NPASS Compound

Structure

NPC212890 OpenBabel07101718302D 34 37 0 0 1 0 0 0 0 0999 V2000 -3.2144 -4.2293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8474 0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1154 3.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2245 -1.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2493 -0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3833 1.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 -1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1559 -1.9498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0279 -2.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2089 -4.1247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3833 0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 -0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 -1.2807 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4346 -1.4886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1154 0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2493 1.7138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 -1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1154 1.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5173 -0.2862 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9346 -0.6226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1070 -1.6408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7967 -4.9338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9814 1.7138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9814 -0.2862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2493 2.7138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7700 -2.0316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6157 -3.2112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 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 -4.6038 0.1205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 13 2 0 0 0 0 5 17 1 0 0 0 0 6 13 1 0 0 0 0 6 18 2 0 0 0 0 7 14 2 0 0 0 0 7 19 1 0 0 0 0 8 14 1 0 0 0 0 8 20 2 0 0 0 0 9 25 1 0 0 0 0 10 31 1 0 0 0 0 11 32 1 0 0 0 0 11 33 1 0 0 0 0 12 26 2 0 0 0 0 12 31 1 0 0 0 0 15 9 1 6 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 10 1 1 0 0 0 16 23 1 0 0 0 0 17 21 2 0 0 0 0 17 28 1 0 0 0 0 18 21 1 0 0 0 0 18 29 1 0 0 0 0 19 24 2 0 0 0 0 19 30 1 0 0 0 0 20 24 1 0 0 0 0 20 32 1 0 0 0 0 21 27 1 0 0 0 0 22 13 1 1 0 0 0 22 34 1 0 0 0 0 23 14 1 6 0 0 0 23 34 1 0 0 0 0 24 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.17
Volume:	458.881
LogP:	2.354
LogD:	2.515
LogS:	-4.393
# Rotatable Bonds:	9
TPSA:	122.14
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.55
Synthetic Accessibility Score:	3.973
Fsp3:	0.458
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:	-4.777
MDCK Permeability:	3.535652285791002e-05
Pgp-inhibitor:	0.918
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.623
Plasma Protein Binding (PPB):	65.54073333740234%
Volume Distribution (VD):	0.569
Pgp-substrate:	16.813947677612305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.858
CYP2C19-inhibitor:	0.09
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.36
CYP2C9-substrate:	0.725
CYP2D6-inhibitor:	0.58
CYP2D6-substrate:	0.503
CYP3A4-inhibitor:	0.91
CYP3A4-substrate:	0.829

ADMET: Excretion

Clearance (CL):	10.259
Half-life (T1/2):	0.579

ADMET: Toxicity

hERG Blockers:	0.308
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.606
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.141
Skin Sensitization:	0.756
Carcinogencity:	0.233
Eye Corrosion:	0.003
Eye Irritation:	0.115
Respiratory Toxicity:	0.285

Download Data

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

Natural Product: NPC212890

Natural Product ID:	NPC212890
*Common Name:**	[(2S,3R,4R,5S)-5-(4-Hydroxy-3,5-Dimethoxyphenyl)-4-(Hydroxymethyl)-2-(7-Methoxy-1,3-Benzodioxol-5-Yl)Oxolan-3-Yl]Methyl Acetate
IUPAC Name:	[(2S,3R,4R,5S)-5-(4-hydroxy-3,5-dimethoxyphenyl)-4-(hydroxymethyl)-2-(7-methoxy-1,3-benzodioxol-5-yl)oxolan-3-yl]methyl acetate
Synonyms:
Standard InCHIKey:	JUEJBEWUMWMVJE-WVZRZZCNSA-N
Standard InCHI:	InChI=1S/C24H28O10/c1-12(26)31-10-16-15(9-25)22(13-5-17(28-2)21(27)18(6-13)29-3)34-23(16)14-7-19(30-4)24-20(8-14)32-11-33-24/h5-8,15-16,22-23,25,27H,9-11H2,1-4H3/t15-,16-,22+,23+/m0/s1
SMILES:	OC[C@H]1[C@H](COC(=O)C)[C@H](O[C@@H]1c1cc(OC)c(c(c1)OC)O)c1cc(OC)c2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL223923
PubChem CID:	44421675
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO25232	Peperomia heyneana	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17291043]
NPO25232	Peperomia heyneana	Species	Piperaceae	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	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	229400.0	nM	PMID[536327]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	49800.0	nM	PMID[536327]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	4.6	n.a.	PMID[536327]

☑ 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 NPC212890 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	307
0.1-0.2	1348
0.2-0.3	3569
0.3-0.4	8638
0.4-0.5	10183
0.5-0.6	5070
0.6-0.7	8242
0.7-0.8	4122
0.8-0.85	803
0.85-0.9	347
0.9-0.95	64
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC477702
0.971	High Similarity	NPC287124
0.9571	High Similarity	NPC141569
0.9571	High Similarity	NPC166884
0.9571	High Similarity	NPC477701
0.9565	High Similarity	NPC177868
0.95	High Similarity	NPC185071
0.95	High Similarity	NPC12728
0.9452	High Similarity	NPC136757
0.942	High Similarity	NPC474039
0.9375	High Similarity	NPC668
0.9375	High Similarity	NPC477695
0.9375	High Similarity	NPC174512
0.9375	High Similarity	NPC293757
0.9375	High Similarity	NPC474965
0.9362	High Similarity	NPC298317
0.9362	High Similarity	NPC255566
0.9348	High Similarity	NPC11453
0.9315	High Similarity	NPC477699
0.931	High Similarity	NPC473989
0.9306	High Similarity	NPC248132
0.9306	High Similarity	NPC130449
0.9296	High Similarity	NPC472713
0.9296	High Similarity	NPC187774
0.9296	High Similarity	NPC473046
0.9296	High Similarity	NPC118385
0.9296	High Similarity	NPC472712
0.9286	High Similarity	NPC46591
0.9281	High Similarity	NPC283949
0.9275	High Similarity	NPC165155
0.9275	High Similarity	NPC24490
0.9275	High Similarity	NPC150534
0.9275	High Similarity	NPC141765
0.9275	High Similarity	NPC34103
0.9247	High Similarity	NPC475756
0.9247	High Similarity	NPC477700
0.9241	High Similarity	NPC145569
0.9241	High Similarity	NPC216223
0.9241	High Similarity	NPC55158
0.9241	High Similarity	NPC51328
0.9241	High Similarity	NPC286235
0.9203	High Similarity	NPC326095
0.9203	High Similarity	NPC244983
0.9184	High Similarity	NPC471154
0.9184	High Similarity	NPC56184
0.9178	High Similarity	NPC24425
0.9172	High Similarity	NPC325720
0.9172	High Similarity	NPC316676
0.9155	High Similarity	NPC472714
0.9155	High Similarity	NPC5262
0.9149	High Similarity	NPC56091
0.9149	High Similarity	NPC226547
0.9143	High Similarity	NPC185908
0.9139	High Similarity	NPC91634
0.9139	High Similarity	NPC150943
0.9139	High Similarity	NPC268718
0.9137	High Similarity	NPC135777
0.9137	High Similarity	NPC142547
0.9137	High Similarity	NPC126409
0.9137	High Similarity	NPC99572
0.9122	High Similarity	NPC474606
0.9116	High Similarity	NPC32079
0.911	High Similarity	NPC125570
0.911	High Similarity	NPC477698
0.9103	High Similarity	NPC39657
0.9091	High Similarity	NPC474808
0.9091	High Similarity	NPC477898
0.9078	High Similarity	NPC88640
0.9078	High Similarity	NPC193666
0.9078	High Similarity	NPC123526
0.9071	High Similarity	NPC143895
0.9071	High Similarity	NPC471988
0.9065	High Similarity	NPC287745
0.9065	High Similarity	NPC67247
0.906	High Similarity	NPC312763
0.9058	High Similarity	NPC72046
0.9058	High Similarity	NPC175067
0.9058	High Similarity	NPC261812
0.9058	High Similarity	NPC204215
0.9058	High Similarity	NPC65183
0.9034	High Similarity	NPC154971
0.9034	High Similarity	NPC252286
0.9028	High Similarity	NPC84181
0.9	High Similarity	NPC101624
0.9	High Similarity	NPC25333
0.9	High Similarity	NPC236522
0.9	High Similarity	NPC49235
0.9	High Similarity	NPC184938
0.9	High Similarity	NPC148893
0.9	High Similarity	NPC476065
0.9	High Similarity	NPC238834
0.8993	High Similarity	NPC158331
0.8993	High Similarity	NPC196937
0.8993	High Similarity	NPC136750
0.8993	High Similarity	NPC266848
0.8993	High Similarity	NPC473236
0.8986	High Similarity	NPC164082
0.8966	High Similarity	NPC279298
0.8966	High Similarity	NPC166506
0.8966	High Similarity	NPC189239
0.8966	High Similarity	NPC110763
0.8966	High Similarity	NPC475868
0.8966	High Similarity	NPC197352
0.8966	High Similarity	NPC180953
0.8966	High Similarity	NPC22150
0.8966	High Similarity	NPC38041
0.8961	High Similarity	NPC14294
0.8961	High Similarity	NPC116759
0.8958	High Similarity	NPC477697
0.8958	High Similarity	NPC470811
0.8958	High Similarity	NPC477696
0.8951	High Similarity	NPC472711
0.8944	High Similarity	NPC9068
0.8944	High Similarity	NPC30951
0.8944	High Similarity	NPC6369
0.894	High Similarity	NPC237946
0.894	High Similarity	NPC32373
0.8936	High Similarity	NPC25695
0.8936	High Similarity	NPC172818
0.8936	High Similarity	NPC121651
0.8933	High Similarity	NPC103197
0.8933	High Similarity	NPC30009
0.8933	High Similarity	NPC198461
0.8929	High Similarity	NPC31530
0.8929	High Similarity	NPC107478
0.8926	High Similarity	NPC302610
0.8921	High Similarity	NPC106739
0.8921	High Similarity	NPC259742
0.8921	High Similarity	NPC147616
0.8921	High Similarity	NPC471505
0.8921	High Similarity	NPC104077
0.8921	High Similarity	NPC219671
0.8919	High Similarity	NPC472709
0.8919	High Similarity	NPC472710
0.8912	High Similarity	NPC102934
0.8912	High Similarity	NPC301961
0.8912	High Similarity	NPC166584
0.8912	High Similarity	NPC252402
0.8904	High Similarity	NPC112861
0.8904	High Similarity	NPC226540
0.8904	High Similarity	NPC474054
0.8897	High Similarity	NPC121661
0.8897	High Similarity	NPC172171
0.8897	High Similarity	NPC297342
0.8897	High Similarity	NPC25292
0.8897	High Similarity	NPC87883
0.8897	High Similarity	NPC239254
0.8897	High Similarity	NPC471415
0.8897	High Similarity	NPC73467
0.8897	High Similarity	NPC470097
0.8897	High Similarity	NPC114119
0.8897	High Similarity	NPC473045
0.8889	High Similarity	NPC40237
0.8889	High Similarity	NPC151423
0.8889	High Similarity	NPC41782
0.8889	High Similarity	NPC189115
0.8882	High Similarity	NPC19947
0.8882	High Similarity	NPC475592
0.8882	High Similarity	NPC207584
0.8882	High Similarity	NPC115281
0.8882	High Similarity	NPC181168
0.8882	High Similarity	NPC163527
0.8881	High Similarity	NPC284464
0.8873	High Similarity	NPC281780
0.8867	High Similarity	NPC24562
0.8865	High Similarity	NPC189474
0.8865	High Similarity	NPC18576
0.8859	High Similarity	NPC224472
0.8857	High Similarity	NPC169973
0.8851	High Similarity	NPC95392
0.8851	High Similarity	NPC106138
0.8851	High Similarity	NPC35877
0.8851	High Similarity	NPC90896
0.8851	High Similarity	NPC55715
0.8851	High Similarity	NPC283839
0.8849	High Similarity	NPC228346
0.8849	High Similarity	NPC158079
0.8849	High Similarity	NPC7171
0.8849	High Similarity	NPC115207
0.8849	High Similarity	NPC40432
0.8849	High Similarity	NPC192255
0.8849	High Similarity	NPC161557
0.8849	High Similarity	NPC474017
0.8849	High Similarity	NPC27843
0.8846	High Similarity	NPC59516
0.8836	High Similarity	NPC307466
0.8836	High Similarity	NPC18979
0.8828	High Similarity	NPC273657
0.8828	High Similarity	NPC473044
0.8828	High Similarity	NPC76415
0.8828	High Similarity	NPC265154
0.8828	High Similarity	NPC470950
0.8828	High Similarity	NPC185307
0.8828	High Similarity	NPC106920
0.8828	High Similarity	NPC324962
0.8828	High Similarity	NPC218510
0.8824	High Similarity	NPC230531
0.8824	High Similarity	NPC215400
0.8819	High Similarity	NPC469661
0.8819	High Similarity	NPC311530

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 NPC212890 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	814
0.2-0.3	1887
0.3-0.4	2771
0.4-0.5	1831
0.5-0.6	1050
0.6-0.7	467
0.7-0.8	73
0.8-0.85	5
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9073	High Similarity	NPD6234	Discontinued
0.894	High Similarity	NPD4966	Approved
0.894	High Similarity	NPD4965	Approved
0.894	High Similarity	NPD4967	Phase 2
0.879	High Similarity	NPD7228	Approved
0.8742	High Similarity	NPD37	Approved
0.8705	High Similarity	NPD3027	Phase 3
0.8354	Intermediate Similarity	NPD7199	Phase 2
0.8235	Intermediate Similarity	NPD1653	Approved
0.8232	Intermediate Similarity	NPD7240	Approved
0.8176	Intermediate Similarity	NPD7266	Discontinued
0.8138	Intermediate Similarity	NPD1613	Approved
0.8138	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3705	Approved
0.7988	Intermediate Similarity	NPD3818	Discontinued
0.7976	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7054	Approved
0.7719	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7472	Approved
0.7667	Intermediate Similarity	NPD7680	Approved
0.766	Intermediate Similarity	NPD1357	Approved
0.7647	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6674	Discontinued
0.7588	Intermediate Similarity	NPD7685	Pre-registration
0.7578	Intermediate Similarity	NPD1934	Approved
0.7533	Intermediate Similarity	NPD4060	Phase 1
0.7533	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3620	Phase 2
0.7529	Intermediate Similarity	NPD6797	Phase 2
0.7517	Intermediate Similarity	NPD2983	Phase 2
0.7517	Intermediate Similarity	NPD2982	Phase 2
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.7482	Intermediate Similarity	NPD5283	Phase 1
0.7448	Intermediate Similarity	NPD2981	Phase 2
0.7442	Intermediate Similarity	NPD7808	Phase 3
0.744	Intermediate Similarity	NPD6166	Phase 2
0.744	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3882	Suspended
0.7432	Intermediate Similarity	NPD3018	Phase 2
0.7423	Intermediate Similarity	NPD2978	Approved
0.7423	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2977	Approved
0.74	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6190	Approved
0.7379	Intermediate Similarity	NPD1091	Approved
0.7379	Intermediate Similarity	NPD1610	Phase 2
0.7378	Intermediate Similarity	NPD3817	Phase 2
0.7368	Intermediate Similarity	NPD230	Phase 1
0.7338	Intermediate Similarity	NPD228	Approved
0.7326	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4110	Phase 3
0.7325	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6232	Discontinued
0.7317	Intermediate Similarity	NPD1465	Phase 2
0.7317	Intermediate Similarity	NPD2801	Approved
0.7315	Intermediate Similarity	NPD2861	Phase 2
0.731	Intermediate Similarity	NPD5844	Phase 1
0.7294	Intermediate Similarity	NPD7473	Discontinued
0.7285	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6355	Discontinued
0.7244	Intermediate Similarity	NPD5762	Approved
0.7244	Intermediate Similarity	NPD5763	Approved
0.7233	Intermediate Similarity	NPD5058	Phase 3
0.7215	Intermediate Similarity	NPD4628	Phase 3
0.7212	Intermediate Similarity	NPD8455	Phase 2
0.7212	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6653	Approved
0.7194	Intermediate Similarity	NPD3022	Approved
0.7194	Intermediate Similarity	NPD3021	Approved
0.7178	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4749	Approved
0.7152	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4380	Phase 2
0.7133	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7095	Approved
0.7103	Intermediate Similarity	NPD1548	Phase 1
0.7101	Intermediate Similarity	NPD5494	Approved
0.7099	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7075	Discontinued
0.7081	Intermediate Similarity	NPD1511	Approved
0.7081	Intermediate Similarity	NPD4357	Discontinued
0.7078	Intermediate Similarity	NPD4140	Approved
0.7073	Intermediate Similarity	NPD4005	Discontinued
0.7068	Intermediate Similarity	NPD7827	Phase 1
0.7059	Intermediate Similarity	NPD8127	Discontinued
0.7051	Intermediate Similarity	NPD7097	Phase 1
0.7045	Intermediate Similarity	NPD7549	Discontinued
0.7044	Intermediate Similarity	NPD4237	Approved
0.7044	Intermediate Similarity	NPD4236	Phase 3
0.7039	Intermediate Similarity	NPD6841	Approved
0.7039	Intermediate Similarity	NPD6842	Approved
0.7039	Intermediate Similarity	NPD6843	Phase 3
0.7037	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2533	Approved
0.7037	Intermediate Similarity	NPD2532	Approved
0.7037	Intermediate Similarity	NPD2534	Approved
0.703	Intermediate Similarity	NPD7028	Phase 2
0.7025	Intermediate Similarity	NPD6005	Phase 3
0.7025	Intermediate Similarity	NPD6002	Phase 3
0.7025	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6004	Phase 3
0.7025	Intermediate Similarity	NPD1375	Discontinued
0.7025	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7296	Approved
0.7014	Intermediate Similarity	NPD7157	Approved
0.7013	Intermediate Similarity	NPD6233	Phase 2
0.7012	Intermediate Similarity	NPD3687	Approved
0.7012	Intermediate Similarity	NPD3686	Approved
0.7007	Intermediate Similarity	NPD5126	Approved
0.7007	Intermediate Similarity	NPD5125	Phase 3
0.7	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1512	Approved
0.6993	Remote Similarity	NPD4625	Phase 3
0.698	Remote Similarity	NPD1608	Approved
0.6968	Remote Similarity	NPD1558	Phase 1
0.6964	Remote Similarity	NPD5402	Approved
0.6962	Remote Similarity	NPD2438	Suspended
0.6957	Remote Similarity	NPD2219	Phase 1
0.6948	Remote Similarity	NPD6798	Discontinued
0.6946	Remote Similarity	NPD6801	Discontinued
0.6943	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3060	Approved
0.6937	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4678	Approved
0.6928	Remote Similarity	NPD4675	Approved
0.6923	Remote Similarity	NPD5735	Approved
0.6923	Remote Similarity	NPD7843	Approved
0.6919	Remote Similarity	NPD7229	Phase 3
0.6919	Remote Similarity	NPD3787	Discontinued
0.6918	Remote Similarity	NPD3540	Phase 1
0.6918	Remote Similarity	NPD5536	Phase 2
0.6914	Remote Similarity	NPD7124	Phase 2
0.6905	Remote Similarity	NPD7819	Suspended
0.6905	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7033	Discontinued
0.6899	Remote Similarity	NPD5588	Approved
0.6894	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3750	Approved
0.689	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5242	Approved
0.6879	Remote Similarity	NPD2684	Approved
0.6871	Remote Similarity	NPD6799	Approved
0.6864	Remote Similarity	NPD5353	Approved
0.6859	Remote Similarity	NPD2238	Phase 2
0.6855	Remote Similarity	NPD3539	Phase 1
0.6855	Remote Similarity	NPD6100	Approved
0.6855	Remote Similarity	NPD2935	Discontinued
0.6855	Remote Similarity	NPD6099	Approved
0.6852	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5403	Approved
0.6845	Remote Similarity	NPD3384	Approved
0.6845	Remote Similarity	NPD3382	Approved
0.6845	Remote Similarity	NPD3383	Approved
0.6835	Remote Similarity	NPD4538	Approved
0.6835	Remote Similarity	NPD6111	Discontinued
0.6835	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4536	Approved
0.6832	Remote Similarity	NPD5177	Phase 3
0.6831	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6599	Discontinued
0.6824	Remote Similarity	NPD5585	Approved
0.6821	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8312	Approved
0.6816	Remote Similarity	NPD8313	Approved
0.6815	Remote Similarity	NPD4340	Discontinued
0.6813	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4210	Discontinued
0.6806	Remote Similarity	NPD5535	Approved
0.6795	Remote Similarity	NPD4062	Phase 3
0.6792	Remote Similarity	NPD4108	Discontinued
0.679	Remote Similarity	NPD6331	Phase 2
0.679	Remote Similarity	NPD3892	Phase 2
0.679	Remote Similarity	NPD8166	Discontinued
0.6779	Remote Similarity	NPD17	Approved
0.6779	Remote Similarity	NPD4626	Approved
0.6776	Remote Similarity	NPD1283	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