NPASS Compound

Structure

NPC31081 OpenBabel07101718182D 28 30 0 0 1 0 0 0 0 0999 V2000 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 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 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 1.7321 -0.0000 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 -3.4641 -3.0000 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 1.7321 -1.0000 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 0.0000 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 -2.5981 -2.5000 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 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -0.8660 -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 -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 -1.5000 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 12 2 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 14 2 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 14 26 1 0 0 0 0 15 11 1 1 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 23 1 6 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 17 24 1 6 0 0 0 18 28 1 1 0 0 0 19 25 2 0 0 0 0 19 28 1 0 0 0 0 20 26 1 1 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.13
Volume:	380.673
LogP:	1.085
LogD:	1.248
LogS:	-2.767
# Rotatable Bonds:	7
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	3.44
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.764
MDCK Permeability:	3.377571192686446e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.309
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.476
Plasma Protein Binding (PPB):	89.8322525024414%
Volume Distribution (VD):	0.677
Pgp-substrate:	5.235151767730713%

ADMET: Metabolism

CYP1A2-inhibitor:	0.169
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.104
CYP2D6-substrate:	0.187
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.091

ADMET: Excretion

Clearance (CL):	4.016
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.213
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.168
Carcinogencity:	0.042
Eye Corrosion:	0.003
Eye Irritation:	0.364
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC31081

Natural Product ID:	NPC31081
*Common Name:**	3'-Benzoylsalicin
IUPAC Name:	[(2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxan-4-yl] benzoate
Synonyms:	3'-Benzoylsalicin
Standard InCHIKey:	WUOFKHTVWRRLNC-YFYQMDMQSA-N
Standard InCHI:	InChI=1S/C20H22O8/c21-10-13-8-4-5-9-14(13)26-20-17(24)18(16(23)15(11-22)27-20)28-19(25)12-6-2-1-3-7-12/h1-9,15-18,20-24H,10-11H2/t15-,16-,17-,18+,20-/m1/s1
SMILES:	c1ccc(cc1)C(=O)O[C@H]1[C@@H]([C@@H](CO)O[C@H]([C@@H]1O)Oc1ccccc1CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467341
PubChem CID:	38361552
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	=	29.7	%	PMID[514915]

☑ 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 NPC31081 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	324
0.1-0.2	1311
0.2-0.3	3437
0.3-0.4	7993
0.4-0.5	10496
0.5-0.6	4563
0.6-0.7	7222
0.7-0.8	6675
0.8-0.85	533
0.85-0.9	118
0.9-0.95	20
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC245219
0.9571	High Similarity	NPC92054
0.9571	High Similarity	NPC140722
0.9571	High Similarity	NPC4958
0.9562	High Similarity	NPC65833
0.9504	High Similarity	NPC22137
0.9433	High Similarity	NPC302989
0.9371	High Similarity	NPC131874
0.9371	High Similarity	NPC93619
0.9286	High Similarity	NPC471028
0.9209	High Similarity	NPC80098
0.9197	High Similarity	NPC166180
0.9178	High Similarity	NPC279281
0.9178	High Similarity	NPC299761
0.9178	High Similarity	NPC92153
0.9178	High Similarity	NPC230439
0.9155	High Similarity	NPC291153
0.911	High Similarity	NPC215811
0.9097	High Similarity	NPC111785
0.9058	High Similarity	NPC471345
0.9048	High Similarity	NPC299435
0.9048	High Similarity	NPC185103
0.9048	High Similarity	NPC260604
0.9034	High Similarity	NPC182350
0.9034	High Similarity	NPC100818
0.903	High Similarity	NPC146540
0.9028	High Similarity	NPC83975
0.8993	High Similarity	NPC476026
0.8993	High Similarity	NPC474441
0.8993	High Similarity	NPC474401
0.8993	High Similarity	NPC43638
0.8993	High Similarity	NPC474398
0.898	High Similarity	NPC259767
0.898	High Similarity	NPC88484
0.8944	High Similarity	NPC242756
0.8933	High Similarity	NPC231475
0.8933	High Similarity	NPC57072
0.8926	High Similarity	NPC127406
0.8913	High Similarity	NPC34456
0.8912	High Similarity	NPC134905
0.8912	High Similarity	NPC36130
0.8905	High Similarity	NPC269421
0.8873	High Similarity	NPC145319
0.8859	High Similarity	NPC99233
0.8851	High Similarity	NPC34965
0.8851	High Similarity	NPC121001
0.8851	High Similarity	NPC183536
0.8851	High Similarity	NPC259182
0.8816	High Similarity	NPC472994
0.8816	High Similarity	NPC195685
0.8816	High Similarity	NPC270675
0.8816	High Similarity	NPC71780
0.8816	High Similarity	NPC477628
0.8816	High Similarity	NPC477629
0.8816	High Similarity	NPC210961
0.8808	High Similarity	NPC43761
0.8803	High Similarity	NPC79908
0.88	High Similarity	NPC149368
0.88	High Similarity	NPC170475
0.88	High Similarity	NPC265480
0.8792	High Similarity	NPC191046
0.8792	High Similarity	NPC143851
0.8792	High Similarity	NPC29763
0.8792	High Similarity	NPC194095
0.8792	High Similarity	NPC39360
0.8792	High Similarity	NPC83283
0.8792	High Similarity	NPC327032
0.8792	High Similarity	NPC106625
0.8792	High Similarity	NPC210003
0.8776	High Similarity	NPC104172
0.8776	High Similarity	NPC88886
0.8759	High Similarity	NPC474044
0.8758	High Similarity	NPC472876
0.875	High Similarity	NPC292443
0.875	High Similarity	NPC328093
0.8742	High Similarity	NPC313163
0.8742	High Similarity	NPC197896
0.8742	High Similarity	NPC161749
0.8742	High Similarity	NPC156457
0.8742	High Similarity	NPC258035
0.8742	High Similarity	NPC23817
0.8733	High Similarity	NPC169248
0.8733	High Similarity	NPC26195
0.8733	High Similarity	NPC72649
0.8733	High Similarity	NPC39351
0.8733	High Similarity	NPC10205
0.8733	High Similarity	NPC95090
0.8733	High Similarity	NPC97052
0.8733	High Similarity	NPC27408
0.8725	High Similarity	NPC157898
0.8725	High Similarity	NPC137813
0.8716	High Similarity	NPC213723
0.8714	High Similarity	NPC212729
0.8707	High Similarity	NPC287294
0.8701	High Similarity	NPC475183
0.8701	High Similarity	NPC80068
0.8701	High Similarity	NPC121290
0.8699	High Similarity	NPC473149
0.8693	High Similarity	NPC224530
0.8693	High Similarity	NPC216496
0.8693	High Similarity	NPC282169
0.8693	High Similarity	NPC101636
0.8693	High Similarity	NPC217950
0.8693	High Similarity	NPC159579
0.8693	High Similarity	NPC132737
0.8693	High Similarity	NPC85707
0.8693	High Similarity	NPC48093
0.8693	High Similarity	NPC259957
0.8693	High Similarity	NPC129217
0.8684	High Similarity	NPC73511
0.8684	High Similarity	NPC160780
0.8684	High Similarity	NPC74319
0.8684	High Similarity	NPC287872
0.8684	High Similarity	NPC289811
0.8681	High Similarity	NPC478250
0.8675	High Similarity	NPC307938
0.8675	High Similarity	NPC323593
0.8675	High Similarity	NPC206378
0.8675	High Similarity	NPC45165
0.8675	High Similarity	NPC471405
0.8675	High Similarity	NPC203500
0.8652	High Similarity	NPC103409
0.8652	High Similarity	NPC294470
0.8645	High Similarity	NPC139060
0.8645	High Similarity	NPC129264
0.8645	High Similarity	NPC19240
0.8645	High Similarity	NPC280923
0.8645	High Similarity	NPC85751
0.8645	High Similarity	NPC205824
0.8639	High Similarity	NPC218685
0.8639	High Similarity	NPC472339
0.8636	High Similarity	NPC22324
0.8636	High Similarity	NPC298171
0.8636	High Similarity	NPC27942
0.863	High Similarity	NPC199928
0.8627	High Similarity	NPC200708
0.8627	High Similarity	NPC239966
0.8627	High Similarity	NPC271479
0.8627	High Similarity	NPC472320
0.8627	High Similarity	NPC203020
0.8627	High Similarity	NPC289346
0.8621	High Similarity	NPC232228
0.8618	High Similarity	NPC473512
0.8618	High Similarity	NPC77672
0.8618	High Similarity	NPC44931
0.8618	High Similarity	NPC133984
0.8618	High Similarity	NPC1913
0.8618	High Similarity	NPC108831
0.8618	High Similarity	NPC129827
0.8618	High Similarity	NPC135391
0.8618	High Similarity	NPC6985
0.8618	High Similarity	NPC133671
0.8618	High Similarity	NPC78263
0.8618	High Similarity	NPC182634
0.8618	High Similarity	NPC60966
0.8618	High Similarity	NPC54802
0.8618	High Similarity	NPC197304
0.8618	High Similarity	NPC122809
0.8618	High Similarity	NPC65003
0.8611	High Similarity	NPC164599
0.8603	High Similarity	NPC114096
0.8591	High Similarity	NPC473966
0.8591	High Similarity	NPC191154
0.859	High Similarity	NPC260504
0.859	High Similarity	NPC473278
0.859	High Similarity	NPC475174
0.859	High Similarity	NPC89809
0.8581	High Similarity	NPC199335
0.8581	High Similarity	NPC121703
0.8571	High Similarity	NPC472859
0.8571	High Similarity	NPC25389
0.8571	High Similarity	NPC311803
0.8571	High Similarity	NPC303913
0.8571	High Similarity	NPC114116
0.8562	High Similarity	NPC41121
0.8562	High Similarity	NPC320283
0.8562	High Similarity	NPC226722
0.8562	High Similarity	NPC473634
0.8562	High Similarity	NPC308265
0.8562	High Similarity	NPC22062
0.8562	High Similarity	NPC138811
0.8562	High Similarity	NPC138915
0.8562	High Similarity	NPC472459
0.8562	High Similarity	NPC111929
0.8562	High Similarity	NPC104677
0.8553	High Similarity	NPC473657
0.8553	High Similarity	NPC261866
0.8553	High Similarity	NPC295613
0.8551	High Similarity	NPC238309
0.8551	High Similarity	NPC295970
0.8542	High Similarity	NPC215512
0.8542	High Similarity	NPC186406
0.8542	High Similarity	NPC476442
0.854	High Similarity	NPC148026
0.8535	High Similarity	NPC116745
0.8533	High Similarity	NPC23253
0.8533	High Similarity	NPC134819
0.8526	High Similarity	NPC178281
0.8526	High Similarity	NPC72016
0.8526	High Similarity	NPC99216

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 NPC31081 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	785
0.2-0.3	1610
0.3-0.4	2588
0.4-0.5	2050
0.5-0.6	1206
0.6-0.7	467
0.7-0.8	157
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8742	High Similarity	NPD4381	Clinical (unspecified phase)
0.8514	High Similarity	NPD5403	Approved
0.8507	High Similarity	NPD1091	Approved
0.8378	Intermediate Similarity	NPD5401	Approved
0.831	Intermediate Similarity	NPD1933	Approved
0.8301	Intermediate Similarity	NPD8455	Phase 2
0.8247	Intermediate Similarity	NPD5402	Approved
0.8231	Intermediate Similarity	NPD4628	Phase 3
0.821	Intermediate Similarity	NPD6559	Discontinued
0.8194	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD3818	Discontinued
0.816	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD7075	Discontinued
0.8137	Intermediate Similarity	NPD7054	Approved
0.8137	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1203	Approved
0.8117	Intermediate Similarity	NPD6801	Discontinued
0.811	Intermediate Similarity	NPD8312	Approved
0.811	Intermediate Similarity	NPD8313	Approved
0.8105	Intermediate Similarity	NPD4380	Phase 2
0.8092	Intermediate Similarity	NPD1653	Approved
0.8086	Intermediate Similarity	NPD7472	Approved
0.8086	Intermediate Similarity	NPD7074	Phase 3
0.8085	Intermediate Similarity	NPD6832	Phase 2
0.8082	Intermediate Similarity	NPD1551	Phase 2
0.8067	Intermediate Similarity	NPD6799	Approved
0.8065	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6797	Phase 2
0.7988	Intermediate Similarity	NPD7251	Discontinued
0.7973	Intermediate Similarity	NPD1549	Phase 2
0.7939	Intermediate Similarity	NPD7808	Phase 3
0.7935	Intermediate Similarity	NPD7411	Suspended
0.7929	Intermediate Similarity	NPD3225	Approved
0.7914	Intermediate Similarity	NPD9717	Approved
0.7905	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD2797	Approved
0.7867	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD3750	Approved
0.7847	Intermediate Similarity	NPD6798	Discontinued
0.7847	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6233	Phase 2
0.7785	Intermediate Similarity	NPD7266	Discontinued
0.7785	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1934	Approved
0.7771	Intermediate Similarity	NPD7685	Pre-registration
0.777	Intermediate Similarity	NPD4308	Phase 3
0.777	Intermediate Similarity	NPD7033	Discontinued
0.7756	Intermediate Similarity	NPD6599	Discontinued
0.7724	Intermediate Similarity	NPD2313	Discontinued
0.7724	Intermediate Similarity	NPD3268	Approved
0.7722	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7819	Suspended
0.7714	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7687	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD447	Suspended
0.7674	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3748	Approved
0.7622	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6166	Phase 2
0.7622	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2796	Approved
0.76	Intermediate Similarity	NPD2935	Discontinued
0.7597	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7458	Discontinued
0.7569	Intermediate Similarity	NPD1019	Discontinued
0.7568	Intermediate Similarity	NPD6355	Discontinued
0.7566	Intermediate Similarity	NPD1652	Phase 2
0.7564	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD37	Approved
0.7546	Intermediate Similarity	NPD7199	Phase 2
0.7533	Intermediate Similarity	NPD1510	Phase 2
0.753	Intermediate Similarity	NPD3751	Discontinued
0.7516	Intermediate Similarity	NPD4967	Phase 2
0.7516	Intermediate Similarity	NPD7768	Phase 2
0.7516	Intermediate Similarity	NPD4965	Approved
0.7516	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD4307	Phase 2
0.7484	Intermediate Similarity	NPD1511	Approved
0.7468	Intermediate Similarity	NPD3226	Approved
0.7468	Intermediate Similarity	NPD6190	Approved
0.7467	Intermediate Similarity	NPD7097	Phase 1
0.7453	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2798	Approved
0.7436	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2346	Discontinued
0.7432	Intermediate Similarity	NPD4062	Phase 3
0.7429	Intermediate Similarity	NPD9545	Approved
0.7425	Intermediate Similarity	NPD7228	Approved
0.7423	Intermediate Similarity	NPD6234	Discontinued
0.7419	Intermediate Similarity	NPD7440	Discontinued
0.7417	Intermediate Similarity	NPD2799	Discontinued
0.741	Intermediate Similarity	NPD9493	Approved
0.741	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3882	Suspended
0.7403	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3787	Discontinued
0.7389	Intermediate Similarity	NPD1512	Approved
0.7383	Intermediate Similarity	NPD1240	Approved
0.7383	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1613	Approved
0.7379	Intermediate Similarity	NPD3267	Approved
0.7379	Intermediate Similarity	NPD3266	Approved
0.7375	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD411	Approved
0.7349	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4340	Discontinued
0.7333	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5124	Phase 1
0.7322	Intermediate Similarity	NPD7583	Approved
0.732	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6002	Phase 3
0.732	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6005	Phase 3
0.732	Intermediate Similarity	NPD6004	Phase 3
0.7305	Intermediate Similarity	NPD1894	Discontinued
0.7292	Intermediate Similarity	NPD1481	Phase 2
0.7292	Intermediate Similarity	NPD1608	Approved
0.7285	Intermediate Similarity	NPD1607	Approved
0.7283	Intermediate Similarity	NPD7585	Approved
0.7259	Intermediate Similarity	NPD290	Approved
0.7256	Intermediate Similarity	NPD3749	Approved
0.7253	Intermediate Similarity	NPD7435	Discontinued
0.7248	Intermediate Similarity	NPD3764	Approved
0.7222	Intermediate Similarity	NPD1535	Discovery
0.7222	Intermediate Similarity	NPD422	Phase 1
0.7219	Intermediate Similarity	NPD230	Phase 1
0.7215	Intermediate Similarity	NPD4662	Approved
0.7215	Intermediate Similarity	NPD4661	Approved
0.7211	Intermediate Similarity	NPD5647	Approved
0.7203	Intermediate Similarity	NPD1778	Approved
0.7202	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6232	Discontinued
0.7184	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1548	Phase 1
0.7182	Intermediate Similarity	NPD6781	Approved
0.7182	Intermediate Similarity	NPD6780	Approved
0.7182	Intermediate Similarity	NPD6778	Approved
0.7182	Intermediate Similarity	NPD6782	Approved
0.7182	Intermediate Similarity	NPD6776	Approved
0.7182	Intermediate Similarity	NPD6777	Approved
0.7182	Intermediate Similarity	NPD6779	Approved
0.7171	Intermediate Similarity	NPD6653	Approved
0.717	Intermediate Similarity	NPD5049	Phase 3
0.717	Intermediate Similarity	NPD6273	Approved
0.7169	Intermediate Similarity	NPD5494	Approved
0.7161	Intermediate Similarity	NPD2424	Discontinued
0.7161	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3496	Discontinued
0.7151	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD7584	Approved
0.7134	Intermediate Similarity	NPD2354	Approved
0.7134	Intermediate Similarity	NPD4288	Approved
0.7134	Intermediate Similarity	NPD3887	Approved
0.7126	Intermediate Similarity	NPD6959	Discontinued
0.7117	Intermediate Similarity	NPD6844	Discontinued
0.7114	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4908	Phase 1
0.7105	Intermediate Similarity	NPD4622	Approved
0.7105	Intermediate Similarity	NPD4618	Approved
0.7104	Intermediate Similarity	NPD6823	Phase 2
0.7103	Intermediate Similarity	NPD1610	Phase 2
0.7095	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5058	Phase 3
0.7083	Intermediate Similarity	NPD17	Approved
0.7074	Intermediate Similarity	NPD7783	Phase 2
0.7074	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1241	Discontinued
0.707	Intermediate Similarity	NPD7003	Approved
0.7067	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7473	Discontinued
0.7052	Intermediate Similarity	NPD7039	Approved
0.7052	Intermediate Similarity	NPD7038	Approved
0.7051	Intermediate Similarity	NPD2897	Discontinued
0.7047	Intermediate Similarity	NPD2861	Phase 2
0.7047	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4060	Phase 1
0.7032	Intermediate Similarity	NPD6032	Approved
0.7027	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD8127	Discontinued
0.7021	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7874	Approved
0.702	Intermediate Similarity	NPD1296	Phase 2
0.702	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD920	Approved
0.7017	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5585	Approved
0.7013	Intermediate Similarity	NPD5689	Approved

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