NPASS Compound

Structure

CID217950 OpenBabel06191716012D 33 35 0 0 1 0 0 0 0 0999 V2000 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -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 3.4641 -2.0000 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 -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 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 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 3.4641 0.0000 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 2.5981 -0.5000 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 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 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 8.6603 1.0000 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 5.1962 0.0000 0.0000 O 0 0 0 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 6.9282 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 -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 29 1 0 0 0 0 2 30 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 11 2 0 0 0 0 6 13 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 31 1 0 0 0 0 11 13 1 0 0 0 0 12 20 2 0 0 0 0 12 24 1 0 0 0 0 13 32 1 0 0 0 0 14 16 2 0 0 0 0 14 29 1 0 0 0 0 15 9 1 1 0 0 0 15 17 1 0 0 0 0 15 33 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 22 1 0 0 0 0 19 27 1 6 0 0 0 20 30 1 0 0 0 0 21 28 2 0 0 0 0 21 31 1 0 0 0 0 22 32 1 1 0 0 0 22 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.15
Volume:	441.636
LogP:	0.688
LogD:	0.433
LogS:	-2.209
# Rotatable Bonds:	9
TPSA:	164.37
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.331
Synthetic Accessibility Score:	3.734
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.342
MDCK Permeability:	2.2531092326971702e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.203
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.36
Plasma Protein Binding (PPB):	71.4698715209961%
Volume Distribution (VD):	0.445
Pgp-substrate:	9.555340766906738%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.32
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.581
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.508
CYP2D6-inhibitor:	0.371
CYP2D6-substrate:	0.392
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	6.983
Half-life (T1/2):	0.926

ADMET: Toxicity

hERG Blockers:	0.366
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.717
AMES Toxicity:	0.456
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.147
Carcinogencity:	0.57
Eye Corrosion:	0.003
Eye Irritation:	0.157
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC217950

Natural Product ID:	NPC217950
*Common Name:**	Curculigoside D
IUPAC Name:	[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl 3-hydroxy-2,6-dimethoxybenzoate
Synonyms:	Curculigoside D
Standard InCHIKey:	FUMJMMSKXPMVAE-DRASZATQSA-N
Standard InCHI:	InChI=1S/C22H26O11/c1-29-14-8-7-12(24)20(30-2)16(14)21(28)31-10-11-5-3-4-6-13(11)32-22-19(27)18(26)17(25)15(9-23)33-22/h3-8,15,17-19,22-27H,9-10H2,1-2H3/t15-,17-,18+,19-,22-/m1/s1
SMILES:	COc1ccc(c(c1C(=O)OCc1ccccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL258047
PubChem CID:	21580518
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20524638]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	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	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	49.0	%	PMID[473845]
NPT2	Others	Unspecified		EC50	=	9500.0	nM	PMID[473845]

☑ 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 NPC217950 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	360
0.1-0.2	1587
0.2-0.3	4060
0.3-0.4	9318
0.4-0.5	9016
0.5-0.6	4131
0.6-0.7	5357
0.7-0.8	6497
0.8-0.85	1736
0.85-0.9	555
0.9-0.95	77
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC299435
0.9605	High Similarity	NPC260604
0.95	High Similarity	NPC254540
0.95	High Similarity	NPC211594
0.95	High Similarity	NPC172807
0.9434	High Similarity	NPC116745
0.9383	High Similarity	NPC477848
0.9379	High Similarity	NPC472386
0.9375	High Similarity	NPC58053
0.9375	High Similarity	NPC105025
0.9375	High Similarity	NPC93337
0.9375	High Similarity	NPC201292
0.9375	High Similarity	NPC226294
0.9375	High Similarity	NPC469931
0.9375	High Similarity	NPC45638
0.9375	High Similarity	NPC475942
0.9375	High Similarity	NPC186807
0.9367	High Similarity	NPC127415
0.9363	High Similarity	NPC25389
0.9363	High Similarity	NPC311803
0.9363	High Similarity	NPC472859
0.9325	High Similarity	NPC472385
0.9325	High Similarity	NPC198324
0.9325	High Similarity	NPC233994
0.9325	High Similarity	NPC211532
0.9317	High Similarity	NPC21190
0.9317	High Similarity	NPC183357
0.9317	High Similarity	NPC22195
0.9313	High Similarity	NPC45618
0.9313	High Similarity	NPC58716
0.9313	High Similarity	NPC146792
0.9299	High Similarity	NPC119125
0.9299	High Similarity	NPC166277
0.9264	High Similarity	NPC101191
0.9264	High Similarity	NPC49344
0.9264	High Similarity	NPC210094
0.9264	High Similarity	NPC43211
0.9264	High Similarity	NPC135277
0.9264	High Similarity	NPC237435
0.9264	High Similarity	NPC264735
0.9264	High Similarity	NPC115760
0.9259	High Similarity	NPC117260
0.9259	High Similarity	NPC48773
0.9259	High Similarity	NPC205076
0.9259	High Similarity	NPC307518
0.9259	High Similarity	NPC476405
0.9255	High Similarity	NPC471457
0.9255	High Similarity	NPC472383
0.9255	High Similarity	NPC112755
0.9255	High Similarity	NPC472381
0.9255	High Similarity	NPC170675
0.9255	High Similarity	NPC95855
0.9255	High Similarity	NPC210042
0.9245	High Similarity	NPC94777
0.9245	High Similarity	NPC88043
0.9236	High Similarity	NPC287872
0.9236	High Similarity	NPC289811
0.9236	High Similarity	NPC74319
0.9236	High Similarity	NPC160780
0.9211	High Similarity	NPC302989
0.9207	High Similarity	NPC472384
0.9207	High Similarity	NPC472991
0.9207	High Similarity	NPC472380
0.9207	High Similarity	NPC268533
0.9207	High Similarity	NPC472992
0.9207	High Similarity	NPC472382
0.9202	High Similarity	NPC169977
0.9202	High Similarity	NPC21666
0.9202	High Similarity	NPC175230
0.9202	High Similarity	NPC42773
0.9202	High Similarity	NPC45522
0.9202	High Similarity	NPC88560
0.9202	High Similarity	NPC4390
0.9202	High Similarity	NPC204693
0.9202	High Similarity	NPC172033
0.9202	High Similarity	NPC51774
0.9202	High Similarity	NPC101026
0.9202	High Similarity	NPC239549
0.9202	High Similarity	NPC236191
0.9202	High Similarity	NPC24043
0.9198	High Similarity	NPC34287
0.9198	High Similarity	NPC149011
0.9198	High Similarity	NPC44558
0.9198	High Similarity	NPC105511
0.9198	High Similarity	NPC471416
0.9198	High Similarity	NPC224462
0.9198	High Similarity	NPC245014
0.9198	High Similarity	NPC474434
0.9198	High Similarity	NPC204937
0.9198	High Similarity	NPC84265
0.9198	High Similarity	NPC282987
0.9193	High Similarity	NPC93099
0.9187	High Similarity	NPC22832
0.9187	High Similarity	NPC165720
0.9187	High Similarity	NPC311830
0.9182	High Similarity	NPC300537
0.9182	High Similarity	NPC127782
0.9177	High Similarity	NPC203020
0.9177	High Similarity	NPC239966
0.9172	High Similarity	NPC1913
0.9161	High Similarity	NPC215811
0.9156	High Similarity	NPC225129
0.9152	High Similarity	NPC476622
0.9152	High Similarity	NPC476621
0.9152	High Similarity	NPC476623
0.9152	High Similarity	NPC476620
0.9152	High Similarity	NPC476618
0.9152	High Similarity	NPC476619
0.9152	High Similarity	NPC472387
0.9141	High Similarity	NPC175107
0.9141	High Similarity	NPC301683
0.9141	High Similarity	NPC259152
0.9141	High Similarity	NPC3583
0.9141	High Similarity	NPC267254
0.9141	High Similarity	NPC153755
0.9141	High Similarity	NPC190003
0.9136	High Similarity	NPC183036
0.9136	High Similarity	NPC229687
0.913	High Similarity	NPC236934
0.913	High Similarity	NPC99957
0.913	High Similarity	NPC181616
0.913	High Similarity	NPC5778
0.9125	High Similarity	NPC222936
0.9125	High Similarity	NPC243930
0.9125	High Similarity	NPC309025
0.9125	High Similarity	NPC19709
0.9125	High Similarity	NPC284960
0.9125	High Similarity	NPC191306
0.9125	High Similarity	NPC88023
0.9125	High Similarity	NPC270335
0.9125	High Similarity	NPC147596
0.9103	High Similarity	NPC299761
0.9103	High Similarity	NPC279281
0.9103	High Similarity	NPC230439
0.9103	High Similarity	NPC92153
0.9102	High Similarity	NPC470447
0.9102	High Similarity	NPC470445
0.9102	High Similarity	NPC470449
0.9102	High Similarity	NPC470446
0.9102	High Similarity	NPC36138
0.9091	High Similarity	NPC169733
0.9085	High Similarity	NPC92054
0.9085	High Similarity	NPC163165
0.9085	High Similarity	NPC472993
0.9085	High Similarity	NPC4958
0.9085	High Similarity	NPC140722
0.9085	High Similarity	NPC83975
0.908	High Similarity	NPC244776
0.908	High Similarity	NPC212748
0.908	High Similarity	NPC235260
0.908	High Similarity	NPC116864
0.908	High Similarity	NPC155763
0.908	High Similarity	NPC20505
0.9074	High Similarity	NPC229729
0.9074	High Similarity	NPC45400
0.9074	High Similarity	NPC135345
0.9062	High Similarity	NPC189142
0.9062	High Similarity	NPC22324
0.9062	High Similarity	NPC4013
0.9062	High Similarity	NPC285108
0.9062	High Similarity	NPC61594
0.9062	High Similarity	NPC90905
0.9062	High Similarity	NPC33298
0.9062	High Similarity	NPC56735
0.9062	High Similarity	NPC473043
0.9062	High Similarity	NPC77660
0.9051	High Similarity	NPC472860
0.9048	High Similarity	NPC470451
0.9048	High Similarity	NPC470455
0.9048	High Similarity	NPC470416
0.9042	High Similarity	NPC222674
0.9038	High Similarity	NPC34965
0.9038	High Similarity	NPC183536
0.9036	High Similarity	NPC168584
0.9032	High Similarity	NPC164527
0.9032	High Similarity	NPC213382
0.903	High Similarity	NPC142996
0.903	High Similarity	NPC102028
0.903	High Similarity	NPC169645
0.903	High Similarity	NPC84482
0.903	High Similarity	NPC472607
0.9024	High Similarity	NPC156977
0.9018	High Similarity	NPC120099
0.9018	High Similarity	NPC195257
0.9018	High Similarity	NPC138927
0.9018	High Similarity	NPC225434
0.9018	High Similarity	NPC203050
0.9018	High Similarity	NPC209296
0.9018	High Similarity	NPC219904
0.9018	High Similarity	NPC223747
0.9012	High Similarity	NPC21100
0.9012	High Similarity	NPC115674
0.9012	High Similarity	NPC210073
0.9012	High Similarity	NPC197285
0.9006	High Similarity	NPC470178
0.9006	High Similarity	NPC29830
0.9006	High Similarity	NPC168822
0.9	High Similarity	NPC182045
0.9	High Similarity	NPC71780
0.8988	High Similarity	NPC107987

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 NPC217950 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	887
0.2-0.3	1931
0.3-0.4	2667
0.4-0.5	1820
0.5-0.6	991
0.6-0.7	380
0.7-0.8	137
0.8-0.85	21
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9264	High Similarity	NPD4338	Clinical (unspecified phase)
0.9018	High Similarity	NPD7054	Approved
0.8963	High Similarity	NPD7074	Phase 3
0.8963	High Similarity	NPD7472	Approved
0.8957	High Similarity	NPD3818	Discontinued
0.8795	High Similarity	NPD6797	Phase 2
0.8743	High Similarity	NPD7251	Discontinued
0.8742	High Similarity	NPD2801	Approved
0.869	High Similarity	NPD7808	Phase 3
0.8679	High Similarity	NPD1934	Approved
0.8662	High Similarity	NPD1653	Approved
0.858	High Similarity	NPD4381	Clinical (unspecified phase)
0.8571	High Similarity	NPD5402	Approved
0.8519	High Similarity	NPD4868	Clinical (unspecified phase)
0.8509	High Similarity	NPD2393	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6166	Phase 2
0.8494	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD3817	Phase 2
0.8412	Intermediate Similarity	NPD6559	Discontinued
0.8293	Intermediate Similarity	NPD3882	Suspended
0.8235	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1511	Approved
0.817	Intermediate Similarity	NPD1933	Approved
0.8137	Intermediate Similarity	NPD5403	Approved
0.8133	Intermediate Similarity	NPD7075	Discontinued
0.8129	Intermediate Similarity	NPD5844	Phase 1
0.8084	Intermediate Similarity	NPD6234	Discontinued
0.8075	Intermediate Similarity	NPD1512	Approved
0.807	Intermediate Similarity	NPD7228	Approved
0.8052	Intermediate Similarity	NPD447	Suspended
0.8047	Intermediate Similarity	NPD6232	Discontinued
0.8036	Intermediate Similarity	NPD5494	Approved
0.8035	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD8313	Approved
0.8	Intermediate Similarity	NPD8312	Approved
0.7989	Intermediate Similarity	NPD7685	Pre-registration
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4380	Phase 2
0.7987	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD4966	Approved
0.7964	Intermediate Similarity	NPD4965	Approved
0.7964	Intermediate Similarity	NPD4967	Phase 2
0.7962	Intermediate Similarity	NPD1551	Phase 2
0.7952	Intermediate Similarity	NPD1465	Phase 2
0.7952	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7473	Discontinued
0.7892	Intermediate Similarity	NPD6801	Discontinued
0.7882	Intermediate Similarity	NPD7199	Phase 2
0.7877	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7819	Suspended
0.784	Intermediate Similarity	NPD6799	Approved
0.7805	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7266	Discontinued
0.7756	Intermediate Similarity	NPD1613	Approved
0.7756	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1549	Phase 2
0.7736	Intermediate Similarity	NPD2935	Discontinued
0.7725	Intermediate Similarity	NPD7411	Suspended
0.7716	Intermediate Similarity	NPD6190	Approved
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7688	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD3751	Discontinued
0.763	Intermediate Similarity	NPD3787	Discontinued
0.7622	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7240	Approved
0.7566	Intermediate Similarity	NPD7435	Discontinued
0.7564	Intermediate Similarity	NPD3027	Phase 3
0.756	Intermediate Similarity	NPD6599	Discontinued
0.7544	Intermediate Similarity	NPD7768	Phase 2
0.7532	Intermediate Similarity	NPD1203	Approved
0.7531	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8455	Phase 2
0.7516	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD1091	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.7484	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7783	Phase 2
0.7471	Intermediate Similarity	NPD6959	Discontinued
0.7453	Intermediate Similarity	NPD1510	Phase 2
0.7443	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4628	Phase 3
0.7439	Intermediate Similarity	NPD3750	Approved
0.7436	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6823	Phase 2
0.7405	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3226	Approved
0.7371	Intermediate Similarity	NPD8151	Discontinued
0.7371	Intermediate Similarity	NPD1247	Approved
0.7365	Intermediate Similarity	NPD2533	Approved
0.7365	Intermediate Similarity	NPD2534	Approved
0.7365	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2532	Approved
0.7362	Intermediate Similarity	NPD2346	Discontinued
0.7356	Intermediate Similarity	NPD919	Approved
0.7338	Intermediate Similarity	NPD9717	Approved
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7874	Approved
0.7312	Intermediate Similarity	NPD943	Approved
0.7312	Intermediate Similarity	NPD1240	Approved
0.7299	Intermediate Similarity	NPD3749	Approved
0.7296	Intermediate Similarity	NPD2313	Discontinued
0.7292	Intermediate Similarity	NPD7696	Phase 3
0.7292	Intermediate Similarity	NPD7697	Approved
0.7292	Intermediate Similarity	NPD7698	Approved
0.7288	Intermediate Similarity	NPD3926	Phase 2
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.7263	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7870	Phase 2
0.7254	Intermediate Similarity	NPD7871	Phase 2
0.725	Intermediate Similarity	NPD6233	Phase 2
0.7239	Intermediate Similarity	NPD7033	Discontinued
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7231	Intermediate Similarity	NPD7701	Phase 2
0.7222	Intermediate Similarity	NPD1607	Approved
0.7202	Intermediate Similarity	NPD7680	Approved
0.7193	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD8434	Phase 2
0.7189	Intermediate Similarity	NPD8150	Discontinued
0.7188	Intermediate Similarity	NPD411	Approved
0.7184	Intermediate Similarity	NPD5353	Approved
0.7179	Intermediate Similarity	NPD7584	Approved
0.7169	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1652	Phase 2
0.715	Intermediate Similarity	NPD5006	Approved
0.715	Intermediate Similarity	NPD5005	Approved
0.7143	Intermediate Similarity	NPD5953	Discontinued
0.7134	Intermediate Similarity	NPD2799	Discontinued
0.7134	Intermediate Similarity	NPD3748	Approved
0.7121	Intermediate Similarity	NPD7801	Approved
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7699	Phase 2
0.711	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD9494	Approved
0.709	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6213	Phase 3
0.709	Intermediate Similarity	NPD6212	Phase 3
0.7089	Intermediate Similarity	NPD2797	Approved
0.7081	Intermediate Similarity	NPD6798	Discontinued
0.7081	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD920	Approved
0.707	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6674	Discontinued
0.7056	Intermediate Similarity	NPD7585	Approved
0.7056	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2798	Approved
0.7044	Intermediate Similarity	NPD1019	Discontinued
0.7033	Intermediate Similarity	NPD7286	Phase 2
0.7031	Intermediate Similarity	NPD4420	Approved
0.703	Intermediate Similarity	NPD4308	Phase 3
0.7025	Intermediate Similarity	NPD3225	Approved
0.7011	Intermediate Similarity	NPD7038	Approved
0.7011	Intermediate Similarity	NPD7039	Approved
0.7006	Intermediate Similarity	NPD9269	Phase 2
0.7005	Intermediate Similarity	NPD7583	Approved
0.7	Intermediate Similarity	NPD5242	Approved
0.6993	Remote Similarity	NPD9493	Approved
0.699	Remote Similarity	NPD8320	Phase 1
0.699	Remote Similarity	NPD8319	Approved
0.6988	Remote Similarity	NPD6099	Approved
0.6988	Remote Similarity	NPD6100	Approved
0.6987	Remote Similarity	NPD3496	Discontinued
0.6983	Remote Similarity	NPD8127	Discontinued
0.6979	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3268	Approved
0.6973	Remote Similarity	NPD7549	Discontinued
0.6964	Remote Similarity	NPD2800	Approved
0.6959	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4908	Phase 1
0.6951	Remote Similarity	NPD5124	Phase 1
0.6951	Remote Similarity	NPD6355	Discontinued
0.6951	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5711	Approved
0.6944	Remote Similarity	NPD5710	Approved
0.6943	Remote Similarity	NPD422	Phase 1
0.6928	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6386	Approved
0.6914	Remote Similarity	NPD6385	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