NPASS Compound

Structure

CID95421 OpenBabel06191715432D 52 56 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 -3.4641 -0.0000 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 0.0000 -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 -1.7321 -0.0000 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 -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 -4.3301 -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 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 -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 -2.5981 1.5000 0.0000 C 0 0 0 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 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -6.0622 -0.5000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -1.7321 1.0000 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 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 15 2 0 0 0 0 2 4 2 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 4 16 1 0 0 0 0 5 12 2 0 0 0 0 5 17 1 0 0 0 0 6 12 1 0 0 0 0 6 18 2 0 0 0 0 7 13 2 0 0 0 0 7 19 1 0 0 0 0 8 13 1 0 0 0 0 8 20 2 0 0 0 0 9 14 2 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 10 22 2 0 0 0 0 11 48 1 0 0 0 0 12 30 1 0 0 0 0 13 31 1 0 0 0 0 14 32 1 0 0 0 0 15 34 1 0 0 0 0 16 49 1 0 0 0 0 17 24 2 0 0 0 0 17 35 1 0 0 0 0 18 24 1 0 0 0 0 18 36 1 0 0 0 0 19 25 2 0 0 0 0 19 37 1 0 0 0 0 20 25 1 0 0 0 0 20 38 1 0 0 0 0 21 26 2 0 0 0 0 21 39 1 0 0 0 0 22 26 1 0 0 0 0 22 40 1 0 0 0 0 23 11 1 1 0 0 0 23 27 1 0 0 0 0 23 50 1 0 0 0 0 24 41 1 0 0 0 0 25 42 1 0 0 0 0 26 43 1 0 0 0 0 27 28 1 0 0 0 0 27 44 1 6 0 0 0 28 29 1 0 0 0 0 28 51 1 1 0 0 0 29 33 1 0 0 0 0 29 52 1 6 0 0 0 30 45 2 0 0 0 0 30 48 1 0 0 0 0 31 46 2 0 0 0 0 31 51 1 0 0 0 0 32 47 2 0 0 0 0 32 52 1 0 0 0 0 33 49 1 1 0 0 0 33 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	728.12
Volume:	664.009
LogP:	2.25
LogD:	0.796
LogS:	-2.911
# Rotatable Bonds:	12
TPSA:	319.89
# H-Bond Aceptor:	19
# H-Bond Donor:	11
# Rings:	5
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.066
Synthetic Accessibility Score:	4.472
Fsp3:	0.182
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:	-6.999
MDCK Permeability:	1.1666338650684338e-05
Pgp-inhibitor:	0.069
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.946
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	88.26703643798828%
Volume Distribution (VD):	0.375
Pgp-substrate:	14.982157707214355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.67
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.023
CYP2C9-inhibitor:	0.487
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.052
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	13.008
Half-life (T1/2):	0.968

ADMET: Toxicity

hERG Blockers:	0.226
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.973
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.935
Respiratory Toxicity:	0.006

Download Data

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

Natural Product: NPC95421

Natural Product ID:	NPC95421
*Common Name:**	Hyemaloside A
IUPAC Name:	[(2R,3R,4S,5R,6S)-3-hydroxy-6-(4-hydroxyphenoxy)-4,5-bis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Synonyms:
Standard InCHIKey:	DTLDDZWHEMEXCO-ILYYIXHASA-N
Standard InCHI:	InChI=1S/C33H28O19/c34-15-1-3-16(4-2-15)49-33-29(52-32(47)14-9-21(39)26(43)22(40)10-14)28(51-31(46)13-7-19(37)25(42)20(38)8-13)27(44)23(50-33)11-48-30(45)12-5-17(35)24(41)18(36)6-12/h1-10,23,27-29,33-44H,11H2/t23-,27-,28+,29-,33-/m1/s1
SMILES:	Oc1ccc(cc1)O[C@@H]1O[C@H](COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H]([C@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509744
PubChem CID:	25058097
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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	=	1460.0	nM	PMID[471311]
NPT2	Others	Unspecified	IC50	=	580.0	nM	PMID[471311]
NPT2	Others	Unspecified	IC50	=	180.0	nM	PMID[471311]

☑ 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 NPC95421 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	402
0.1-0.2	1774
0.2-0.3	4518
0.3-0.4	9528
0.4-0.5	8477
0.5-0.6	4442
0.6-0.7	6164
0.7-0.8	5785
0.8-0.85	1046
0.85-0.9	465
0.9-0.95	84
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC198125
0.9684	High Similarity	NPC4013
0.9684	High Similarity	NPC90905
0.963	High Similarity	NPC5786
0.963	High Similarity	NPC102851
0.9557	High Similarity	NPC289346
0.9506	High Similarity	NPC658
0.9506	High Similarity	NPC149300
0.9506	High Similarity	NPC197708
0.9494	High Similarity	NPC287872
0.9494	High Similarity	NPC74319
0.9437	High Similarity	NPC285108
0.9437	High Similarity	NPC33298
0.943	High Similarity	NPC172419
0.943	High Similarity	NPC238419
0.9401	High Similarity	NPC8940
0.9375	High Similarity	NPC311803
0.9375	High Similarity	NPC472859
0.9375	High Similarity	NPC25389
0.9367	High Similarity	NPC247629
0.9367	High Similarity	NPC239019
0.9313	High Similarity	NPC166277
0.9313	High Similarity	NPC119125
0.925	High Similarity	NPC114791
0.925	High Similarity	NPC289811
0.925	High Similarity	NPC141331
0.925	High Similarity	NPC160780
0.925	High Similarity	NPC104222
0.925	High Similarity	NPC210501
0.925	High Similarity	NPC318826
0.9235	High Similarity	NPC111490
0.9235	High Similarity	NPC261623
0.9231	High Similarity	NPC97119
0.9231	High Similarity	NPC297503
0.9231	High Similarity	NPC135831
0.9226	High Similarity	NPC80956
0.9222	High Similarity	NPC472991
0.9222	High Similarity	NPC472992
0.9217	High Similarity	NPC163165
0.9207	High Similarity	NPC473818
0.9193	High Similarity	NPC239966
0.9193	High Similarity	NPC203020
0.9187	High Similarity	NPC133984
0.9187	High Similarity	NPC1913
0.9177	High Similarity	NPC3746
0.9177	High Similarity	NPC205037
0.9177	High Similarity	NPC44260
0.9177	High Similarity	NPC61152
0.9177	High Similarity	NPC16024
0.9176	High Similarity	NPC231254
0.9167	High Similarity	NPC476622
0.9167	High Similarity	NPC476618
0.9167	High Similarity	NPC476619
0.9167	High Similarity	NPC476623
0.9167	High Similarity	NPC476621
0.9167	High Similarity	NPC476620
0.9141	High Similarity	NPC121290
0.9141	High Similarity	NPC227297
0.9123	High Similarity	NPC469650
0.9112	High Similarity	NPC471030
0.9107	High Similarity	NPC472723
0.9102	High Similarity	NPC172033
0.9102	High Similarity	NPC88560
0.9102	High Similarity	NPC175230
0.9096	High Similarity	NPC204937
0.9096	High Similarity	NPC149011
0.9075	High Similarity	NPC160543
0.9075	High Similarity	NPC469652
0.9075	High Similarity	NPC472724
0.9075	High Similarity	NPC93065
0.9075	High Similarity	NPC472720
0.9075	High Similarity	NPC472721
0.9075	High Similarity	NPC31208
0.9074	High Similarity	NPC476373
0.907	High Similarity	NPC260521
0.907	High Similarity	NPC65489
0.907	High Similarity	NPC469649
0.9068	High Similarity	NPC472860
0.9064	High Similarity	NPC470416
0.9053	High Similarity	NPC37668
0.9053	High Similarity	NPC472387
0.9053	High Similarity	NPC253521
0.9053	High Similarity	NPC113836
0.9048	High Similarity	NPC169645
0.9048	High Similarity	NPC84482
0.9042	High Similarity	NPC47140
0.9042	High Similarity	NPC67134
0.9017	High Similarity	NPC240200
0.9017	High Similarity	NPC477081
0.9017	High Similarity	NPC290289
0.9017	High Similarity	NPC158214
0.9017	High Similarity	NPC223534
0.9017	High Similarity	NPC477083
0.9012	High Similarity	NPC474093
0.9012	High Similarity	NPC104910
0.9006	High Similarity	NPC36138
0.9	High Similarity	NPC194095
0.9	High Similarity	NPC327032
0.9	High Similarity	NPC191046
0.8994	High Similarity	NPC61904
0.8994	High Similarity	NPC144097
0.8994	High Similarity	NPC79736
0.8994	High Similarity	NPC67629
0.8994	High Similarity	NPC297574
0.8988	High Similarity	NPC470438
0.8988	High Similarity	NPC472993
0.8976	High Similarity	NPC311389
0.8976	High Similarity	NPC128403
0.8976	High Similarity	NPC470271
0.897	High Similarity	NPC142614
0.8966	High Similarity	NPC187632
0.8963	High Similarity	NPC476372
0.8963	High Similarity	NPC476371
0.896	High Similarity	NPC30011
0.896	High Similarity	NPC97817
0.896	High Similarity	NPC179947
0.896	High Similarity	NPC475179
0.896	High Similarity	NPC72554
0.8957	High Similarity	NPC24164
0.8951	High Similarity	NPC68324
0.8951	High Similarity	NPC114179
0.8951	High Similarity	NPC156818
0.8951	High Similarity	NPC160512
0.8951	High Similarity	NPC289322
0.8951	High Similarity	NPC38779
0.8947	High Similarity	NPC469371
0.8941	High Similarity	NPC267680
0.8941	High Similarity	NPC196127
0.8941	High Similarity	NPC217387
0.8941	High Similarity	NPC267549
0.8941	High Similarity	NPC293626
0.8941	High Similarity	NPC258044
0.8941	High Similarity	NPC35167
0.8938	High Similarity	NPC310661
0.8938	High Similarity	NPC105827
0.8935	High Similarity	NPC34267
0.8935	High Similarity	NPC81042
0.8935	High Similarity	NPC214621
0.8935	High Similarity	NPC223426
0.8931	High Similarity	NPC140151
0.8929	High Similarity	NPC254540
0.8929	High Similarity	NPC211594
0.8929	High Similarity	NPC65333
0.8929	High Similarity	NPC259152
0.8929	High Similarity	NPC172807
0.8929	High Similarity	NPC3583
0.8924	High Similarity	NPC92117
0.8916	High Similarity	NPC175793
0.8914	High Similarity	NPC471091
0.8914	High Similarity	NPC40078
0.8914	High Similarity	NPC97924
0.8914	High Similarity	NPC264302
0.8908	High Similarity	NPC119094
0.8908	High Similarity	NPC473618
0.8908	High Similarity	NPC173872
0.8908	High Similarity	NPC7839
0.8908	High Similarity	NPC142291
0.8895	High Similarity	NPC470718
0.8895	High Similarity	NPC123259
0.8895	High Similarity	NPC35924
0.8895	High Similarity	NPC199172
0.8895	High Similarity	NPC162394
0.8895	High Similarity	NPC241781
0.8895	High Similarity	NPC156785
0.8895	High Similarity	NPC129533
0.8895	High Similarity	NPC132111
0.8889	High Similarity	NPC300845
0.8889	High Similarity	NPC88803
0.8889	High Similarity	NPC291948
0.8889	High Similarity	NPC104983
0.8889	High Similarity	NPC471405
0.8889	High Similarity	NPC250436
0.8876	High Similarity	NPC98583
0.8875	High Similarity	NPC134905
0.8875	High Similarity	NPC36130
0.8869	High Similarity	NPC470272
0.8869	High Similarity	NPC471416
0.8869	High Similarity	NPC34287
0.8862	High Similarity	NPC146792
0.8862	High Similarity	NPC43918
0.8862	High Similarity	NPC190204
0.8862	High Similarity	NPC45618
0.8862	High Similarity	NPC58716
0.8862	High Similarity	NPC261411
0.8862	High Similarity	NPC116745
0.8861	High Similarity	NPC120621
0.8861	High Similarity	NPC248257
0.8861	High Similarity	NPC142528
0.8848	High Similarity	NPC148273
0.8844	High Similarity	NPC21359
0.8844	High Similarity	NPC249560
0.8844	High Similarity	NPC470713
0.8844	High Similarity	NPC470720
0.8844	High Similarity	NPC223860
0.8844	High Similarity	NPC470451
0.8844	High Similarity	NPC275977
0.8844	High Similarity	NPC470455
0.8844	High Similarity	NPC25946
0.8844	High Similarity	NPC470717
0.8844	High Similarity	NPC460984

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 NPC95421 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	935
0.2-0.3	1987
0.3-0.4	2688
0.4-0.5	1821
0.5-0.6	918
0.6-0.7	316
0.7-0.8	102
0.8-0.85	17
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD7993	Clinical (unspecified phase)
0.8889	High Similarity	NPD4868	Clinical (unspecified phase)
0.8824	High Similarity	NPD4338	Clinical (unspecified phase)
0.8647	High Similarity	NPD7472	Approved
0.8596	High Similarity	NPD6797	Phase 2
0.8588	High Similarity	NPD7054	Approved
0.8547	High Similarity	NPD7251	Discontinued
0.8538	High Similarity	NPD7074	Phase 3
0.8529	High Similarity	NPD3818	Discontinued
0.8497	Intermediate Similarity	NPD7808	Phase 3
0.8383	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1653	Approved
0.8304	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD6166	Phase 2
0.8266	Intermediate Similarity	NPD5844	Phase 1
0.8229	Intermediate Similarity	NPD7685	Pre-registration
0.8136	Intermediate Similarity	NPD8313	Approved
0.8136	Intermediate Similarity	NPD8312	Approved
0.8095	Intermediate Similarity	NPD2801	Approved
0.8095	Intermediate Similarity	NPD8455	Phase 2
0.8086	Intermediate Similarity	NPD6190	Approved
0.8061	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD1934	Approved
0.8022	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD1465	Phase 2
0.7988	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD5402	Approved
0.7921	Intermediate Similarity	NPD6559	Discontinued
0.7862	Intermediate Similarity	NPD230	Phase 1
0.7845	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7266	Discontinued
0.7836	Intermediate Similarity	NPD3817	Phase 2
0.7816	Intermediate Similarity	NPD7199	Phase 2
0.7811	Intermediate Similarity	NPD4380	Phase 2
0.7803	Intermediate Similarity	NPD6234	Discontinued
0.7791	Intermediate Similarity	NPD3882	Suspended
0.7784	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1511	Approved
0.7746	Intermediate Similarity	NPD7075	Discontinued
0.7719	Intermediate Similarity	NPD37	Approved
0.7697	Intermediate Similarity	NPD3751	Discontinued
0.7688	Intermediate Similarity	NPD4965	Approved
0.7688	Intermediate Similarity	NPD4967	Phase 2
0.7688	Intermediate Similarity	NPD4966	Approved
0.768	Intermediate Similarity	NPD8151	Discontinued
0.7679	Intermediate Similarity	NPD1512	Approved
0.767	Intermediate Similarity	NPD6232	Discontinued
0.767	Intermediate Similarity	NPD3787	Discontinued
0.7661	Intermediate Similarity	NPD7411	Suspended
0.7657	Intermediate Similarity	NPD5494	Approved
0.7627	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7240	Approved
0.7614	Intermediate Similarity	NPD6959	Discontinued
0.759	Intermediate Similarity	NPD4628	Phase 3
0.7586	Intermediate Similarity	NPD7768	Phase 2
0.7572	Intermediate Similarity	NPD7819	Suspended
0.7572	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7473	Discontinued
0.7529	Intermediate Similarity	NPD5403	Approved
0.7529	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6801	Discontinued
0.7513	Intermediate Similarity	NPD7783	Phase 2
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.7513	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1549	Phase 2
0.7469	Intermediate Similarity	NPD1613	Approved
0.7469	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6799	Approved
0.7448	Intermediate Similarity	NPD6780	Approved
0.7448	Intermediate Similarity	NPD6778	Approved
0.7448	Intermediate Similarity	NPD6782	Approved
0.7448	Intermediate Similarity	NPD6781	Approved
0.7448	Intermediate Similarity	NPD6776	Approved
0.7448	Intermediate Similarity	NPD6777	Approved
0.7448	Intermediate Similarity	NPD6779	Approved
0.7443	Intermediate Similarity	NPD3749	Approved
0.7412	Intermediate Similarity	NPD5401	Approved
0.741	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7870	Phase 2
0.7385	Intermediate Similarity	NPD7871	Phase 2
0.7381	Intermediate Similarity	NPD3750	Approved
0.7374	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7874	Approved
0.7333	Intermediate Similarity	NPD7697	Approved
0.7333	Intermediate Similarity	NPD7680	Approved
0.7333	Intermediate Similarity	NPD7696	Phase 3
0.7333	Intermediate Similarity	NPD7698	Approved
0.7321	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6233	Phase 2
0.7284	Intermediate Similarity	NPD3027	Phase 3
0.7278	Intermediate Similarity	NPD9269	Phase 2
0.7273	Intermediate Similarity	NPD7701	Phase 2
0.7246	Intermediate Similarity	NPD1551	Phase 2
0.7241	Intermediate Similarity	NPD7458	Discontinued
0.7239	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5353	Approved
0.7222	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1933	Approved
0.7209	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6599	Discontinued
0.7194	Intermediate Similarity	NPD6823	Phase 2
0.7188	Intermediate Similarity	NPD6534	Approved
0.7188	Intermediate Similarity	NPD6535	Approved
0.7186	Intermediate Similarity	NPD1510	Phase 2
0.7176	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7699	Phase 2
0.7165	Intermediate Similarity	NPD7700	Phase 2
0.7164	Intermediate Similarity	NPD7801	Approved
0.716	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2796	Approved
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7127	Intermediate Similarity	NPD8127	Discontinued
0.7108	Intermediate Similarity	NPD447	Suspended
0.7101	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7585	Approved
0.7083	Intermediate Similarity	NPD3748	Approved
0.7059	Intermediate Similarity	NPD7039	Approved
0.7059	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7038	Approved
0.7053	Intermediate Similarity	NPD8150	Discontinued
0.705	Intermediate Similarity	NPD7583	Approved
0.7049	Intermediate Similarity	NPD5242	Approved
0.7048	Intermediate Similarity	NPD943	Approved
0.7035	Intermediate Similarity	NPD8320	Phase 1
0.7035	Intermediate Similarity	NPD8319	Approved
0.7026	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9268	Approved
0.7024	Intermediate Similarity	NPD7097	Phase 1
0.7021	Intermediate Similarity	NPD7549	Discontinued
0.7	Intermediate Similarity	NPD1091	Approved
0.6977	Remote Similarity	NPD8166	Discontinued
0.6971	Remote Similarity	NPD6273	Approved
0.6966	Remote Similarity	NPD6386	Approved
0.6966	Remote Similarity	NPD6385	Approved
0.6965	Remote Similarity	NPD7584	Approved
0.6959	Remote Similarity	NPD6213	Phase 3
0.6959	Remote Similarity	NPD6212	Phase 3
0.6959	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3926	Phase 2
0.6947	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1240	Approved
0.694	Remote Similarity	NPD1247	Approved
0.6928	Remote Similarity	NPD3764	Approved
0.6928	Remote Similarity	NPD6798	Discontinued
0.6923	Remote Similarity	NPD919	Approved
0.6914	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2533	Approved
0.6914	Remote Similarity	NPD2532	Approved
0.6914	Remote Similarity	NPD2534	Approved
0.6909	Remote Similarity	NPD4908	Phase 1
0.6879	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6971	Discontinued
0.6864	Remote Similarity	NPD1607	Approved
0.6855	Remote Similarity	NPD9545	Approved
0.6854	Remote Similarity	NPD3226	Approved
0.6829	Remote Similarity	NPD1203	Approved
0.6826	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5953	Discontinued
0.6821	Remote Similarity	NPD6674	Discontinued
0.6821	Remote Similarity	NPD1652	Phase 2
0.6811	Remote Similarity	NPD7229	Phase 3
0.68	Remote Similarity	NPD7440	Discontinued
0.6778	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3225	Approved
0.6761	Remote Similarity	NPD7390	Discontinued
0.676	Remote Similarity	NPD3455	Phase 2
0.6755	Remote Similarity	NPD7177	Discontinued
0.6748	Remote Similarity	NPD1481	Phase 2
0.6748	Remote Similarity	NPD1608	Approved
0.6742	Remote Similarity	NPD920	Approved
0.6723	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7286	Phase 2
0.6707	Remote Similarity	NPD6832	Phase 2
0.6706	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5124	Phase 1
0.6698	Remote Similarity	NPD8059	Phase 3
0.6698	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1535	Discovery
0.6686	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7033	Discontinued
0.6686	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD4288	Approved
0.6667	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4357	Discontinued
0.6648	Remote Similarity	NPD6844	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