NPASS Compound

Structure

NPC471849 OpenBabel07101718242D 52 56 0 0 1 0 0 0 0 0999 V2000 2.5085 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.8276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 3.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3616 6.7586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6893 2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8531 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3446 -0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5255 3.3793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6893 4.8276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3616 3.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5255 5.3103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3446 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8362 3.3793 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1978 6.2759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6893 1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0170 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6893 3.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3616 4.8276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0170 2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3446 1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5085 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 3.3793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3446 2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0170 1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 1.4483 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5085 1.4483 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 0.4828 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.0339 6.7586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5255 1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0170 -0.9655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 4.3448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 3.3793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 -0.9655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 2.8966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3446 1.9310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 -0.4828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1978 5.3103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8531 1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 0.4828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9310 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 8 1 0 0 0 0 2 9 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 13 1 0 0 0 0 10 22 2 0 0 0 0 11 14 2 0 0 0 0 11 22 1 0 0 0 0 12 15 2 0 0 0 0 12 23 1 0 0 0 0 13 24 2 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 23 2 0 0 0 0 16 26 1 0 0 0 0 17 3 1 1 0 0 0 17 29 1 0 0 0 0 18 4 1 1 0 0 0 19 39 2 0 0 0 0 19 48 1 0 0 0 0 20 40 2 0 0 0 0 20 49 1 0 0 0 0 21 41 2 0 0 0 0 21 50 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 48 1 0 0 0 0 25 26 2 0 0 0 0 25 52 1 0 0 0 0 26 51 1 0 0 0 0 27 30 2 0 0 0 0 27 32 1 0 0 0 0 28 31 2 0 0 0 0 28 33 1 0 0 0 0 29 34 2 0 0 0 0 29 37 1 0 0 0 0 30 31 1 0 0 0 0 30 42 1 0 0 0 0 31 43 1 0 0 0 0 32 33 2 0 0 0 0 32 49 1 0 0 0 0 33 50 1 0 0 0 0 34 38 1 0 0 0 0 34 44 1 0 0 0 0 35 36 1 0 0 0 0 35 37 1 0 0 0 0 35 45 2 0 0 0 0 36 18 1 1 0 0 0 36 38 1 0 0 0 0 36 51 1 0 0 0 0 37 46 1 0 0 0 0 38 47 2 0 0 0 0 38 52 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	722.23
Volume:	696.576
LogP:	4.148
LogD:	1.436
LogS:	-1.025
# Rotatable Bonds:	12
TPSA:	218.49
# H-Bond Aceptor:	16
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.065
Synthetic Accessibility Score:	5.102
Fsp3:	0.361
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.028
MDCK Permeability:	2.4622553610242903e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.989
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	98.11445617675781%
Volume Distribution (VD):	0.763
Pgp-substrate:	12.150849342346191%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.119
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.902
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.205
CYP3A4-substrate:	0.946

ADMET: Excretion

Clearance (CL):	2.51
Half-life (T1/2):	0.861

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.358
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.075
Carcinogencity:	0.762
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC471849

Natural Product ID:	NPC471849
*Common Name:**	Episarcodonin
IUPAC Name:	[4-[4-[(5R,11aR)-3-[(2S)-butan-2-yl]-11a-[(2R)-butan-2-yl]-2,4-dihydroxy-5-oxido-1-oxopyrazino[1,2-b][1,4,2]benzodioxazin-5-ium-9-yl]-2,3-diacetyloxy-5,6-dihydroxyphenyl]phenyl] acetate
Synonyms:
Standard InCHIKey:	ULLCSSTZNGODKE-YOAXYMDMSA-N
Standard InCHI:	InChI=1S/C36H38N2O14/c1-8-17(3)29-34(44)38(47)36(18(4)9-2,35(45)37(29)46)51-26-16-23(12-15-25(26)52-38)28-31(43)30(42)27(22-10-13-24(14-11-22)48-19(5)39)32(49-20(6)40)33(28)50-21(7)41/h10-18,42-44,46H,8-9H2,1-7H3/t17-,18+,36+,38+/m0/s1
SMILES:	CCC(C)C1=C([N+]2(C(C(=O)N1O)(OC3=C(O2)C=CC(=C3)C4=C(C(=C(C(=C4OC(=O)C)OC(=O)C)C5=CC=C(C=C5)OC(=O)C)O)O)C(C)CC)[O-])O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3238011
PubChem CID:	90671616
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26394	Sarcodon leucopus	Species	Thelephoraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10757716]
NPO26394	Sarcodon leucopus	Species	Thelephoraceae	Eukaryota	n.a.	Tibet, China	n.a.	PMID[24645629]
NPO26394	Sarcodon leucopus	Species	Thelephoraceae	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
EC50	1
IC50	3
Others	1

Activity Type	# Activity
NON-MOLECULAR	2
Others	2
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	13000.0	nM	PMID[514280]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	85.0	U	PMID[514280]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	17000.0	nM	PMID[514280]
NPT625	Tissue	Liver	Mus musculus	IC50	=	54000.0	nM	PMID[514280]
NPT2	Others	Unspecified		IC50	=	4200.0	nM	PMID[514280]

☑ 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 NPC471849 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	348
0.1-0.2	1604
0.2-0.3	6245
0.3-0.4	12399
0.4-0.5	5387
0.5-0.6	8999
0.6-0.7	7585
0.7-0.8	124
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC161144
1.0	High Similarity	NPC119291
1.0	High Similarity	NPC471848
0.8245	Intermediate Similarity	NPC18633
0.8245	Intermediate Similarity	NPC471847
0.7166	Intermediate Similarity	NPC113790
0.7135	Intermediate Similarity	NPC36077
0.712	Intermediate Similarity	NPC292385
0.712	Intermediate Similarity	NPC125709
0.7098	Intermediate Similarity	NPC36354
0.7087	Intermediate Similarity	NPC471563
0.707	Intermediate Similarity	NPC92235
0.7059	Intermediate Similarity	NPC170239
0.7059	Intermediate Similarity	NPC275125
0.7059	Intermediate Similarity	NPC97937
0.7005	Intermediate Similarity	NPC475896
0.699	Remote Similarity	NPC140346
0.699	Remote Similarity	NPC174311
0.6979	Remote Similarity	NPC7178
0.6979	Remote Similarity	NPC62903
0.6976	Remote Similarity	NPC29531
0.6968	Remote Similarity	NPC231149
0.6952	Remote Similarity	NPC292256
0.6952	Remote Similarity	NPC125617
0.6943	Remote Similarity	NPC155015
0.6943	Remote Similarity	NPC142479
0.694	Remote Similarity	NPC476171
0.693	Remote Similarity	NPC185031
0.6923	Remote Similarity	NPC252095
0.6904	Remote Similarity	NPC55121
0.6904	Remote Similarity	NPC476200
0.6904	Remote Similarity	NPC192258
0.6898	Remote Similarity	NPC185127
0.6856	Remote Similarity	NPC316292
0.6848	Remote Similarity	NPC105493
0.6845	Remote Similarity	NPC7439
0.6845	Remote Similarity	NPC256555
0.6845	Remote Similarity	NPC34245
0.6845	Remote Similarity	NPC91492
0.6845	Remote Similarity	NPC110067
0.6842	Remote Similarity	NPC139839
0.6842	Remote Similarity	NPC48366
0.6839	Remote Similarity	NPC476154
0.6813	Remote Similarity	NPC474810
0.6806	Remote Similarity	NPC176903
0.6806	Remote Similarity	NPC30688
0.68	Remote Similarity	NPC471823
0.6788	Remote Similarity	NPC163598
0.6788	Remote Similarity	NPC120774
0.6788	Remote Similarity	NPC264875
0.6786	Remote Similarity	NPC44040
0.6771	Remote Similarity	NPC294522
0.6771	Remote Similarity	NPC205727
0.6771	Remote Similarity	NPC120426
0.6771	Remote Similarity	NPC21184
0.6768	Remote Similarity	NPC124747
0.6768	Remote Similarity	NPC109061
0.6768	Remote Similarity	NPC155754
0.6758	Remote Similarity	NPC474635
0.6755	Remote Similarity	NPC236419
0.6755	Remote Similarity	NPC230157
0.6754	Remote Similarity	NPC315914
0.6748	Remote Similarity	NPC475566
0.6742	Remote Similarity	NPC473746
0.6733	Remote Similarity	NPC476637
0.6733	Remote Similarity	NPC280493
0.6733	Remote Similarity	NPC476279
0.6719	Remote Similarity	NPC476969
0.6718	Remote Similarity	NPC268484
0.6718	Remote Similarity	NPC80918
0.6718	Remote Similarity	NPC188578
0.6717	Remote Similarity	NPC130955
0.6717	Remote Similarity	NPC301089
0.6703	Remote Similarity	NPC147317
0.6703	Remote Similarity	NPC142530
0.6702	Remote Similarity	NPC472332
0.6702	Remote Similarity	NPC469564
0.6702	Remote Similarity	NPC472335
0.67	Remote Similarity	NPC265214
0.6699	Remote Similarity	NPC226725
0.6697	Remote Similarity	NPC257728
0.6696	Remote Similarity	NPC211215
0.6684	Remote Similarity	NPC476642
0.6683	Remote Similarity	NPC99591
0.6682	Remote Similarity	NPC475180
0.6667	Remote Similarity	NPC94220
0.6667	Remote Similarity	NPC24339
0.6667	Remote Similarity	NPC187398
0.6667	Remote Similarity	NPC7543
0.6667	Remote Similarity	NPC148835
0.6667	Remote Similarity	NPC85057
0.6667	Remote Similarity	NPC20511
0.6667	Remote Similarity	NPC142614
0.6667	Remote Similarity	NPC473748
0.6667	Remote Similarity	NPC153365
0.6667	Remote Similarity	NPC139548
0.6667	Remote Similarity	NPC52086
0.6667	Remote Similarity	NPC76336
0.6667	Remote Similarity	NPC223720
0.6667	Remote Similarity	NPC130920
0.6667	Remote Similarity	NPC476348
0.6667	Remote Similarity	NPC475669
0.6667	Remote Similarity	NPC83019
0.6667	Remote Similarity	NPC38874
0.6667	Remote Similarity	NPC166456
0.6667	Remote Similarity	NPC95162
0.6667	Remote Similarity	NPC98083
0.6651	Remote Similarity	NPC154527
0.6651	Remote Similarity	NPC257266
0.665	Remote Similarity	NPC284810
0.665	Remote Similarity	NPC67424
0.665	Remote Similarity	NPC165483
0.6636	Remote Similarity	NPC477666
0.6635	Remote Similarity	NPC41845
0.6635	Remote Similarity	NPC6709
0.6634	Remote Similarity	NPC9309
0.6633	Remote Similarity	NPC8712
0.6632	Remote Similarity	NPC10010
0.6631	Remote Similarity	NPC25966
0.6631	Remote Similarity	NPC127218
0.6631	Remote Similarity	NPC13067
0.6631	Remote Similarity	NPC245207
0.6631	Remote Similarity	NPC319647
0.663	Remote Similarity	NPC277021
0.662	Remote Similarity	NPC204580
0.662	Remote Similarity	NPC281629
0.6618	Remote Similarity	NPC109827
0.6618	Remote Similarity	NPC297807
0.6618	Remote Similarity	NPC72696
0.6618	Remote Similarity	NPC101107
0.6618	Remote Similarity	NPC124470
0.6618	Remote Similarity	NPC98546
0.6616	Remote Similarity	NPC125495
0.6615	Remote Similarity	NPC15577
0.6615	Remote Similarity	NPC160196
0.6615	Remote Similarity	NPC476347
0.6613	Remote Similarity	NPC126682
0.6613	Remote Similarity	NPC82271
0.6605	Remote Similarity	NPC469689
0.6605	Remote Similarity	NPC471031
0.6603	Remote Similarity	NPC234069
0.6601	Remote Similarity	NPC10871
0.66	Remote Similarity	NPC177100
0.66	Remote Similarity	NPC139540
0.6595	Remote Similarity	NPC474600
0.6589	Remote Similarity	NPC50548
0.6588	Remote Similarity	NPC174486
0.6585	Remote Similarity	NPC32064
0.6584	Remote Similarity	NPC156432
0.6583	Remote Similarity	NPC130894
0.6583	Remote Similarity	NPC143828
0.6583	Remote Similarity	NPC9609
0.6583	Remote Similarity	NPC18607
0.6583	Remote Similarity	NPC4481
0.6583	Remote Similarity	NPC7846
0.6583	Remote Similarity	NPC115798
0.6583	Remote Similarity	NPC300943
0.6583	Remote Similarity	NPC176300
0.6583	Remote Similarity	NPC261004
0.6583	Remote Similarity	NPC18772
0.6583	Remote Similarity	NPC152166
0.6583	Remote Similarity	NPC288669
0.6583	Remote Similarity	NPC19687
0.6583	Remote Similarity	NPC253634
0.6583	Remote Similarity	NPC22472
0.6583	Remote Similarity	NPC191459
0.6583	Remote Similarity	NPC204854
0.6583	Remote Similarity	NPC105242
0.6583	Remote Similarity	NPC25495
0.6582	Remote Similarity	NPC150442
0.6582	Remote Similarity	NPC149735
0.658	Remote Similarity	NPC281549
0.658	Remote Similarity	NPC477879
0.6579	Remote Similarity	NPC477616
0.6578	Remote Similarity	NPC474886
0.6578	Remote Similarity	NPC276490
0.6571	Remote Similarity	NPC470451
0.6571	Remote Similarity	NPC174122
0.6571	Remote Similarity	NPC64140
0.6571	Remote Similarity	NPC470455
0.657	Remote Similarity	NPC216307
0.6569	Remote Similarity	NPC475805
0.6567	Remote Similarity	NPC471745
0.6567	Remote Similarity	NPC8300
0.6566	Remote Similarity	NPC55619
0.6566	Remote Similarity	NPC200388
0.6566	Remote Similarity	NPC100916
0.6564	Remote Similarity	NPC213197
0.6562	Remote Similarity	NPC287275
0.6562	Remote Similarity	NPC205361
0.6561	Remote Similarity	NPC471389
0.6555	Remote Similarity	NPC47883
0.6553	Remote Similarity	NPC470942
0.6553	Remote Similarity	NPC329816
0.6552	Remote Similarity	NPC470462
0.655	Remote Similarity	NPC155101
0.6548	Remote Similarity	NPC77430
0.6543	Remote Similarity	NPC19869
0.6543	Remote Similarity	NPC43500
0.6543	Remote Similarity	NPC164148

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 NPC471849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	721
0.2-0.3	1537
0.3-0.4	2636
0.4-0.5	2298
0.5-0.6	1351
0.6-0.7	369
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6765	Remote Similarity	NPD7549	Discontinued
0.6697	Remote Similarity	NPD7585	Approved
0.6684	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7583	Approved
0.6633	Remote Similarity	NPD5677	Discontinued
0.662	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD1653	Approved
0.6442	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD8127	Discontinued
0.6432	Remote Similarity	NPD3817	Phase 2
0.6429	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5844	Phase 1
0.6406	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7447	Phase 1
0.6392	Remote Similarity	NPD3146	Approved
0.6392	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4666	Phase 3
0.6382	Remote Similarity	NPD2801	Approved
0.6381	Remote Similarity	NPD8054	Approved
0.6381	Remote Similarity	NPD8053	Approved
0.6376	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7906	Approved
0.6364	Remote Similarity	NPD7808	Phase 3
0.6359	Remote Similarity	NPD7228	Approved
0.6354	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD8153	Approved
0.6352	Remote Similarity	NPD8152	Approved
0.6348	Remote Similarity	NPD7907	Approved
0.6347	Remote Similarity	NPD2494	Approved
0.6347	Remote Similarity	NPD2493	Approved
0.6341	Remote Similarity	NPD6166	Phase 2
0.6341	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6234	Discontinued
0.6337	Remote Similarity	NPD5709	Phase 3
0.6335	Remote Similarity	NPD4582	Approved
0.6335	Remote Similarity	NPD4583	Approved
0.6335	Remote Similarity	NPD7891	Discontinued
0.6333	Remote Similarity	NPD7311	Approved
0.6333	Remote Similarity	NPD7313	Approved
0.6333	Remote Similarity	NPD7312	Approved
0.6333	Remote Similarity	NPD7310	Approved
0.6318	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7251	Discontinued
0.6303	Remote Similarity	NPD7309	Approved
0.63	Remote Similarity	NPD1465	Phase 2
0.629	Remote Similarity	NPD4002	Approved
0.629	Remote Similarity	NPD4004	Approved
0.6287	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD7584	Approved
0.6278	Remote Similarity	NPD7263	Phase 2
0.6276	Remote Similarity	NPD7048	Phase 3
0.6273	Remote Similarity	NPD3452	Approved
0.6273	Remote Similarity	NPD3450	Approved
0.627	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5402	Approved
0.6268	Remote Similarity	NPD6797	Phase 2
0.6268	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7213	Phase 3
0.6256	Remote Similarity	NPD7212	Phase 2
0.625	Remote Similarity	NPD7054	Approved
0.6244	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5676	Approved
0.6238	Remote Similarity	NPD7038	Approved
0.6238	Remote Similarity	NPD7039	Approved
0.6237	Remote Similarity	NPD2219	Phase 1
0.6232	Remote Similarity	NPD7473	Discontinued
0.6226	Remote Similarity	NPD6851	Approved
0.6226	Remote Similarity	NPD6853	Approved
0.6225	Remote Similarity	NPD6746	Phase 2
0.6223	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7074	Phase 3
0.622	Remote Similarity	NPD7472	Approved
0.6216	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5242	Approved
0.6212	Remote Similarity	NPD3687	Approved
0.6212	Remote Similarity	NPD3686	Approved
0.6201	Remote Similarity	NPD7047	Phase 3
0.6197	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7199	Phase 2
0.6193	Remote Similarity	NPD1512	Approved
0.619	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD7701	Phase 2
0.6169	Remote Similarity	NPD37	Approved
0.6169	Remote Similarity	NPD1934	Approved
0.6168	Remote Similarity	NPD4663	Approved
0.6167	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7783	Phase 2
0.6165	Remote Similarity	NPD6232	Discontinued
0.6164	Remote Similarity	NPD2974	Approved
0.6164	Remote Similarity	NPD2973	Approved
0.6164	Remote Similarity	NPD2975	Approved
0.6158	Remote Similarity	NPD4967	Phase 2
0.6158	Remote Similarity	NPD4966	Approved
0.6158	Remote Similarity	NPD3882	Suspended
0.6158	Remote Similarity	NPD4965	Approved
0.6157	Remote Similarity	NPD2490	Approved
0.6157	Remote Similarity	NPD2488	Approved
0.6154	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4580	Approved
0.6151	Remote Similarity	NPD6723	Discontinued
0.6142	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7827	Phase 1
0.6138	Remote Similarity	NPD1613	Approved
0.6138	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD7075	Discontinued
0.6126	Remote Similarity	NPD7476	Discontinued
0.6122	Remote Similarity	NPD6667	Approved
0.6122	Remote Similarity	NPD6666	Approved
0.6121	Remote Similarity	NPD4111	Phase 1
0.6121	Remote Similarity	NPD4665	Approved
0.6114	Remote Similarity	NPD6297	Approved
0.6108	Remote Similarity	NPD5353	Approved
0.6106	Remote Similarity	NPD4481	Phase 3
0.6103	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD4578	Approved
0.6103	Remote Similarity	NPD3750	Approved
0.6103	Remote Similarity	NPD4577	Approved
0.6095	Remote Similarity	NPD42	Phase 2
0.6095	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6042	Phase 2
0.6091	Remote Similarity	NPD1774	Approved
0.6091	Remote Similarity	NPD1511	Approved
0.6091	Remote Similarity	NPD5297	Approved
0.6087	Remote Similarity	NPD7608	Discontinued
0.6087	Remote Similarity	NPD4749	Approved
0.6073	Remote Similarity	NPD7256	Discontinued
0.607	Remote Similarity	NPD4675	Approved
0.607	Remote Similarity	NPD4678	Approved
0.6068	Remote Similarity	NPD3251	Approved
0.6068	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7095	Approved
0.6064	Remote Similarity	NPD3027	Phase 3
0.6062	Remote Similarity	NPD6099	Approved
0.6062	Remote Similarity	NPD6100	Approved
0.6061	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD3536	Discontinued
0.6059	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD4482	Phase 3
0.6053	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4060	Phase 1
0.6053	Remote Similarity	NPD7874	Approved
0.605	Remote Similarity	NPD4210	Discontinued
0.6048	Remote Similarity	NPD3818	Discontinued
0.6048	Remote Similarity	NPD8099	Discontinued
0.6048	Remote Similarity	NPD8251	Approved
0.6048	Remote Similarity	NPD8252	Approved
0.6044	Remote Similarity	NPD8320	Phase 1
0.6044	Remote Similarity	NPD8319	Approved
0.6043	Remote Similarity	NPD6997	Phase 2
0.604	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.603	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD2489	Approved
0.6029	Remote Similarity	NPD27	Approved
0.6028	Remote Similarity	NPD7280	Phase 3
0.6028	Remote Similarity	NPD7281	Phase 3
0.6027	Remote Similarity	NPD3533	Approved
0.6027	Remote Similarity	NPD2972	Approved
0.6027	Remote Similarity	NPD2491	Approved
0.6021	Remote Similarity	NPD6355	Discontinued
0.602	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4110	Phase 3
0.6019	Remote Similarity	NPD8156	Discontinued
0.6019	Remote Similarity	NPD8150	Discontinued
0.6009	Remote Similarity	NPD7240	Approved
0.6	Remote Similarity	NPD5403	Approved
0.6	Remote Similarity	NPD2122	Discontinued
0.6	Remote Similarity	NPD5745	Approved
0.6	Remote Similarity	NPD8366	Approved
0.599	Remote Similarity	NPD6599	Discontinued
0.5982	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD2970	Approved
0.5981	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD2969	Approved
0.598	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5773	Approved
0.598	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7972	Discontinued
0.598	Remote Similarity	NPD5772	Approved
0.5979	Remote Similarity	NPD6032	Approved
0.5978	Remote Similarity	NPD422	Phase 1
0.5973	Remote Similarity	NPD4040	Phase 1
0.5972	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD6620	Discovery
0.5972	Remote Similarity	NPD7177	Discontinued
0.5971	Remote Similarity	NPD3453	Discontinued
0.5966	Remote Similarity	NPD8491	Approved
0.5963	Remote Similarity	NPD7861	Discontinued
0.5961	Remote Similarity	NPD5089	Approved
0.5961	Remote Similarity	NPD5090	Approved
0.596	Remote Similarity	NPD7124	Phase 2
0.5959	Remote Similarity	NPD6111	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