NPASS Compound

Structure

NPC138227 OpenBabel07101718192D 31 34 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 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 -4.3301 -1.5000 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 -5.1962 2.0000 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 -3.4641 -1.0000 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 -3.4641 2.0000 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 -3.4641 3.0000 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 -4.3301 1.5000 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 -0.0000 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 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 -6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 -5.1962 -3.0000 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 -1.7321 2.0000 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 -4.3301 0.5000 0.0000 O 0 3 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 2 2 0 0 0 0 1 7 1 0 0 0 0 2 10 1 0 0 0 0 3 7 2 0 0 0 0 3 12 1 0 0 0 0 4 8 1 0 0 0 0 4 11 2 0 0 0 0 5 8 2 0 0 0 0 5 13 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 9 13 1 0 0 0 0 10 12 2 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 29 2 0 0 0 0 14 18 2 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 1 0 0 0 16 19 1 0 0 0 0 16 26 1 6 0 0 0 17 20 1 0 0 0 0 17 27 1 6 0 0 0 18 29 1 0 0 0 0 19 28 1 1 0 0 0 19 31 1 0 0 0 0 20 30 1 1 0 0 0 20 31 1 0 0 0 0 M CHG 1 29 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	435.09
Volume:	397.169
LogP:	0.874
LogD:	0.703
LogS:	-3.088
# Rotatable Bonds:	3
TPSA:	191.6
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	4.328
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.437
MDCK Permeability:	5.572723694058368e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.778
Human Intestinal Absorption (HIA):	0.588
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	93.43966674804688%
Volume Distribution (VD):	0.647
Pgp-substrate:	11.0813570022583%

ADMET: Metabolism

CYP1A2-inhibitor:	0.232
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.223
CYP2D6-inhibitor:	0.116
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.011

ADMET: Excretion

Clearance (CL):	7.165
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.775
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.854
Carcinogencity:	0.106
Eye Corrosion:	0.003
Eye Irritation:	0.794
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC138227

Natural Product ID:	NPC138227
*Common Name:**	E163
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxyoxane-2,3,4,5-tetrol
Synonyms:
Standard InCHIKey:	IUKZBFPSIRTYSG-VBYALHQYSA-O
Standard InCHI:	InChI=1S/C20H18O11/c21-8-4-11(23)9-6-14(30-20-17(27)15(25)16(26)19(28)31-20)18(29-13(9)5-8)7-1-2-10(22)12(24)3-7/h1-6,15-17,19-20,25-28H,(H3-,21,22,23,24)/p+1/t15-,16-,17+,19-,20+/m0/s1
SMILES:	c1cc(c(cc1c1c(cc2c(cc(cc2[o+]1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452482
PubChem CID:	10252404
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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
NPO33237	tart cherries	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10075763]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	75.0	%	PMID[466065]

☑ 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 NPC138227 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	459
0.1-0.2	1877
0.2-0.3	4345
0.3-0.4	9924
0.4-0.5	7999
0.5-0.6	4198
0.6-0.7	5199
0.7-0.8	5329
0.8-0.85	1656
0.85-0.9	1114
0.9-0.95	427
0.95-1	170

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469313
1.0	High Similarity	NPC76176
1.0	High Similarity	NPC168579
0.9926	High Similarity	NPC37793
0.9855	High Similarity	NPC125755
0.9784	High Similarity	NPC15538
0.9784	High Similarity	NPC473480
0.9783	High Similarity	NPC161700
0.9783	High Similarity	NPC277867
0.9714	High Similarity	NPC280945
0.964	High Similarity	NPC475096
0.9635	High Similarity	NPC469661
0.9571	High Similarity	NPC99515
0.9571	High Similarity	NPC190714
0.9565	High Similarity	NPC189115
0.9565	High Similarity	NPC475084
0.951	High Similarity	NPC473621
0.9504	High Similarity	NPC227902
0.9496	High Similarity	NPC252169
0.9496	High Similarity	NPC473044
0.9485	High Similarity	NPC203230
0.9485	High Similarity	NPC242028
0.9437	High Similarity	NPC175976
0.9429	High Similarity	NPC25292
0.9429	High Similarity	NPC473045
0.9424	High Similarity	NPC469559
0.942	High Similarity	NPC106944
0.9416	High Similarity	NPC65530
0.9416	High Similarity	NPC87777
0.9416	High Similarity	NPC59324
0.9416	High Similarity	NPC262328
0.9353	High Similarity	NPC210192
0.9348	High Similarity	NPC98777
0.9348	High Similarity	NPC212770
0.9338	High Similarity	NPC188555
0.9338	High Similarity	NPC130496
0.931	High Similarity	NPC53587
0.931	High Similarity	NPC21902
0.931	High Similarity	NPC169404
0.931	High Similarity	NPC176186
0.9286	High Similarity	NPC472353
0.9275	High Similarity	NPC211549
0.927	High Similarity	NPC164787
0.927	High Similarity	NPC238243
0.9247	High Similarity	NPC150442
0.9247	High Similarity	NPC78809
0.9231	High Similarity	NPC39657
0.922	High Similarity	NPC81638
0.9214	High Similarity	NPC178054
0.9209	High Similarity	NPC292487
0.9203	High Similarity	NPC16435
0.9203	High Similarity	NPC165482
0.9203	High Similarity	NPC40664
0.9203	High Similarity	NPC302701
0.9203	High Similarity	NPC197723
0.9203	High Similarity	NPC3293
0.9203	High Similarity	NPC269091
0.9203	High Similarity	NPC138350
0.9203	High Similarity	NPC306441
0.9197	High Similarity	NPC87696
0.9191	High Similarity	NPC15658
0.9191	High Similarity	NPC126029
0.9191	High Similarity	NPC85799
0.9191	High Similarity	NPC26080
0.9191	High Similarity	NPC219876
0.9191	High Similarity	NPC303422
0.9191	High Similarity	NPC261619
0.9191	High Similarity	NPC61477
0.9191	High Similarity	NPC185604
0.9191	High Similarity	NPC165686
0.9191	High Similarity	NPC78770
0.9178	High Similarity	NPC226108
0.9178	High Similarity	NPC272552
0.9178	High Similarity	NPC322899
0.9178	High Similarity	NPC134911
0.9178	High Similarity	NPC46283
0.9178	High Similarity	NPC44192
0.9178	High Similarity	NPC469944
0.9172	High Similarity	NPC472710
0.9172	High Similarity	NPC472709
0.9172	High Similarity	NPC238140
0.9155	High Similarity	NPC28440
0.9155	High Similarity	NPC171932
0.9149	High Similarity	NPC5253
0.9149	High Similarity	NPC139976
0.9149	High Similarity	NPC49542
0.9149	High Similarity	NPC128337
0.9149	High Similarity	NPC472714
0.9149	High Similarity	NPC84207
0.9149	High Similarity	NPC230718
0.9149	High Similarity	NPC5262
0.9137	High Similarity	NPC138738
0.9137	High Similarity	NPC134260
0.9137	High Similarity	NPC470413
0.913	High Similarity	NPC234333
0.913	High Similarity	NPC94750
0.913	High Similarity	NPC61946
0.913	High Similarity	NPC47398
0.913	High Similarity	NPC151224
0.913	High Similarity	NPC121812
0.913	High Similarity	NPC112246
0.913	High Similarity	NPC260898
0.913	High Similarity	NPC112939
0.913	High Similarity	NPC474206
0.913	High Similarity	NPC470356
0.9124	High Similarity	NPC115022
0.9124	High Similarity	NPC294166
0.9124	High Similarity	NPC11060
0.9118	High Similarity	NPC268266
0.9118	High Similarity	NPC121376
0.9118	High Similarity	NPC268342
0.9118	High Similarity	NPC220825
0.9118	High Similarity	NPC42760
0.9116	High Similarity	NPC20050
0.9116	High Similarity	NPC306267
0.9103	High Similarity	NPC55158
0.9103	High Similarity	NPC286235
0.9103	High Similarity	NPC51328
0.9078	High Similarity	NPC108674
0.9067	High Similarity	NPC185231
0.9065	High Similarity	NPC164857
0.9065	High Similarity	NPC230734
0.9065	High Similarity	NPC199459
0.9065	High Similarity	NPC52277
0.9065	High Similarity	NPC227503
0.9065	High Similarity	NPC470802
0.9065	High Similarity	NPC474639
0.9065	High Similarity	NPC177035
0.9058	High Similarity	NPC48863
0.9058	High Similarity	NPC476411
0.9058	High Similarity	NPC107478
0.9058	High Similarity	NPC13745
0.9058	High Similarity	NPC251981
0.9058	High Similarity	NPC170694
0.9051	High Similarity	NPC254275
0.9041	High Similarity	NPC225815
0.9041	High Similarity	NPC469707
0.9041	High Similarity	NPC218041
0.9041	High Similarity	NPC214326
0.9041	High Similarity	NPC260781
0.9041	High Similarity	NPC145979
0.9041	High Similarity	NPC185955
0.9041	High Similarity	NPC9933
0.9041	High Similarity	NPC182368
0.9041	High Similarity	NPC469706
0.9034	High Similarity	NPC130449
0.9034	High Similarity	NPC270751
0.9034	High Similarity	NPC248132
0.9021	High Similarity	NPC187774
0.9021	High Similarity	NPC472713
0.9021	High Similarity	NPC292443
0.9021	High Similarity	NPC473046
0.9021	High Similarity	NPC225445
0.9021	High Similarity	NPC472712
0.9021	High Similarity	NPC118385
0.9007	High Similarity	NPC1253
0.9007	High Similarity	NPC100936
0.9	High Similarity	NPC176051
0.9	High Similarity	NPC103976
0.9	High Similarity	NPC474282
0.9	High Similarity	NPC107551
0.9	High Similarity	NPC326797
0.9	High Similarity	NPC102904
0.8993	High Similarity	NPC470236
0.8993	High Similarity	NPC473413
0.8986	High Similarity	NPC215833
0.8986	High Similarity	NPC69513
0.8986	High Similarity	NPC263064
0.8986	High Similarity	NPC49074
0.8986	High Similarity	NPC475840
0.8986	High Similarity	NPC132895
0.8978	High Similarity	NPC9912
0.8978	High Similarity	NPC475067
0.8978	High Similarity	NPC166168
0.8973	High Similarity	NPC106138
0.8971	High Similarity	NPC218003
0.8966	High Similarity	NPC202742
0.8966	High Similarity	NPC114505
0.8966	High Similarity	NPC15956
0.8966	High Similarity	NPC193473
0.8966	High Similarity	NPC18185
0.8966	High Similarity	NPC213074
0.8966	High Similarity	NPC294558
0.8966	High Similarity	NPC31325
0.8966	High Similarity	NPC263940
0.8966	High Similarity	NPC170103
0.8966	High Similarity	NPC262911
0.8966	High Similarity	NPC224674
0.8966	High Similarity	NPC275284
0.8966	High Similarity	NPC204770
0.8966	High Similarity	NPC236202
0.8966	High Similarity	NPC58190
0.8966	High Similarity	NPC82917
0.8966	High Similarity	NPC70409
0.8966	High Similarity	NPC108811
0.8958	High Similarity	NPC307466
0.8951	High Similarity	NPC46092
0.8951	High Similarity	NPC470950
0.8951	High Similarity	NPC472451
0.8951	High Similarity	NPC278961

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 NPC138227 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	418
0.1-0.2	953
0.2-0.3	1980
0.3-0.4	2678
0.4-0.5	1751
0.5-0.6	909
0.6-0.7	300
0.7-0.8	122
0.8-0.85	11
0.85-0.9	15
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9191	High Similarity	NPD1613	Approved
0.9191	High Similarity	NPD1612	Clinical (unspecified phase)
0.8897	High Similarity	NPD1529	Clinical (unspecified phase)
0.8824	High Similarity	NPD1530	Clinical (unspecified phase)
0.8716	High Similarity	NPD1653	Approved
0.8696	High Similarity	NPD3027	Phase 3
0.8553	High Similarity	NPD7074	Phase 3
0.8491	Intermediate Similarity	NPD7054	Approved
0.8438	Intermediate Similarity	NPD7472	Approved
0.8414	Intermediate Similarity	NPD7266	Discontinued
0.8385	Intermediate Similarity	NPD6797	Phase 2
0.8382	Intermediate Similarity	NPD1091	Approved
0.8333	Intermediate Similarity	NPD7251	Discontinued
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8269	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD4908	Phase 1
0.8205	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7228	Approved
0.8176	Intermediate Similarity	NPD6674	Discontinued
0.8171	Intermediate Similarity	NPD7808	Phase 3
0.8171	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD1610	Phase 2
0.8112	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6166	Phase 2
0.8013	Intermediate Similarity	NPD1934	Approved
0.7987	Intermediate Similarity	NPD6234	Discontinued
0.7962	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD1548	Phase 1
0.7927	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD2861	Phase 2
0.7898	Intermediate Similarity	NPD37	Approved
0.7888	Intermediate Similarity	NPD7199	Phase 2
0.7862	Intermediate Similarity	NPD4967	Phase 2
0.7862	Intermediate Similarity	NPD4965	Approved
0.7862	Intermediate Similarity	NPD4966	Approved
0.7848	Intermediate Similarity	NPD8455	Phase 2
0.7831	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7683	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7240	Approved
0.7671	Intermediate Similarity	NPD4625	Phase 3
0.7658	Intermediate Similarity	NPD4380	Phase 2
0.7655	Intermediate Similarity	NPD3018	Phase 2
0.7625	Intermediate Similarity	NPD1465	Phase 2
0.7625	Intermediate Similarity	NPD2801	Approved
0.7622	Intermediate Similarity	NPD4749	Approved
0.7619	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1511	Approved
0.7582	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD5058	Phase 3
0.7516	Intermediate Similarity	NPD1512	Approved
0.7515	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD2982	Phase 2
0.7485	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3705	Approved
0.7469	Intermediate Similarity	NPD3817	Phase 2
0.7468	Intermediate Similarity	NPD1652	Phase 2
0.7467	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5124	Phase 1
0.7431	Intermediate Similarity	NPD2981	Phase 2
0.7423	Intermediate Similarity	NPD3882	Suspended
0.74	Intermediate Similarity	NPD4060	Phase 1
0.7394	Intermediate Similarity	NPD1357	Approved
0.7389	Intermediate Similarity	NPD7212	Phase 2
0.7389	Intermediate Similarity	NPD7213	Phase 3
0.7383	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7075	Discontinued
0.7368	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4538	Approved
0.7368	Intermediate Similarity	NPD4536	Approved
0.7362	Intermediate Similarity	NPD5402	Approved
0.7342	Intermediate Similarity	NPD7447	Phase 1
0.7338	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3751	Discontinued
0.7333	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5960	Phase 3
0.732	Intermediate Similarity	NPD5588	Approved
0.7319	Intermediate Similarity	NPD228	Approved
0.729	Intermediate Similarity	NPD1549	Phase 2
0.7289	Intermediate Similarity	NPD5494	Approved
0.7283	Intermediate Similarity	NPD8312	Approved
0.7283	Intermediate Similarity	NPD8313	Approved
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7680	Approved
0.7267	Intermediate Similarity	NPD7685	Pre-registration
0.7266	Intermediate Similarity	NPD7843	Approved
0.7261	Intermediate Similarity	NPD6190	Approved
0.7255	Intermediate Similarity	NPD7097	Phase 1
0.725	Intermediate Similarity	NPD5403	Approved
0.725	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD422	Phase 1
0.7234	Intermediate Similarity	NPD7157	Approved
0.7234	Intermediate Similarity	NPD6671	Approved
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2684	Approved
0.7216	Intermediate Similarity	NPD6841	Approved
0.7216	Intermediate Similarity	NPD6842	Approved
0.7216	Intermediate Similarity	NPD6843	Phase 3
0.7214	Intermediate Similarity	NPD5283	Phase 1
0.7211	Intermediate Similarity	NPD8651	Approved
0.72	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3750	Approved
0.7195	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2978	Approved
0.7195	Intermediate Similarity	NPD2977	Approved
0.7171	Intermediate Similarity	NPD1558	Phase 1
0.7171	Intermediate Similarity	NPD3620	Phase 2
0.7171	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD290	Approved
0.7152	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7152	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8053	Approved
0.7143	Intermediate Similarity	NPD8054	Approved
0.7143	Intermediate Similarity	NPD6959	Discontinued
0.7134	Intermediate Similarity	NPD6801	Discontinued
0.7134	Intermediate Similarity	NPD5177	Phase 3
0.7126	Intermediate Similarity	NPD7549	Discontinued
0.7125	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5401	Approved
0.7117	Intermediate Similarity	NPD4678	Approved
0.7117	Intermediate Similarity	NPD4675	Approved
0.7115	Intermediate Similarity	NPD3540	Phase 1
0.7114	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5846	Approved
0.7103	Intermediate Similarity	NPD6516	Phase 2
0.7101	Intermediate Similarity	NPD6232	Discontinued
0.7097	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7819	Suspended
0.7089	Intermediate Similarity	NPD3892	Phase 2
0.7073	Intermediate Similarity	NPD7411	Suspended
0.7073	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6100	Approved
0.7051	Intermediate Similarity	NPD6099	Approved
0.7051	Intermediate Similarity	NPD3539	Phase 1
0.705	Intermediate Similarity	NPD3021	Approved
0.705	Intermediate Similarity	NPD3022	Approved
0.7044	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2677	Approved
0.7019	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6355	Discontinued
0.7006	Intermediate Similarity	NPD1375	Discontinued
0.7006	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD6584	Phase 3
0.7	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6233	Phase 2
0.6987	Remote Similarity	NPD4108	Discontinued
0.6987	Remote Similarity	NPD7033	Discontinued
0.6987	Remote Similarity	NPD1510	Phase 2
0.6986	Remote Similarity	NPD5126	Approved
0.6986	Remote Similarity	NPD5125	Phase 3
0.6981	Remote Similarity	NPD4628	Phase 3
0.6981	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7473	Discontinued
0.6975	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7095	Approved
0.6966	Remote Similarity	NPD4663	Approved
0.6962	Remote Similarity	NPD2424	Discontinued
0.6957	Remote Similarity	NPD6799	Approved
0.6957	Remote Similarity	NPD968	Approved
0.6951	Remote Similarity	NPD4005	Discontinued
0.6949	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2796	Approved
0.6928	Remote Similarity	NPD3384	Approved
0.6928	Remote Similarity	NPD3382	Approved
0.6928	Remote Similarity	NPD3383	Approved
0.6927	Remote Similarity	NPD7906	Approved
0.6919	Remote Similarity	NPD27	Approved
0.6919	Remote Similarity	NPD2489	Approved
0.6918	Remote Similarity	NPD5061	Approved
0.6918	Remote Similarity	NPD5062	Approved
0.6918	Remote Similarity	NPD3060	Approved
0.6914	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7768	Phase 2
0.6903	Remote Similarity	NPD230	Phase 1
0.6903	Remote Similarity	NPD5735	Approved
0.6903	Remote Similarity	NPD4340	Discontinued
0.6894	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4578	Approved
0.6893	Remote Similarity	NPD4577	Approved
0.6889	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3748	Approved
0.6875	Remote Similarity	NPD4535	Phase 3
0.6875	Remote Similarity	NPD7466	Approved
0.6867	Remote Similarity	NPD3225	Approved
0.686	Remote Similarity	NPD2970	Approved
0.686	Remote Similarity	NPD2969	Approved
0.6852	Remote Similarity	NPD1774	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