NPASS Compound

Structure

NPC472381 OpenBabel07101719252D 35 38 0 0 1 0 0 0 0 0999 V2000 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 -6.0622 -1.5000 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 -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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 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 -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 1.7321 0.0000 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 0.8660 -1.5000 0.0000 C 0 0 2 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 -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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 2.5981 0.5000 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 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 O 0 0 0 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 -0.8660 -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 31 1 0 0 0 0 2 32 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 9 1 0 0 0 0 5 12 2 0 0 0 0 6 10 1 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 24 1 0 0 0 0 9 17 2 0 0 0 0 9 25 1 0 0 0 0 10 16 1 0 0 0 0 10 26 2 0 0 0 0 11 16 1 0 0 0 0 11 27 1 0 0 0 0 12 17 1 0 0 0 0 12 34 1 0 0 0 0 13 17 1 1 0 0 0 13 33 1 0 0 0 0 14 21 2 0 0 0 0 14 31 1 0 0 0 0 15 8 1 6 0 0 0 15 18 1 0 0 0 0 15 35 1 0 0 0 0 16 22 2 0 0 0 0 18 19 1 0 0 0 0 18 28 1 1 0 0 0 19 20 1 0 0 0 0 19 29 1 6 0 0 0 20 23 1 0 0 0 0 20 30 1 1 0 0 0 21 22 1 0 0 0 0 21 32 1 0 0 0 0 22 33 1 0 0 0 0 23 34 1 6 0 0 0 23 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.14
Volume:	459.166
LogP:	1.067
LogD:	0.376
LogS:	-3.942
# Rotatable Bonds:	6
TPSA:	184.6
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	4.286
Fsp3:	0.435
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.219
MDCK Permeability:	3.2100986572913826e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.917
Human Intestinal Absorption (HIA):	0.325
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.629

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.289
Plasma Protein Binding (PPB):	68.82213592529297%
Volume Distribution (VD):	0.467
Pgp-substrate:	28.25432777404785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.596
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.708
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	8.282
Half-life (T1/2):	0.603

ADMET: Toxicity

hERG Blockers:	0.285
Human Hepatotoxicity (H-HT):	0.361
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.441
Rat Oral Acute Toxicity:	0.737
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.762
Carcinogencity:	0.338
Eye Corrosion:	0.003
Eye Irritation:	0.093
Respiratory Toxicity:	0.718

Download Data

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

Natural Product: NPC472381

Natural Product ID:	NPC472381
*Common Name:**	JWFFWURECCTPGO-DYRYEQCVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JWFFWURECCTPGO-DYRYEQCVSA-N
Standard InCHI:	InChI=1S/C23H26O12/c1-31-14-7-11(27)16-10(26)6-13(33-22(16)21(14)32-2)17-9(25)4-3-5-12(17)34-23-20(30)19(29)18(28)15(8-24)35-23/h3-5,7,13,15,18-20,23-25,27-30H,6,8H2,1-2H3/t13-,15+,18+,19-,20+,23+/m0/s1
SMILES:	COC1=C(C2=C(C(=O)CC(O2)C3=C(C=CC=C3OC4C(C(C(C(O4)CO)O)O)O)O)C(=C1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397949
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002593] 8-O-methylated flavonoids

*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
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	whole plant	n.a.	n.a.	PMID[25637363]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	30000.0	nM	PMID[480998]

☑ 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 NPC472381 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	406
0.1-0.2	1664
0.2-0.3	3874
0.3-0.4	9376
0.4-0.5	8832
0.5-0.6	4036
0.6-0.7	4969
0.7-0.8	5691
0.8-0.85	2413
0.85-0.9	1080
0.9-0.95	335
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472383
0.9937	High Similarity	NPC93099
0.9937	High Similarity	NPC22195
0.9937	High Similarity	NPC21190
0.9937	High Similarity	NPC44558
0.9937	High Similarity	NPC183357
0.9875	High Similarity	NPC472386
0.9875	High Similarity	NPC267254
0.9874	High Similarity	NPC112755
0.9874	High Similarity	NPC95855
0.9874	High Similarity	NPC170675
0.9874	High Similarity	NPC210042
0.9874	High Similarity	NPC471457
0.9814	High Similarity	NPC51774
0.9814	High Similarity	NPC239549
0.9814	High Similarity	NPC236191
0.9812	High Similarity	NPC474434
0.9812	High Similarity	NPC105511
0.9812	High Similarity	NPC471416
0.9812	High Similarity	NPC34287
0.9753	High Similarity	NPC102028
0.9752	High Similarity	NPC156977
0.9752	High Similarity	NPC301683
0.9752	High Similarity	NPC205076
0.9752	High Similarity	NPC307518
0.9752	High Similarity	NPC48773
0.975	High Similarity	NPC105025
0.975	High Similarity	NPC229687
0.975	High Similarity	NPC45638
0.975	High Similarity	NPC469931
0.975	High Similarity	NPC183036
0.975	High Similarity	NPC475942
0.975	High Similarity	NPC93337
0.975	High Similarity	NPC186807
0.975	High Similarity	NPC58053
0.975	High Similarity	NPC201292
0.975	High Similarity	NPC226294
0.9748	High Similarity	NPC5778
0.9748	High Similarity	NPC236934
0.9693	High Similarity	NPC472382
0.9693	High Similarity	NPC472380
0.9693	High Similarity	NPC472384
0.9691	High Similarity	NPC204693
0.9689	High Similarity	NPC224462
0.9689	High Similarity	NPC293004
0.9688	High Similarity	NPC45618
0.9688	High Similarity	NPC58716
0.9688	High Similarity	NPC146792
0.9688	High Similarity	NPC135345
0.9688	High Similarity	NPC45400
0.9634	High Similarity	NPC472387
0.9632	High Similarity	NPC142996
0.963	High Similarity	NPC3583
0.963	High Similarity	NPC117260
0.963	High Similarity	NPC211594
0.963	High Similarity	NPC476405
0.963	High Similarity	NPC254540
0.963	High Similarity	NPC475155
0.963	High Similarity	NPC172807
0.963	High Similarity	NPC259152
0.9627	High Similarity	NPC293629
0.9625	High Similarity	NPC181616
0.9625	High Similarity	NPC99957
0.9623	High Similarity	NPC29830
0.9623	High Similarity	NPC309025
0.9623	High Similarity	NPC127415
0.9623	High Similarity	NPC243930
0.9623	High Similarity	NPC88023
0.9573	High Similarity	NPC169733
0.9573	High Similarity	NPC268533
0.9571	High Similarity	NPC42773
0.9571	High Similarity	NPC101026
0.9571	High Similarity	NPC21666
0.9571	High Similarity	NPC45522
0.9571	High Similarity	NPC24043
0.9571	High Similarity	NPC169977
0.9568	High Similarity	NPC245014
0.9568	High Similarity	NPC177731
0.9568	High Similarity	NPC231194
0.9568	High Similarity	NPC84265
0.9568	High Similarity	NPC79056
0.9568	High Similarity	NPC194483
0.9568	High Similarity	NPC51326
0.9568	High Similarity	NPC105095
0.9568	High Similarity	NPC282987
0.9568	High Similarity	NPC52353
0.9568	High Similarity	NPC44328
0.9565	High Similarity	NPC477502
0.9565	High Similarity	NPC229729
0.9563	High Similarity	NPC311830
0.9563	High Similarity	NPC22832
0.9563	High Similarity	NPC165720
0.956	High Similarity	NPC300537
0.956	High Similarity	NPC127782
0.9515	High Similarity	NPC476621
0.9515	High Similarity	NPC476623
0.9515	High Similarity	NPC476620
0.9515	High Similarity	NPC476618
0.9515	High Similarity	NPC476619
0.9515	High Similarity	NPC476622
0.9515	High Similarity	NPC168584
0.9512	High Similarity	NPC264735
0.9512	High Similarity	NPC477848
0.9512	High Similarity	NPC472607
0.9509	High Similarity	NPC256760
0.9509	High Similarity	NPC261254
0.9506	High Similarity	NPC61791
0.9506	High Similarity	NPC209296
0.9506	High Similarity	NPC43587
0.9506	High Similarity	NPC270578
0.9506	High Similarity	NPC52382
0.9506	High Similarity	NPC195257
0.9503	High Similarity	NPC115674
0.9503	High Similarity	NPC70441
0.9503	High Similarity	NPC210073
0.95	High Similarity	NPC94777
0.95	High Similarity	NPC270335
0.95	High Similarity	NPC19709
0.95	High Similarity	NPC284960
0.95	High Similarity	NPC222936
0.95	High Similarity	NPC191306
0.95	High Similarity	NPC88043
0.9497	High Similarity	NPC182045
0.9458	High Similarity	NPC470443
0.9458	High Similarity	NPC470444
0.9458	High Similarity	NPC110941
0.9458	High Similarity	NPC241423
0.9458	High Similarity	NPC473571
0.9458	High Similarity	NPC126784
0.9458	High Similarity	NPC473682
0.9455	High Similarity	NPC233994
0.9455	High Similarity	NPC211532
0.9455	High Similarity	NPC65563
0.9455	High Similarity	NPC8573
0.9455	High Similarity	NPC472385
0.9455	High Similarity	NPC198324
0.9455	High Similarity	NPC470949
0.9451	High Similarity	NPC208668
0.9448	High Similarity	NPC150767
0.9448	High Similarity	NPC212748
0.9448	High Similarity	NPC78734
0.9444	High Similarity	NPC116745
0.9444	High Similarity	NPC160156
0.9444	High Similarity	NPC92565
0.9441	High Similarity	NPC475497
0.9441	High Similarity	NPC284277
0.9441	High Similarity	NPC475366
0.9437	High Similarity	NPC189142
0.9437	High Similarity	NPC77660
0.9437	High Similarity	NPC473043
0.9437	High Similarity	NPC148273
0.9434	High Similarity	NPC110349
0.9405	High Similarity	NPC148710
0.9401	High Similarity	NPC473071
0.9401	High Similarity	NPC473073
0.9398	High Similarity	NPC475261
0.9394	High Similarity	NPC210094
0.9394	High Similarity	NPC43211
0.9394	High Similarity	NPC115760
0.9394	High Similarity	NPC108202
0.9394	High Similarity	NPC237435
0.9394	High Similarity	NPC135277
0.9394	High Similarity	NPC49344
0.9394	High Similarity	NPC101191
0.939	High Similarity	NPC235575
0.9387	High Similarity	NPC203050
0.9387	High Similarity	NPC219904
0.9387	High Similarity	NPC225434
0.9387	High Similarity	NPC86008
0.9387	High Similarity	NPC471287
0.9387	High Similarity	NPC105283
0.9387	High Similarity	NPC223747
0.9387	High Similarity	NPC120099
0.9383	High Similarity	NPC21100
0.9383	High Similarity	NPC197285
0.9383	High Similarity	NPC8856
0.9379	High Similarity	NPC470178
0.9379	High Similarity	NPC168822
0.9367	High Similarity	NPC206378
0.9345	High Similarity	NPC470446
0.9345	High Similarity	NPC473072
0.9345	High Similarity	NPC470445
0.9345	High Similarity	NPC470449
0.9345	High Similarity	NPC470447
0.9341	High Similarity	NPC473895
0.9337	High Similarity	NPC257714
0.9337	High Similarity	NPC472991
0.9337	High Similarity	NPC472992
0.9333	High Similarity	NPC4390
0.9333	High Similarity	NPC175230
0.9333	High Similarity	NPC172033
0.9333	High Similarity	NPC88560
0.9329	High Similarity	NPC199079
0.9329	High Similarity	NPC210808
0.9329	High Similarity	NPC149011
0.9329	High Similarity	NPC204937
0.9329	High Similarity	NPC67105
0.9329	High Similarity	NPC206123
0.9329	High Similarity	NPC218488
0.9329	High Similarity	NPC95866

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 NPC472381 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	902
0.2-0.3	1869
0.3-0.4	2688
0.4-0.5	1802
0.5-0.6	958
0.6-0.7	395
0.7-0.8	129
0.8-0.85	24
0.85-0.9	12
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9568	High Similarity	NPD7074	Phase 3
0.9506	High Similarity	NPD7054	Approved
0.9448	High Similarity	NPD7472	Approved
0.9394	High Similarity	NPD4338	Clinical (unspecified phase)
0.9325	High Similarity	NPD3818	Discontinued
0.9277	High Similarity	NPD7808	Phase 3
0.9273	High Similarity	NPD6797	Phase 2
0.9217	High Similarity	NPD7251	Discontinued
0.9187	High Similarity	NPD4381	Clinical (unspecified phase)
0.9085	High Similarity	NPD6167	Clinical (unspecified phase)
0.9085	High Similarity	NPD6166	Phase 2
0.9085	High Similarity	NPD6168	Clinical (unspecified phase)
0.9057	High Similarity	NPD1934	Approved
0.9	High Similarity	NPD2801	Approved
0.8922	High Similarity	NPD7804	Clinical (unspecified phase)
0.8882	High Similarity	NPD2393	Clinical (unspecified phase)
0.8727	High Similarity	NPD5494	Approved
0.8659	High Similarity	NPD4868	Clinical (unspecified phase)
0.8598	High Similarity	NPD3817	Phase 2
0.858	High Similarity	NPD4380	Phase 2
0.8547	High Similarity	NPD6559	Discontinued
0.8545	High Similarity	NPD3882	Suspended
0.8438	Intermediate Similarity	NPD1511	Approved
0.8383	Intermediate Similarity	NPD7075	Discontinued
0.8382	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD5402	Approved
0.8372	Intermediate Similarity	NPD5844	Phase 1
0.8333	Intermediate Similarity	NPD1512	Approved
0.8291	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1549	Phase 2
0.8232	Intermediate Similarity	NPD1653	Approved
0.8222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD1465	Phase 2
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.816	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD7473	Discontinued
0.8144	Intermediate Similarity	NPD6801	Discontinued
0.8129	Intermediate Similarity	NPD6959	Discontinued
0.8103	Intermediate Similarity	NPD7228	Approved
0.8095	Intermediate Similarity	NPD7819	Suspended
0.8084	Intermediate Similarity	NPD7411	Suspended
0.8061	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD8312	Approved
0.8034	Intermediate Similarity	NPD8313	Approved
0.8023	Intermediate Similarity	NPD7199	Phase 2
0.8011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD2796	Approved
0.7988	Intermediate Similarity	NPD6799	Approved
0.7977	Intermediate Similarity	NPD3787	Discontinued
0.7952	Intermediate Similarity	NPD5403	Approved
0.7939	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1510	Phase 2
0.7929	Intermediate Similarity	NPD37	Approved
0.7921	Intermediate Similarity	NPD7685	Pre-registration
0.7914	Intermediate Similarity	NPD6780	Approved
0.7914	Intermediate Similarity	NPD6779	Approved
0.7914	Intermediate Similarity	NPD6776	Approved
0.7914	Intermediate Similarity	NPD6781	Approved
0.7914	Intermediate Similarity	NPD6778	Approved
0.7914	Intermediate Similarity	NPD6782	Approved
0.7914	Intermediate Similarity	NPD6777	Approved
0.7907	Intermediate Similarity	NPD6234	Discontinued
0.7895	Intermediate Similarity	NPD4966	Approved
0.7895	Intermediate Similarity	NPD4967	Phase 2
0.7895	Intermediate Similarity	NPD4965	Approved
0.7845	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD5401	Approved
0.7829	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD1247	Approved
0.7811	Intermediate Similarity	NPD6599	Discontinued
0.7799	Intermediate Similarity	NPD1240	Approved
0.7799	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1613	Approved
0.7789	Intermediate Similarity	NPD7698	Approved
0.7789	Intermediate Similarity	NPD7696	Phase 3
0.7789	Intermediate Similarity	NPD7435	Discontinued
0.7789	Intermediate Similarity	NPD7697	Approved
0.7784	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7783	Phase 2
0.7772	Intermediate Similarity	NPD8151	Discontinued
0.7771	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7266	Discontinued
0.7727	Intermediate Similarity	NPD3926	Phase 2
0.7722	Intermediate Similarity	NPD7240	Approved
0.772	Intermediate Similarity	NPD7701	Phase 2
0.7702	Intermediate Similarity	NPD1607	Approved
0.7697	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD943	Approved
0.7674	Intermediate Similarity	NPD8455	Phase 2
0.7669	Intermediate Similarity	NPD2935	Discontinued
0.7668	Intermediate Similarity	NPD7584	Approved
0.7656	Intermediate Similarity	NPD7870	Phase 2
0.7656	Intermediate Similarity	NPD7871	Phase 2
0.7647	Intermediate Similarity	NPD6535	Approved
0.7647	Intermediate Similarity	NPD6534	Approved
0.7644	Intermediate Similarity	NPD6823	Phase 2
0.7644	Intermediate Similarity	NPD3749	Approved
0.764	Intermediate Similarity	NPD1933	Approved
0.7619	Intermediate Similarity	NPD7699	Phase 2
0.7619	Intermediate Similarity	NPD7700	Phase 2
0.761	Intermediate Similarity	NPD3027	Phase 3
0.76	Intermediate Similarity	NPD919	Approved
0.759	Intermediate Similarity	NPD3750	Approved
0.759	Intermediate Similarity	NPD4628	Phase 3
0.7586	Intermediate Similarity	NPD7768	Phase 2
0.7576	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7874	Approved
0.7547	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6190	Approved
0.7531	Intermediate Similarity	NPD230	Phase 1
0.7531	Intermediate Similarity	NPD447	Suspended
0.7515	Intermediate Similarity	NPD2532	Approved
0.7515	Intermediate Similarity	NPD2534	Approved
0.7515	Intermediate Similarity	NPD2533	Approved
0.7513	Intermediate Similarity	NPD7801	Approved
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1551	Phase 2
0.7453	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2800	Approved
0.7425	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6213	Phase 3
0.7407	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6212	Phase 3
0.7377	Intermediate Similarity	NPD5953	Discontinued
0.7341	Intermediate Similarity	NPD3226	Approved
0.7326	Intermediate Similarity	NPD8150	Discontinued
0.7326	Intermediate Similarity	NPD920	Approved
0.7326	Intermediate Similarity	NPD8434	Phase 2
0.7321	Intermediate Similarity	NPD6674	Discontinued
0.7314	Intermediate Similarity	NPD6844	Discontinued
0.731	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8319	Approved
0.7296	Intermediate Similarity	NPD8320	Phase 1
0.7292	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3748	Approved
0.7273	Intermediate Similarity	NPD7585	Approved
0.7268	Intermediate Similarity	NPD7286	Phase 2
0.7246	Intermediate Similarity	NPD6099	Approved
0.7246	Intermediate Similarity	NPD6100	Approved
0.7245	Intermediate Similarity	NPD7680	Approved
0.7241	Intermediate Similarity	NPD7458	Discontinued
0.7222	Intermediate Similarity	NPD7583	Approved
0.7222	Intermediate Similarity	NPD4908	Phase 1
0.7215	Intermediate Similarity	NPD1091	Approved
0.7209	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2344	Approved
0.7202	Intermediate Similarity	NPD2346	Discontinued
0.7188	Intermediate Similarity	NPD4360	Phase 2
0.7188	Intermediate Similarity	NPD4363	Phase 3
0.7186	Intermediate Similarity	NPD7033	Discontinued
0.7186	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2799	Discontinued
0.7184	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6651	Approved
0.716	Intermediate Similarity	NPD9494	Approved
0.7151	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD5242	Approved
0.7135	Intermediate Similarity	NPD5353	Approved
0.7134	Intermediate Similarity	NPD2313	Discontinued
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1243	Approved
0.7117	Intermediate Similarity	NPD6832	Phase 2
0.7107	Intermediate Similarity	NPD5006	Approved
0.7107	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5005	Approved
0.7099	Intermediate Similarity	NPD2798	Approved
0.7093	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6233	Phase 2
0.7088	Intermediate Similarity	NPD5711	Approved
0.7088	Intermediate Similarity	NPD5710	Approved
0.7085	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2861	Phase 2
0.7045	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1203	Approved
0.7035	Intermediate Similarity	NPD2309	Approved
0.7033	Intermediate Similarity	NPD8127	Discontinued
0.7033	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6798	Discontinued
0.7021	Intermediate Similarity	NPD7549	Discontinued
0.7019	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1652	Phase 2
0.7016	Intermediate Similarity	NPD6843	Phase 3
0.7016	Intermediate Similarity	NPD6841	Approved
0.7016	Intermediate Similarity	NPD6842	Approved
0.7014	Intermediate Similarity	NPD8059	Phase 3
0.7014	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1899	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