NPASS Compound

Structure

CID112749 OpenBabel06191715462D 33 35 0 0 1 0 0 0 0 0999 V2000 5.8938 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 -4.8611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -4.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3559 1.3281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3281 1.3281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0518 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0518 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 -4.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.2098 -3.4028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0518 -2.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 -2.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0518 -4.8611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -4.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 0.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8938 -3.4028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 -3.4028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -2.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 -2.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 -0.4861 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 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 6 32 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 8 15 1 0 0 0 0 9 18 1 0 0 0 0 9 22 2 0 0 0 0 10 16 1 0 0 0 0 10 25 2 0 0 0 0 11 17 1 0 0 0 0 11 26 2 0 0 0 0 12 19 2 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 23 2 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 15 27 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.17
Volume:	456.011
LogP:	4.483
LogD:	1.534
LogS:	-3.036
# Rotatable Bonds:	5
TPSA:	153.75
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	3.817
Fsp3:	0.417
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:	-5.868
MDCK Permeability:	1.0053789992525708e-05
Pgp-inhibitor:	0.49
Pgp-substrate:	0.891
Human Intestinal Absorption (HIA):	0.516
20% Bioavailability (F20%):	0.106
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	98.23192596435547%
Volume Distribution (VD):	0.375
Pgp-substrate:	4.079526901245117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.77
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.177
CYP2C9-inhibitor:	0.287
CYP2C9-substrate:	0.617
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.096
CYP3A4-substrate:	0.439

ADMET: Excretion

Clearance (CL):	3.844
Half-life (T1/2):	0.202

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.473
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.046
Skin Sensitization:	0.927
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.757
Respiratory Toxicity:	0.117

Download Data

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

Natural Product: NPC112749

Natural Product ID:	NPC112749
*Common Name:**	Isomallotochromanol
IUPAC Name:	1-[3-[(6-acetyl-3,5,7-trihydroxy-2,2-dimethyl-3,4-dihydrochromen-8-yl)methyl]-2,6-dihydroxy-4-methoxy-5-methylphenyl]ethanone
Synonyms:	Isomallotochromanol
Standard InCHIKey:	XBXKUYYCBXJGEN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H28O9/c1-9-18(28)16(10(2)25)19(29)12(22(9)32-6)7-13-20(30)17(11(3)26)21(31)14-8-15(27)24(4,5)33-23(13)14/h15,27-31H,7-8H2,1-6H3
SMILES:	COc1c(Cc2c3OC(C)(C)C(Cc3c(c(c2O)C(=O)C)O)O)c(O)c(c(c1C)O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523152
PubChem CID:	159574
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800639]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[2347013]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3210017]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3734813]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4040956]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	100.0	%	PMID[467805]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	95.5	%	PMID[467805]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	0.0	%	PMID[467805]

☑ 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 NPC112749 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	367
0.1-0.2	1524
0.2-0.3	3803
0.3-0.4	9478
0.4-0.5	9704
0.5-0.6	4117
0.6-0.7	5725
0.7-0.8	5299
0.8-0.85	1876
0.85-0.9	687
0.9-0.95	111
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9441	High Similarity	NPC472345
0.9433	High Similarity	NPC18886
0.9379	High Similarity	NPC471677
0.9379	High Similarity	NPC474021
0.9379	High Similarity	NPC471676
0.9379	High Similarity	NPC472420
0.9379	High Similarity	NPC474023
0.9379	High Similarity	NPC244577
0.9379	High Similarity	NPC263384
0.9379	High Similarity	NPC472422
0.9315	High Similarity	NPC56232
0.9315	High Similarity	NPC10807
0.9315	High Similarity	NPC475790
0.9315	High Similarity	NPC150123
0.9315	High Similarity	NPC161881
0.9315	High Similarity	NPC244583
0.931	High Similarity	NPC105136
0.9306	High Similarity	NPC10097
0.9257	High Similarity	NPC215917
0.9257	High Similarity	NPC10754
0.9257	High Similarity	NPC20530
0.9252	High Similarity	NPC7989
0.9252	High Similarity	NPC469405
0.9252	High Similarity	NPC180301
0.9252	High Similarity	NPC223701
0.9252	High Similarity	NPC248793
0.9252	High Similarity	NPC472583
0.9247	High Similarity	NPC472636
0.9247	High Similarity	NPC262039
0.9247	High Similarity	NPC262038
0.9247	High Similarity	NPC477897
0.9247	High Similarity	NPC328740
0.9247	High Similarity	NPC254412
0.9247	High Similarity	NPC289774
0.9247	High Similarity	NPC278476
0.9247	High Similarity	NPC319910
0.9247	High Similarity	NPC209846
0.9241	High Similarity	NPC139966
0.9241	High Similarity	NPC89442
0.9241	High Similarity	NPC472628
0.9241	High Similarity	NPC307052
0.9236	High Similarity	NPC47388
0.9236	High Similarity	NPC472627
0.9236	High Similarity	NPC473133
0.9236	High Similarity	NPC470670
0.9236	High Similarity	NPC85773
0.9236	High Similarity	NPC91902
0.9231	High Similarity	NPC470890
0.9225	High Similarity	NPC276565
0.9189	High Similarity	NPC259710
0.9189	High Similarity	NPC304207
0.9189	High Similarity	NPC304745
0.9189	High Similarity	NPC207809
0.9189	High Similarity	NPC470681
0.9189	High Similarity	NPC477958
0.9189	High Similarity	NPC111341
0.9189	High Similarity	NPC48579
0.9189	High Similarity	NPC217706
0.9184	High Similarity	NPC243171
0.9184	High Similarity	NPC138288
0.9184	High Similarity	NPC216035
0.9184	High Similarity	NPC171651
0.9184	High Similarity	NPC35567
0.9184	High Similarity	NPC473996
0.9184	High Similarity	NPC217149
0.9178	High Similarity	NPC476509
0.9167	High Similarity	NPC474302
0.9167	High Similarity	NPC472629
0.9155	High Similarity	NPC157497
0.9155	High Similarity	NPC285659
0.9155	High Similarity	NPC74397
0.9155	High Similarity	NPC81337
0.9122	High Similarity	NPC293286
0.9122	High Similarity	NPC268193
0.9122	High Similarity	NPC112701
0.9122	High Similarity	NPC109594
0.9122	High Similarity	NPC326592
0.9116	High Similarity	NPC472580
0.9116	High Similarity	NPC474772
0.9116	High Similarity	NPC472423
0.9116	High Similarity	NPC471675
0.9116	High Similarity	NPC474744
0.9097	High Similarity	NPC124780
0.9097	High Similarity	NPC87486
0.9097	High Similarity	NPC224714
0.9078	High Similarity	NPC248995
0.9078	High Similarity	NPC254168
0.9078	High Similarity	NPC272844
0.9073	High Similarity	NPC472631
0.9073	High Similarity	NPC472630
0.9054	High Similarity	NPC256141
0.9054	High Similarity	NPC477957
0.9054	High Similarity	NPC31627
0.9054	High Similarity	NPC476238
0.9054	High Similarity	NPC285623
0.9054	High Similarity	NPC210597
0.9054	High Similarity	NPC327269
0.9048	High Similarity	NPC472421
0.9048	High Similarity	NPC177308
0.9048	High Similarity	NPC124478
0.9048	High Similarity	NPC38775
0.9034	High Similarity	NPC290133
0.9034	High Similarity	NPC316769
0.9034	High Similarity	NPC24136
0.9034	High Similarity	NPC187282
0.9028	High Similarity	NPC316816
0.9028	High Similarity	NPC478086
0.9028	High Similarity	NPC214166
0.9021	High Similarity	NPC96408
0.9021	High Similarity	NPC156190
0.9021	High Similarity	NPC248372
0.9021	High Similarity	NPC166689
0.9021	High Similarity	NPC17170
0.9021	High Similarity	NPC279650
0.9021	High Similarity	NPC258630
0.9021	High Similarity	NPC110038
0.9014	High Similarity	NPC240305
0.9013	High Similarity	NPC472634
0.9007	High Similarity	NPC473990
0.9	High Similarity	NPC208152
0.9	High Similarity	NPC78492
0.8993	High Similarity	NPC74924
0.8993	High Similarity	NPC236756
0.8993	High Similarity	NPC100134
0.8993	High Similarity	NPC209760
0.8993	High Similarity	NPC88983
0.8993	High Similarity	NPC20907
0.8993	High Similarity	NPC311579
0.8993	High Similarity	NPC244250
0.898	High Similarity	NPC5173
0.8978	High Similarity	NPC186628
0.8973	High Similarity	NPC122828
0.8973	High Similarity	NPC211466
0.8973	High Similarity	NPC51070
0.8973	High Similarity	NPC202494
0.8973	High Similarity	NPC176869
0.8973	High Similarity	NPC40086
0.8973	High Similarity	NPC3779
0.8973	High Similarity	NPC44721
0.8973	High Similarity	NPC296998
0.8973	High Similarity	NPC476182
0.8973	High Similarity	NPC472918
0.8973	High Similarity	NPC473077
0.8973	High Similarity	NPC222298
0.8966	High Similarity	NPC131579
0.8966	High Similarity	NPC131568
0.8966	High Similarity	NPC209040
0.8958	High Similarity	NPC223500
0.8958	High Similarity	NPC220998
0.8958	High Similarity	NPC227579
0.8958	High Similarity	NPC66515
0.8958	High Similarity	NPC228504
0.8958	High Similarity	NPC265040
0.8958	High Similarity	NPC1089
0.8958	High Similarity	NPC64915
0.8958	High Similarity	NPC328164
0.8958	High Similarity	NPC10937
0.8958	High Similarity	NPC32739
0.8958	High Similarity	NPC182852
0.8958	High Similarity	NPC166934
0.8958	High Similarity	NPC40833
0.8958	High Similarity	NPC148757
0.8958	High Similarity	NPC37496
0.8958	High Similarity	NPC76372
0.8958	High Similarity	NPC324134
0.8958	High Similarity	NPC306829
0.8958	High Similarity	NPC161506
0.8958	High Similarity	NPC76338
0.8958	High Similarity	NPC296917
0.8958	High Similarity	NPC125855
0.8958	High Similarity	NPC78
0.8958	High Similarity	NPC177354
0.8958	High Similarity	NPC107572
0.8958	High Similarity	NPC167624
0.8958	High Similarity	NPC194432
0.8958	High Similarity	NPC166482
0.8958	High Similarity	NPC324436
0.8954	High Similarity	NPC472635
0.8947	High Similarity	NPC470326
0.8947	High Similarity	NPC174953
0.8947	High Similarity	NPC471976
0.8947	High Similarity	NPC475784
0.894	High Similarity	NPC27337
0.894	High Similarity	NPC474055
0.894	High Similarity	NPC23817
0.894	High Similarity	NPC472598
0.8936	High Similarity	NPC470982
0.8936	High Similarity	NPC470983
0.8933	High Similarity	NPC321779
0.8933	High Similarity	NPC470604
0.8933	High Similarity	NPC108937
0.8933	High Similarity	NPC477530
0.8933	High Similarity	NPC470605
0.8933	High Similarity	NPC470603
0.8933	High Similarity	NPC279218
0.8933	High Similarity	NPC470327
0.8933	High Similarity	NPC471116
0.8933	High Similarity	NPC45849
0.8933	High Similarity	NPC200761
0.8933	High Similarity	NPC476169

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 NPC112749 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	1009
0.2-0.3	2076
0.3-0.4	2634
0.4-0.5	1738
0.5-0.6	921
0.6-0.7	308
0.7-0.8	115
0.8-0.85	20
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9048	High Similarity	NPD4380	Phase 2
0.8867	High Similarity	NPD2393	Clinical (unspecified phase)
0.8816	High Similarity	NPD7075	Discontinued
0.8707	High Similarity	NPD4378	Clinical (unspecified phase)
0.8693	High Similarity	NPD4381	Clinical (unspecified phase)
0.8675	High Similarity	NPD1934	Approved
0.8675	High Similarity	NPD6801	Discontinued
0.8618	High Similarity	NPD7096	Clinical (unspecified phase)
0.8611	High Similarity	NPD1552	Clinical (unspecified phase)
0.8611	High Similarity	NPD1550	Clinical (unspecified phase)
0.8581	High Similarity	NPD7410	Clinical (unspecified phase)
0.8562	High Similarity	NPD8443	Clinical (unspecified phase)
0.8553	High Similarity	NPD7804	Clinical (unspecified phase)
0.8552	High Similarity	NPD1549	Phase 2
0.8481	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6166	Phase 2
0.8481	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6651	Approved
0.8408	Intermediate Similarity	NPD6959	Discontinued
0.8367	Intermediate Similarity	NPD2800	Approved
0.8366	Intermediate Similarity	NPD7411	Suspended
0.8288	Intermediate Similarity	NPD2796	Approved
0.8272	Intermediate Similarity	NPD7074	Phase 3
0.8258	Intermediate Similarity	NPD7819	Suspended
0.8258	Intermediate Similarity	NPD2801	Approved
0.8219	Intermediate Similarity	NPD1510	Phase 2
0.821	Intermediate Similarity	NPD7054	Approved
0.8171	Intermediate Similarity	NPD6559	Discontinued
0.816	Intermediate Similarity	NPD7472	Approved
0.8153	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD3818	Discontinued
0.8146	Intermediate Similarity	NPD1511	Approved
0.8146	Intermediate Similarity	NPD6799	Approved
0.811	Intermediate Similarity	NPD6797	Phase 2
0.8089	Intermediate Similarity	NPD3817	Phase 2
0.8069	Intermediate Similarity	NPD1240	Approved
0.8061	Intermediate Similarity	NPD7251	Discontinued
0.8039	Intermediate Similarity	NPD1512	Approved
0.8038	Intermediate Similarity	NPD3882	Suspended
0.8025	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD5494	Approved
0.7987	Intermediate Similarity	NPD5403	Approved
0.7974	Intermediate Similarity	NPD2532	Approved
0.7974	Intermediate Similarity	NPD2534	Approved
0.7974	Intermediate Similarity	NPD2533	Approved
0.7959	Intermediate Similarity	NPD1607	Approved
0.7949	Intermediate Similarity	NPD6599	Discontinued
0.7904	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD5402	Approved
0.7857	Intermediate Similarity	NPD5401	Approved
0.7812	Intermediate Similarity	NPD7768	Phase 2
0.7791	Intermediate Similarity	NPD6232	Discontinued
0.7784	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5844	Phase 1
0.7763	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7473	Discontinued
0.7712	Intermediate Similarity	NPD4628	Phase 3
0.7654	Intermediate Similarity	NPD3749	Approved
0.7651	Intermediate Similarity	NPD5124	Phase 1
0.7651	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD920	Approved
0.7597	Intermediate Similarity	NPD3750	Approved
0.7588	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1465	Phase 2
0.7574	Intermediate Similarity	NPD5953	Discontinued
0.7568	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD2935	Discontinued
0.7566	Intermediate Similarity	NPD1551	Phase 2
0.756	Intermediate Similarity	NPD7286	Phase 2
0.7543	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1243	Approved
0.7486	Intermediate Similarity	NPD7584	Approved
0.7472	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5710	Approved
0.747	Intermediate Similarity	NPD5711	Approved
0.7467	Intermediate Similarity	NPD1613	Approved
0.7467	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD4360	Phase 2
0.7458	Intermediate Similarity	NPD4363	Phase 3
0.7451	Intermediate Similarity	NPD6100	Approved
0.7451	Intermediate Similarity	NPD6099	Approved
0.745	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2313	Discontinued
0.7405	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2799	Discontinued
0.7386	Intermediate Similarity	NPD7033	Discontinued
0.7372	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2424	Discontinued
0.7342	Intermediate Similarity	NPD7390	Discontinued
0.7341	Intermediate Similarity	NPD8313	Approved
0.7341	Intermediate Similarity	NPD8312	Approved
0.7329	Intermediate Similarity	NPD3226	Approved
0.7315	Intermediate Similarity	NPD4908	Phase 1
0.731	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1247	Approved
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.729	Intermediate Similarity	NPD2344	Approved
0.729	Intermediate Similarity	NPD2346	Discontinued
0.7289	Intermediate Similarity	NPD919	Approved
0.7273	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3748	Approved
0.7262	Intermediate Similarity	NPD3787	Discontinued
0.7261	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD8455	Phase 2
0.7253	Intermediate Similarity	NPD6780	Approved
0.7253	Intermediate Similarity	NPD6781	Approved
0.7253	Intermediate Similarity	NPD6777	Approved
0.7253	Intermediate Similarity	NPD6776	Approved
0.7253	Intermediate Similarity	NPD6778	Approved
0.7253	Intermediate Similarity	NPD6779	Approved
0.7253	Intermediate Similarity	NPD6782	Approved
0.7248	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD943	Approved
0.7219	Intermediate Similarity	NPD3926	Phase 2
0.7216	Intermediate Similarity	NPD8434	Phase 2
0.72	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6832	Phase 2
0.7192	Intermediate Similarity	NPD1610	Phase 2
0.7168	Intermediate Similarity	NPD3823	Discontinued
0.7158	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3027	Phase 3
0.7135	Intermediate Similarity	NPD7435	Discontinued
0.7128	Intermediate Similarity	NPD8151	Discontinued
0.7127	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4361	Phase 2
0.7119	Intermediate Similarity	NPD8150	Discontinued
0.7114	Intermediate Similarity	NPD1203	Approved
0.7107	Intermediate Similarity	NPD2309	Approved
0.7105	Intermediate Similarity	NPD6798	Discontinued
0.7105	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7199	Phase 2
0.7099	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD37	Approved
0.7089	Intermediate Similarity	NPD1652	Phase 2
0.7083	Intermediate Similarity	NPD6234	Discontinued
0.7081	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD230	Phase 1
0.7076	Intermediate Similarity	NPD2403	Approved
0.7074	Intermediate Similarity	NPD7585	Approved
0.7072	Intermediate Similarity	NPD6534	Approved
0.7072	Intermediate Similarity	NPD6535	Approved
0.7066	Intermediate Similarity	NPD4966	Approved
0.7066	Intermediate Similarity	NPD4967	Phase 2
0.7066	Intermediate Similarity	NPD4965	Approved
0.7053	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7783	Phase 2
0.7043	Intermediate Similarity	NPD7696	Phase 3
0.7043	Intermediate Similarity	NPD7698	Approved
0.7043	Intermediate Similarity	NPD7697	Approved
0.7039	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4625	Phase 3
0.7034	Intermediate Similarity	NPD1548	Phase 1
0.7021	Intermediate Similarity	NPD7583	Approved
0.7012	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7458	Discontinued
0.7011	Intermediate Similarity	NPD1729	Discontinued
0.7005	Intermediate Similarity	NPD7871	Phase 2
0.7005	Intermediate Similarity	NPD7870	Phase 2
0.7	Intermediate Similarity	NPD6190	Approved
0.6994	Remote Similarity	NPD7228	Approved
0.6993	Remote Similarity	NPD3268	Approved
0.6993	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6823	Phase 2
0.6984	Remote Similarity	NPD7701	Phase 2
0.6982	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2654	Approved
0.6975	Remote Similarity	NPD4662	Approved
0.6975	Remote Similarity	NPD4661	Approved
0.6968	Remote Similarity	NPD6355	Discontinued
0.6968	Remote Similarity	NPD1933	Approved
0.6966	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7699	Phase 2
0.6957	Remote Similarity	NPD7700	Phase 2
0.6954	Remote Similarity	NPD2798	Approved
0.6951	Remote Similarity	NPD1653	Approved
0.6948	Remote Similarity	NPD6233	Phase 2
0.6943	Remote Similarity	NPD4308	Phase 3
0.6933	Remote Similarity	NPD5049	Phase 3
0.6919	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD9717	Approved
0.6911	Remote Similarity	NPD7874	Approved
0.6911	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2797	Approved
0.6886	Remote Similarity	NPD6844	Discontinued
0.6879	Remote Similarity	NPD4538	Approved
0.6879	Remote Similarity	NPD4536	Approved
0.6879	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7801	Approved
0.6871	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4749	Approved
0.686	Remote Similarity	NPD7229	Phase 3
0.6859	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD447	Suspended
0.6855	Remote Similarity	NPD6003	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