NPASS Compound

Structure

NPC92153 OpenBabel07101719512D 38 41 0 0 1 0 0 0 0 0999 V2000 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 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 -5.1962 1.0000 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 5.1962 0.0000 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 -4.3301 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 -0.8660 -1.5000 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 -3.4641 -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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 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 -2.5981 -0.5000 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 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 18 2 0 0 0 0 9 19 2 0 0 0 0 10 11 1 0 0 0 0 10 17 2 0 0 0 0 11 20 2 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 35 1 0 0 0 0 15 25 1 0 0 0 0 16 20 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 30 1 0 0 0 0 20 36 1 0 0 0 0 21 13 1 6 0 0 0 21 22 1 0 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 1 0 0 0 23 24 1 0 0 0 0 23 32 1 6 0 0 0 24 27 1 0 0 0 0 24 38 1 1 0 0 0 25 33 2 0 0 0 0 25 38 1 0 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 27 36 1 6 0 0 0 27 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.15
Volume:	509.014
LogP:	3.003
LogD:	2.166
LogS:	-3.649
# Rotatable Bonds:	10
TPSA:	172.21
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.269
Synthetic Accessibility Score:	3.712
Fsp3:	0.259
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.292
MDCK Permeability:	2.0491803297773004e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.636
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.467
Plasma Protein Binding (PPB):	100.37596893310547%
Volume Distribution (VD):	0.646
Pgp-substrate:	1.9102228879928589%

ADMET: Metabolism

CYP1A2-inhibitor:	0.46
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.149
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.344
CYP2C9-substrate:	0.259
CYP2D6-inhibitor:	0.977
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.104

ADMET: Excretion

Clearance (CL):	13.029
Half-life (T1/2):	0.955

ADMET: Toxicity

hERG Blockers:	0.141
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.154
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.253
Carcinogencity:	0.297
Eye Corrosion:	0.003
Eye Irritation:	0.713
Respiratory Toxicity:	0.005

Download Data

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

Natural Product: NPC92153

Natural Product ID:	NPC92153
*Common Name:**	Itoside E
IUPAC Name:	[2-[(2S,3R,4S,5S,6R)-3-benzoyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxyphenyl]methyl 2-hydroxybenzoate
Synonyms:	Itoside E
Standard InCHIKey:	UTRVZPDCXSMOPG-YIHAFMAISA-N
Standard InCHI:	InChI=1S/C27H26O11/c28-13-21-22(31)23(32)24(38-25(33)15-6-2-1-3-7-15)27(37-21)36-20-11-10-17(29)12-16(20)14-35-26(34)18-8-4-5-9-19(18)30/h1-12,21-24,27-32H,13-14H2/t21-,22-,23+,24-,27-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2COC(=O)c2ccccc2O)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512449
PubChem CID:	44577125
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
NPO9317	Itoa orientalis	Species	Salicaceae	Eukaryota	bark, twigs, and leaves	n.a.	n.a.	PMID[18412396]
NPO9317	Itoa orientalis	Species	Salicaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	31.7	%	PMID[509169]

☑ 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 NPC92153 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	1535
0.2-0.3	3784
0.3-0.4	8514
0.4-0.5	9792
0.5-0.6	4438
0.6-0.7	6391
0.7-0.8	6638
0.8-0.85	986
0.85-0.9	224
0.9-0.95	27
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC279281
1.0	High Similarity	NPC299761
1.0	High Similarity	NPC230439
0.9795	High Similarity	NPC93619
0.9589	High Similarity	NPC140722
0.9589	High Similarity	NPC4958
0.9589	High Similarity	NPC92054
0.953	High Similarity	NPC215811
0.9477	High Similarity	NPC132737
0.9467	High Similarity	NPC260604
0.9467	High Similarity	NPC299435
0.9456	High Similarity	NPC83975
0.9408	High Similarity	NPC476026
0.9408	High Similarity	NPC474398
0.9408	High Similarity	NPC474441
0.9408	High Similarity	NPC474401
0.9355	High Similarity	NPC475183
0.9346	High Similarity	NPC231475
0.9346	High Similarity	NPC57072
0.9295	High Similarity	NPC280923
0.9272	High Similarity	NPC34965
0.9272	High Similarity	NPC183536
0.9236	High Similarity	NPC475174
0.9211	High Similarity	NPC185103
0.9195	High Similarity	NPC302989
0.9178	High Similarity	NPC245219
0.9178	High Similarity	NPC65833
0.9178	High Similarity	NPC31081
0.9133	High Similarity	NPC22137
0.9103	High Similarity	NPC217950
0.9062	High Similarity	NPC280385
0.9038	High Similarity	NPC328093
0.9013	High Similarity	NPC131874
0.8993	High Similarity	NPC138915
0.8987	High Similarity	NPC127415
0.8981	High Similarity	NPC477629
0.8981	High Similarity	NPC210961
0.8981	High Similarity	NPC71780
0.8981	High Similarity	NPC195685
0.8981	High Similarity	NPC477628
0.8981	High Similarity	NPC472994
0.8981	High Similarity	NPC270675
0.8957	High Similarity	NPC472992
0.8957	High Similarity	NPC472991
0.8951	High Similarity	NPC470438
0.8944	High Similarity	NPC149011
0.8944	High Similarity	NPC204937
0.8931	High Similarity	NPC178281
0.8924	High Similarity	NPC472876
0.8924	High Similarity	NPC90905
0.8924	High Similarity	NPC4013
0.8919	High Similarity	NPC145319
0.891	High Similarity	NPC177742
0.8902	High Similarity	NPC472387
0.8902	High Similarity	NPC476621
0.8902	High Similarity	NPC476623
0.8902	High Similarity	NPC476622
0.8902	High Similarity	NPC476620
0.8902	High Similarity	NPC476618
0.8902	High Similarity	NPC476619
0.8889	High Similarity	NPC47140
0.8889	High Similarity	NPC67134
0.8889	High Similarity	NPC475890
0.8868	High Similarity	NPC80068
0.8868	High Similarity	NPC121290
0.8846	High Similarity	NPC261866
0.8839	High Similarity	NPC470331
0.8834	High Similarity	NPC88560
0.8834	High Similarity	NPC172033
0.8834	High Similarity	NPC472993
0.8834	High Similarity	NPC175230
0.8827	High Similarity	NPC210808
0.8827	High Similarity	NPC199079
0.8824	High Similarity	NPC182350
0.8812	High Similarity	NPC19240
0.8812	High Similarity	NPC129264
0.8812	High Similarity	NPC99216
0.8812	High Similarity	NPC85751
0.8812	High Similarity	NPC139060
0.8812	High Similarity	NPC205824
0.8805	High Similarity	NPC212099
0.8805	High Similarity	NPC101116
0.8805	High Similarity	NPC22324
0.8805	High Similarity	NPC146837
0.8805	High Similarity	NPC278329
0.8797	High Similarity	NPC289346
0.879	High Similarity	NPC156457
0.879	High Similarity	NPC43638
0.879	High Similarity	NPC60966
0.879	High Similarity	NPC258035
0.879	High Similarity	NPC133984
0.879	High Similarity	NPC197896
0.879	High Similarity	NPC161749
0.879	High Similarity	NPC313163
0.878	High Similarity	NPC223426
0.878	High Similarity	NPC34267
0.878	High Similarity	NPC214621
0.878	High Similarity	NPC81042
0.8774	High Similarity	NPC259767
0.8774	High Similarity	NPC88484
0.8773	High Similarity	NPC288152
0.8773	High Similarity	NPC257011
0.8773	High Similarity	NPC172807
0.8773	High Similarity	NPC137871
0.8773	High Similarity	NPC211594
0.8773	High Similarity	NPC472386
0.8773	High Similarity	NPC9002
0.8773	High Similarity	NPC254540
0.8765	High Similarity	NPC472133
0.8758	High Similarity	NPC70441
0.8758	High Similarity	NPC473278
0.8758	High Similarity	NPC260504
0.8758	High Similarity	NPC89809
0.8758	High Similarity	NPC111785
0.875	High Similarity	NPC168822
0.875	High Similarity	NPC474422
0.875	High Similarity	NPC17432
0.8743	High Similarity	NPC36138
0.8734	High Similarity	NPC43761
0.8734	High Similarity	NPC287872
0.8734	High Similarity	NPC74319
0.8734	High Similarity	NPC73511
0.8727	High Similarity	NPC61904
0.8727	High Similarity	NPC144097
0.8726	High Similarity	NPC170475
0.8726	High Similarity	NPC127406
0.8718	High Similarity	NPC83283
0.8718	High Similarity	NPC210003
0.8718	High Similarity	NPC29763
0.8718	High Similarity	NPC143851
0.8718	High Similarity	NPC39360
0.8712	High Similarity	NPC76047
0.8712	High Similarity	NPC471416
0.8712	High Similarity	NPC44558
0.8712	High Similarity	NPC105511
0.8712	High Similarity	NPC34287
0.8712	High Similarity	NPC43434
0.8712	High Similarity	NPC472129
0.8704	High Similarity	NPC146792
0.8704	High Similarity	NPC116745
0.8704	High Similarity	NPC298847
0.8704	High Similarity	NPC45618
0.8704	High Similarity	NPC58716
0.8696	High Similarity	NPC472130
0.8696	High Similarity	NPC472131
0.869	High Similarity	NPC470416
0.8688	High Similarity	NPC77660
0.8688	High Similarity	NPC189142
0.8688	High Similarity	NPC56735
0.8688	High Similarity	NPC61594
0.8688	High Similarity	NPC33298
0.8688	High Similarity	NPC285108
0.8679	High Similarity	NPC271479
0.8679	High Similarity	NPC472320
0.8675	High Similarity	NPC35167
0.8675	High Similarity	NPC477895
0.8675	High Similarity	NPC253521
0.8675	High Similarity	NPC37668
0.8675	High Similarity	NPC113836
0.8675	High Similarity	NPC139571
0.8675	High Similarity	NPC471028
0.8675	High Similarity	NPC217520
0.8667	High Similarity	NPC264735
0.8667	High Similarity	NPC49344
0.8667	High Similarity	NPC477848
0.8667	High Similarity	NPC164599
0.8667	High Similarity	NPC135277
0.8667	High Similarity	NPC43211
0.8667	High Similarity	NPC101191
0.8667	High Similarity	NPC210094
0.8667	High Similarity	NPC237435
0.8667	High Similarity	NPC115760
0.8662	High Similarity	NPC97052
0.8662	High Similarity	NPC99233
0.8662	High Similarity	NPC27408
0.8662	High Similarity	NPC26195
0.8662	High Similarity	NPC95090
0.8662	High Similarity	NPC39351
0.8662	High Similarity	NPC169248
0.8662	High Similarity	NPC72649
0.8659	High Similarity	NPC48773
0.8659	High Similarity	NPC205076
0.8659	High Similarity	NPC307518
0.8654	High Similarity	NPC259182
0.8654	High Similarity	NPC121001
0.865	High Similarity	NPC58053
0.865	High Similarity	NPC472383
0.865	High Similarity	NPC45638
0.865	High Similarity	NPC222455
0.865	High Similarity	NPC471457
0.865	High Similarity	NPC226294
0.865	High Similarity	NPC469931
0.865	High Similarity	NPC112755
0.865	High Similarity	NPC95421
0.865	High Similarity	NPC201292
0.865	High Similarity	NPC105025
0.865	High Similarity	NPC93337
0.865	High Similarity	NPC186807
0.865	High Similarity	NPC198125
0.865	High Similarity	NPC170675

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 NPC92153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	848
0.2-0.3	1805
0.3-0.4	2618
0.4-0.5	1941
0.5-0.6	1089
0.6-0.7	375
0.7-0.8	147
0.8-0.85	13
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.879	High Similarity	NPD4381	Clinical (unspecified phase)
0.8667	High Similarity	NPD4338	Clinical (unspecified phase)
0.8662	High Similarity	NPD5402	Approved
0.8614	High Similarity	NPD8313	Approved
0.8614	High Similarity	NPD8312	Approved
0.8494	Intermediate Similarity	NPD6559	Discontinued
0.8424	Intermediate Similarity	NPD7054	Approved
0.8375	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7472	Approved
0.8373	Intermediate Similarity	NPD7074	Phase 3
0.8364	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD5403	Approved
0.8323	Intermediate Similarity	NPD6797	Phase 2
0.8274	Intermediate Similarity	NPD7251	Discontinued
0.8266	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7808	Phase 3
0.8205	Intermediate Similarity	NPD5401	Approved
0.8204	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4380	Phase 2
0.8165	Intermediate Similarity	NPD1653	Approved
0.8137	Intermediate Similarity	NPD8455	Phase 2
0.8133	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6166	Phase 2
0.8098	Intermediate Similarity	NPD7075	Discontinued
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8039	Intermediate Similarity	NPD1551	Phase 2
0.8013	Intermediate Similarity	NPD1933	Approved
0.8012	Intermediate Similarity	NPD7411	Suspended
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7963	Intermediate Similarity	NPD1934	Approved
0.7959	Intermediate Similarity	NPD1203	Approved
0.7914	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2801	Approved
0.7895	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD3817	Phase 2
0.7862	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6801	Discontinued
0.7841	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3751	Discontinued
0.7821	Intermediate Similarity	NPD1549	Phase 2
0.7818	Intermediate Similarity	NPD7768	Phase 2
0.7814	Intermediate Similarity	NPD7435	Discontinued
0.7808	Intermediate Similarity	NPD1091	Approved
0.7805	Intermediate Similarity	NPD7819	Suspended
0.78	Intermediate Similarity	NPD6832	Phase 2
0.7799	Intermediate Similarity	NPD6799	Approved
0.7778	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD447	Suspended
0.7758	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7266	Discontinued
0.7756	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD6780	Approved
0.7747	Intermediate Similarity	NPD6782	Approved
0.7747	Intermediate Similarity	NPD6776	Approved
0.7747	Intermediate Similarity	NPD6778	Approved
0.7747	Intermediate Similarity	NPD6781	Approved
0.7747	Intermediate Similarity	NPD6777	Approved
0.7747	Intermediate Similarity	NPD6779	Approved
0.7746	Intermediate Similarity	NPD7685	Pre-registration
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7713	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD7783	Phase 2
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3787	Discontinued
0.7688	Intermediate Similarity	NPD1511	Approved
0.7669	Intermediate Similarity	NPD3226	Approved
0.7663	Intermediate Similarity	NPD6823	Phase 2
0.7658	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6233	Phase 2
0.764	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD9717	Approved
0.7633	Intermediate Similarity	NPD6959	Discontinued
0.761	Intermediate Similarity	NPD3750	Approved
0.7605	Intermediate Similarity	NPD3882	Suspended
0.7593	Intermediate Similarity	NPD1512	Approved
0.7588	Intermediate Similarity	NPD6232	Discontinued
0.7582	Intermediate Similarity	NPD2313	Discontinued
0.7581	Intermediate Similarity	NPD7870	Phase 2
0.7581	Intermediate Similarity	NPD7871	Phase 2
0.7578	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5494	Approved
0.7566	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7874	Approved
0.7562	Intermediate Similarity	NPD6190	Approved
0.756	Intermediate Similarity	NPD3749	Approved
0.7546	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7531	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6844	Discontinued
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.7527	Intermediate Similarity	NPD7697	Approved
0.7527	Intermediate Similarity	NPD7696	Phase 3
0.7527	Intermediate Similarity	NPD7698	Approved
0.7516	Intermediate Similarity	NPD1510	Phase 2
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.7514	Intermediate Similarity	NPD7228	Approved
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7473	Intermediate Similarity	NPD6535	Approved
0.7473	Intermediate Similarity	NPD6534	Approved
0.7468	Intermediate Similarity	NPD2796	Approved
0.7468	Intermediate Similarity	NPD411	Approved
0.7468	Intermediate Similarity	NPD6798	Discontinued
0.746	Intermediate Similarity	NPD7701	Phase 2
0.7457	Intermediate Similarity	NPD7473	Discontinued
0.745	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8150	Discontinued
0.7425	Intermediate Similarity	NPD37	Approved
0.7421	Intermediate Similarity	NPD8151	Discontinued
0.7418	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD6212	Phase 3
0.7418	Intermediate Similarity	NPD6213	Phase 3
0.7417	Intermediate Similarity	NPD3225	Approved
0.7412	Intermediate Similarity	NPD6234	Discontinued
0.7405	Intermediate Similarity	NPD7033	Discontinued
0.7396	Intermediate Similarity	NPD4966	Approved
0.7396	Intermediate Similarity	NPD4965	Approved
0.7396	Intermediate Similarity	NPD4967	Phase 2
0.7375	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7699	Phase 2
0.7351	Intermediate Similarity	NPD7700	Phase 2
0.7349	Intermediate Similarity	NPD7458	Discontinued
0.7344	Intermediate Similarity	NPD7801	Approved
0.7341	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1019	Discontinued
0.732	Intermediate Similarity	NPD2798	Approved
0.7296	Intermediate Similarity	NPD2799	Discontinued
0.7296	Intermediate Similarity	NPD4308	Phase 3
0.7296	Intermediate Similarity	NPD3748	Approved
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD9493	Approved
0.7273	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1613	Approved
0.7261	Intermediate Similarity	NPD1240	Approved
0.7261	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2797	Approved
0.725	Intermediate Similarity	NPD5406	Approved
0.725	Intermediate Similarity	NPD5408	Approved
0.725	Intermediate Similarity	NPD5405	Approved
0.725	Intermediate Similarity	NPD5404	Approved
0.7244	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7584	Approved
0.7211	Intermediate Similarity	NPD8319	Approved
0.7211	Intermediate Similarity	NPD8320	Phase 1
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1607	Approved
0.7169	Intermediate Similarity	NPD6273	Approved
0.7161	Intermediate Similarity	NPD2861	Phase 2
0.7152	Intermediate Similarity	NPD3496	Discontinued
0.7151	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7134	Intermediate Similarity	NPD3764	Approved
0.7134	Intermediate Similarity	NPD3268	Approved
0.7125	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7097	Phase 1
0.7115	Intermediate Similarity	NPD4908	Phase 1
0.7108	Intermediate Similarity	NPD2533	Approved
0.7108	Intermediate Similarity	NPD2532	Approved
0.7108	Intermediate Similarity	NPD2534	Approved
0.7107	Intermediate Similarity	NPD6355	Discontinued
0.7107	Intermediate Similarity	NPD230	Phase 1
0.7102	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7585	Approved
0.7091	Intermediate Similarity	NPD7440	Discontinued
0.7059	Intermediate Similarity	NPD1481	Phase 2
0.7059	Intermediate Similarity	NPD1608	Approved
0.7056	Intermediate Similarity	NPD7039	Approved
0.7056	Intermediate Similarity	NPD7038	Approved
0.7047	Intermediate Similarity	NPD7583	Approved
0.7044	Intermediate Similarity	NPD4307	Phase 2
0.7029	Intermediate Similarity	NPD8127	Discontinued
0.7025	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7177	Discontinued
0.7012	Intermediate Similarity	NPD6674	Discontinued
0.7012	Intermediate Similarity	NPD1652	Phase 2
0.7006	Intermediate Similarity	NPD4661	Approved
0.7006	Intermediate Similarity	NPD4662	Approved
0.7006	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5953	Discontinued
0.6994	Remote Similarity	NPD2344	Approved
0.6994	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1535	Discovery
0.6974	Remote Similarity	NPD1778	Approved
0.697	Remote Similarity	NPD7930	Approved
0.697	Remote Similarity	NPD7003	Approved
0.6957	Remote Similarity	NPD6653	Approved
0.6954	Remote Similarity	NPD9545	Approved
0.6943	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD920	Approved
0.6923	Remote Similarity	NPD1470	Approved
0.6918	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD919	Approved
0.6907	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD642	Clinical (unspecified phase)

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