NPASS Compound

Structure

NPC472694 OpenBabel07101718232D 44 48 0 0 1 0 0 0 0 0999 V2000 1.3694 -9.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0151 -10.1253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7499 1.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4042 1.7254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6349 -5.3745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7995 -4.3566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7177 -4.0828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -0.2622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4231 -1.2201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0492 -1.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0492 -2.7794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2193 -1.3421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2630 -8.2250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3870 -7.2748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3782 -8.5927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6261 -6.6924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2193 -3.2584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3895 -1.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9892 -5.1598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2372 -3.2595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6925 0.2261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3961 -2.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8992 -3.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2542 -9.5428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6155 1.1812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7501 -5.7422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3895 -2.7794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0753 -3.2728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0377 -1.5499 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9038 -0.3182 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5597 -3.2584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4686 -1.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6542 -2.6014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6672 -1.8232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0214 -3.4245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5819 -0.7613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4763 -2.6771 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8806 -1.2761 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7299 -2.7794 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5597 -4.2166 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2322 -1.1033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0126 -1.7128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5014 -1.3519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 35 1 0 0 0 0 7 35 1 0 0 0 0 8 36 1 0 0 0 0 9 36 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 13 14 1 0 0 0 0 13 15 2 0 0 0 0 14 16 1 0 0 0 0 15 24 1 0 0 0 0 16 26 1 0 0 0 0 17 27 2 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 26 2 0 0 0 0 21 25 2 0 0 0 0 21 30 1 0 0 0 0 22 29 1 0 0 0 0 23 28 1 0 0 0 0 23 37 1 0 0 0 0 27 31 1 0 0 0 0 28 22 1 6 0 0 0 28 35 1 0 0 0 0 29 36 1 0 0 0 0 29 38 1 1 0 0 0 30 38 1 1 0 0 0 30 44 1 0 0 0 0 31 40 2 0 0 0 0 32 37 1 0 0 0 0 32 41 2 0 0 0 0 33 37 1 0 0 0 0 33 39 1 0 0 0 0 33 42 2 0 0 0 0 34 38 1 0 0 0 0 34 39 1 0 0 0 0 34 43 2 0 0 0 0 35 39 1 0 0 0 0 36 44 1 0 0 0 0 37 20 1 6 0 0 0 38 32 1 6 0 0 0 39 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	598.37
Volume:	657.904
LogP:	7.561
LogD:	6.125
LogS:	-5.648
# Rotatable Bonds:	9
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	6.676
Fsp3:	0.59
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.235
MDCK Permeability:	2.5140170691884123e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.259
30% Bioavailability (F30%):	0.884

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.479
Plasma Protein Binding (PPB):	99.8684310913086%
Volume Distribution (VD):	1.37
Pgp-substrate:	4.174734115600586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.535
CYP2C19-inhibitor:	0.563
CYP2C19-substrate:	0.96
CYP2C9-inhibitor:	0.687
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.73
CYP3A4-substrate:	0.926

ADMET: Excretion

Clearance (CL):	7.85
Half-life (T1/2):	0.078

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.561
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.236
Rat Oral Acute Toxicity:	0.892
Maximum Recommended Daily Dose:	0.848
Skin Sensitization:	0.645
Carcinogencity:	0.053
Eye Corrosion:	0.112
Eye Irritation:	0.188
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC472694

Natural Product ID:	NPC472694
*Common Name:**	NQIJROSKTOJIMN-KUNHJYBOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NQIJROSKTOJIMN-KUNHJYBOSA-N
Standard InCHI:	InChI=1S/C39H50O5/c1-24(2)15-13-14-16-26(5)19-20-37-23-28-22-29-36(8,9)44-30(21-25(3)4)38(29,32(37)41)34(43)39(33(37)42,35(28,6)7)31(40)27-17-11-10-12-18-27/h10-13,15,17-19,21,24,28-30H,14,16,20,22-23H2,1-9H3/b15-13+,26-19+/t28-,29+,30+,37+,38+,39+/m1/s1
SMILES:	C/C(=CC[C@]12C[C@H]3C[C@@H]4[C@@](C1=O)([C@H](C=C(C)C)OC4(C)C)C(=O)[C@](C2=O)(C3(C)C)C(=O)c1ccccc1)/CC/C=C/C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581598
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	aerial parts	Yunnan, China	n.a.	PMID[25871261]
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19915	Hypericum henryi	Species	Hypericaceae	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[458402]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[458402]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[458402]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[458402]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[458402]

☑ 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 NPC472694 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	359
0.1-0.2	1347
0.2-0.3	2318
0.3-0.4	7103
0.4-0.5	14842
0.5-0.6	14196
0.6-0.7	2256
0.7-0.8	249
0.8-0.85	19
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472693
0.8833	High Similarity	NPC61651
0.875	High Similarity	NPC472692
0.875	High Similarity	NPC472682
0.8699	High Similarity	NPC476234
0.8618	High Similarity	NPC476225
0.8605	High Similarity	NPC471334
0.8525	High Similarity	NPC268930
0.8516	High Similarity	NPC316553
0.8455	Intermediate Similarity	NPC472697
0.8455	Intermediate Similarity	NPC472698
0.8438	Intermediate Similarity	NPC146239
0.8361	Intermediate Similarity	NPC260886
0.8359	Intermediate Similarity	NPC328997
0.8359	Intermediate Similarity	NPC294050
0.8346	Intermediate Similarity	NPC325740
0.8203	Intermediate Similarity	NPC472681
0.8197	Intermediate Similarity	NPC130591
0.8197	Intermediate Similarity	NPC234637
0.814	Intermediate Similarity	NPC478108
0.8115	Intermediate Similarity	NPC471481
0.806	Intermediate Similarity	NPC144257
0.8033	Intermediate Similarity	NPC218855
0.8031	Intermediate Similarity	NPC472679
0.8031	Intermediate Similarity	NPC472680
0.8015	Intermediate Similarity	NPC48992
0.8	Intermediate Similarity	NPC472683
0.8	Intermediate Similarity	NPC472696
0.8	Intermediate Similarity	NPC472701
0.8	Intermediate Similarity	NPC472695
0.7984	Intermediate Similarity	NPC215419
0.7937	Intermediate Similarity	NPC152812
0.7937	Intermediate Similarity	NPC94425
0.7926	Intermediate Similarity	NPC472656
0.7923	Intermediate Similarity	NPC51079
0.7917	Intermediate Similarity	NPC472700
0.7917	Intermediate Similarity	NPC472699
0.791	Intermediate Similarity	NPC470278
0.7902	Intermediate Similarity	NPC473403
0.7886	Intermediate Similarity	NPC280789
0.7879	Intermediate Similarity	NPC470648
0.7879	Intermediate Similarity	NPC473423
0.7868	Intermediate Similarity	NPC329913
0.7836	Intermediate Similarity	NPC471832
0.7836	Intermediate Similarity	NPC147561
0.782	Intermediate Similarity	NPC115797
0.782	Intermediate Similarity	NPC472678
0.782	Intermediate Similarity	NPC51448
0.7817	Intermediate Similarity	NPC471107
0.7817	Intermediate Similarity	NPC471100
0.7815	Intermediate Similarity	NPC474866
0.7815	Intermediate Similarity	NPC475939
0.7815	Intermediate Similarity	NPC472691
0.7815	Intermediate Similarity	NPC471829
0.7812	Intermediate Similarity	NPC202015
0.7786	Intermediate Similarity	NPC85511
0.777	Intermediate Similarity	NPC118366
0.7762	Intermediate Similarity	NPC475552
0.7752	Intermediate Similarity	NPC474222
0.7752	Intermediate Similarity	NPC474223
0.7752	Intermediate Similarity	NPC475804
0.7752	Intermediate Similarity	NPC475827
0.7752	Intermediate Similarity	NPC238861
0.7752	Intermediate Similarity	NPC77000
0.7744	Intermediate Similarity	NPC470753
0.7744	Intermediate Similarity	NPC473220
0.7737	Intermediate Similarity	NPC126516
0.7737	Intermediate Similarity	NPC203486
0.7724	Intermediate Similarity	NPC254558
0.771	Intermediate Similarity	NPC474159
0.771	Intermediate Similarity	NPC474254
0.7698	Intermediate Similarity	NPC184109
0.7687	Intermediate Similarity	NPC268607
0.7671	Intermediate Similarity	NPC51602
0.7669	Intermediate Similarity	NPC470649
0.7669	Intermediate Similarity	NPC473082
0.7669	Intermediate Similarity	NPC470765
0.7669	Intermediate Similarity	NPC470818
0.7669	Intermediate Similarity	NPC478107
0.7661	Intermediate Similarity	NPC265513
0.766	Intermediate Similarity	NPC187566
0.7638	Intermediate Similarity	NPC226093
0.7634	Intermediate Similarity	NPC269923
0.7634	Intermediate Similarity	NPC167323
0.7622	Intermediate Similarity	NPC80895
0.7622	Intermediate Similarity	NPC471912
0.7619	Intermediate Similarity	NPC294458
0.7615	Intermediate Similarity	NPC473243
0.7615	Intermediate Similarity	NPC232958
0.7612	Intermediate Similarity	NPC169913
0.7609	Intermediate Similarity	NPC4242
0.7609	Intermediate Similarity	NPC474608
0.7609	Intermediate Similarity	NPC471911
0.7606	Intermediate Similarity	NPC475135
0.7591	Intermediate Similarity	NPC209851
0.7591	Intermediate Similarity	NPC472394
0.7591	Intermediate Similarity	NPC475493
0.7589	Intermediate Similarity	NPC477904
0.7589	Intermediate Similarity	NPC475400
0.7589	Intermediate Similarity	NPC183270
0.7574	Intermediate Similarity	NPC25736
0.7571	Intermediate Similarity	NPC475373
0.7569	Intermediate Similarity	NPC277053
0.7569	Intermediate Similarity	NPC301946
0.7569	Intermediate Similarity	NPC127857
0.7559	Intermediate Similarity	NPC474095
0.7557	Intermediate Similarity	NPC144547
0.7557	Intermediate Similarity	NPC50872
0.7554	Intermediate Similarity	NPC195647
0.7554	Intermediate Similarity	NPC17877
0.7554	Intermediate Similarity	NPC66761
0.7554	Intermediate Similarity	NPC472577
0.7554	Intermediate Similarity	NPC291638
0.7551	Intermediate Similarity	NPC132810
0.7551	Intermediate Similarity	NPC46549
0.7551	Intermediate Similarity	NPC264229
0.7551	Intermediate Similarity	NPC471103
0.754	Intermediate Similarity	NPC93287
0.7537	Intermediate Similarity	NPC476599
0.7537	Intermediate Similarity	NPC275576
0.7519	Intermediate Similarity	NPC328107
0.7519	Intermediate Similarity	NPC84129
0.7519	Intermediate Similarity	NPC140118
0.7519	Intermediate Similarity	NPC469742
0.7519	Intermediate Similarity	NPC12881
0.7518	Intermediate Similarity	NPC210591
0.7518	Intermediate Similarity	NPC214550
0.7518	Intermediate Similarity	NPC475652
0.7517	Intermediate Similarity	NPC282239
0.7517	Intermediate Similarity	NPC473670
0.7517	Intermediate Similarity	NPC21410
0.75	Intermediate Similarity	NPC477905
0.75	Intermediate Similarity	NPC472548
0.75	Intermediate Similarity	NPC149691
0.7483	Intermediate Similarity	NPC112216
0.7483	Intermediate Similarity	NPC7095
0.7481	Intermediate Similarity	NPC988
0.7481	Intermediate Similarity	NPC474106
0.7481	Intermediate Similarity	NPC289432
0.748	Intermediate Similarity	NPC477411
0.748	Intermediate Similarity	NPC196075
0.748	Intermediate Similarity	NPC307651
0.7467	Intermediate Similarity	NPC217091
0.7467	Intermediate Similarity	NPC106895
0.7466	Intermediate Similarity	NPC233763
0.7465	Intermediate Similarity	NPC473613
0.7465	Intermediate Similarity	NPC473109
0.7465	Intermediate Similarity	NPC43241
0.7465	Intermediate Similarity	NPC211137
0.7465	Intermediate Similarity	NPC473112
0.7465	Intermediate Similarity	NPC48017
0.7465	Intermediate Similarity	NPC184747
0.7465	Intermediate Similarity	NPC251294
0.7465	Intermediate Similarity	NPC473758
0.7465	Intermediate Similarity	NPC473081
0.7465	Intermediate Similarity	NPC476094
0.7465	Intermediate Similarity	NPC473085
0.7465	Intermediate Similarity	NPC200592
0.7465	Intermediate Similarity	NPC473060
0.7465	Intermediate Similarity	NPC4341
0.7465	Intermediate Similarity	NPC147880
0.7463	Intermediate Similarity	NPC473083
0.7451	Intermediate Similarity	NPC55744
0.7448	Intermediate Similarity	NPC471162
0.7447	Intermediate Similarity	NPC183122
0.7447	Intermediate Similarity	NPC283375
0.7445	Intermediate Similarity	NPC262819
0.7442	Intermediate Similarity	NPC190298
0.7431	Intermediate Similarity	NPC95449
0.7429	Intermediate Similarity	NPC473399
0.7429	Intermediate Similarity	NPC477893
0.7429	Intermediate Similarity	NPC473216
0.7429	Intermediate Similarity	NPC477896
0.7426	Intermediate Similarity	NPC195224
0.7424	Intermediate Similarity	NPC472981
0.7422	Intermediate Similarity	NPC470764
0.7419	Intermediate Similarity	NPC470007
0.7417	Intermediate Similarity	NPC472393
0.7415	Intermediate Similarity	NPC60509
0.7415	Intermediate Similarity	NPC81698
0.7415	Intermediate Similarity	NPC471970
0.7415	Intermediate Similarity	NPC250046
0.7415	Intermediate Similarity	NPC281398
0.7415	Intermediate Similarity	NPC273798
0.7413	Intermediate Similarity	NPC16912
0.741	Intermediate Similarity	NPC15850
0.7405	Intermediate Similarity	NPC204784
0.7402	Intermediate Similarity	NPC128368
0.74	Intermediate Similarity	NPC472549
0.7397	Intermediate Similarity	NPC469856
0.7397	Intermediate Similarity	NPC469854
0.7394	Intermediate Similarity	NPC472371
0.7394	Intermediate Similarity	NPC472395
0.7391	Intermediate Similarity	NPC472361
0.7391	Intermediate Similarity	NPC472418
0.7388	Intermediate Similarity	NPC472704
0.7388	Intermediate Similarity	NPC8990
0.7379	Intermediate Similarity	NPC471971
0.7379	Intermediate Similarity	NPC30846
0.7379	Intermediate Similarity	NPC470231

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 NPC472694 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	842
0.2-0.3	1419
0.3-0.4	3472
0.4-0.5	2142
0.5-0.6	903
0.6-0.7	55
0.7-0.8	5
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
0.7969	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD7094	Approved
0.754	Intermediate Similarity	NPD6858	Approved
0.7381	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7961	Discontinued
0.7329	Intermediate Similarity	NPD7236	Approved
0.7323	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD7610	Discontinued
0.7244	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD3317	Approved
0.7163	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3495	Discontinued
0.7086	Intermediate Similarity	NPD7239	Suspended
0.7	Intermediate Similarity	NPD7055	Discontinued
0.6986	Remote Similarity	NPD1471	Phase 3
0.6972	Remote Similarity	NPD7713	Phase 3
0.6953	Remote Similarity	NPD2182	Approved
0.695	Remote Similarity	NPD7008	Discontinued
0.6947	Remote Similarity	NPD6010	Discontinued
0.694	Remote Similarity	NPD7009	Phase 2
0.6934	Remote Similarity	NPD3972	Approved
0.6917	Remote Similarity	NPD7631	Approved
0.6894	Remote Similarity	NPD5951	Approved
0.6861	Remote Similarity	NPD6287	Discontinued
0.6833	Remote Similarity	NPD7609	Phase 3
0.6825	Remote Similarity	NPD6647	Phase 2
0.6812	Remote Similarity	NPD6637	Approved
0.681	Remote Similarity	NPD7799	Discontinued
0.6772	Remote Similarity	NPD5909	Discontinued
0.6757	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7798	Approved
0.6693	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1930	Approved
0.6693	Remote Similarity	NPD1929	Approved
0.6692	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7741	Discontinued
0.6667	Remote Similarity	NPD7057	Phase 3
0.6667	Remote Similarity	NPD7058	Phase 2
0.6641	Remote Similarity	NPD2067	Discontinued
0.6641	Remote Similarity	NPD164	Approved
0.6623	Remote Similarity	NPD8166	Discontinued
0.6614	Remote Similarity	NPD1932	Approved
0.6604	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1876	Approved
0.6594	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2066	Phase 3
0.6587	Remote Similarity	NPD1238	Approved
0.6573	Remote Similarity	NPD7084	Phase 3
0.6565	Remote Similarity	NPD2329	Discontinued
0.6552	Remote Similarity	NPD3764	Approved
0.655	Remote Similarity	NPD8434	Phase 2
0.6541	Remote Similarity	NPD5761	Phase 2
0.6541	Remote Similarity	NPD5760	Phase 2
0.6529	Remote Similarity	NPD8407	Phase 2
0.6522	Remote Similarity	NPD3024	Approved
0.6522	Remote Similarity	NPD3025	Approved
0.6519	Remote Similarity	NPD2629	Approved
0.6516	Remote Similarity	NPD6273	Approved
0.6512	Remote Similarity	NPD1237	Approved
0.651	Remote Similarity	NPD2799	Discontinued
0.651	Remote Similarity	NPD7305	Phase 1
0.6507	Remote Similarity	NPD8032	Phase 2
0.6506	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD1508	Approved
0.6503	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2798	Approved
0.65	Remote Similarity	NPD650	Approved
0.65	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7458	Discontinued
0.6496	Remote Similarity	NPD6065	Approved
0.6483	Remote Similarity	NPD6039	Approved
0.648	Remote Similarity	NPD1989	Approved
0.6471	Remote Similarity	NPD4198	Discontinued
0.6467	Remote Similarity	NPD2796	Approved
0.6462	Remote Similarity	NPD5048	Discontinued
0.6454	Remote Similarity	NPD4878	Approved
0.6452	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.645	Remote Similarity	NPD8368	Discontinued
0.6447	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1470	Approved
0.6429	Remote Similarity	NPD3023	Approved
0.6429	Remote Similarity	NPD3026	Approved
0.6424	Remote Similarity	NPD2346	Discontinued
0.6424	Remote Similarity	NPD2344	Approved
0.6405	Remote Similarity	NPD4628	Phase 3
0.6395	Remote Similarity	NPD6663	Approved
0.6392	Remote Similarity	NPD3226	Approved
0.6389	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6085	Phase 2
0.638	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD3019	Approved
0.6349	Remote Similarity	NPD1843	Approved
0.6345	Remote Similarity	NPD5736	Approved
0.6341	Remote Similarity	NPD3672	Approved
0.6341	Remote Similarity	NPD3673	Approved
0.6341	Remote Similarity	NPD5494	Approved
0.6335	Remote Similarity	NPD7819	Suspended
0.6333	Remote Similarity	NPD2567	Approved
0.6333	Remote Similarity	NPD2569	Approved
0.6327	Remote Similarity	NPD2313	Discontinued
0.6316	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD4879	Approved
0.6301	Remote Similarity	NPD6832	Phase 2
0.6299	Remote Similarity	NPD7003	Approved
0.6289	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD8435	Approved
0.6286	Remote Similarity	NPD8360	Approved
0.6286	Remote Similarity	NPD8361	Approved
0.6284	Remote Similarity	NPD7714	Approved
0.6284	Remote Similarity	NPD7715	Approved
0.6277	Remote Similarity	NPD1711	Phase 2
0.6277	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD942	Approved
0.6269	Remote Similarity	NPD1317	Discontinued
0.6268	Remote Similarity	NPD1201	Approved
0.6265	Remote Similarity	NPD6808	Phase 2
0.6258	Remote Similarity	NPD2309	Approved
0.625	Remote Similarity	NPD5926	Approved
0.625	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD2932	Approved
0.6211	Remote Similarity	NPD7411	Suspended
0.6207	Remote Similarity	NPD3266	Approved
0.6207	Remote Similarity	NPD3267	Approved
0.619	Remote Similarity	NPD1202	Approved
0.6184	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD5327	Phase 3
0.6178	Remote Similarity	NPD8165	Discontinued
0.6178	Remote Similarity	NPD3950	Discontinued
0.6173	Remote Similarity	NPD6279	Approved
0.6173	Remote Similarity	NPD6280	Approved
0.6171	Remote Similarity	NPD8150	Discontinued
0.6171	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD6685	Approved
0.6159	Remote Similarity	NPD4766	Approved
0.6149	Remote Similarity	NPD6599	Discontinued
0.6142	Remote Similarity	NPD1693	Approved
0.6139	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD2800	Approved
0.6114	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1088	Approved
0.6107	Remote Similarity	NPD3268	Approved
0.6098	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD1087	Approved
0.6095	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.609	Remote Similarity	NPD7487	Discontinued
0.6087	Remote Similarity	NPD1241	Discontinued
0.6087	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD2652	Approved
0.6087	Remote Similarity	NPD2650	Approved
0.6078	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD1510	Phase 2
0.6077	Remote Similarity	NPD8485	Approved
0.6069	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD5157	Phase 1
0.6069	Remote Similarity	NPD6764	Approved
0.6069	Remote Similarity	NPD5159	Phase 2
0.6069	Remote Similarity	NPD6765	Approved
0.6065	Remote Similarity	NPD1549	Phase 2
0.6056	Remote Similarity	NPD1651	Approved
0.6051	Remote Similarity	NPD3887	Approved
0.6049	Remote Similarity	NPD4380	Phase 2
0.6039	Remote Similarity	NPD6099	Approved
0.6039	Remote Similarity	NPD6100	Approved
0.6038	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD2533	Approved
0.6038	Remote Similarity	NPD2532	Approved
0.6038	Remote Similarity	NPD2534	Approved
0.6031	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD2347	Approved
0.6027	Remote Similarity	NPD5667	Approved
0.6027	Remote Similarity	NPD2199	Approved
0.6027	Remote Similarity	NPD2198	Approved
0.6026	Remote Similarity	NPD4307	Phase 2
0.6026	Remote Similarity	NPD2979	Phase 3
0.6024	Remote Similarity	NPD3749	Approved
0.6024	Remote Similarity	NPD7075	Discontinued
0.6016	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6049	Phase 2
0.6014	Remote Similarity	NPD5125	Phase 3
0.6014	Remote Similarity	NPD5126	Approved
0.6014	Remote Similarity	NPD2345	Approved
0.6012	Remote Similarity	NPD5889	Approved
0.6012	Remote Similarity	NPD5890	Approved
0.6012	Remote Similarity	NPD8127	Discontinued
0.6	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD9545	Approved
0.5985	Remote Similarity	NPD2196	Discontinued
0.5978	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD7577	Discontinued
0.5965	Remote Similarity	NPD7473	Discontinued

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