NPASS Compound

Structure

NPC295082 OpenBabel07101719512D 35 39 0 0 1 0 0 0 0 0999 V2000 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -3.4641 0.0000 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 5.1962 3.0000 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 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 -1.7321 0.0000 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 -3.4641 1.0000 0.0000 C 0 0 0 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 1.7321 -2.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 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 -2.0000 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 3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 1.7321 -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 6.9282 1.0000 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 1.7321 1.0000 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 32 1 0 0 0 0 2 5 1 0 0 0 0 2 11 2 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 7 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 26 1 0 0 0 0 11 23 1 0 0 0 0 13 27 1 0 0 0 0 14 16 2 0 0 0 0 14 28 1 0 0 0 0 15 19 1 0 0 0 0 15 29 1 0 0 0 0 16 32 1 0 0 0 0 17 24 2 0 0 0 0 17 33 1 0 0 0 0 18 10 1 6 0 0 0 18 22 1 0 0 0 0 18 34 1 0 0 0 0 19 20 1 0 0 0 0 19 25 2 0 0 0 0 20 21 1 0 0 0 0 20 30 2 0 0 0 0 21 23 2 0 0 0 0 21 31 1 0 0 0 0 22 12 1 1 0 0 0 22 33 1 0 0 0 0 23 35 1 0 0 0 0 24 25 1 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.11
Volume:	457.075
LogP:	3.546
LogD:	2.481
LogS:	-4.711
# Rotatable Bonds:	4
TPSA:	159.05
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.294
Synthetic Accessibility Score:	3.679
Fsp3:	0.16
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.719
MDCK Permeability:	1.292312936129747e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.257

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	95.1539535522461%
Volume Distribution (VD):	0.506
Pgp-substrate:	9.644318580627441%

ADMET: Metabolism

CYP1A2-inhibitor:	0.302
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.155
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.852
CYP2C9-substrate:	0.7
CYP2D6-inhibitor:	0.137
CYP2D6-substrate:	0.23
CYP3A4-inhibitor:	0.332
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	3.087
Half-life (T1/2):	0.845

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.461
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.689
Rat Oral Acute Toxicity:	0.329
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.371
Carcinogencity:	0.384
Eye Corrosion:	0.003
Eye Irritation:	0.775
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC295082

Natural Product ID:	NPC295082
*Common Name:**	Rhodiolinin
IUPAC Name:	(2R,3R)-6,8-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-9-(4-hydroxyphenyl)-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-7-one
Synonyms:	Rhodiolinin
Standard InCHIKey:	POVCYOFRCMBMKD-XMSQKQJNSA-N
Standard InCHI:	InChI=1S/C25H20O10/c1-32-16-8-12(4-7-14(16)28)22-18(10-26)34-24-17(33-22)9-15(29)19-20(30)21(31)23(35-25(19)24)11-2-5-13(27)6-3-11/h2-9,18,22,26-29,31H,10H2,1H3/t18-,22-/m1/s1
SMILES:	COc1cc(ccc1O)[C@@H]1[C@@H](CO)Oc2c(cc(c3c(=O)c(c(c4ccc(cc4)O)oc23)O)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL594871
PubChem CID:	14778358
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001844] Flavonolignans

*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
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	roots	n.a.	n.a.	PMID[19729316]
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16239	Rhodiola rosea	Species	Crassulaceae	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
EC50	2
IC50	2
Ki	1
Others	3

Activity Type	# Activity
Cell Line	1
Individual Protein	3
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	>	300000.0	nM	PMID[469569]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	Ki	=	14100.0	nM	PMID[469569]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	10300.0	nM	PMID[469569]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	6100.0	nM	PMID[469569]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	7.19	n.a.	PMID[469569]
NPT742	Organism	Influenza A virus	Influenza A virus	EC50	=	29300.0	nM	PMID[469569]
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	EC50	=	41700.0	nM	PMID[469569]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	10.24	n.a.	PMID[469569]

☑ 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 NPC295082 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	458
0.1-0.2	1839
0.2-0.3	4731
0.3-0.4	10639
0.4-0.5	7181
0.5-0.6	3941
0.6-0.7	5260
0.7-0.8	4855
0.8-0.85	1778
0.85-0.9	1293
0.9-0.95	694
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC243877
0.9682	High Similarity	NPC66618
0.9682	High Similarity	NPC113163
0.9682	High Similarity	NPC84324
0.9682	High Similarity	NPC165970
0.9682	High Similarity	NPC305987
0.9682	High Similarity	NPC288131
0.9625	High Similarity	NPC14662
0.9623	High Similarity	NPC7688
0.9623	High Similarity	NPC7154
0.9623	High Similarity	NPC125039
0.9623	High Similarity	NPC58223
0.9623	High Similarity	NPC36916
0.9623	High Similarity	NPC72787
0.9623	High Similarity	NPC36
0.9618	High Similarity	NPC101731
0.9554	High Similarity	NPC172202
0.9554	High Similarity	NPC284127
0.9554	High Similarity	NPC476410
0.9503	High Similarity	NPC260266
0.9494	High Similarity	NPC263449
0.949	High Similarity	NPC93376
0.949	High Similarity	NPC75215
0.949	High Similarity	NPC189179
0.949	High Similarity	NPC227192
0.949	High Similarity	NPC183851
0.949	High Similarity	NPC470402
0.949	High Similarity	NPC63454
0.949	High Similarity	NPC224137
0.9448	High Similarity	NPC476405
0.9448	High Similarity	NPC117260
0.9437	High Similarity	NPC272064
0.9434	High Similarity	NPC308992
0.9434	High Similarity	NPC158188
0.943	High Similarity	NPC204854
0.943	High Similarity	NPC191459
0.943	High Similarity	NPC253634
0.943	High Similarity	NPC7846
0.943	High Similarity	NPC130894
0.943	High Similarity	NPC4481
0.943	High Similarity	NPC25495
0.943	High Similarity	NPC9609
0.943	High Similarity	NPC22472
0.943	High Similarity	NPC19687
0.943	High Similarity	NPC18772
0.943	High Similarity	NPC261004
0.943	High Similarity	NPC18607
0.943	High Similarity	NPC288669
0.943	High Similarity	NPC176300
0.943	High Similarity	NPC152166
0.943	High Similarity	NPC143828
0.943	High Similarity	NPC300943
0.943	High Similarity	NPC115798
0.943	High Similarity	NPC105242
0.9427	High Similarity	NPC49824
0.9427	High Similarity	NPC247017
0.9427	High Similarity	NPC474520
0.9427	High Similarity	NPC98661
0.9401	High Similarity	NPC36138
0.9394	High Similarity	NPC169733
0.939	High Similarity	NPC101026
0.939	High Similarity	NPC169977
0.939	High Similarity	NPC24043
0.939	High Similarity	NPC21666
0.939	High Similarity	NPC42773
0.939	High Similarity	NPC45522
0.9387	High Similarity	NPC245014
0.9387	High Similarity	NPC84265
0.9387	High Similarity	NPC282987
0.9379	High Similarity	NPC470457
0.9379	High Similarity	NPC224280
0.9375	High Similarity	NPC219927
0.9367	High Similarity	NPC176665
0.9367	High Similarity	NPC29841
0.9367	High Similarity	NPC475267
0.9367	High Similarity	NPC162869
0.9367	High Similarity	NPC305663
0.9367	High Similarity	NPC156057
0.9367	High Similarity	NPC235215
0.9367	High Similarity	NPC163524
0.9367	High Similarity	NPC203891
0.9367	High Similarity	NPC110070
0.9367	High Similarity	NPC474208
0.9367	High Similarity	NPC287979
0.9367	High Similarity	NPC101830
0.9367	High Similarity	NPC48208
0.9367	High Similarity	NPC7973
0.9367	High Similarity	NPC472438
0.9367	High Similarity	NPC474836
0.9367	High Similarity	NPC78302
0.9363	High Similarity	NPC201136
0.9363	High Similarity	NPC196439
0.9363	High Similarity	NPC4455
0.9363	High Similarity	NPC138360
0.9363	High Similarity	NPC280339
0.9363	High Similarity	NPC201451
0.9363	High Similarity	NPC213622
0.9363	High Similarity	NPC146165
0.9363	High Similarity	NPC92659
0.9363	High Similarity	NPC183597
0.9363	High Similarity	NPC227325
0.9363	High Similarity	NPC44079
0.9363	High Similarity	NPC167815
0.9363	High Similarity	NPC26227
0.9363	High Similarity	NPC163780
0.9363	High Similarity	NPC50715
0.9363	High Similarity	NPC2476
0.9363	High Similarity	NPC128863
0.9345	High Similarity	NPC470416
0.9333	High Similarity	NPC477848
0.9325	High Similarity	NPC280493
0.9325	High Similarity	NPC226294
0.9325	High Similarity	NPC469931
0.9325	High Similarity	NPC45638
0.9325	High Similarity	NPC93337
0.9325	High Similarity	NPC186807
0.9325	High Similarity	NPC475942
0.9325	High Similarity	NPC177480
0.9325	High Similarity	NPC58053
0.9325	High Similarity	NPC105025
0.9325	High Similarity	NPC475212
0.9325	High Similarity	NPC201292
0.9317	High Similarity	NPC470459
0.9317	High Similarity	NPC472625
0.9313	High Similarity	NPC34089
0.9313	High Similarity	NPC471499
0.9313	High Similarity	NPC289771
0.9313	High Similarity	NPC142252
0.9313	High Similarity	NPC26326
0.9313	High Similarity	NPC196179
0.9308	High Similarity	NPC193842
0.9308	High Similarity	NPC152904
0.9304	High Similarity	NPC320825
0.9304	High Similarity	NPC235165
0.9304	High Similarity	NPC201837
0.9304	High Similarity	NPC43243
0.9304	High Similarity	NPC250922
0.9304	High Similarity	NPC13858
0.9304	High Similarity	NPC266960
0.9304	High Similarity	NPC178854
0.9304	High Similarity	NPC292107
0.9304	High Similarity	NPC200388
0.9304	High Similarity	NPC245546
0.9304	High Similarity	NPC472916
0.9304	High Similarity	NPC100916
0.9304	High Similarity	NPC268161
0.9304	High Similarity	NPC326037
0.9304	High Similarity	NPC55619
0.9304	High Similarity	NPC255106
0.9299	High Similarity	NPC69394
0.9299	High Similarity	NPC22519
0.9299	High Similarity	NPC145379
0.9299	High Similarity	NPC231018
0.9299	High Similarity	NPC276409
0.9299	High Similarity	NPC274327
0.9299	High Similarity	NPC183878
0.9299	High Similarity	NPC255350
0.9299	High Similarity	NPC86485
0.9299	High Similarity	NPC176775
0.9299	High Similarity	NPC250822
0.9299	High Similarity	NPC75279
0.9299	High Similarity	NPC160951
0.9299	High Similarity	NPC47781
0.9281	High Similarity	NPC470444
0.9281	High Similarity	NPC473682
0.9281	High Similarity	NPC241423
0.9281	High Similarity	NPC324742
0.9281	High Similarity	NPC110941
0.9281	High Similarity	NPC126784
0.9281	High Similarity	NPC473571
0.9281	High Similarity	NPC470443
0.9277	High Similarity	NPC472385
0.9277	High Similarity	NPC198324
0.9277	High Similarity	NPC470949
0.9277	High Similarity	NPC472992
0.9277	High Similarity	NPC472991
0.9277	High Similarity	NPC211532
0.9277	High Similarity	NPC65563
0.9277	High Similarity	NPC8573
0.9277	High Similarity	NPC233994
0.9273	High Similarity	NPC204693
0.9268	High Similarity	NPC102277
0.9268	High Similarity	NPC279209
0.9264	High Similarity	NPC146792
0.9264	High Similarity	NPC158761
0.9264	High Similarity	NPC45618
0.9264	High Similarity	NPC470456
0.9264	High Similarity	NPC58716
0.9259	High Similarity	NPC142614
0.9259	High Similarity	NPC477840
0.9259	High Similarity	NPC234052
0.9255	High Similarity	NPC476247
0.9255	High Similarity	NPC477841
0.925	High Similarity	NPC470326
0.925	High Similarity	NPC282009
0.925	High Similarity	NPC287328
0.9245	High Similarity	NPC471515
0.9245	High Similarity	NPC472911
0.9245	High Similarity	NPC96167
0.9245	High Similarity	NPC472914

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 NPC295082 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	420
0.1-0.2	975
0.2-0.3	1942
0.3-0.4	2673
0.4-0.5	1720
0.5-0.6	919
0.6-0.7	338
0.7-0.8	115
0.8-0.85	20
0.85-0.9	21
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9623	High Similarity	NPD6166	Phase 2
0.9623	High Similarity	NPD6167	Clinical (unspecified phase)
0.9623	High Similarity	NPD6168	Clinical (unspecified phase)
0.9299	High Similarity	NPD2801	Approved
0.9217	High Similarity	NPD4338	Clinical (unspecified phase)
0.9114	High Similarity	NPD1934	Approved
0.9096	High Similarity	NPD6797	Phase 2
0.9091	High Similarity	NPD7054	Approved
0.9042	High Similarity	NPD7251	Discontinued
0.9036	High Similarity	NPD7472	Approved
0.8988	High Similarity	NPD7808	Phase 3
0.8944	High Similarity	NPD3882	Suspended
0.8938	High Similarity	NPD2393	Clinical (unspecified phase)
0.8922	High Similarity	NPD7074	Phase 3
0.8882	High Similarity	NPD3817	Phase 2
0.8854	High Similarity	NPD1512	Approved
0.8827	High Similarity	NPD4868	Clinical (unspecified phase)
0.8802	High Similarity	NPD3818	Discontinued
0.8757	High Similarity	NPD7993	Clinical (unspecified phase)
0.8726	High Similarity	NPD1511	Approved
0.865	High Similarity	NPD5402	Approved
0.8634	High Similarity	NPD4380	Phase 2
0.8554	High Similarity	NPD5494	Approved
0.8545	High Similarity	NPD4381	Clinical (unspecified phase)
0.8529	High Similarity	NPD7804	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD7075	Discontinued
0.8421	Intermediate Similarity	NPD5844	Phase 1
0.8313	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6801	Discontinued
0.8284	Intermediate Similarity	NPD6959	Discontinued
0.8253	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6232	Discontinued
0.8228	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD5403	Approved
0.821	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD7473	Discontinued
0.8176	Intermediate Similarity	NPD1549	Phase 2
0.8148	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD7411	Suspended
0.8098	Intermediate Similarity	NPD5401	Approved
0.807	Intermediate Similarity	NPD1247	Approved
0.805	Intermediate Similarity	NPD2796	Approved
0.8046	Intermediate Similarity	NPD3751	Discontinued
0.8036	Intermediate Similarity	NPD1465	Phase 2
0.8023	Intermediate Similarity	NPD3787	Discontinued
0.7987	Intermediate Similarity	NPD1510	Phase 2
0.7977	Intermediate Similarity	NPD3926	Phase 2
0.7967	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD6559	Discontinued
0.7956	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7819	Suspended
0.7914	Intermediate Similarity	NPD6190	Approved
0.7857	Intermediate Similarity	NPD6599	Discontinued
0.7848	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1613	Approved
0.7844	Intermediate Similarity	NPD1653	Approved
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD919	Approved
0.7736	Intermediate Similarity	NPD1240	Approved
0.7736	Intermediate Similarity	NPD943	Approved
0.7688	Intermediate Similarity	NPD3749	Approved
0.7679	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD6778	Approved
0.7672	Intermediate Similarity	NPD6776	Approved
0.7672	Intermediate Similarity	NPD6777	Approved
0.7672	Intermediate Similarity	NPD6779	Approved
0.7672	Intermediate Similarity	NPD6781	Approved
0.7672	Intermediate Similarity	NPD6782	Approved
0.7672	Intermediate Similarity	NPD6780	Approved
0.767	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD3027	Phase 3
0.7657	Intermediate Similarity	NPD7199	Phase 2
0.764	Intermediate Similarity	NPD1607	Approved
0.764	Intermediate Similarity	NPD7228	Approved
0.763	Intermediate Similarity	NPD7768	Phase 2
0.7622	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8312	Approved
0.7582	Intermediate Similarity	NPD8313	Approved
0.7578	Intermediate Similarity	NPD230	Phase 1
0.7569	Intermediate Similarity	NPD7685	Pre-registration
0.7554	Intermediate Similarity	NPD8150	Discontinued
0.7552	Intermediate Similarity	NPD7435	Discontinued
0.7546	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD6234	Discontinued
0.7532	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3750	Approved
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD2935	Discontinued
0.747	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD447	Suspended
0.7461	Intermediate Similarity	NPD7698	Approved
0.7461	Intermediate Similarity	NPD7696	Phase 3
0.7461	Intermediate Similarity	NPD7697	Approved
0.7457	Intermediate Similarity	NPD6844	Discontinued
0.7457	Intermediate Similarity	NPD37	Approved
0.7453	Intermediate Similarity	NPD6233	Phase 2
0.7429	Intermediate Similarity	NPD4965	Approved
0.7429	Intermediate Similarity	NPD4967	Phase 2
0.7429	Intermediate Similarity	NPD4966	Approved
0.7425	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4628	Phase 3
0.7407	Intermediate Similarity	NPD6534	Approved
0.7407	Intermediate Similarity	NPD6535	Approved
0.7398	Intermediate Similarity	NPD7701	Phase 2
0.7396	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7390	Discontinued
0.7396	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1551	Phase 2
0.7391	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4908	Phase 1
0.7374	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7783	Phase 2
0.7366	Intermediate Similarity	NPD8434	Phase 2
0.7365	Intermediate Similarity	NPD2800	Approved
0.736	Intermediate Similarity	NPD8151	Discontinued
0.7353	Intermediate Similarity	NPD2533	Approved
0.7353	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2534	Approved
0.7353	Intermediate Similarity	NPD2532	Approved
0.7323	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7874	Approved
0.7312	Intermediate Similarity	NPD9494	Approved
0.7292	Intermediate Similarity	NPD7700	Phase 2
0.7292	Intermediate Similarity	NPD7699	Phase 2
0.7286	Intermediate Similarity	NPD7801	Approved
0.7284	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6798	Discontinued
0.7283	Intermediate Similarity	NPD3226	Approved
0.7267	Intermediate Similarity	NPD920	Approved
0.7256	Intermediate Similarity	NPD1933	Approved
0.7251	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2344	Approved
0.7243	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7549	Discontinued
0.7231	Intermediate Similarity	NPD6823	Phase 2
0.7229	Intermediate Similarity	NPD3748	Approved
0.7228	Intermediate Similarity	NPD5953	Discontinued
0.7225	Intermediate Similarity	NPD4363	Phase 3
0.7225	Intermediate Similarity	NPD4360	Phase 2
0.7216	Intermediate Similarity	NPD8455	Phase 2
0.7189	Intermediate Similarity	NPD7240	Approved
0.7186	Intermediate Similarity	NPD6099	Approved
0.7186	Intermediate Similarity	NPD6100	Approved
0.7172	Intermediate Similarity	NPD7584	Approved
0.717	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7126	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7033	Discontinued
0.712	Intermediate Similarity	NPD7286	Phase 2
0.7108	Intermediate Similarity	NPD6651	Approved
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5353	Approved
0.7076	Intermediate Similarity	NPD2309	Approved
0.7073	Intermediate Similarity	NPD2313	Discontinued
0.7059	Intermediate Similarity	NPD1652	Phase 2
0.7059	Intermediate Similarity	NPD1243	Approved
0.7055	Intermediate Similarity	NPD6832	Phase 2
0.7053	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2346	Discontinued
0.7035	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2799	Discontinued
0.7006	Intermediate Similarity	NPD1548	Phase 1
0.7005	Intermediate Similarity	NPD7039	Approved
0.7005	Intermediate Similarity	NPD7038	Approved
0.7005	Intermediate Similarity	NPD2494	Approved
0.7005	Intermediate Similarity	NPD2493	Approved
0.6995	Remote Similarity	NPD6212	Phase 3
0.6995	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5242	Approved
0.6995	Remote Similarity	NPD6213	Phase 3
0.6994	Remote Similarity	NPD2861	Phase 2
0.6985	Remote Similarity	NPD8320	Phase 1
0.6985	Remote Similarity	NPD8319	Approved
0.6978	Remote Similarity	NPD8127	Discontinued
0.6975	Remote Similarity	NPD1203	Approved
0.6973	Remote Similarity	NPD2163	Approved
0.6971	Remote Similarity	NPD7907	Approved
0.6957	Remote Similarity	NPD4665	Approved
0.6957	Remote Similarity	NPD2403	Approved
0.6957	Remote Similarity	NPD4111	Phase 1
0.6946	Remote Similarity	NPD5124	Phase 1
0.6946	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6355	Discontinued
0.6946	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5711	Approved
0.694	Remote Similarity	NPD5710	Approved
0.694	Remote Similarity	NPD7229	Phase 3
0.6937	Remote Similarity	NPD1610	Phase 2
0.6935	Remote Similarity	NPD7680	Approved
0.6919	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3452	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