NPASS Compound

Structure

NPC472380 OpenBabel07101719252D 36 39 0 0 1 0 0 0 0 0999 V2000 5.1962 2.0000 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 -1.7321 3.0000 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 -4.0000 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 0.0000 -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 5.1962 -0.0000 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 4.3301 -2.5000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 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 3.4641 -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 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 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 6.0622 -1.5000 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 -2.5000 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 4.3301 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 -1.7321 2.0000 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 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 33 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 10 2 0 0 0 0 7 13 2 0 0 0 0 8 11 1 0 0 0 0 8 14 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 11 16 1 0 0 0 0 11 25 2 0 0 0 0 12 16 1 0 0 0 0 12 26 1 0 0 0 0 13 35 1 0 0 0 0 14 10 1 1 0 0 0 14 34 1 0 0 0 0 15 20 2 0 0 0 0 15 31 1 0 0 0 0 16 21 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 1 0 0 0 18 22 1 0 0 0 0 18 28 1 6 0 0 0 19 24 1 0 0 0 0 19 29 1 6 0 0 0 20 21 1 0 0 0 0 20 32 1 0 0 0 0 21 34 1 0 0 0 0 22 23 1 1 0 0 0 22 36 1 0 0 0 0 23 30 2 0 0 0 0 23 33 1 0 0 0 0 24 35 1 1 0 0 0 24 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.14
Volume:	473.825
LogP:	1.535
LogD:	1.39
LogS:	-3.964
# Rotatable Bonds:	7
TPSA:	170.44
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	4.211
Fsp3:	0.417
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.683
MDCK Permeability:	3.892067979904823e-05
Pgp-inhibitor:	0.088
Pgp-substrate:	0.151
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.413

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.483
Plasma Protein Binding (PPB):	65.89886474609375%
Volume Distribution (VD):	0.514
Pgp-substrate:	27.305646896362305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.694
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.797
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.685
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.303
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	7.069
Half-life (T1/2):	0.297

ADMET: Toxicity

hERG Blockers:	0.188
Human Hepatotoxicity (H-HT):	0.606
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.156
Rat Oral Acute Toxicity:	0.534
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.147
Carcinogencity:	0.191
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.449

Download Data

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

Natural Product: NPC472380

Natural Product ID:	NPC472380
*Common Name:**	NXOJDMDERVDHQN-RKHOIXOUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NXOJDMDERVDHQN-RKHOIXOUSA-N
Standard InCHI:	InChI=1S/C24H26O12/c1-31-15-9-12(26)16-11(25)8-14(34-21(16)20(15)32-2)10-6-4-5-7-13(10)35-24-19(29)17(27)18(28)22(36-24)23(30)33-3/h4-7,9,14,17-19,22,24,26-29H,8H2,1-3H3/t14-,17-,18-,19+,22-,24+/m0/s1
SMILES:	COC(=O)[C@H]1O[C@@H](Oc2ccccc2[C@@H]2CC(=O)c3c(O2)c(OC)c(cc3O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397948
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[473862]

☑ 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 NPC472380 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	395
0.1-0.2	1696
0.2-0.3	4012
0.3-0.4	8876
0.4-0.5	8959
0.5-0.6	4430
0.6-0.7	5171
0.7-0.8	5723
0.8-0.85	2128
0.85-0.9	939
0.9-0.95	351
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472384
1.0	High Similarity	NPC472382
0.9878	High Similarity	NPC268533
0.9817	High Similarity	NPC264735
0.9816	High Similarity	NPC472386
0.9758	High Similarity	NPC472385
0.9758	High Similarity	NPC198324
0.9697	High Similarity	NPC210094
0.9697	High Similarity	NPC115760
0.9697	High Similarity	NPC477848
0.9697	High Similarity	NPC49344
0.9697	High Similarity	NPC135277
0.9697	High Similarity	NPC101191
0.9697	High Similarity	NPC237435
0.9697	High Similarity	NPC43211
0.9693	High Similarity	NPC472381
0.9693	High Similarity	NPC472383
0.9643	High Similarity	NPC470447
0.9643	High Similarity	NPC470445
0.9643	High Similarity	NPC470446
0.9643	High Similarity	NPC470449
0.9639	High Similarity	NPC233994
0.9639	High Similarity	NPC211532
0.9636	High Similarity	NPC21666
0.9636	High Similarity	NPC42773
0.9636	High Similarity	NPC169977
0.9636	High Similarity	NPC45522
0.9636	High Similarity	NPC24043
0.9636	High Similarity	NPC4390
0.9636	High Similarity	NPC101026
0.9634	High Similarity	NPC22195
0.9634	High Similarity	NPC183357
0.9634	High Similarity	NPC21190
0.9634	High Similarity	NPC44558
0.9632	High Similarity	NPC93099
0.9586	High Similarity	NPC470455
0.9586	High Similarity	NPC470451
0.9581	High Similarity	NPC168584
0.9581	High Similarity	NPC472387
0.9576	High Similarity	NPC172807
0.9576	High Similarity	NPC211594
0.9576	High Similarity	NPC190003
0.9576	High Similarity	NPC267254
0.9576	High Similarity	NPC117260
0.9576	High Similarity	NPC254540
0.9576	High Similarity	NPC175107
0.9576	High Similarity	NPC476405
0.9576	High Similarity	NPC153755
0.9573	High Similarity	NPC471457
0.9573	High Similarity	NPC210042
0.9573	High Similarity	NPC112755
0.9573	High Similarity	NPC270578
0.9573	High Similarity	NPC95855
0.9573	High Similarity	NPC170675
0.9573	High Similarity	NPC52382
0.9527	High Similarity	NPC36138
0.9524	High Similarity	NPC110941
0.9524	High Similarity	NPC241423
0.9524	High Similarity	NPC473682
0.9524	High Similarity	NPC473571
0.9524	High Similarity	NPC126784
0.9524	High Similarity	NPC470444
0.9524	High Similarity	NPC470443
0.9521	High Similarity	NPC470949
0.9521	High Similarity	NPC8573
0.9521	High Similarity	NPC169733
0.9521	High Similarity	NPC65563
0.9518	High Similarity	NPC51774
0.9518	High Similarity	NPC239549
0.9518	High Similarity	NPC236191
0.9515	High Similarity	NPC282987
0.9515	High Similarity	NPC34287
0.9515	High Similarity	NPC105511
0.9515	High Similarity	NPC245014
0.9515	High Similarity	NPC116864
0.9515	High Similarity	NPC235260
0.9515	High Similarity	NPC20505
0.9515	High Similarity	NPC471416
0.9515	High Similarity	NPC155763
0.9515	High Similarity	NPC474434
0.9515	High Similarity	NPC244776
0.9515	High Similarity	NPC84265
0.9512	High Similarity	NPC160156
0.9512	High Similarity	NPC92565
0.9471	High Similarity	NPC148710
0.9471	High Similarity	NPC470416
0.9467	High Similarity	NPC473071
0.9467	High Similarity	NPC473073
0.9467	High Similarity	NPC222674
0.9464	High Similarity	NPC476619
0.9464	High Similarity	NPC476622
0.9464	High Similarity	NPC476621
0.9464	High Similarity	NPC476618
0.9464	High Similarity	NPC476623
0.9464	High Similarity	NPC173837
0.9464	High Similarity	NPC476620
0.9461	High Similarity	NPC253685
0.9461	High Similarity	NPC102028
0.9458	High Similarity	NPC307518
0.9458	High Similarity	NPC48773
0.9458	High Similarity	NPC156977
0.9458	High Similarity	NPC301683
0.9458	High Similarity	NPC205076
0.9455	High Similarity	NPC186807
0.9455	High Similarity	NPC203050
0.9455	High Similarity	NPC105025
0.9455	High Similarity	NPC223747
0.9455	High Similarity	NPC93337
0.9455	High Similarity	NPC183036
0.9455	High Similarity	NPC469931
0.9455	High Similarity	NPC45638
0.9455	High Similarity	NPC120099
0.9455	High Similarity	NPC225434
0.9455	High Similarity	NPC201292
0.9455	High Similarity	NPC226294
0.9455	High Similarity	NPC229687
0.9455	High Similarity	NPC219904
0.9455	High Similarity	NPC58053
0.9455	High Similarity	NPC138927
0.9455	High Similarity	NPC475942
0.9451	High Similarity	NPC236934
0.9451	High Similarity	NPC5778
0.9412	High Similarity	NPC473072
0.9412	High Similarity	NPC107987
0.9405	High Similarity	NPC89127
0.9405	High Similarity	NPC471669
0.9401	High Similarity	NPC204693
0.9398	High Similarity	NPC95866
0.9398	High Similarity	NPC224462
0.9398	High Similarity	NPC293004
0.9398	High Similarity	NPC206123
0.9394	High Similarity	NPC173637
0.9394	High Similarity	NPC58716
0.9394	High Similarity	NPC45618
0.9394	High Similarity	NPC146792
0.9394	High Similarity	NPC317489
0.9394	High Similarity	NPC127546
0.9394	High Similarity	NPC265530
0.9394	High Similarity	NPC135345
0.9394	High Similarity	NPC52550
0.9394	High Similarity	NPC84362
0.9394	High Similarity	NPC226304
0.9394	High Similarity	NPC45400
0.9394	High Similarity	NPC116745
0.9394	High Similarity	NPC223424
0.9394	High Similarity	NPC325555
0.9349	High Similarity	NPC217520
0.9349	High Similarity	NPC139571
0.9349	High Similarity	NPC35167
0.9349	High Similarity	NPC477895
0.9345	High Similarity	NPC294629
0.9345	High Similarity	NPC108202
0.9345	High Similarity	NPC473327
0.9345	High Similarity	NPC16194
0.9345	High Similarity	NPC142996
0.9345	High Similarity	NPC220173
0.9345	High Similarity	NPC294815
0.9345	High Similarity	NPC476472
0.9345	High Similarity	NPC19108
0.9341	High Similarity	NPC203259
0.9341	High Similarity	NPC471725
0.9341	High Similarity	NPC475155
0.9341	High Similarity	NPC471748
0.9341	High Similarity	NPC259152
0.9341	High Similarity	NPC176740
0.9341	High Similarity	NPC3583
0.9341	High Similarity	NPC26230
0.9341	High Similarity	NPC134532
0.9341	High Similarity	NPC155877
0.9341	High Similarity	NPC60735
0.9341	High Similarity	NPC33054
0.9337	High Similarity	NPC293629
0.9333	High Similarity	NPC21100
0.9333	High Similarity	NPC145038
0.9333	High Similarity	NPC88789
0.9333	High Similarity	NPC56077
0.9333	High Similarity	NPC253662
0.9333	High Similarity	NPC179950
0.9333	High Similarity	NPC197285
0.9333	High Similarity	NPC276222
0.9333	High Similarity	NPC113968
0.9333	High Similarity	NPC118284
0.9333	High Similarity	NPC277174
0.9333	High Similarity	NPC73855
0.9333	High Similarity	NPC328940
0.9333	High Similarity	NPC135599
0.9333	High Similarity	NPC274618
0.9333	High Similarity	NPC99957
0.9333	High Similarity	NPC281131
0.9333	High Similarity	NPC181616
0.9333	High Similarity	NPC308404
0.9329	High Similarity	NPC127415
0.9329	High Similarity	NPC309025
0.9329	High Similarity	NPC29830
0.9329	High Similarity	NPC243930
0.9329	High Similarity	NPC88023
0.929	High Similarity	NPC472991
0.929	High Similarity	NPC48984
0.929	High Similarity	NPC61904
0.929	High Similarity	NPC472992

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 NPC472380 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	922
0.2-0.3	1947
0.3-0.4	2631
0.4-0.5	1849
0.5-0.6	911
0.6-0.7	367
0.7-0.8	125
0.8-0.85	28
0.85-0.9	10
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9697	High Similarity	NPD4338	Clinical (unspecified phase)
0.9345	High Similarity	NPD7808	Phase 3
0.9341	High Similarity	NPD6797	Phase 2
0.9286	High Similarity	NPD7251	Discontinued
0.9281	High Similarity	NPD7074	Phase 3
0.9222	High Similarity	NPD7054	Approved
0.9167	High Similarity	NPD7472	Approved
0.9048	High Similarity	NPD3818	Discontinued
0.9042	High Similarity	NPD6168	Clinical (unspecified phase)
0.9042	High Similarity	NPD6167	Clinical (unspecified phase)
0.9042	High Similarity	NPD6166	Phase 2
0.8994	High Similarity	NPD7804	Clinical (unspecified phase)
0.8909	High Similarity	NPD4381	Clinical (unspecified phase)
0.8902	High Similarity	NPD3817	Phase 2
0.878	High Similarity	NPD1934	Approved
0.8727	High Similarity	NPD2801	Approved
0.8683	High Similarity	NPD7075	Discontinued
0.8675	High Similarity	NPD5402	Approved
0.8623	High Similarity	NPD4868	Clinical (unspecified phase)
0.8623	High Similarity	NPD3882	Suspended
0.8614	High Similarity	NPD2393	Clinical (unspecified phase)
0.8563	High Similarity	NPD7993	Clinical (unspecified phase)
0.8503	High Similarity	NPD7096	Clinical (unspecified phase)
0.85	High Similarity	NPD7879	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD5494	Approved
0.8443	Intermediate Similarity	NPD6801	Discontinued
0.8409	Intermediate Similarity	NPD6559	Discontinued
0.8343	Intermediate Similarity	NPD5844	Phase 1
0.8323	Intermediate Similarity	NPD4380	Phase 2
0.8303	Intermediate Similarity	NPD1512	Approved
0.8293	Intermediate Similarity	NPD6799	Approved
0.8253	Intermediate Similarity	NPD5403	Approved
0.8204	Intermediate Similarity	NPD1653	Approved
0.8182	Intermediate Similarity	NPD1511	Approved
0.8176	Intermediate Similarity	NPD1465	Phase 2
0.8161	Intermediate Similarity	NPD6232	Discontinued
0.8133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5401	Approved
0.8125	Intermediate Similarity	NPD7473	Discontinued
0.8114	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6599	Discontinued
0.8079	Intermediate Similarity	NPD7228	Approved
0.8079	Intermediate Similarity	NPD3751	Discontinued
0.807	Intermediate Similarity	NPD7819	Suspended
0.8059	Intermediate Similarity	NPD7411	Suspended
0.8057	Intermediate Similarity	NPD3787	Discontinued
0.8053	Intermediate Similarity	NPD7435	Discontinued
0.8037	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD8313	Approved
0.8011	Intermediate Similarity	NPD8312	Approved
0.8	Intermediate Similarity	NPD7199	Phase 2
0.7989	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1549	Phase 2
0.7919	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD37	Approved
0.7901	Intermediate Similarity	NPD7685	Pre-registration
0.7898	Intermediate Similarity	NPD6959	Discontinued
0.7898	Intermediate Similarity	NPD1247	Approved
0.7895	Intermediate Similarity	NPD6776	Approved
0.7895	Intermediate Similarity	NPD6777	Approved
0.7895	Intermediate Similarity	NPD6779	Approved
0.7895	Intermediate Similarity	NPD6782	Approved
0.7895	Intermediate Similarity	NPD6781	Approved
0.7895	Intermediate Similarity	NPD6778	Approved
0.7895	Intermediate Similarity	NPD6780	Approved
0.7886	Intermediate Similarity	NPD6234	Discontinued
0.7886	Intermediate Similarity	NPD919	Approved
0.7874	Intermediate Similarity	NPD4967	Phase 2
0.7874	Intermediate Similarity	NPD4966	Approved
0.7874	Intermediate Similarity	NPD4965	Approved
0.7844	Intermediate Similarity	NPD6190	Approved
0.7806	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7874	Approved
0.7772	Intermediate Similarity	NPD7698	Approved
0.7772	Intermediate Similarity	NPD7696	Phase 3
0.7772	Intermediate Similarity	NPD7697	Approved
0.7766	Intermediate Similarity	NPD7783	Phase 2
0.7766	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2796	Approved
0.7755	Intermediate Similarity	NPD8151	Discontinued
0.7751	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7266	Discontinued
0.7709	Intermediate Similarity	NPD3926	Phase 2
0.7706	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD7240	Approved
0.7704	Intermediate Similarity	NPD7701	Phase 2
0.7697	Intermediate Similarity	NPD1510	Phase 2
0.7679	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD8455	Phase 2
0.7651	Intermediate Similarity	NPD2935	Discontinued
0.7641	Intermediate Similarity	NPD7870	Phase 2
0.7641	Intermediate Similarity	NPD7871	Phase 2
0.7632	Intermediate Similarity	NPD6534	Approved
0.7632	Intermediate Similarity	NPD6535	Approved
0.7627	Intermediate Similarity	NPD3749	Approved
0.7622	Intermediate Similarity	NPD1933	Approved
0.7604	Intermediate Similarity	NPD7699	Phase 2
0.7604	Intermediate Similarity	NPD7700	Phase 2
0.7574	Intermediate Similarity	NPD3750	Approved
0.7574	Intermediate Similarity	NPD4628	Phase 3
0.7571	Intermediate Similarity	NPD7768	Phase 2
0.7561	Intermediate Similarity	NPD1240	Approved
0.7561	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1613	Approved
0.756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD8320	Phase 1
0.7551	Intermediate Similarity	NPD8319	Approved
0.7515	Intermediate Similarity	NPD447	Suspended
0.7515	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD7801	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD8150	Discontinued
0.7475	Intermediate Similarity	NPD7584	Approved
0.747	Intermediate Similarity	NPD1607	Approved
0.7455	Intermediate Similarity	NPD943	Approved
0.7449	Intermediate Similarity	NPD6823	Phase 2
0.744	Intermediate Similarity	NPD1551	Phase 2
0.7439	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6233	Phase 2
0.7378	Intermediate Similarity	NPD3027	Phase 3
0.7366	Intermediate Similarity	NPD5953	Discontinued
0.7333	Intermediate Similarity	NPD6798	Discontinued
0.733	Intermediate Similarity	NPD3226	Approved
0.7317	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD920	Approved
0.7299	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3748	Approved
0.7273	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7585	Approved
0.7259	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7286	Phase 2
0.7256	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7680	Approved
0.7232	Intermediate Similarity	NPD7458	Discontinued
0.7216	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6212	Phase 3
0.7216	Intermediate Similarity	NPD6213	Phase 3
0.7214	Intermediate Similarity	NPD7583	Approved
0.7209	Intermediate Similarity	NPD2800	Approved
0.7202	Intermediate Similarity	NPD6355	Discontinued
0.72	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2346	Discontinued
0.7189	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7033	Discontinued
0.7176	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2799	Discontinued
0.7135	Intermediate Similarity	NPD5242	Approved
0.7127	Intermediate Similarity	NPD5353	Approved
0.7126	Intermediate Similarity	NPD2313	Discontinued
0.7111	Intermediate Similarity	NPD6844	Discontinued
0.711	Intermediate Similarity	NPD1243	Approved
0.711	Intermediate Similarity	NPD6674	Discontinued
0.7108	Intermediate Similarity	NPD6832	Phase 2
0.71	Intermediate Similarity	NPD5005	Approved
0.71	Intermediate Similarity	NPD5006	Approved
0.7086	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5711	Approved
0.7081	Intermediate Similarity	NPD5710	Approved
0.7079	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4060	Phase 1
0.7039	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6099	Approved
0.7035	Intermediate Similarity	NPD6100	Approved
0.703	Intermediate Similarity	NPD1203	Approved
0.7027	Intermediate Similarity	NPD8127	Discontinued
0.7016	Intermediate Similarity	NPD7549	Discontinued
0.7016	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1652	Phase 2
0.7006	Intermediate Similarity	NPD4908	Phase 1
0.7005	Intermediate Similarity	NPD4363	Phase 3
0.7005	Intermediate Similarity	NPD4360	Phase 2
0.7	Intermediate Similarity	NPD5124	Phase 1
0.7	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2344	Approved
0.6994	Remote Similarity	NPD1091	Approved
0.6985	Remote Similarity	NPD4420	Approved
0.6971	Remote Similarity	NPD7930	Approved
0.6961	Remote Similarity	NPD6386	Approved
0.6961	Remote Similarity	NPD6385	Approved
0.6959	Remote Similarity	NPD6651	Approved
0.6949	Remote Similarity	NPD7390	Discontinued
0.6946	Remote Similarity	NPD9494	Approved
0.6943	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3887	Approved
0.6932	Remote Similarity	NPD2354	Approved
0.6923	Remote Similarity	NPD3268	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