NPASS Compound

Structure

NPC177742 OpenBabel07101719132D 31 33 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 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 -6.9282 -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 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 -3.4641 2.0000 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 -3.4641 -1.0000 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 -7.7942 -2.5000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 -0.8660 0.5000 0.0000 C 0 0 2 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 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 -1.7321 -0.0000 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 11 1 0 0 0 0 2 5 1 0 0 0 0 2 12 2 0 0 0 0 3 6 2 0 0 0 0 3 12 1 0 0 0 0 4 7 1 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 9 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 23 1 0 0 0 0 11 18 1 0 0 0 0 11 24 2 0 0 0 0 13 25 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 26 1 0 0 0 0 16 18 2 0 0 0 0 16 30 1 0 0 0 0 17 10 1 1 0 0 0 17 19 1 0 0 0 0 17 31 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 6 0 0 0 20 21 1 0 0 0 0 20 28 1 1 0 0 0 21 22 1 0 0 0 0 21 29 1 6 0 0 0 22 30 1 1 0 0 0 22 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.16
Volume:	424.056
LogP:	0.722
LogD:	0.488
LogS:	-2.813
# Rotatable Bonds:	7
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.337
Synthetic Accessibility Score:	3.805
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.221
MDCK Permeability:	6.5043627728300635e-06
Pgp-inhibitor:	0.015
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.881
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	91.31731414794922%
Volume Distribution (VD):	0.766
Pgp-substrate:	3.7398529052734375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.316
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.657
CYP2D6-inhibitor:	0.541
CYP2D6-substrate:	0.431
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.091

ADMET: Excretion

Clearance (CL):	5.1
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.168
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.066
AMES Toxicity:	0.368
Rat Oral Acute Toxicity:	0.184
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.751
Carcinogencity:	0.286
Eye Corrosion:	0.003
Eye Irritation:	0.086
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC177742

Natural Product ID:	NPC177742
*Common Name:**	Scorzodihydrostilbene C
IUPAC Name:	1-[3-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone
Synonyms:	Scorzodihydrostilbene C
Standard InCHIKey:	IBJOXGCAQZPNTD-MIUGBVLSSA-N
Standard InCHI:	InChI=1S/C22H26O9/c1-11(24)18-14(7-4-12-2-5-13(25)6-3-12)15(26)8-9-16(18)30-22-21(29)20(28)19(27)17(10-23)31-22/h2-3,5-6,8-9,17,19-23,25-29H,4,7,10H2,1H3/t17-,19-,20+,21-,22-/m1/s1
SMILES:	CC(=O)c1c(CCc2ccc(cc2)O)c(ccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL556267
PubChem CID:	42638804
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0000142] Stilbene glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10471	Scorzonera radiata	Species	Asteraceae	Eukaryota	n.a.	Mongolian	n.a.	PMID[19271716]
NPO10471	Scorzonera radiata	Species	Asteraceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	486380.0	nM	PMID[490870]

☑ 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 NPC177742 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	375
0.1-0.2	1413
0.2-0.3	3094
0.3-0.4	7531
0.4-0.5	10383
0.5-0.6	4550
0.6-0.7	5499
0.7-0.8	7697
0.8-0.85	1765
0.85-0.9	355
0.9-0.95	31
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9739	High Similarity	NPC61594
0.9739	High Similarity	NPC56735
0.9675	High Similarity	NPC147596
0.9408	High Similarity	NPC185103
0.9236	High Similarity	NPC146837
0.9236	High Similarity	NPC278329
0.9231	High Similarity	NPC328093
0.9187	High Similarity	NPC246274
0.9119	High Similarity	NPC178281
0.9119	High Similarity	NPC99216
0.9114	High Similarity	NPC101116
0.9114	High Similarity	NPC22324
0.9114	High Similarity	NPC216752
0.9114	High Similarity	NPC212099
0.9091	High Similarity	NPC215811
0.9074	High Similarity	NPC315619
0.9068	High Similarity	NPC472381
0.9068	High Similarity	NPC222455
0.9068	High Similarity	NPC472383
0.9062	High Similarity	NPC178851
0.9062	High Similarity	NPC70441
0.9032	High Similarity	NPC260604
0.9032	High Similarity	NPC106625
0.9032	High Similarity	NPC299435
0.9032	High Similarity	NPC470331
0.9018	High Similarity	NPC199357
0.9012	High Similarity	NPC22195
0.9012	High Similarity	NPC44558
0.9012	High Similarity	NPC183357
0.9012	High Similarity	NPC105511
0.9012	High Similarity	NPC21190
0.9006	High Similarity	NPC93099
0.9006	High Similarity	NPC298847
0.9006	High Similarity	NPC63470
0.9	High Similarity	NPC7752
0.8994	High Similarity	NPC300537
0.8994	High Similarity	NPC127782
0.8981	High Similarity	NPC60966
0.8981	High Similarity	NPC6985
0.8974	High Similarity	NPC99233
0.8968	High Similarity	NPC474843
0.8968	High Similarity	NPC259182
0.8968	High Similarity	NPC121001
0.8963	High Similarity	NPC199533
0.8963	High Similarity	NPC470454
0.8957	High Similarity	NPC472386
0.8957	High Similarity	NPC5029
0.8957	High Similarity	NPC205076
0.8957	High Similarity	NPC111536
0.8957	High Similarity	NPC48773
0.8957	High Similarity	NPC271385
0.8957	High Similarity	NPC76128
0.8957	High Similarity	NPC30432
0.8957	High Similarity	NPC307518
0.8957	High Similarity	NPC267254
0.8957	High Similarity	NPC301683
0.8951	High Similarity	NPC475942
0.8951	High Similarity	NPC471457
0.8951	High Similarity	NPC259905
0.8951	High Similarity	NPC170675
0.8951	High Similarity	NPC469931
0.8951	High Similarity	NPC45638
0.8951	High Similarity	NPC95855
0.8951	High Similarity	NPC112755
0.8951	High Similarity	NPC226294
0.8951	High Similarity	NPC210042
0.8951	High Similarity	NPC105025
0.8951	High Similarity	NPC58053
0.8951	High Similarity	NPC186807
0.8951	High Similarity	NPC93337
0.8951	High Similarity	NPC201292
0.8938	High Similarity	NPC17432
0.8938	High Similarity	NPC127415
0.8924	High Similarity	NPC73511
0.8924	High Similarity	NPC308265
0.8922	High Similarity	NPC476203
0.8917	High Similarity	NPC206378
0.8917	High Similarity	NPC261866
0.8917	High Similarity	NPC127406
0.891	High Similarity	NPC230439
0.891	High Similarity	NPC299761
0.891	High Similarity	NPC92153
0.891	High Similarity	NPC279281
0.8909	High Similarity	NPC198893
0.8909	High Similarity	NPC475246
0.8909	High Similarity	NPC232818
0.8909	High Similarity	NPC102053
0.8909	High Similarity	NPC314489
0.8902	High Similarity	NPC236191
0.8902	High Similarity	NPC239549
0.8902	High Similarity	NPC51774
0.8896	High Similarity	NPC298778
0.8896	High Similarity	NPC199079
0.8896	High Similarity	NPC224462
0.8896	High Similarity	NPC471416
0.8896	High Similarity	NPC34287
0.8896	High Similarity	NPC241874
0.8896	High Similarity	NPC210808
0.8896	High Similarity	NPC474434
0.8889	High Similarity	NPC146792
0.8889	High Similarity	NPC135345
0.8889	High Similarity	NPC103633
0.8889	High Similarity	NPC140722
0.8889	High Similarity	NPC4958
0.8889	High Similarity	NPC58716
0.8889	High Similarity	NPC45618
0.8889	High Similarity	NPC92054
0.8889	High Similarity	NPC249977
0.8889	High Similarity	NPC83975
0.8882	High Similarity	NPC165720
0.8868	High Similarity	NPC271479
0.8861	High Similarity	NPC43638
0.8861	High Similarity	NPC161749
0.8861	High Similarity	NPC313163
0.8861	High Similarity	NPC197896
0.8861	High Similarity	NPC258035
0.8861	High Similarity	NPC23817
0.8861	High Similarity	NPC156457
0.8854	High Similarity	NPC27408
0.8854	High Similarity	NPC72649
0.8854	High Similarity	NPC95090
0.8854	High Similarity	NPC97052
0.8854	High Similarity	NPC169248
0.8854	High Similarity	NPC39351
0.8854	High Similarity	NPC26195
0.8848	High Similarity	NPC102028
0.8848	High Similarity	NPC68381
0.8848	High Similarity	NPC3718
0.8846	High Similarity	NPC183536
0.8846	High Similarity	NPC259767
0.8846	High Similarity	NPC34965
0.8846	High Similarity	NPC88484
0.8841	High Similarity	NPC257011
0.8841	High Similarity	NPC288152
0.8841	High Similarity	NPC117260
0.8841	High Similarity	NPC476405
0.8841	High Similarity	NPC137871
0.8841	High Similarity	NPC254540
0.8841	High Similarity	NPC260263
0.8841	High Similarity	NPC156977
0.8841	High Similarity	NPC211594
0.8841	High Similarity	NPC172807
0.8841	High Similarity	NPC9002
0.8834	High Similarity	NPC183036
0.8834	High Similarity	NPC229687
0.8827	High Similarity	NPC5778
0.8827	High Similarity	NPC236934
0.882	High Similarity	NPC94777
0.882	High Similarity	NPC309025
0.882	High Similarity	NPC19709
0.882	High Similarity	NPC243930
0.882	High Similarity	NPC29830
0.882	High Similarity	NPC88043
0.882	High Similarity	NPC88023
0.8812	High Similarity	NPC303913
0.8812	High Similarity	NPC217950
0.8812	High Similarity	NPC73148
0.8805	High Similarity	NPC57072
0.8805	High Similarity	NPC329091
0.8805	High Similarity	NPC231475
0.8802	High Similarity	NPC277710
0.8802	High Similarity	NPC114257
0.8802	High Similarity	NPC84494
0.8802	High Similarity	NPC153578
0.8802	High Similarity	NPC245059
0.8802	High Similarity	NPC299149
0.8802	High Similarity	NPC58538
0.8797	High Similarity	NPC45165
0.8797	High Similarity	NPC170475
0.8795	High Similarity	NPC472382
0.8795	High Similarity	NPC472384
0.8795	High Similarity	NPC475233
0.8795	High Similarity	NPC472380
0.8795	High Similarity	NPC46958
0.879	High Similarity	NPC210003
0.879	High Similarity	NPC83283
0.879	High Similarity	NPC135522
0.879	High Similarity	NPC143851
0.879	High Similarity	NPC39360
0.879	High Similarity	NPC29763
0.8788	High Similarity	NPC213052
0.8788	High Similarity	NPC45522
0.8788	High Similarity	NPC204693
0.8788	High Similarity	NPC24043
0.8788	High Similarity	NPC101026
0.8788	High Similarity	NPC42773
0.8788	High Similarity	NPC169977
0.8788	High Similarity	NPC85368
0.8788	High Similarity	NPC21666
0.8788	High Similarity	NPC98776
0.8788	High Similarity	NPC203751
0.8782	High Similarity	NPC190217
0.878	High Similarity	NPC212748
0.878	High Similarity	NPC293004
0.878	High Similarity	NPC84265
0.878	High Similarity	NPC282987
0.878	High Similarity	NPC245014
0.8773	High Similarity	NPC116745
0.8773	High Similarity	NPC229729
0.8773	High Similarity	NPC45400

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 NPC177742 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	848
0.2-0.3	1630
0.3-0.4	2586
0.4-0.5	1980
0.5-0.6	1068
0.6-0.7	524
0.7-0.8	160
0.8-0.85	26
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8861	High Similarity	NPD4381	Clinical (unspecified phase)
0.8667	High Similarity	NPD7074	Phase 3
0.8659	High Similarity	NPD3818	Discontinued
0.8623	High Similarity	NPD4338	Clinical (unspecified phase)
0.8606	High Similarity	NPD7054	Approved
0.8571	High Similarity	NPD8312	Approved
0.8571	High Similarity	NPD8313	Approved
0.8563	High Similarity	NPD6559	Discontinued
0.8554	High Similarity	NPD7472	Approved
0.8503	High Similarity	NPD6797	Phase 2
0.8494	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7251	Discontinued
0.8439	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD7808	Phase 3
0.8375	Intermediate Similarity	NPD1934	Approved
0.8323	Intermediate Similarity	NPD2801	Approved
0.8323	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD5402	Approved
0.825	Intermediate Similarity	NPD4380	Phase 2
0.821	Intermediate Similarity	NPD7819	Suspended
0.8204	Intermediate Similarity	NPD6166	Phase 2
0.8204	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7075	Discontinued
0.8114	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD6776	Approved
0.8111	Intermediate Similarity	NPD6782	Approved
0.8111	Intermediate Similarity	NPD6777	Approved
0.8111	Intermediate Similarity	NPD6781	Approved
0.8111	Intermediate Similarity	NPD6778	Approved
0.8111	Intermediate Similarity	NPD6779	Approved
0.8111	Intermediate Similarity	NPD6780	Approved
0.8065	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6959	Discontinued
0.8022	Intermediate Similarity	NPD6823	Phase 2
0.8013	Intermediate Similarity	NPD1549	Phase 2
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD8455	Phase 2
0.7978	Intermediate Similarity	NPD7435	Discontinued
0.7976	Intermediate Similarity	NPD3787	Discontinued
0.7964	Intermediate Similarity	NPD5494	Approved
0.7963	Intermediate Similarity	NPD3226	Approved
0.7953	Intermediate Similarity	NPD5844	Phase 1
0.7949	Intermediate Similarity	NPD2346	Discontinued
0.7939	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3817	Phase 2
0.7937	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6801	Discontinued
0.7911	Intermediate Similarity	NPD4628	Phase 3
0.7892	Intermediate Similarity	NPD3882	Suspended
0.788	Intermediate Similarity	NPD7697	Approved
0.788	Intermediate Similarity	NPD7696	Phase 3
0.788	Intermediate Similarity	NPD7698	Approved
0.7875	Intermediate Similarity	NPD1511	Approved
0.7872	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD7783	Phase 2
0.787	Intermediate Similarity	NPD6232	Discontinued
0.784	Intermediate Similarity	NPD5403	Approved
0.7838	Intermediate Similarity	NPD7870	Phase 2
0.7838	Intermediate Similarity	NPD7871	Phase 2
0.7836	Intermediate Similarity	NPD7473	Discontinued
0.7833	Intermediate Similarity	NPD6535	Approved
0.7833	Intermediate Similarity	NPD6534	Approved
0.7818	Intermediate Similarity	NPD37	Approved
0.7807	Intermediate Similarity	NPD7701	Phase 2
0.7799	Intermediate Similarity	NPD3750	Approved
0.7798	Intermediate Similarity	NPD6234	Discontinued
0.7791	Intermediate Similarity	NPD7228	Approved
0.7791	Intermediate Similarity	NPD1653	Approved
0.7784	Intermediate Similarity	NPD4967	Phase 2
0.7784	Intermediate Similarity	NPD4966	Approved
0.7784	Intermediate Similarity	NPD4965	Approved
0.7778	Intermediate Similarity	NPD1512	Approved
0.7771	Intermediate Similarity	NPD2796	Approved
0.7764	Intermediate Similarity	NPD6799	Approved
0.7758	Intermediate Similarity	NPD7411	Suspended
0.7725	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7874	Approved
0.7716	Intermediate Similarity	NPD5401	Approved
0.7714	Intermediate Similarity	NPD7685	Pre-registration
0.7707	Intermediate Similarity	NPD1510	Phase 2
0.7707	Intermediate Similarity	NPD2799	Discontinued
0.7706	Intermediate Similarity	NPD7199	Phase 2
0.7705	Intermediate Similarity	NPD7700	Phase 2
0.7705	Intermediate Similarity	NPD7699	Phase 2
0.7697	Intermediate Similarity	NPD6599	Discontinued
0.7688	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7801	Approved
0.768	Intermediate Similarity	NPD6213	Phase 3
0.768	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6212	Phase 3
0.7673	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1465	Phase 2
0.7657	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3749	Approved
0.7632	Intermediate Similarity	NPD2798	Approved
0.7625	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7266	Discontinued
0.7607	Intermediate Similarity	NPD2532	Approved
0.7607	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2534	Approved
0.7607	Intermediate Similarity	NPD2533	Approved
0.7605	Intermediate Similarity	NPD6844	Discontinued
0.7582	Intermediate Similarity	NPD2861	Phase 2
0.7579	Intermediate Similarity	NPD8151	Discontinued
0.7574	Intermediate Similarity	NPD7768	Phase 2
0.7572	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1240	Approved
0.7548	Intermediate Similarity	NPD2313	Discontinued
0.7546	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1091	Approved
0.753	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1933	Approved
0.7516	Intermediate Similarity	NPD6674	Discontinued
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD8434	Phase 2
0.7484	Intermediate Similarity	NPD3748	Approved
0.7468	Intermediate Similarity	NPD1607	Approved
0.7452	Intermediate Similarity	NPD4060	Phase 1
0.7452	Intermediate Similarity	NPD1613	Approved
0.7452	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1551	Phase 2
0.7436	Intermediate Similarity	NPD6798	Discontinued
0.7425	Intermediate Similarity	NPD7458	Discontinued
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.7416	Intermediate Similarity	NPD7240	Approved
0.741	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6355	Discontinued
0.7405	Intermediate Similarity	NPD447	Suspended
0.7394	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7584	Approved
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.7368	Intermediate Similarity	NPD8320	Phase 1
0.7368	Intermediate Similarity	NPD8319	Approved
0.7349	Intermediate Similarity	NPD6273	Approved
0.7338	Intermediate Similarity	NPD1203	Approved
0.7338	Intermediate Similarity	NPD1470	Approved
0.7337	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3764	Approved
0.7317	Intermediate Similarity	NPD2309	Approved
0.7317	Intermediate Similarity	NPD6190	Approved
0.7303	Intermediate Similarity	NPD1201	Approved
0.7301	Intermediate Similarity	NPD2800	Approved
0.7296	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7930	Approved
0.7289	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2424	Discontinued
0.7226	Intermediate Similarity	NPD2797	Approved
0.7222	Intermediate Similarity	NPD6099	Approved
0.7222	Intermediate Similarity	NPD6100	Approved
0.7219	Intermediate Similarity	NPD2651	Approved
0.7219	Intermediate Similarity	NPD2649	Approved
0.7216	Intermediate Similarity	NPD3926	Phase 2
0.7215	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3268	Approved
0.7205	Intermediate Similarity	NPD7097	Phase 1
0.72	Intermediate Similarity	NPD1247	Approved
0.7197	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4908	Phase 1
0.7186	Intermediate Similarity	NPD4661	Approved
0.7186	Intermediate Similarity	NPD4662	Approved
0.7167	Intermediate Similarity	NPD5953	Discontinued
0.716	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5710	Approved
0.7159	Intermediate Similarity	NPD5711	Approved
0.7158	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD8059	Phase 3
0.7157	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD4420	Approved
0.7134	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7390	Discontinued
0.7125	Intermediate Similarity	NPD943	Approved
0.7117	Intermediate Similarity	NPD5404	Approved
0.7117	Intermediate Similarity	NPD5406	Approved
0.7117	Intermediate Similarity	NPD5405	Approved
0.7117	Intermediate Similarity	NPD5408	Approved
0.7117	Intermediate Similarity	NPD2438	Suspended
0.7107	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD8127	Discontinued
0.7101	Intermediate Similarity	NPD920	Approved
0.7097	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1610	Phase 2
0.7073	Intermediate Similarity	NPD2343	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