NPASS Compound

Structure

CID8940 OpenBabel06191715332D 63 69 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7519 -0.6832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4954 3.5963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4067 -0.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -4.0619 0.0405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3061 2.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7238 -0.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4404 3.9234 0.0000 C 0 0 0 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 -4.3436 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0619 1.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0055 0.5120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1961 3.2685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3154 1.2358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0069 2.2866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3061 -0.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3163 2.7567 0.0000 C 0 0 0 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 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4138 -1.1712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6296 4.9053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9773 0.7478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1411 3.5956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5971 2.1953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7626 1.6317 0.0000 O 0 0 0 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 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7215 -1.5240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1740 3.7465 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3163 -0.7567 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4067 2.3413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 14 2 0 0 0 0 2 4 2 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 4 15 1 0 0 0 0 5 12 2 0 0 0 0 5 18 1 0 0 0 0 6 12 1 0 0 0 0 6 19 2 0 0 0 0 7 13 2 0 0 0 0 7 20 1 0 0 0 0 8 13 1 0 0 0 0 8 21 2 0 0 0 0 9 16 2 0 0 0 0 9 22 1 0 0 0 0 10 17 2 0 0 0 0 10 23 1 0 0 0 0 11 58 1 0 0 0 0 12 36 1 0 0 0 0 13 37 1 0 0 0 0 14 41 1 0 0 0 0 15 59 1 0 0 0 0 16 25 1 0 0 0 0 16 38 1 0 0 0 0 17 26 1 0 0 0 0 17 39 1 0 0 0 0 18 27 2 0 0 0 0 18 42 1 0 0 0 0 19 27 1 0 0 0 0 19 43 1 0 0 0 0 20 28 2 0 0 0 0 20 44 1 0 0 0 0 21 28 1 0 0 0 0 21 45 1 0 0 0 0 22 29 2 0 0 0 0 22 46 1 0 0 0 0 23 30 2 0 0 0 0 23 47 1 0 0 0 0 24 11 1 6 0 0 0 24 33 1 0 0 0 0 24 60 1 0 0 0 0 25 26 1 0 0 0 0 25 31 2 0 0 0 0 26 32 2 0 0 0 0 27 48 1 0 0 0 0 28 49 1 0 0 0 0 29 31 1 0 0 0 0 29 50 1 0 0 0 0 30 32 1 0 0 0 0 30 51 1 0 0 0 0 31 52 1 0 0 0 0 32 53 1 0 0 0 0 33 34 1 0 0 0 0 33 61 1 1 0 0 0 34 35 1 0 0 0 0 34 62 1 6 0 0 0 35 40 1 0 0 0 0 35 63 1 1 0 0 0 36 54 2 0 0 0 0 36 62 1 0 0 0 0 37 55 2 0 0 0 0 37 63 1 0 0 0 0 38 56 2 0 0 0 0 38 58 1 0 0 0 0 39 57 2 0 0 0 0 39 61 1 0 0 0 0 40 59 1 6 0 0 0 40 60 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	878.12
Volume:	792.583
LogP:	2.689
LogD:	0.976
LogS:	-3.716
# Rotatable Bonds:	8
TPSA:	386.65
# H-Bond Aceptor:	23
# H-Bond Donor:	13
# Rings:	7
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.066
Synthetic Accessibility Score:	5.516
Fsp3:	0.15
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.148
MDCK Permeability:	7.91685852163937e-06
Pgp-inhibitor:	0.247
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.992
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	91.2754135131836%
Volume Distribution (VD):	0.266
Pgp-substrate:	24.65106773376465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.539
CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.017
CYP2C9-inhibitor:	0.346
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	13.398
Half-life (T1/2):	0.969

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.271
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.97
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.942
Respiratory Toxicity:	0.002

Download Data

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

Natural Product: NPC8940

Natural Product ID:	NPC8940
*Common Name:**	Hyemaloside C
IUPAC Name:	n.a.
Synonyms:	Hyemaloside C
Standard InCHIKey:	BIUWKTLZFMHRQE-RYQQTUIDSA-N
Standard InCHI:	InChI=1S/C40H30O23/c41-14-1-3-15(4-2-14)59-40-35(63-37(55)13-7-20(44)28(49)21(45)8-13)34(62-36(54)12-5-18(42)27(48)19(43)6-12)33-24(60-40)11-58-38(56)16-9-22(46)29(50)31(52)25(16)26-17(39(57)61-33)10-23(47)30(51)32(26)53/h1-10,24,33-35,40-53H,11H2/t24-,33-,34+,35-,40-/m1/s1
SMILES:	c1cc(ccc1O)O[C@H]1[C@@H]([C@H]([C@H]2[C@@H](COC(=O)c3cc(c(c(c3-c3c(cc(c(c3O)O)O)C(=O)O2)O)O)O)O1)OC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506679
PubChem CID:	25110930
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO27524	Eugenia hyemalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18763827]
NPO27524	Eugenia hyemalis	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18763827]
NPO27524	Eugenia hyemalis	Species	Myrtaceae	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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	=	1190.0	nM	PMID[532989]
NPT2	Others	Unspecified	IC50	=	840.0	nM	PMID[532989]
NPT2	Others	Unspecified	IC50	=	70.0	nM	PMID[532989]

☑ 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 NPC8940 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	428
0.1-0.2	1798
0.2-0.3	4018
0.3-0.4	9190
0.4-0.5	8700
0.5-0.6	4364
0.6-0.7	5582
0.7-0.8	6488
0.8-0.85	1460
0.85-0.9	543
0.9-0.95	105
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9649	High Similarity	NPC469649
0.9649	High Similarity	NPC260521
0.9593	High Similarity	NPC158214
0.9593	High Similarity	NPC240200
0.9593	High Similarity	NPC223534
0.9593	High Similarity	NPC290289
0.9591	High Similarity	NPC469650
0.9591	High Similarity	NPC261623
0.9591	High Similarity	NPC111490
0.9586	High Similarity	NPC80956
0.9538	High Similarity	NPC472724
0.9538	High Similarity	NPC31208
0.9538	High Similarity	NPC160543
0.9538	High Similarity	NPC469652
0.9538	High Similarity	NPC472721
0.9538	High Similarity	NPC93065
0.9538	High Similarity	NPC187632
0.9538	High Similarity	NPC472720
0.9535	High Similarity	NPC65489
0.9532	High Similarity	NPC231254
0.9483	High Similarity	NPC97924
0.9483	High Similarity	NPC471091
0.9483	High Similarity	NPC40078
0.9467	High Similarity	NPC472723
0.9458	High Similarity	NPC43918
0.9458	High Similarity	NPC190204
0.9458	High Similarity	NPC261411
0.9401	High Similarity	NPC95421
0.9401	High Similarity	NPC198125
0.9368	High Similarity	NPC477083
0.9368	High Similarity	NPC477081
0.9353	High Similarity	NPC297574
0.9345	High Similarity	NPC47521
0.9341	High Similarity	NPC470271
0.9341	High Similarity	NPC311389
0.9281	High Similarity	NPC175793
0.927	High Similarity	NPC189312
0.927	High Similarity	NPC3474
0.9266	High Similarity	NPC477082
0.9261	High Similarity	NPC264302
0.9257	High Similarity	NPC269046
0.9257	High Similarity	NPC173872
0.9257	High Similarity	NPC119094
0.9249	High Similarity	NPC129533
0.9249	High Similarity	NPC123259
0.9231	High Similarity	NPC470272
0.9226	High Similarity	NPC473818
0.9205	High Similarity	NPC201814
0.92	High Similarity	NPC237202
0.9191	High Similarity	NPC53680
0.9191	High Similarity	NPC208797
0.9172	High Similarity	NPC149300
0.9167	High Similarity	NPC174140
0.9157	High Similarity	NPC476358
0.9148	High Similarity	NPC142291
0.9148	High Similarity	NPC7839
0.9133	High Similarity	NPC472725
0.9133	High Similarity	NPC472726
0.9128	High Similarity	NPC79736
0.9128	High Similarity	NPC67629
0.9123	High Similarity	NPC473550
0.9123	High Similarity	NPC98583
0.9112	High Similarity	NPC31034
0.9102	High Similarity	NPC4013
0.9102	High Similarity	NPC291957
0.9102	High Similarity	NPC90905
0.9102	High Similarity	NPC14030
0.9091	High Similarity	NPC179947
0.9075	High Similarity	NPC476619
0.9075	High Similarity	NPC476623
0.9075	High Similarity	NPC476621
0.9075	High Similarity	NPC476622
0.9075	High Similarity	NPC476620
0.9075	High Similarity	NPC267549
0.9075	High Similarity	NPC476618
0.9064	High Similarity	NPC102851
0.9064	High Similarity	NPC100251
0.9064	High Similarity	NPC5786
0.9064	High Similarity	NPC65333
0.9048	High Similarity	NPC470898
0.9048	High Similarity	NPC121290
0.904	High Similarity	NPC473618
0.9029	High Similarity	NPC97119
0.9029	High Similarity	NPC135831
0.9029	High Similarity	NPC297503
0.9017	High Similarity	NPC472992
0.9017	High Similarity	NPC472991
0.9012	High Similarity	NPC263119
0.9012	High Similarity	NPC34436
0.9012	High Similarity	NPC166674
0.9012	High Similarity	NPC46640
0.9012	High Similarity	NPC219600
0.9006	High Similarity	NPC181778
0.8983	High Similarity	NPC269625
0.8983	High Similarity	NPC105591
0.8982	High Similarity	NPC289346
0.8976	High Similarity	NPC114179
0.8976	High Similarity	NPC156818
0.8976	High Similarity	NPC289322
0.8976	High Similarity	NPC160512
0.8976	High Similarity	NPC68324
0.8976	High Similarity	NPC38779
0.8971	High Similarity	NPC125352
0.8966	High Similarity	NPC472387
0.8953	High Similarity	NPC67134
0.8953	High Similarity	NPC47140
0.8947	High Similarity	NPC197708
0.8947	High Similarity	NPC658
0.8935	High Similarity	NPC67959
0.8922	High Similarity	NPC141331
0.8922	High Similarity	NPC74319
0.8922	High Similarity	NPC114791
0.8922	High Similarity	NPC104222
0.8922	High Similarity	NPC210501
0.8922	High Similarity	NPC287872
0.8922	High Similarity	NPC318826
0.892	High Similarity	NPC132111
0.8916	High Similarity	NPC104983
0.8916	High Similarity	NPC291948
0.8916	High Similarity	NPC250436
0.8916	High Similarity	NPC300845
0.8916	High Similarity	NPC88803
0.8914	High Similarity	NPC471030
0.8908	High Similarity	NPC473713
0.8902	High Similarity	NPC163165
0.8902	High Similarity	NPC172033
0.8902	High Similarity	NPC88560
0.8902	High Similarity	NPC175230
0.8895	High Similarity	NPC204937
0.8895	High Similarity	NPC149011
0.8889	High Similarity	NPC217781
0.8882	High Similarity	NPC142614
0.8876	High Similarity	NPC285108
0.8876	High Similarity	NPC33298
0.8876	High Similarity	NPC475179
0.887	High Similarity	NPC470416
0.887	High Similarity	NPC49690
0.8869	High Similarity	NPC24164
0.8869	High Similarity	NPC53889
0.8864	High Similarity	NPC469371
0.8862	High Similarity	NPC172419
0.8862	High Similarity	NPC238419
0.8857	High Similarity	NPC253521
0.8857	High Similarity	NPC37668
0.8857	High Similarity	NPC113836
0.883	High Similarity	NPC317671
0.883	High Similarity	NPC142707
0.883	High Similarity	NPC26536
0.883	High Similarity	NPC49983
0.882	High Similarity	NPC474093
0.882	High Similarity	NPC104910
0.882	High Similarity	NPC112380
0.8817	High Similarity	NPC311803
0.8817	High Similarity	NPC472859
0.8817	High Similarity	NPC25389
0.8814	High Similarity	NPC476203
0.8814	High Similarity	NPC36138
0.881	High Similarity	NPC87317
0.8804	High Similarity	NPC470450
0.8802	High Similarity	NPC318432
0.8802	High Similarity	NPC247629
0.8802	High Similarity	NPC239019
0.88	High Similarity	NPC144097
0.88	High Similarity	NPC61904
0.8793	High Similarity	NPC472993
0.8786	High Similarity	NPC476365
0.8786	High Similarity	NPC34287
0.8786	High Similarity	NPC471416
0.8772	High Similarity	NPC166851
0.8772	High Similarity	NPC162169
0.8771	High Similarity	NPC30011
0.8771	High Similarity	NPC97817
0.8771	High Similarity	NPC72554
0.8765	High Similarity	NPC476372
0.8765	High Similarity	NPC476371
0.8764	High Similarity	NPC318119
0.8757	High Similarity	NPC119125
0.8757	High Similarity	NPC203020
0.8757	High Similarity	NPC166277
0.8757	High Similarity	NPC170203
0.8757	High Similarity	NPC239966
0.875	High Similarity	NPC258044
0.875	High Similarity	NPC293626
0.875	High Similarity	NPC267680
0.875	High Similarity	NPC217387
0.875	High Similarity	NPC265380
0.875	High Similarity	NPC196127
0.875	High Similarity	NPC35167
0.8743	High Similarity	NPC34267
0.8743	High Similarity	NPC81042
0.8743	High Similarity	NPC214621
0.8743	High Similarity	NPC84482
0.8743	High Similarity	NPC169645
0.8743	High Similarity	NPC223426
0.8736	High Similarity	NPC254540
0.8736	High Similarity	NPC271848
0.8736	High Similarity	NPC172807
0.8736	High Similarity	NPC205076
0.8736	High Similarity	NPC211594
0.8736	High Similarity	NPC48773

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 NPC8940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	948
0.2-0.3	1878
0.3-0.4	2686
0.4-0.5	1815
0.5-0.6	917
0.6-0.7	366
0.7-0.8	127
0.8-0.85	22
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8916	High Similarity	NPD4868	Clinical (unspecified phase)
0.8844	High Similarity	NPD7993	Clinical (unspecified phase)
0.8636	High Similarity	NPD4338	Clinical (unspecified phase)
0.8621	High Similarity	NPD5844	Phase 1
0.8556	High Similarity	NPD8397	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD8312	Approved
0.8483	Intermediate Similarity	NPD8313	Approved
0.8466	Intermediate Similarity	NPD7472	Approved
0.8466	Intermediate Similarity	NPD7074	Phase 3
0.8462	Intermediate Similarity	NPD1465	Phase 2
0.8457	Intermediate Similarity	NPD3818	Discontinued
0.8418	Intermediate Similarity	NPD6797	Phase 2
0.8409	Intermediate Similarity	NPD7054	Approved
0.8371	Intermediate Similarity	NPD7251	Discontinued
0.8324	Intermediate Similarity	NPD7808	Phase 3
0.8314	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD8455	Phase 2
0.8239	Intermediate Similarity	NPD6166	Phase 2
0.8239	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD7228	Approved
0.8125	Intermediate Similarity	NPD6232	Discontinued
0.8093	Intermediate Similarity	NPD8151	Discontinued
0.8081	Intermediate Similarity	NPD1934	Approved
0.8068	Intermediate Similarity	NPD6959	Discontinued
0.8068	Intermediate Similarity	NPD7199	Phase 2
0.8059	Intermediate Similarity	NPD1653	Approved
0.8057	Intermediate Similarity	NPD6234	Discontinued
0.8035	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD2801	Approved
0.8034	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7473	Discontinued
0.7989	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD6559	Discontinued
0.7944	Intermediate Similarity	NPD3751	Discontinued
0.7931	Intermediate Similarity	NPD7819	Suspended
0.7921	Intermediate Similarity	NPD3787	Discontinued
0.7898	Intermediate Similarity	NPD3749	Approved
0.7895	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD37	Approved
0.7869	Intermediate Similarity	NPD7685	Pre-registration
0.7841	Intermediate Similarity	NPD7768	Phase 2
0.7841	Intermediate Similarity	NPD4965	Approved
0.7841	Intermediate Similarity	NPD4966	Approved
0.7841	Intermediate Similarity	NPD4967	Phase 2
0.7828	Intermediate Similarity	NPD7783	Phase 2
0.7828	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD5494	Approved
0.7797	Intermediate Similarity	NPD7075	Discontinued
0.7784	Intermediate Similarity	NPD3817	Phase 2
0.7784	Intermediate Similarity	NPD5402	Approved
0.7772	Intermediate Similarity	NPD7240	Approved
0.7759	Intermediate Similarity	NPD4380	Phase 2
0.7751	Intermediate Similarity	NPD3750	Approved
0.7744	Intermediate Similarity	NPD7435	Discontinued
0.774	Intermediate Similarity	NPD3882	Suspended
0.7719	Intermediate Similarity	NPD1511	Approved
0.7714	Intermediate Similarity	NPD7411	Suspended
0.7704	Intermediate Similarity	NPD7870	Phase 2
0.7704	Intermediate Similarity	NPD7871	Phase 2
0.7684	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6782	Approved
0.768	Intermediate Similarity	NPD6777	Approved
0.768	Intermediate Similarity	NPD6781	Approved
0.768	Intermediate Similarity	NPD6776	Approved
0.768	Intermediate Similarity	NPD6778	Approved
0.768	Intermediate Similarity	NPD6780	Approved
0.768	Intermediate Similarity	NPD6779	Approved
0.763	Intermediate Similarity	NPD1512	Approved
0.7627	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6190	Approved
0.76	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7874	Approved
0.7563	Intermediate Similarity	NPD7696	Phase 3
0.7563	Intermediate Similarity	NPD7698	Approved
0.7563	Intermediate Similarity	NPD7697	Approved
0.7529	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7701	Phase 2
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7485	Intermediate Similarity	NPD230	Phase 1
0.7475	Intermediate Similarity	NPD7680	Approved
0.7472	Intermediate Similarity	NPD6801	Discontinued
0.7471	Intermediate Similarity	NPD7266	Discontinued
0.7471	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3748	Approved
0.7442	Intermediate Similarity	NPD4628	Phase 3
0.7425	Intermediate Similarity	NPD1613	Approved
0.7425	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD6823	Phase 2
0.7423	Intermediate Similarity	NPD6535	Approved
0.7423	Intermediate Similarity	NPD6534	Approved
0.7414	Intermediate Similarity	NPD6799	Approved
0.7404	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7700	Phase 2
0.7398	Intermediate Similarity	NPD7699	Phase 2
0.7389	Intermediate Similarity	NPD7801	Approved
0.7386	Intermediate Similarity	NPD5403	Approved
0.7384	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6599	Discontinued
0.7326	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7390	Discontinued
0.7292	Intermediate Similarity	NPD8150	Discontinued
0.7289	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2534	Approved
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2533	Approved
0.7273	Intermediate Similarity	NPD5401	Approved
0.7273	Intermediate Similarity	NPD2532	Approved
0.7264	Intermediate Similarity	NPD8320	Phase 1
0.7264	Intermediate Similarity	NPD8319	Approved
0.7251	Intermediate Similarity	NPD1510	Phase 2
0.7243	Intermediate Similarity	NPD7229	Phase 3
0.7241	Intermediate Similarity	NPD7003	Approved
0.7229	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2796	Approved
0.7209	Intermediate Similarity	NPD2935	Discontinued
0.7207	Intermediate Similarity	NPD3226	Approved
0.7204	Intermediate Similarity	NPD3926	Phase 2
0.7202	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8434	Phase 2
0.7194	Intermediate Similarity	NPD6213	Phase 3
0.7194	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6212	Phase 3
0.7189	Intermediate Similarity	NPD8127	Discontinued
0.7181	Intermediate Similarity	NPD7177	Discontinued
0.7175	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7549	Discontinued
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7118	Intermediate Similarity	NPD943	Approved
0.711	Intermediate Similarity	NPD5405	Approved
0.711	Intermediate Similarity	NPD5406	Approved
0.711	Intermediate Similarity	NPD5404	Approved
0.711	Intermediate Similarity	NPD5408	Approved
0.711	Intermediate Similarity	NPD1551	Phase 2
0.7101	Intermediate Similarity	NPD3764	Approved
0.7098	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1247	Approved
0.7086	Intermediate Similarity	NPD6674	Discontinued
0.7083	Intermediate Similarity	NPD4908	Phase 1
0.7081	Intermediate Similarity	NPD919	Approved
0.7076	Intermediate Similarity	NPD1933	Approved
0.7073	Intermediate Similarity	NPD7585	Approved
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7045	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3027	Phase 3
0.7041	Intermediate Similarity	NPD4287	Approved
0.7039	Intermediate Similarity	NPD6273	Approved
0.7024	Intermediate Similarity	NPD7583	Approved
0.7021	Intermediate Similarity	NPD5242	Approved
0.7018	Intermediate Similarity	NPD1240	Approved
0.7011	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7097	Phase 1
0.698	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD447	Suspended
0.6976	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2346	Discontinued
0.6954	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7584	Approved
0.6936	Remote Similarity	NPD1607	Approved
0.693	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD9269	Phase 2
0.6919	Remote Similarity	NPD5353	Approved
0.6914	Remote Similarity	NPD6100	Approved
0.6914	Remote Similarity	NPD6099	Approved
0.6912	Remote Similarity	NPD8059	Phase 3
0.6912	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD920	Approved
0.6891	Remote Similarity	NPD5953	Discontinued
0.6889	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5711	Approved
0.6878	Remote Similarity	NPD5710	Approved
0.6872	Remote Similarity	NPD7930	Approved
0.6866	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5006	Approved
0.6829	Remote Similarity	NPD5005	Approved
0.6824	Remote Similarity	NPD9494	Approved
0.6824	Remote Similarity	NPD2861	Phase 2
0.6821	Remote Similarity	NPD4060	Phase 1
0.6788	Remote Similarity	NPD7286	Phase 2
0.6782	Remote Similarity	NPD6355	Discontinued
0.678	Remote Similarity	NPD2344	Approved
0.6778	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7039	Approved
0.6769	Remote Similarity	NPD7038	Approved
0.6766	Remote Similarity	NPD1091	Approved
0.6766	Remote Similarity	NPD1610	Phase 2

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