity	NPC37992
0.8182	Intermediate Similarity	NPC241349
0.8176	Intermediate Similarity	NPC146014
0.8169	Intermediate Similarity	NPC116742
0.8169	Intermediate Similarity	NPC182249
0.8169	Intermediate Similarity	NPC61590
0.8169	Intermediate Similarity	NPC139243
0.8163	Intermediate Similarity	NPC5568
0.8162	Intermediate Similarity	NPC72667
0.8151	Intermediate Similarity	NPC75295
0.8148	Intermediate Similarity	NPC275576
0.8143	Intermediate Similarity	NPC477594
0.8143	Intermediate Similarity	NPC27394
0.8143	Intermediate Similarity	NPC202225
0.8138	Intermediate Similarity	NPC476473
0.8125	Intermediate Similarity	NPC477595
0.8125	Intermediate Similarity	NPC272907
0.8125	Intermediate Similarity	NPC2681
0.8121	Intermediate Similarity	NPC118033
0.812	Intermediate Similarity	NPC154696
0.812	Intermediate Similarity	NPC162935
0.812	Intermediate Similarity	NPC249340
0.8112	Intermediate Similarity	NPC216312
0.8112	Intermediate Similarity	NPC470616
0.8112	Intermediate Similarity	NPC29771
0.8112	Intermediate Similarity	NPC470617
0.8112	Intermediate Similarity	NPC473591
0.8112	Intermediate Similarity	NPC476477
0.8112	Intermediate Similarity	NPC111422
0.8112	Intermediate Similarity	NPC155192
0.8112	Intermediate Similarity	NPC306835
0.8112	Intermediate Similarity	NPC299405
0.8112	Intermediate Similarity	NPC471602
0.8112	Intermediate Similarity	NPC256463
0.8112	Intermediate Similarity	NPC271494
0.8108	Intermediate Similarity	NPC46549
0.8108	Intermediate Similarity	NPC264229
0.8106	Intermediate Similarity	NPC478121
0.8099	Intermediate Similarity	NPC475957
0.8095	Intermediate Similarity	NPC472938
0.8095	Intermediate Similarity	NPC470330
0.8095	Intermediate Similarity	NPC472936
0.8095	Intermediate Similarity	NPC472937
0.8088	Intermediate Similarity	NPC254492
0.8085	Intermediate Similarity	NPC279463
0.8085	Intermediate Similarity	NPC477596
0.8074	Intermediate Similarity	NPC181334
0.8071	Intermediate Similarity	NPC472591
0.8071	Intermediate Similarity	NPC59459
0.8071	Intermediate Similarity	NPC78307
0.8071	Intermediate Similarity	NPC329913
0.8069	Intermediate Similarity	NPC477209
0.8067	Intermediate Similarity	NPC473773
0.8067	Intermediate Similarity	NPC475579
0.8058	Intermediate Similarity	NPC471851
0.8056	Intermediate Similarity	NPC82336
0.8056	Intermediate Similarity	NPC3218
0.8056	Intermediate Similarity	NPC78987
0.8056	Intermediate Similarity	NPC476534
0.8054	Intermediate Similarity	NPC247219
0.8045	Intermediate Similarity	NPC32322
0.8045	Intermediate Similarity	NPC259703
0.8043	Intermediate Similarity	NPC171460
0.8043	Intermediate Similarity	NPC214246
0.8042	Intermediate Similarity	NPC202260
0.8041	Intermediate Similarity	NPC81835
0.8041	Intermediate Similarity	NPC66991
0.8029	Intermediate Similarity	NPC84672
0.8029	Intermediate Similarity	NPC176130
0.8029	Intermediate Similarity	NPC69424
0.8029	Intermediate Similarity	NPC78364
0.8028	Intermediate Similarity	NPC38158
0.8028	Intermediate Similarity	NPC476699
0.8027	Intermediate Similarity	NPC84786
0.8027	Intermediate Similarity	NPC320734
0.8026	Intermediate Similarity	NPC472807
0.8015	Intermediate Similarity	NPC325295
0.8015	Intermediate Similarity	NPC49938
0.8015	Intermediate Similarity	NPC87985
0.8015	Intermediate Similarity	NPC76308
0.8014	Intermediate Similarity	NPC477893
0.8014	Intermediate Similarity	NPC66593
0.8014	Intermediate Similarity	NPC21873
0.8014	Intermediate Similarity	NPC477896
0.8	Intermediate Similarity	NPC261659
0.8	Intermediate Similarity	NPC174991
0.8	Intermediate Similarity	NPC257003
0.8	Intermediate Similarity	NPC475454
0.8	Intermediate Similarity	NPC475311
0.8	Intermediate Similarity	NPC477407
0.8	Intermediate Similarity	NPC37642
0.8	Intermediate Similarity	NPC470842
0.8	Intermediate Similarity	NPC471444
0.8	Intermediate Similarity	NPC473680
0.8	Intermediate Similarity	NPC473579
0.8	Intermediate Similarity	NPC327204
0.8	Intermediate Similarity	NPC323379
0.7987	Intermediate Similarity	NPC146388
0.7987	Intermediate Similarity	NPC17600
0.7987	Intermediate Similarity	NPC94781
0.7986	Intermediate Similarity	NPC108129
0.7986	Intermediate Similarity	NPC245395
0.7986	Intermediate Similarity	NPC471875
0.7973	Intermediate Similarity	NPC286038
0.7973	Intermediate Similarity	NPC191899
0.7973	Intermediate Similarity	NPC147250
0.7973	Intermediate Similarity	NPC202112
0.7973	Intermediate Similarity	NPC477208
0.7973	Intermediate Similarity	NPC273798
0.7973	Intermediate Similarity	NPC246229
0.7973	Intermediate Similarity	NPC474991
0.7973	Intermediate Similarity	NPC51513
0.7972	Intermediate Similarity	NPC118366
0.7971	Intermediate Similarity	NPC473744
0.7971	Intermediate Similarity	NPC96024
0.7969	Intermediate Similarity	NPC139946
0.7961	Intermediate Similarity	NPC470102

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 NPC194970 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	826
0.2-0.3	1344
0.3-0.4	2373
0.4-0.5	2223
0.5-0.6	1454
0.6-0.7	619
0.7-0.8	71
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.838	Intermediate Similarity	NPD8166	Discontinued
0.8188	Intermediate Similarity	NPD6663	Approved
0.8162	Intermediate Similarity	NPD5736	Approved
0.797	Intermediate Similarity	NPD2932	Approved
0.7877	Intermediate Similarity	NPD4628	Phase 3
0.7836	Intermediate Similarity	NPD3019	Approved
0.7755	Intermediate Similarity	NPD7003	Approved
0.7733	Intermediate Similarity	NPD6273	Approved
0.773	Intermediate Similarity	NPD3764	Approved
0.7697	Intermediate Similarity	NPD7458	Discontinued
0.7687	Intermediate Similarity	NPD9545	Approved
0.7635	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1283	Approved
0.7534	Intermediate Similarity	NPD2799	Discontinued
0.7533	Intermediate Similarity	NPD7236	Approved
0.75	Intermediate Similarity	NPD4140	Approved
0.75	Intermediate Similarity	NPD2797	Approved
0.7483	Intermediate Similarity	NPD2935	Discontinued
0.7483	Intermediate Similarity	NPD3268	Approved
0.7467	Intermediate Similarity	NPD6190	Approved
0.7448	Intermediate Similarity	NPD6355	Discontinued
0.7445	Intermediate Similarity	NPD4626	Approved
0.7434	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD8032	Phase 2
0.7426	Intermediate Similarity	NPD3091	Approved
0.7413	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3972	Approved
0.74	Intermediate Similarity	NPD4110	Phase 3
0.74	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3026	Approved
0.7391	Intermediate Similarity	NPD3023	Approved
0.7388	Intermediate Similarity	NPD2629	Approved
0.7379	Intermediate Similarity	NPD2979	Phase 3
0.7379	Intermediate Similarity	NPD4060	Phase 1
0.7376	Intermediate Similarity	NPD1470	Approved
0.7372	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3025	Approved
0.7372	Intermediate Similarity	NPD5691	Approved
0.7372	Intermediate Similarity	NPD3024	Approved
0.7361	Intermediate Similarity	NPD6798	Discontinued
0.7355	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1281	Approved
0.7337	Intermediate Similarity	NPD8434	Phase 2
0.7329	Intermediate Similarity	NPD8127	Discontinued
0.7319	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2346	Discontinued
0.7297	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7008	Discontinued
0.729	Intermediate Similarity	NPD7239	Suspended
0.7286	Intermediate Similarity	NPD1608	Approved
0.7285	Intermediate Similarity	NPD3750	Approved
0.7278	Intermediate Similarity	NPD7819	Suspended
0.7267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5951	Approved
0.7248	Intermediate Similarity	NPD5404	Approved
0.7248	Intermediate Similarity	NPD2438	Suspended
0.7248	Intermediate Similarity	NPD5405	Approved
0.7248	Intermediate Similarity	NPD5406	Approved
0.7248	Intermediate Similarity	NPD5408	Approved
0.7248	Intermediate Similarity	NPD6099	Approved
0.7248	Intermediate Similarity	NPD6100	Approved
0.7244	Intermediate Similarity	NPD3226	Approved
0.7241	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7097	Phase 1
0.7214	Intermediate Similarity	NPD3092	Approved
0.7211	Intermediate Similarity	NPD230	Phase 1
0.7208	Intermediate Similarity	NPD2533	Approved
0.7208	Intermediate Similarity	NPD2532	Approved
0.7208	Intermediate Similarity	NPD2534	Approved
0.72	Intermediate Similarity	NPD2344	Approved
0.7197	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1778	Approved
0.7194	Intermediate Similarity	NPD3095	Discontinued
0.7181	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6232	Discontinued
0.7172	Intermediate Similarity	NPD7095	Approved
0.7154	Intermediate Similarity	NPD5909	Discontinued
0.7153	Intermediate Similarity	NPD9493	Approved
0.7153	Intermediate Similarity	NPD9494	Approved
0.7153	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7133	Intermediate Similarity	NPD1164	Approved
0.7133	Intermediate Similarity	NPD4476	Approved
0.7133	Intermediate Similarity	NPD2531	Phase 2
0.7133	Intermediate Similarity	NPD3266	Approved
0.7133	Intermediate Similarity	NPD4477	Approved
0.7133	Intermediate Similarity	NPD3094	Phase 2
0.7133	Intermediate Similarity	NPD3267	Approved
0.7123	Intermediate Similarity	NPD2313	Discontinued
0.7122	Intermediate Similarity	NPD1651	Approved
0.7122	Intermediate Similarity	NPD5585	Approved
0.7121	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD3020	Approved
0.7107	Intermediate Similarity	NPD37	Approved
0.7099	Intermediate Similarity	NPD6234	Discontinued
0.7097	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1201	Approved
0.709	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6599	Discontinued
0.7089	Intermediate Similarity	NPD7028	Phase 2
0.7083	Intermediate Similarity	NPD2798	Approved
0.7081	Intermediate Similarity	NPD4965	Approved
0.7081	Intermediate Similarity	NPD4966	Approved
0.7081	Intermediate Similarity	NPD4967	Phase 2
0.7081	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4198	Discontinued
0.7076	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6233	Phase 2
0.7071	Intermediate Similarity	NPD17	Approved
0.7071	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2182	Approved
0.7067	Intermediate Similarity	NPD1510	Phase 2
0.7067	Intermediate Similarity	NPD7033	Discontinued
0.7067	Intermediate Similarity	NPD4308	Phase 3
0.7066	Intermediate Similarity	NPD5844	Phase 1
0.7063	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5761	Phase 2
0.7063	Intermediate Similarity	NPD5760	Phase 2
0.7063	Intermediate Similarity	NPD1876	Approved
0.7059	Intermediate Similarity	NPD1241	Discontinued
0.7059	Intermediate Similarity	NPD6010	Discontinued
0.705	Intermediate Similarity	NPD1894	Discontinued
0.7045	Intermediate Similarity	NPD3134	Approved
0.7044	Intermediate Similarity	NPD7411	Suspended
0.7041	Intermediate Similarity	NPD6765	Approved
0.7041	Intermediate Similarity	NPD6764	Approved
0.7039	Intermediate Similarity	NPD4534	Discontinued
0.7039	Intermediate Similarity	NPD1549	Phase 2
0.7021	Intermediate Similarity	NPD3496	Discontinued
0.7021	Intermediate Similarity	NPD3847	Discontinued
0.702	Intermediate Similarity	NPD1551	Phase 2
0.7019	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2309	Approved
0.6993	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5327	Phase 3
0.6987	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2614	Approved
0.6985	Remote Similarity	NPD6858	Approved
0.6985	Remote Similarity	NPD7094	Approved
0.6981	Remote Similarity	NPD4380	Phase 2
0.6975	Remote Similarity	NPD7058	Phase 2
0.6975	Remote Similarity	NPD7057	Phase 3
0.6975	Remote Similarity	NPD7768	Phase 2
0.6974	Remote Similarity	NPD7266	Discontinued
0.6974	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1535	Discovery
0.6959	Remote Similarity	NPD4062	Phase 3
0.6957	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7305	Phase 1
0.6954	Remote Similarity	NPD3748	Approved
0.695	Remote Similarity	NPD4059	Approved
0.6936	Remote Similarity	NPD8150	Discontinued
0.6933	Remote Similarity	NPD1607	Approved
0.6929	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1481	Phase 2
0.6918	Remote Similarity	NPD3455	Phase 2
0.6913	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3620	Phase 2
0.6913	Remote Similarity	NPD1240	Approved
0.6912	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2796	Approved
0.6897	Remote Similarity	NPD1203	Approved
0.6894	Remote Similarity	NPD6801	Discontinued
0.6889	Remote Similarity	NPD3022	Approved
0.6889	Remote Similarity	NPD3021	Approved
0.6886	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6785	Approved
0.6879	Remote Similarity	NPD6784	Approved
0.6875	Remote Similarity	NPD2859	Approved
0.6875	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4359	Approved
0.6875	Remote Similarity	NPD2860	Approved
0.6871	Remote Similarity	NPD6832	Phase 2
0.6867	Remote Similarity	NPD5735	Approved
0.6867	Remote Similarity	NPD7229	Phase 3
0.6866	Remote Similarity	NPD1358	Approved
0.6863	Remote Similarity	NPD6005	Phase 3
0.6863	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6002	Phase 3
0.6863	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6004	Phase 3
0.6863	Remote Similarity	NPD1471	Phase 3
0.6863	Remote Similarity	NPD5763	Approved
0.6863	Remote Similarity	NPD5762	Approved
0.6861	Remote Similarity	NPD5535	Approved
0.6857	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4624	Approved
0.6849	Remote Similarity	NPD5647	Approved
0.6846	Remote Similarity	NPD2066	Phase 3
0.6846	Remote Similarity	NPD7961	Discontinued
0.6839	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3749	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