NPASS Compound

Structure

NPC470456 OpenBabel07101718292D 36 38 0 0 1 0 0 0 0 0999 V2000 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 3.4641 3.0000 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 1.5000 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 -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 -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 -6.0622 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 -5.1962 2.0000 0.0000 C 0 0 3 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 -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 3 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 0.8660 0.5000 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 -3.4641 -1.0000 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 0.0000 2.0000 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 2.5981 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 -6.9282 2.0000 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 3.4641 -0.0000 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 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 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 34 1 0 0 0 0 5 35 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 15 1 0 0 0 0 8 17 2 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 28 1 0 0 0 0 13 18 1 0 0 0 0 15 22 2 0 0 0 0 16 22 1 0 0 0 0 17 25 1 0 0 0 0 18 29 1 0 0 0 0 19 26 1 0 0 0 0 19 30 1 0 0 0 0 20 21 2 0 0 0 0 20 36 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 31 1 0 0 0 0 23 26 2 0 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 24 33 2 0 0 0 0 25 27 2 0 0 0 0 25 36 1 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.2
Volume:	505.263
LogP:	3.569
LogD:	2.392
LogS:	-3.943
# Rotatable Bonds:	10
TPSA:	149.82
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.263
Synthetic Accessibility Score:	3.956
Fsp3:	0.37
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.972
MDCK Permeability:	7.01380122336559e-06
Pgp-inhibitor:	0.968
Pgp-substrate:	0.479
Human Intestinal Absorption (HIA):	0.191
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	94.72832489013672%
Volume Distribution (VD):	0.678
Pgp-substrate:	5.672953128814697%

ADMET: Metabolism

CYP1A2-inhibitor:	0.369
CYP1A2-substrate:	0.927
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.344
CYP2C9-substrate:	0.495
CYP2D6-inhibitor:	0.296
CYP2D6-substrate:	0.232
CYP3A4-inhibitor:	0.188
CYP3A4-substrate:	0.151

ADMET: Excretion

Clearance (CL):	5.098
Half-life (T1/2):	0.691

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.16
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.783
Skin Sensitization:	0.873
Carcinogencity:	0.015
Eye Corrosion:	0.003
Eye Irritation:	0.386
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC470456

Natural Product ID:	NPC470456
*Common Name:**	Dodoviscin A
IUPAC Name:	5,7-dihydroxy-2-[4-hydroxy-3-(2-hydroxy-3-methylbut-3-enyl)-5-(4-hydroxy-3-methylbutyl)phenyl]-3,6-dimethoxychromen-4-one
Synonyms:	dodoviscin A
Standard InCHIKey:	JOFIZXLDARFSIK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H32O9/c1-13(2)18(29)10-16-9-17(8-15(22(16)31)7-6-14(3)12-28)25-27(35-5)24(33)21-20(36-25)11-19(30)26(34-4)23(21)32/h8-9,11,14,18,28-32H,1,6-7,10,12H2,2-5H3
SMILES:	OCC(CCc1cc(cc(c1O)CC(C(=C)C)O)c1oc2cc(O)c(c(c2c(=O)c1OC)O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2037148
PubChem CID:	57409962
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003502] 3'-prenylated flavones

*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
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719093]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22512738]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	138.5	%	PMID[476898]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	248.3	%	PMID[476898]

☑ 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 NPC470456 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	446
0.1-0.2	1702
0.2-0.3	4270
0.3-0.4	9952
0.4-0.5	8256
0.5-0.6	3910
0.6-0.7	5031
0.7-0.8	4864
0.8-0.85	2240
0.85-0.9	1370
0.9-0.95	641
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC470462
0.9873	High Similarity	NPC158761
0.9873	High Similarity	NPC470457
0.9809	High Similarity	NPC470459
0.9618	High Similarity	NPC246478
0.9494	High Similarity	NPC470326
0.949	High Similarity	NPC235215
0.949	High Similarity	NPC29841
0.949	High Similarity	NPC7973
0.949	High Similarity	NPC472438
0.949	High Similarity	NPC78302
0.9437	High Similarity	NPC41301
0.9434	High Similarity	NPC471499
0.9434	High Similarity	NPC266314
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	NPC25495
0.943	High Similarity	NPC9609
0.943	High Similarity	NPC22472
0.943	High Similarity	NPC261004
0.943	High Similarity	NPC105242
0.943	High Similarity	NPC4481
0.943	High Similarity	NPC18607
0.943	High Similarity	NPC176300
0.943	High Similarity	NPC18772
0.943	High Similarity	NPC152166
0.943	High Similarity	NPC19687
0.943	High Similarity	NPC143828
0.943	High Similarity	NPC300943
0.943	High Similarity	NPC115798
0.943	High Similarity	NPC288669
0.9427	High Similarity	NPC268161
0.9427	High Similarity	NPC100916
0.9427	High Similarity	NPC200388
0.9427	High Similarity	NPC474520
0.9427	High Similarity	NPC55619
0.9375	High Similarity	NPC81679
0.9371	High Similarity	NPC282009
0.9371	High Similarity	NPC287328
0.9371	High Similarity	NPC472630
0.9371	High Similarity	NPC263449
0.9371	High Similarity	NPC472631
0.9367	High Similarity	NPC176665
0.9367	High Similarity	NPC224137
0.9367	High Similarity	NPC305663
0.9367	High Similarity	NPC203891
0.9367	High Similarity	NPC189179
0.9367	High Similarity	NPC78103
0.9367	High Similarity	NPC470402
0.9367	High Similarity	NPC93376
0.9367	High Similarity	NPC163524
0.9367	High Similarity	NPC227192
0.9367	High Similarity	NPC110070
0.9367	High Similarity	NPC287979
0.9367	High Similarity	NPC101830
0.9367	High Similarity	NPC75215
0.9367	High Similarity	NPC223787
0.9337	High Similarity	NPC168584
0.9321	High Similarity	NPC471213
0.9317	High Similarity	NPC472625
0.9317	High Similarity	NPC7483
0.9313	High Similarity	NPC472634
0.9313	High Similarity	NPC308992
0.9313	High Similarity	NPC289771
0.9313	High Similarity	NPC26326
0.9308	High Similarity	NPC193842
0.9308	High Similarity	NPC250214
0.9308	High Similarity	NPC95936
0.9308	High Similarity	NPC469658
0.9308	High Similarity	NPC22192
0.9304	High Similarity	NPC250922
0.9304	High Similarity	NPC266960
0.9304	High Similarity	NPC292107
0.9304	High Similarity	NPC317383
0.9304	High Similarity	NPC245546
0.9304	High Similarity	NPC98661
0.9304	High Similarity	NPC43243
0.9304	High Similarity	NPC209614
0.9304	High Similarity	NPC247017
0.9304	High Similarity	NPC178854
0.9304	High Similarity	NPC49824
0.9304	High Similarity	NPC470328
0.9304	High Similarity	NPC472626
0.9299	High Similarity	NPC58382
0.9299	High Similarity	NPC276409
0.9299	High Similarity	NPC162351
0.9299	High Similarity	NPC250822
0.9299	High Similarity	NPC75279
0.9299	High Similarity	NPC246204
0.9264	High Similarity	NPC295082
0.9259	High Similarity	NPC50960
0.9259	High Similarity	NPC475888
0.9255	High Similarity	NPC220912
0.9255	High Similarity	NPC211107
0.925	High Similarity	NPC476980
0.9245	High Similarity	NPC162869
0.9245	High Similarity	NPC471515
0.9245	High Similarity	NPC156057
0.9245	High Similarity	NPC474208
0.9245	High Similarity	NPC474055
0.9245	High Similarity	NPC472913
0.9245	High Similarity	NPC262286
0.9245	High Similarity	NPC78225
0.9245	High Similarity	NPC96167
0.9245	High Similarity	NPC472914
0.9245	High Similarity	NPC471479
0.9245	High Similarity	NPC472598
0.9245	High Similarity	NPC222814
0.9245	High Similarity	NPC472911
0.9245	High Similarity	NPC36852
0.9245	High Similarity	NPC474836
0.9245	High Similarity	NPC472910
0.9245	High Similarity	NPC245758
0.9245	High Similarity	NPC48208
0.9245	High Similarity	NPC469584
0.9245	High Similarity	NPC475267
0.9241	High Similarity	NPC163780
0.9241	High Similarity	NPC44079
0.9241	High Similarity	NPC4455
0.9241	High Similarity	NPC138360
0.9241	High Similarity	NPC280339
0.9241	High Similarity	NPC213622
0.9241	High Similarity	NPC201136
0.9241	High Similarity	NPC130589
0.9241	High Similarity	NPC183597
0.9241	High Similarity	NPC477503
0.9241	High Similarity	NPC201451
0.9241	High Similarity	NPC208197
0.9241	High Similarity	NPC45849
0.9241	High Similarity	NPC200761
0.9241	High Similarity	NPC146165
0.9241	High Similarity	NPC32557
0.9241	High Similarity	NPC50715
0.9241	High Similarity	NPC128863
0.9241	High Similarity	NPC227325
0.9241	High Similarity	NPC133392
0.9241	High Similarity	NPC189960
0.9241	High Similarity	NPC134287
0.9241	High Similarity	NPC167815
0.9241	High Similarity	NPC214138
0.9241	High Similarity	NPC26227
0.9241	High Similarity	NPC92659
0.9241	High Similarity	NPC196439
0.9241	High Similarity	NPC2476
0.9241	High Similarity	NPC470327
0.9236	High Similarity	NPC249570
0.9236	High Similarity	NPC471982
0.9236	High Similarity	NPC123886
0.9231	High Similarity	NPC148710
0.9217	High Similarity	NPC99591
0.9207	High Similarity	NPC326877
0.9207	High Similarity	NPC177480
0.9202	High Similarity	NPC13481
0.9202	High Similarity	NPC207575
0.9198	High Similarity	NPC474240
0.9193	High Similarity	NPC471211
0.9193	High Similarity	NPC278052
0.9193	High Similarity	NPC228383
0.9193	High Similarity	NPC198829
0.9193	High Similarity	NPC474186
0.9193	High Similarity	NPC40491
0.9193	High Similarity	NPC471212
0.9193	High Similarity	NPC474038
0.9193	High Similarity	NPC258331
0.9187	High Similarity	NPC117418
0.9187	High Similarity	NPC152904
0.9187	High Similarity	NPC53545
0.9182	High Similarity	NPC278778
0.9182	High Similarity	NPC255106
0.9182	High Similarity	NPC68093
0.9182	High Similarity	NPC13858
0.9182	High Similarity	NPC265511
0.9182	High Similarity	NPC320825
0.9182	High Similarity	NPC326037
0.9182	High Similarity	NPC235165
0.9182	High Similarity	NPC201837
0.9182	High Similarity	NPC291878
0.9182	High Similarity	NPC195796
0.9182	High Similarity	NPC191146
0.9182	High Similarity	NPC471500
0.9182	High Similarity	NPC35038
0.9182	High Similarity	NPC138243
0.9177	High Similarity	NPC298692
0.9177	High Similarity	NPC280937
0.9177	High Similarity	NPC176775
0.9177	High Similarity	NPC231018
0.9177	High Similarity	NPC145379
0.9177	High Similarity	NPC183878
0.9177	High Similarity	NPC250557
0.9177	High Similarity	NPC22519
0.9177	High Similarity	NPC274327
0.9177	High Similarity	NPC86485
0.9177	High Similarity	NPC270620
0.9177	High Similarity	NPC255350
0.9177	High Similarity	NPC69394
0.9177	High Similarity	NPC47781
0.9177	High Similarity	NPC78326

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 NPC470456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	952
0.2-0.3	1957
0.3-0.4	2645
0.4-0.5	1762
0.5-0.6	916
0.6-0.7	350
0.7-0.8	118
0.8-0.85	25
0.85-0.9	25
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9177	High Similarity	NPD2801	Approved
0.9057	High Similarity	NPD2393	Clinical (unspecified phase)
0.9024	High Similarity	NPD6168	Clinical (unspecified phase)
0.9024	High Similarity	NPD6167	Clinical (unspecified phase)
0.9024	High Similarity	NPD6166	Phase 2
0.8994	High Similarity	NPD1934	Approved
0.8988	High Similarity	NPD4338	Clinical (unspecified phase)
0.8944	High Similarity	NPD3882	Suspended
0.8882	High Similarity	NPD3817	Phase 2
0.8817	High Similarity	NPD7251	Discontinued
0.8802	High Similarity	NPD3818	Discontinued
0.8773	High Similarity	NPD7075	Discontinued
0.8765	High Similarity	NPD7808	Phase 3
0.8757	High Similarity	NPD6797	Phase 2
0.875	High Similarity	NPD7054	Approved
0.8734	High Similarity	NPD1512	Approved
0.8698	High Similarity	NPD7074	Phase 3
0.8698	High Similarity	NPD7472	Approved
0.8671	High Similarity	NPD4378	Clinical (unspecified phase)
0.8667	High Similarity	NPD5494	Approved
0.8642	High Similarity	NPD6801	Discontinued
0.8639	High Similarity	NPD7804	Clinical (unspecified phase)
0.8634	High Similarity	NPD4380	Phase 2
0.8608	High Similarity	NPD1511	Approved
0.8589	High Similarity	NPD7096	Clinical (unspecified phase)
0.8537	High Similarity	NPD5402	Approved
0.8485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD7473	Discontinued
0.8393	Intermediate Similarity	NPD1247	Approved
0.8324	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6232	Discontinued
0.8208	Intermediate Similarity	NPD5844	Phase 1
0.8148	Intermediate Similarity	NPD6799	Approved
0.8144	Intermediate Similarity	NPD7819	Suspended
0.8113	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5403	Approved
0.8098	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD6959	Discontinued
0.8063	Intermediate Similarity	NPD1549	Phase 2
0.8059	Intermediate Similarity	NPD919	Approved
0.805	Intermediate Similarity	NPD2796	Approved
0.7988	Intermediate Similarity	NPD5401	Approved
0.7987	Intermediate Similarity	NPD1510	Phase 2
0.7967	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD6559	Discontinued
0.7964	Intermediate Similarity	NPD6599	Discontinued
0.7929	Intermediate Similarity	NPD1465	Phase 2
0.7917	Intermediate Similarity	NPD7411	Suspended
0.7874	Intermediate Similarity	NPD3926	Phase 2
0.7857	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6190	Approved
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6234	Discontinued
0.7736	Intermediate Similarity	NPD1240	Approved
0.7736	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD943	Approved
0.7736	Intermediate Similarity	NPD1613	Approved
0.773	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD2935	Discontinued
0.7701	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD2800	Approved
0.767	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD2533	Approved
0.7665	Intermediate Similarity	NPD2534	Approved
0.7665	Intermediate Similarity	NPD2532	Approved
0.7661	Intermediate Similarity	NPD37	Approved
0.7658	Intermediate Similarity	NPD3027	Phase 3
0.765	Intermediate Similarity	NPD8434	Phase 2
0.764	Intermediate Similarity	NPD1607	Approved
0.764	Intermediate Similarity	NPD7228	Approved
0.764	Intermediate Similarity	NPD6651	Approved
0.764	Intermediate Similarity	NPD3751	Discontinued
0.7633	Intermediate Similarity	NPD1653	Approved
0.763	Intermediate Similarity	NPD7768	Phase 2
0.763	Intermediate Similarity	NPD4967	Phase 2
0.763	Intermediate Similarity	NPD4965	Approved
0.763	Intermediate Similarity	NPD4966	Approved
0.7627	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD3787	Discontinued
0.7579	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD230	Phase 1
0.7557	Intermediate Similarity	NPD7199	Phase 2
0.7554	Intermediate Similarity	NPD8150	Discontinued
0.7552	Intermediate Similarity	NPD7435	Discontinued
0.7532	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7486	Intermediate Similarity	NPD8312	Approved
0.7486	Intermediate Similarity	NPD8313	Approved
0.7484	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7685	Pre-registration
0.7471	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD920	Approved
0.747	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3750	Approved
0.7425	Intermediate Similarity	NPD4628	Phase 3
0.7418	Intermediate Similarity	NPD5953	Discontinued
0.7403	Intermediate Similarity	NPD7286	Phase 2
0.7394	Intermediate Similarity	NPD6100	Approved
0.7394	Intermediate Similarity	NPD6099	Approved
0.7391	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3226	Approved
0.7371	Intermediate Similarity	NPD7697	Approved
0.7371	Intermediate Similarity	NPD7696	Phase 3
0.7371	Intermediate Similarity	NPD7698	Approved
0.7365	Intermediate Similarity	NPD1243	Approved
0.7362	Intermediate Similarity	NPD447	Suspended
0.7353	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7870	Phase 2
0.7333	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7871	Phase 2
0.7333	Intermediate Similarity	NPD2799	Discontinued
0.7323	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7874	Approved
0.7321	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD4360	Phase 2
0.7316	Intermediate Similarity	NPD4363	Phase 3
0.731	Intermediate Similarity	NPD7701	Phase 2
0.7294	Intermediate Similarity	NPD7390	Discontinued
0.7289	Intermediate Similarity	NPD1551	Phase 2
0.7288	Intermediate Similarity	NPD3749	Approved
0.7286	Intermediate Similarity	NPD7801	Approved
0.7284	Intermediate Similarity	NPD2313	Discontinued
0.7273	Intermediate Similarity	NPD8151	Discontinued
0.7259	Intermediate Similarity	NPD7584	Approved
0.7257	Intermediate Similarity	NPD6844	Discontinued
0.7256	Intermediate Similarity	NPD6355	Discontinued
0.7239	Intermediate Similarity	NPD6233	Phase 2
0.7238	Intermediate Similarity	NPD2403	Approved
0.7235	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6535	Approved
0.7225	Intermediate Similarity	NPD6534	Approved
0.7219	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD9494	Approved
0.7202	Intermediate Similarity	NPD7699	Phase 2
0.7202	Intermediate Similarity	NPD7700	Phase 2
0.72	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7783	Phase 2
0.7195	Intermediate Similarity	NPD4060	Phase 1
0.7193	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7240	Approved
0.7178	Intermediate Similarity	NPD6798	Discontinued
0.7178	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD2344	Approved
0.7127	Intermediate Similarity	NPD5710	Approved
0.7127	Intermediate Similarity	NPD7229	Phase 3
0.7127	Intermediate Similarity	NPD5711	Approved
0.7126	Intermediate Similarity	NPD7033	Discontinued
0.7126	Intermediate Similarity	NPD3748	Approved
0.7098	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4361	Phase 2
0.7072	Intermediate Similarity	NPD8127	Discontinued
0.7071	Intermediate Similarity	NPD8319	Approved
0.7071	Intermediate Similarity	NPD8320	Phase 1
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4908	Phase 1
0.7055	Intermediate Similarity	NPD6832	Phase 2
0.7053	Intermediate Similarity	NPD7907	Approved
0.7052	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1933	Approved
0.7048	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5124	Phase 1
0.7022	Intermediate Similarity	NPD8455	Phase 2
0.7	Intermediate Similarity	NPD2424	Discontinued
0.6995	Remote Similarity	NPD5242	Approved
0.6994	Remote Similarity	NPD2861	Phase 2
0.6989	Remote Similarity	NPD7458	Discontinued
0.6989	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2309	Approved
0.6973	Remote Similarity	NPD2163	Approved
0.6971	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3268	Approved
0.6959	Remote Similarity	NPD6674	Discontinued
0.6957	Remote Similarity	NPD4665	Approved
0.6957	Remote Similarity	NPD4111	Phase 1
0.6941	Remote Similarity	NPD7266	Discontinued
0.6937	Remote Similarity	NPD1610	Phase 2
0.6937	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2798	Approved
0.6927	Remote Similarity	NPD5761	Phase 2
0.6927	Remote Similarity	NPD5760	Phase 2
0.6919	Remote Similarity	NPD2494	Approved
0.6919	Remote Similarity	NPD2493	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