NPASS Compound

Structure

NPC473044 OpenBabel07101718192D 28 30 0 0 1 0 0 0 0 0999 V2000 -1.7321 -5.0000 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 -4.3301 -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 -0.8660 -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 -3.0000 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 -2.5981 -1.5000 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 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 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 -3.4641 0.0000 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 0.8660 -0.5000 0.0000 C 0 0 2 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 -5.1962 0.0000 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 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 1 26 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 13 1 0 0 0 0 4 10 2 0 0 0 0 4 11 1 0 0 0 0 5 10 1 0 0 0 0 5 12 2 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 14 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 8 1 6 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 1 0 0 0 17 18 1 0 0 0 0 17 24 1 6 0 0 0 18 19 1 0 0 0 0 18 25 1 1 0 0 0 19 27 1 6 0 0 0 19 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.13
Volume:	374.804
LogP:	0.86
LogD:	0.812
LogS:	-2.782
# Rotatable Bonds:	5
TPSA:	149.07
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.384
Synthetic Accessibility Score:	3.589
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.255
MDCK Permeability:	1.8833910871762782e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.142
Human Intestinal Absorption (HIA):	0.542
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	94.59585571289062%
Volume Distribution (VD):	0.541
Pgp-substrate:	3.846122980117798%

ADMET: Metabolism

CYP1A2-inhibitor:	0.339
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.408
CYP2D6-inhibitor:	0.258
CYP2D6-substrate:	0.613
CYP3A4-inhibitor:	0.09
CYP3A4-substrate:	0.047

ADMET: Excretion

Clearance (CL):	9.665
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.124
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.573
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.941
Carcinogencity:	0.145
Eye Corrosion:	0.003
Eye Irritation:	0.166
Respiratory Toxicity:	0.069

Download Data

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

Natural Product: NPC473044

Natural Product ID:	NPC473044
*Common Name:**	XBEXOBHATDOZLZ-UJWQCDCRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XBEXOBHATDOZLZ-UJWQCDCRSA-N
Standard InCHI:	InChI=1S/C19H22O9/c1-26-11-4-10(9-2-3-13(21)14(22)6-9)5-12(7-11)27-19-18(25)17(24)16(23)15(8-20)28-19/h2-7,15-25H,8H2,1H3/t15-,16-,17+,18-,19-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(OC)cc(c2)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3608477
PubChem CID:	n.a.
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
NPO32985	osteomeles schwerinae	Species	Rosaceae	Eukaryota	Leaves and Twigs	n.a.	n.a.	PMID[26331986]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	5600.0	nM	PMID[575567]

☑ 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 NPC473044 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	426
0.1-0.2	1612
0.2-0.3	4214
0.3-0.4	10603
0.4-0.5	7778
0.5-0.6	4595
0.6-0.7	6789
0.7-0.8	4969
0.8-0.85	1110
0.85-0.9	473
0.9-0.95	113
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC25292
0.9926	High Similarity	NPC473045
0.9783	High Similarity	NPC99515
0.9783	High Similarity	NPC190714
0.9779	High Similarity	NPC189115
0.9706	High Similarity	NPC469661
0.9643	High Similarity	NPC175976
0.9635	High Similarity	NPC469559
0.9571	High Similarity	NPC39657
0.9568	High Similarity	NPC475096
0.9559	High Similarity	NPC98777
0.9559	High Similarity	NPC212770
0.9556	High Similarity	NPC203230
0.9556	High Similarity	NPC242028
0.95	High Similarity	NPC125755
0.9496	High Similarity	NPC168579
0.9496	High Similarity	NPC76176
0.9496	High Similarity	NPC138227
0.9496	High Similarity	NPC469313
0.9493	High Similarity	NPC475084
0.9493	High Similarity	NPC5262
0.9493	High Similarity	NPC472714
0.9485	High Similarity	NPC59324
0.9485	High Similarity	NPC65530
0.9437	High Similarity	NPC55158
0.9437	High Similarity	NPC51328
0.9437	High Similarity	NPC286235
0.9433	High Similarity	NPC227902
0.9433	High Similarity	NPC15538
0.9433	High Similarity	NPC473480
0.9429	High Similarity	NPC161700
0.9429	High Similarity	NPC277867
0.9424	High Similarity	NPC37793
0.9375	High Similarity	NPC21902
0.9366	High Similarity	NPC248132
0.9366	High Similarity	NPC130449
0.9357	High Similarity	NPC118385
0.9357	High Similarity	NPC472712
0.9357	High Similarity	NPC187774
0.9357	High Similarity	NPC472713
0.9357	High Similarity	NPC473046
0.9343	High Similarity	NPC470413
0.9343	High Similarity	NPC138738
0.9333	High Similarity	NPC115022
0.9333	High Similarity	NPC294166
0.931	High Similarity	NPC78809
0.9286	High Similarity	NPC46092
0.9286	High Similarity	NPC470950
0.9286	High Similarity	NPC185307
0.9286	High Similarity	NPC252169
0.9281	High Similarity	NPC210192
0.9275	High Similarity	NPC22517
0.927	High Similarity	NPC199459
0.927	High Similarity	NPC177035
0.927	High Similarity	NPC52277
0.9265	High Similarity	NPC107478
0.9265	High Similarity	NPC251981
0.9265	High Similarity	NPC170694
0.9265	High Similarity	NPC48863
0.9265	High Similarity	NPC13745
0.9259	High Similarity	NPC165686
0.9259	High Similarity	NPC303422
0.9259	High Similarity	NPC85799
0.9259	High Similarity	NPC26080
0.9236	High Similarity	NPC472710
0.9236	High Similarity	NPC472709
0.9231	High Similarity	NPC280945
0.922	High Similarity	NPC470235
0.922	High Similarity	NPC129417
0.922	High Similarity	NPC283995
0.9214	High Similarity	NPC48309
0.9214	High Similarity	NPC476356
0.9214	High Similarity	NPC60249
0.9209	High Similarity	NPC106944
0.9197	High Similarity	NPC238243
0.9191	High Similarity	NPC49074
0.9191	High Similarity	NPC215833
0.9191	High Similarity	NPC69513
0.9191	High Similarity	NPC132895
0.9185	High Similarity	NPC475067
0.9185	High Similarity	NPC121376
0.9172	High Similarity	NPC473621
0.9167	High Similarity	NPC106138
0.9155	High Similarity	NPC38041
0.9155	High Similarity	NPC18979
0.9155	High Similarity	NPC22150
0.9155	High Similarity	NPC279298
0.9149	High Similarity	NPC81638
0.9143	High Similarity	NPC472711
0.9143	High Similarity	NPC76871
0.913	High Similarity	NPC40664
0.913	High Similarity	NPC197723
0.913	High Similarity	NPC25695
0.913	High Similarity	NPC16435
0.913	High Similarity	NPC306441
0.913	High Similarity	NPC165482
0.913	High Similarity	NPC172818
0.913	High Similarity	NPC138350
0.913	High Similarity	NPC164857
0.913	High Similarity	NPC3293
0.9124	High Similarity	NPC188555
0.9124	High Similarity	NPC130496
0.9124	High Similarity	NPC476411
0.9124	High Similarity	NPC187194
0.9118	High Similarity	NPC160991
0.9118	High Similarity	NPC7903
0.9118	High Similarity	NPC299144
0.9118	High Similarity	NPC184447
0.9118	High Similarity	NPC201587
0.9118	High Similarity	NPC253105
0.9118	High Similarity	NPC162093
0.9118	High Similarity	NPC470270
0.9118	High Similarity	NPC16208
0.9118	High Similarity	NPC35932
0.911	High Similarity	NPC53587
0.911	High Similarity	NPC176186
0.911	High Similarity	NPC169404
0.9097	High Similarity	NPC270751
0.9091	High Similarity	NPC112861
0.9071	High Similarity	NPC291101
0.9071	High Similarity	NPC266197
0.9065	High Similarity	NPC87777
0.9065	High Similarity	NPC124149
0.9065	High Similarity	NPC474039
0.9065	High Similarity	NPC134260
0.9065	High Similarity	NPC304152
0.9065	High Similarity	NPC262328
0.9058	High Similarity	NPC474206
0.9058	High Similarity	NPC234333
0.9058	High Similarity	NPC61946
0.9058	High Similarity	NPC47398
0.9058	High Similarity	NPC151224
0.9058	High Similarity	NPC164787
0.9058	High Similarity	NPC470236
0.9058	High Similarity	NPC470356
0.9058	High Similarity	NPC94750
0.9058	High Similarity	NPC112939
0.9058	High Similarity	NPC121812
0.9058	High Similarity	NPC112246
0.9058	High Similarity	NPC260898
0.9051	High Similarity	NPC11060
0.9048	High Similarity	NPC150442
0.9044	High Similarity	NPC65942
0.9044	High Similarity	NPC248307
0.9044	High Similarity	NPC472597
0.9037	High Similarity	NPC218003
0.9028	High Similarity	NPC275284
0.9028	High Similarity	NPC193473
0.9028	High Similarity	NPC15956
0.9028	High Similarity	NPC224674
0.9028	High Similarity	NPC31325
0.9028	High Similarity	NPC114505
0.9028	High Similarity	NPC213074
0.9021	High Similarity	NPC469586
0.9021	High Similarity	NPC307466
0.9014	High Similarity	NPC278961
0.9014	High Similarity	NPC477898
0.9014	High Similarity	NPC113680
0.9007	High Similarity	NPC178054
0.9007	High Similarity	NPC471389
0.9	High Similarity	NPC292487
0.8993	High Similarity	NPC227503
0.8993	High Similarity	NPC269091
0.8993	High Similarity	NPC470802
0.8993	High Similarity	NPC162659
0.8993	High Similarity	NPC474639
0.8993	High Similarity	NPC302701
0.8993	High Similarity	NPC230734
0.8993	High Similarity	NPC270456
0.8993	High Similarity	NPC248727
0.8993	High Similarity	NPC265433
0.8993	High Similarity	NPC234952
0.8986	High Similarity	NPC35731
0.8986	High Similarity	NPC310854
0.8978	High Similarity	NPC61477
0.8978	High Similarity	NPC261619
0.8978	High Similarity	NPC185604
0.8978	High Similarity	NPC219876
0.8978	High Similarity	NPC15658
0.8978	High Similarity	NPC78770
0.8978	High Similarity	NPC470752
0.8978	High Similarity	NPC126029
0.8973	High Similarity	NPC145979
0.8973	High Similarity	NPC260781
0.8973	High Similarity	NPC225815
0.8973	High Similarity	NPC469707
0.8973	High Similarity	NPC185955
0.8973	High Similarity	NPC469706
0.8973	High Similarity	NPC214326
0.8973	High Similarity	NPC218041
0.8973	High Similarity	NPC9933
0.8973	High Similarity	NPC182368
0.8971	High Similarity	NPC80600
0.8971	High Similarity	NPC262606
0.8971	High Similarity	NPC472338
0.8971	High Similarity	NPC472024
0.8966	High Similarity	NPC301961
0.8966	High Similarity	NPC478237
0.8966	High Similarity	NPC166584
0.8951	High Similarity	NPC84181

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 NPC473044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	874
0.2-0.3	1852
0.3-0.4	2740
0.4-0.5	1697
0.5-0.6	929
0.6-0.7	580
0.7-0.8	118
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8978	High Similarity	NPD1612	Clinical (unspecified phase)
0.8978	High Similarity	NPD1613	Approved
0.8897	High Similarity	NPD3027	Phase 3
0.8686	High Similarity	NPD1529	Clinical (unspecified phase)
0.8613	High Similarity	NPD1530	Clinical (unspecified phase)
0.8523	High Similarity	NPD1653	Approved
0.8345	Intermediate Similarity	NPD7266	Discontinued
0.8261	Intermediate Similarity	NPD7074	Phase 3
0.8199	Intermediate Similarity	NPD7054	Approved
0.8175	Intermediate Similarity	NPD1091	Approved
0.8156	Intermediate Similarity	NPD4908	Phase 1
0.8153	Intermediate Similarity	NPD6234	Discontinued
0.8148	Intermediate Similarity	NPD7472	Approved
0.8137	Intermediate Similarity	NPD7228	Approved
0.8137	Intermediate Similarity	NPD3818	Discontinued
0.8108	Intermediate Similarity	NPD6674	Discontinued
0.8098	Intermediate Similarity	NPD6797	Phase 2
0.8065	Intermediate Similarity	NPD37	Approved
0.8049	Intermediate Similarity	NPD7251	Discontinued
0.8043	Intermediate Similarity	NPD1610	Phase 2
0.8042	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4965	Approved
0.8025	Intermediate Similarity	NPD4967	Phase 2
0.8025	Intermediate Similarity	NPD4966	Approved
0.7975	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1934	Approved
0.7937	Intermediate Similarity	NPD7199	Phase 2
0.7911	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7808	Phase 3
0.7892	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD4625	Phase 3
0.7832	Intermediate Similarity	NPD2861	Phase 2
0.7831	Intermediate Similarity	NPD6559	Discontinued
0.7791	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6166	Phase 2
0.7786	Intermediate Similarity	NPD3705	Approved
0.7754	Intermediate Similarity	NPD1548	Phase 1
0.773	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD5058	Phase 3
0.7676	Intermediate Similarity	NPD4749	Approved
0.7676	Intermediate Similarity	NPD2983	Phase 2
0.7676	Intermediate Similarity	NPD2982	Phase 2
0.7673	Intermediate Similarity	NPD8455	Phase 2
0.7671	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7240	Approved
0.7606	Intermediate Similarity	NPD2981	Phase 2
0.7586	Intermediate Similarity	NPD3018	Phase 2
0.7571	Intermediate Similarity	NPD1357	Approved
0.7562	Intermediate Similarity	NPD2801	Approved
0.7545	Intermediate Similarity	NPD5844	Phase 1
0.7536	Intermediate Similarity	NPD7157	Approved
0.7533	Intermediate Similarity	NPD4536	Approved
0.7533	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4538	Approved
0.7518	Intermediate Similarity	NPD5283	Phase 1
0.75	Intermediate Similarity	NPD228	Approved
0.7456	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3787	Discontinued
0.7453	Intermediate Similarity	NPD1465	Phase 2
0.745	Intermediate Similarity	NPD3620	Phase 2
0.745	Intermediate Similarity	NPD4060	Phase 1
0.745	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD7843	Approved
0.7436	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1511	Approved
0.7423	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7685	Pre-registration
0.7407	Intermediate Similarity	NPD2684	Approved
0.7407	Intermediate Similarity	NPD3817	Phase 2
0.7405	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1652	Phase 2
0.7375	Intermediate Similarity	NPD4380	Phase 2
0.7368	Intermediate Similarity	NPD5960	Phase 3
0.7368	Intermediate Similarity	NPD4108	Discontinued
0.7368	Intermediate Similarity	NPD5588	Approved
0.7362	Intermediate Similarity	NPD3882	Suspended
0.7353	Intermediate Similarity	NPD3021	Approved
0.7353	Intermediate Similarity	NPD3022	Approved
0.7346	Intermediate Similarity	NPD2977	Approved
0.7346	Intermediate Similarity	NPD2978	Approved
0.7342	Intermediate Similarity	NPD1512	Approved
0.7333	Intermediate Similarity	NPD1558	Phase 1
0.7317	Intermediate Similarity	NPD7075	Discontinued
0.7315	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6190	Approved
0.7301	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5124	Phase 1
0.7285	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3751	Discontinued
0.7278	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5125	Phase 3
0.7273	Intermediate Similarity	NPD1375	Discontinued
0.7273	Intermediate Similarity	NPD5126	Approved
0.7273	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4675	Approved
0.7267	Intermediate Similarity	NPD4678	Approved
0.726	Intermediate Similarity	NPD8651	Approved
0.7257	Intermediate Similarity	NPD6842	Approved
0.7257	Intermediate Similarity	NPD6841	Approved
0.7257	Intermediate Similarity	NPD6843	Phase 3
0.7248	Intermediate Similarity	NPD7095	Approved
0.7246	Intermediate Similarity	NPD6232	Discontinued
0.7244	Intermediate Similarity	NPD4628	Phase 3
0.7241	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7213	Phase 3
0.7215	Intermediate Similarity	NPD7212	Phase 2
0.7213	Intermediate Similarity	NPD7680	Approved
0.7205	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4005	Discontinued
0.719	Intermediate Similarity	NPD7097	Phase 1
0.7184	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD422	Phase 1
0.7171	Intermediate Similarity	NPD5735	Approved
0.717	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7447	Phase 1
0.7163	Intermediate Similarity	NPD6671	Approved
0.7162	Intermediate Similarity	NPD6584	Phase 3
0.7162	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5846	Approved
0.7153	Intermediate Similarity	NPD6516	Phase 2
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7134	Intermediate Similarity	NPD7819	Suspended
0.7134	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5494	Approved
0.7125	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7473	Discontinued
0.7115	Intermediate Similarity	NPD1549	Phase 2
0.7105	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6100	Approved
0.7097	Intermediate Similarity	NPD6099	Approved
0.7091	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5402	Approved
0.7089	Intermediate Similarity	NPD2677	Approved
0.7086	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD6959	Discontinued
0.708	Intermediate Similarity	NPD290	Approved
0.7073	Intermediate Similarity	NPD3382	Approved
0.7073	Intermediate Similarity	NPD3383	Approved
0.7073	Intermediate Similarity	NPD6801	Discontinued
0.7073	Intermediate Similarity	NPD3384	Approved
0.707	Intermediate Similarity	NPD5177	Phase 3
0.707	Intermediate Similarity	NPD3060	Approved
0.7069	Intermediate Similarity	NPD7549	Discontinued
0.7063	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD230	Phase 1
0.7059	Intermediate Similarity	NPD6355	Discontinued
0.7051	Intermediate Similarity	NPD3540	Phase 1
0.7051	Intermediate Similarity	NPD5763	Approved
0.7051	Intermediate Similarity	NPD5762	Approved
0.7029	Intermediate Similarity	NPD8313	Approved
0.7029	Intermediate Similarity	NPD8312	Approved
0.7025	Intermediate Similarity	NPD4535	Phase 3
0.7025	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3892	Phase 2
0.7025	Intermediate Similarity	NPD4110	Phase 3
0.7025	Intermediate Similarity	NPD3750	Approved
0.7025	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6331	Phase 2
0.7013	Intermediate Similarity	NPD6653	Approved
0.7012	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD968	Approved
0.6993	Remote Similarity	NPD4140	Approved
0.6993	Remote Similarity	NPD2238	Phase 2
0.6989	Remote Similarity	NPD8053	Approved
0.6989	Remote Similarity	NPD8054	Approved
0.6987	Remote Similarity	NPD3539	Phase 1
0.6975	Remote Similarity	NPD5403	Approved
0.6968	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4162	Approved
0.6962	Remote Similarity	NPD4237	Approved
0.6962	Remote Similarity	NPD4236	Phase 3
0.6959	Remote Similarity	NPD6583	Phase 3
0.6959	Remote Similarity	NPD3685	Discontinued
0.6959	Remote Similarity	NPD6582	Phase 2
0.6959	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4123	Phase 3
0.695	Remote Similarity	NPD5535	Approved
0.6948	Remote Similarity	NPD4340	Discontinued
0.6946	Remote Similarity	NPD7768	Phase 2
0.6944	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7124	Phase 2
0.6933	Remote Similarity	NPD3687	Approved
0.6933	Remote Similarity	NPD3686	Approved
0.6927	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7033	Discontinued
0.6914	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7411	Suspended
0.6899	Remote Similarity	NPD2424	Discontinued
0.6894	Remote Similarity	NPD4357	Discontinued
0.6894	Remote Similarity	NPD6799	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