NPASS Compound

Structure

CID36434 OpenBabel06191715362D 21 22 0 0 1 0 0 0 0 0999 V2000 1.7321 -0.0000 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 -3.4641 -2.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 1 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 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 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 1 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 N 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 0.0000 -0.0000 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 -6.0622 0.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 15 2 0 0 0 0 7 21 2 0 0 0 0 8 1 1 1 0 0 0 8 11 1 0 0 0 0 8 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 6 0 0 0 12 13 1 0 0 0 0 12 17 1 1 0 0 0 13 14 1 0 0 0 0 13 18 1 1 0 0 0 14 19 1 0 0 0 0 14 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	311.08
Volume:	293.862
LogP:	2.18
LogD:	0.901
LogS:	-2.746
# Rotatable Bonds:	4
TPSA:	91.51
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	3.868
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.501
MDCK Permeability:	2.5338335035485215e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.251
Human Intestinal Absorption (HIA):	0.264
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.598

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.187
Plasma Protein Binding (PPB):	29.60245132446289%
Volume Distribution (VD):	0.817
Pgp-substrate:	64.97614288330078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.163
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.626
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.357
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.545
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.09

ADMET: Excretion

Clearance (CL):	3.689
Half-life (T1/2):	0.482

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.604
AMES Toxicity:	0.636
Rat Oral Acute Toxicity:	0.366
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.897
Carcinogencity:	0.17
Eye Corrosion:	0.067
Eye Irritation:	0.581
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC36434

Natural Product ID:	NPC36434
*Common Name:**	4(Alpha-L-Rhamnosyloxy)-Benzyl Isothiocyanate
IUPAC Name:	(2S,3R,4R,5R,6S)-2-[4-(isothiocyanatomethyl)phenoxy]-6-methyloxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	QAZIHHJTZPNRCM-CNJBRALLSA-N
Standard InCHI:	InChI=1S/C14H17NO5S/c1-8-11(16)12(17)13(18)14(19-8)20-10-4-2-9(3-5-10)6-15-7-21/h2-5,8,11-14,16-18H,6H2,1H3/t8-,11-,12+,13+,14-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1ccc(cc1)CN=C=S)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223970
PubChem CID:	153557
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
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)83306-8]
NPO4410	Laggera alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932128]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24024688]
NPO3302	Fusarium avenaceum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25475336]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798960]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3905	Medinilla magnifica	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4410	Laggera alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4221	Fusarium sacchari	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3905	Medinilla magnifica	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7963	Excoecaria acerifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4410	Laggera alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3302	Fusarium avenaceum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8339	Lithothamnion corallioides	Species	Hapalidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7266	Goupia glabra	Species	Goupiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1585	Onobrychis bobrovii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2501	Trifolium strepens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5937	Garrya laurifolia	Species	Garryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2703	Petteria ramentacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4858	Helipterum gnaphaloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5021	Podospora curvicolla	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO823	Senecio cathcartensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8703	Monopteryx uaucu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO495	Daemonorops draco	Species	Arecaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	14430.0	nM	PMID[544605]

☑ 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 NPC36434 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	182
0.1-0.2	1302
0.2-0.3	5355
0.3-0.4	12172
0.4-0.5	6546
0.5-0.6	11653
0.6-0.7	4914
0.7-0.8	537
0.8-0.85	24
0.85-0.9	3
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC298821
0.9699	High Similarity	NPC123761
0.963	High Similarity	NPC161155
0.963	High Similarity	NPC136951
0.963	High Similarity	NPC97004
0.9416	High Similarity	NPC97282
0.8519	High Similarity	NPC198798
0.8473	Intermediate Similarity	NPC469708
0.8473	Intermediate Similarity	NPC60589
0.8462	Intermediate Similarity	NPC178466
0.8462	Intermediate Similarity	NPC63628
0.8451	Intermediate Similarity	NPC195814
0.8409	Intermediate Similarity	NPC469412
0.8409	Intermediate Similarity	NPC269242
0.8409	Intermediate Similarity	NPC198734
0.8367	Intermediate Similarity	NPC114659
0.8367	Intermediate Similarity	NPC139699
0.8162	Intermediate Similarity	NPC287429
0.8148	Intermediate Similarity	NPC476142
0.8146	Intermediate Similarity	NPC197741
0.8146	Intermediate Similarity	NPC140915
0.8146	Intermediate Similarity	NPC305700
0.8146	Intermediate Similarity	NPC18249
0.8146	Intermediate Similarity	NPC10221
0.8146	Intermediate Similarity	NPC187028
0.812	Intermediate Similarity	NPC14950
0.8074	Intermediate Similarity	NPC226712
0.8058	Intermediate Similarity	NPC302378
0.8	Intermediate Similarity	NPC295970
0.8	Intermediate Similarity	NPC248355
0.8	Intermediate Similarity	NPC270849
0.8	Intermediate Similarity	NPC166040
0.8	Intermediate Similarity	NPC26653
0.7943	Intermediate Similarity	NPC80600
0.7943	Intermediate Similarity	NPC472024
0.7895	Intermediate Similarity	NPC175771
0.7879	Intermediate Similarity	NPC313193
0.7842	Intermediate Similarity	NPC12308
0.7842	Intermediate Similarity	NPC470510
0.7832	Intermediate Similarity	NPC162093
0.7826	Intermediate Similarity	NPC212176
0.7817	Intermediate Similarity	NPC474491
0.7778	Intermediate Similarity	NPC294166
0.7778	Intermediate Similarity	NPC25821
0.7778	Intermediate Similarity	NPC49074
0.7778	Intermediate Similarity	NPC115022
0.7762	Intermediate Similarity	NPC9912
0.7762	Intermediate Similarity	NPC121376
0.7746	Intermediate Similarity	NPC307110
0.7746	Intermediate Similarity	NPC97326
0.7733	Intermediate Similarity	NPC313414
0.7724	Intermediate Similarity	NPC187194
0.7724	Intermediate Similarity	NPC471029
0.7708	Intermediate Similarity	NPC165686
0.7708	Intermediate Similarity	NPC26080
0.7708	Intermediate Similarity	NPC303422
0.7708	Intermediate Similarity	NPC85799
0.7708	Intermediate Similarity	NPC299144
0.7697	Intermediate Similarity	NPC471032
0.7697	Intermediate Similarity	NPC470935
0.7676	Intermediate Similarity	NPC40377
0.7676	Intermediate Similarity	NPC146540
0.7671	Intermediate Similarity	NPC470236
0.7671	Intermediate Similarity	NPC238243
0.7671	Intermediate Similarity	NPC55040
0.7655	Intermediate Similarity	NPC69513
0.7655	Intermediate Similarity	NPC215833
0.7643	Intermediate Similarity	NPC95733
0.7643	Intermediate Similarity	NPC62101
0.7639	Intermediate Similarity	NPC248307
0.7639	Intermediate Similarity	NPC65942
0.7632	Intermediate Similarity	NPC277857
0.7632	Intermediate Similarity	NPC115144
0.763	Intermediate Similarity	NPC148055
0.7622	Intermediate Similarity	NPC218003
0.7622	Intermediate Similarity	NPC49353
0.7619	Intermediate Similarity	NPC40664
0.7619	Intermediate Similarity	NPC3293
0.7619	Intermediate Similarity	NPC37468
0.7619	Intermediate Similarity	NPC165482
0.7619	Intermediate Similarity	NPC138350
0.7619	Intermediate Similarity	NPC294470
0.7619	Intermediate Similarity	NPC197723
0.7619	Intermediate Similarity	NPC164857
0.7612	Intermediate Similarity	NPC157338
0.7612	Intermediate Similarity	NPC142319
0.7603	Intermediate Similarity	NPC476411
0.7603	Intermediate Similarity	NPC188555
0.7603	Intermediate Similarity	NPC130496
0.7603	Intermediate Similarity	NPC48863
0.7603	Intermediate Similarity	NPC251981
0.7603	Intermediate Similarity	NPC13745
0.7589	Intermediate Similarity	NPC29477
0.7586	Intermediate Similarity	NPC252833
0.7578	Intermediate Similarity	NPC198741
0.7576	Intermediate Similarity	NPC46844
0.7569	Intermediate Similarity	NPC262606
0.7568	Intermediate Similarity	NPC138738
0.7568	Intermediate Similarity	NPC87777
0.7568	Intermediate Similarity	NPC470413
0.7568	Intermediate Similarity	NPC262328
0.7568	Intermediate Similarity	NPC124149
0.7551	Intermediate Similarity	NPC212729
0.7551	Intermediate Similarity	NPC79957
0.7536	Intermediate Similarity	NPC263835
0.7534	Intermediate Similarity	NPC6836
0.7534	Intermediate Similarity	NPC132895
0.7517	Intermediate Similarity	NPC100389
0.7517	Intermediate Similarity	NPC98777
0.7517	Intermediate Similarity	NPC212770
0.7517	Intermediate Similarity	NPC166168
0.7516	Intermediate Similarity	NPC476743
0.75	Intermediate Similarity	NPC242028
0.75	Intermediate Similarity	NPC103409
0.75	Intermediate Similarity	NPC166180
0.75	Intermediate Similarity	NPC203230
0.75	Intermediate Similarity	NPC186418
0.7483	Intermediate Similarity	NPC470881
0.7483	Intermediate Similarity	NPC264956
0.7483	Intermediate Similarity	NPC35731
0.7483	Intermediate Similarity	NPC34456
0.7468	Intermediate Similarity	NPC476744
0.7467	Intermediate Similarity	NPC210478
0.7466	Intermediate Similarity	NPC470270
0.7466	Intermediate Similarity	NPC269421
0.745	Intermediate Similarity	NPC59324
0.745	Intermediate Similarity	NPC65530
0.7447	Intermediate Similarity	NPC211218
0.7445	Intermediate Similarity	NPC9248
0.7436	Intermediate Similarity	NPC474560
0.7432	Intermediate Similarity	NPC185778
0.7429	Intermediate Similarity	NPC11724
0.7417	Intermediate Similarity	NPC89686
0.7417	Intermediate Similarity	NPC79908
0.7417	Intermediate Similarity	NPC273932
0.7417	Intermediate Similarity	NPC76871
0.7417	Intermediate Similarity	NPC257095
0.7417	Intermediate Similarity	NPC108674
0.7417	Intermediate Similarity	NPC210192
0.741	Intermediate Similarity	NPC282409
0.741	Intermediate Similarity	NPC469702
0.7397	Intermediate Similarity	NPC475067
0.7391	Intermediate Similarity	NPC228907
0.7383	Intermediate Similarity	NPC104167
0.7383	Intermediate Similarity	NPC14600
0.7383	Intermediate Similarity	NPC160607
0.7383	Intermediate Similarity	NPC157554
0.7383	Intermediate Similarity	NPC254610
0.7383	Intermediate Similarity	NPC204848
0.7383	Intermediate Similarity	NPC199459
0.7383	Intermediate Similarity	NPC172818
0.7383	Intermediate Similarity	NPC312770
0.7383	Intermediate Similarity	NPC52277
0.7383	Intermediate Similarity	NPC469383
0.7383	Intermediate Similarity	NPC41473
0.7383	Intermediate Similarity	NPC25695
0.7383	Intermediate Similarity	NPC177035
0.7383	Intermediate Similarity	NPC475628
0.7376	Intermediate Similarity	NPC52097
0.7372	Intermediate Similarity	NPC476742
0.7368	Intermediate Similarity	NPC157816
0.7368	Intermediate Similarity	NPC139976
0.7368	Intermediate Similarity	NPC189115
0.7368	Intermediate Similarity	NPC128337
0.7368	Intermediate Similarity	NPC230718
0.7368	Intermediate Similarity	NPC475084
0.7368	Intermediate Similarity	NPC84207
0.7368	Intermediate Similarity	NPC5253
0.7368	Intermediate Similarity	NPC49542
0.7368	Intermediate Similarity	NPC60249
0.7368	Intermediate Similarity	NPC469559
0.7368	Intermediate Similarity	NPC246947
0.7365	Intermediate Similarity	NPC87696
0.7365	Intermediate Similarity	NPC107478
0.7357	Intermediate Similarity	NPC476872
0.7357	Intermediate Similarity	NPC476445
0.7357	Intermediate Similarity	NPC469548
0.7357	Intermediate Similarity	NPC476448
0.7351	Intermediate Similarity	NPC202700
0.7351	Intermediate Similarity	NPC106944
0.7333	Intermediate Similarity	NPC134260
0.7333	Intermediate Similarity	NPC299583
0.7333	Intermediate Similarity	NPC115379
0.7333	Intermediate Similarity	NPC304152
0.7333	Intermediate Similarity	NPC195196
0.7329	Intermediate Similarity	NPC308885
0.7329	Intermediate Similarity	NPC255550
0.7328	Intermediate Similarity	NPC152384
0.7328	Intermediate Similarity	NPC37714
0.7325	Intermediate Similarity	NPC476741
0.732	Intermediate Similarity	NPC478239
0.732	Intermediate Similarity	NPC185307
0.732	Intermediate Similarity	NPC46092
0.732	Intermediate Similarity	NPC473044
0.732	Intermediate Similarity	NPC470950
0.732	Intermediate Similarity	NPC469367
0.732	Intermediate Similarity	NPC116922
0.7315	Intermediate Similarity	NPC416184
0.7305	Intermediate Similarity	NPC55608
0.7303	Intermediate Similarity	NPC80098

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 NPC36434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	645
0.2-0.3	1064
0.3-0.4	2437
0.4-0.5	2550
0.5-0.6	1600
0.6-0.7	680
0.7-0.8	39
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8074	Intermediate Similarity	NPD1091	Approved
0.7755	Intermediate Similarity	NPD1375	Discontinued
0.7698	Intermediate Similarity	NPD3685	Discontinued
0.7632	Intermediate Similarity	NPD4123	Phase 3
0.75	Intermediate Similarity	NPD4678	Approved
0.75	Intermediate Similarity	NPD4675	Approved
0.74	Intermediate Similarity	NPD3656	Approved
0.7379	Intermediate Similarity	NPD3180	Approved
0.7379	Intermediate Similarity	NPD3179	Approved
0.7329	Intermediate Similarity	NPD3144	Approved
0.7329	Intermediate Similarity	NPD3145	Approved
0.7279	Intermediate Similarity	NPD7477	Discontinued
0.7279	Intermediate Similarity	NPD2674	Phase 3
0.7267	Intermediate Similarity	NPD6841	Approved
0.7267	Intermediate Similarity	NPD6842	Approved
0.7267	Intermediate Similarity	NPD6843	Phase 3
0.7267	Intermediate Similarity	NPD4108	Discontinued
0.725	Intermediate Similarity	NPD5772	Approved
0.725	Intermediate Similarity	NPD5773	Approved
0.7237	Intermediate Similarity	NPD7153	Discontinued
0.7222	Intermediate Similarity	NPD5604	Discontinued
0.7218	Intermediate Similarity	NPD290	Approved
0.7183	Intermediate Similarity	NPD776	Approved
0.7179	Intermediate Similarity	NPD3536	Discontinued
0.7172	Intermediate Similarity	NPD558	Phase 2
0.7171	Intermediate Similarity	NPD521	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2684	Approved
0.7161	Intermediate Similarity	NPD5756	Phase 2
0.716	Intermediate Similarity	NPD7007	Discovery
0.7152	Intermediate Similarity	NPD3686	Approved
0.7152	Intermediate Similarity	NPD3693	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3687	Approved
0.7143	Intermediate Similarity	NPD2978	Approved
0.7143	Intermediate Similarity	NPD2977	Approved
0.7133	Intermediate Similarity	NPD3052	Approved
0.7133	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3054	Approved
0.7117	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2161	Phase 2
0.7105	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3567	Approved
0.7103	Intermediate Similarity	NPD1817	Approved
0.7103	Intermediate Similarity	NPD1819	Approved
0.7103	Intermediate Similarity	NPD1818	Approved
0.7103	Intermediate Similarity	NPD3568	Approved
0.7103	Intermediate Similarity	NPD1820	Approved
0.7099	Intermediate Similarity	NPD2560	Approved
0.7099	Intermediate Similarity	NPD2563	Approved
0.7095	Intermediate Similarity	NPD1048	Approved
0.7092	Intermediate Similarity	NPD2595	Approved
0.7092	Intermediate Similarity	NPD2594	Approved
0.7083	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4433	Discontinued
0.708	Intermediate Similarity	NPD821	Approved
0.708	Intermediate Similarity	NPD7843	Approved
0.7078	Intermediate Similarity	NPD4162	Approved
0.7078	Intermediate Similarity	NPD44	Approved
0.7078	Intermediate Similarity	NPD1652	Phase 2
0.7078	Intermediate Similarity	NPD6364	Approved
0.707	Intermediate Similarity	NPD4739	Approved
0.7051	Intermediate Similarity	NPD5058	Phase 3
0.7047	Intermediate Similarity	NPD840	Approved
0.7047	Intermediate Similarity	NPD839	Approved
0.7047	Intermediate Similarity	NPD1423	Approved
0.7032	Intermediate Similarity	NPD6331	Phase 2
0.7025	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7526	Approved
0.7025	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD52	Approved
0.7014	Intermediate Similarity	NPD2231	Phase 2
0.7014	Intermediate Similarity	NPD2235	Phase 2
0.7	Intermediate Similarity	NPD2238	Phase 2
0.6987	Remote Similarity	NPD2677	Approved
0.6985	Remote Similarity	NPD556	Approved
0.698	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD696	Discontinued
0.6972	Remote Similarity	NPD1357	Approved
0.6968	Remote Similarity	NPD2459	Approved
0.6968	Remote Similarity	NPD3060	Approved
0.6968	Remote Similarity	NPD4236	Phase 3
0.6968	Remote Similarity	NPD4237	Approved
0.6968	Remote Similarity	NPD2460	Phase 3
0.6968	Remote Similarity	NPD2458	Approved
0.6966	Remote Similarity	NPD4129	Approved
0.6962	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6419	Discontinued
0.6959	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6071	Discontinued
0.6943	Remote Similarity	NPD5295	Discontinued
0.6937	Remote Similarity	NPD1653	Approved
0.6933	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7157	Approved
0.6923	Remote Similarity	NPD2667	Approved
0.6923	Remote Similarity	NPD2668	Approved
0.6914	Remote Similarity	NPD6072	Discontinued
0.6913	Remote Similarity	NPD3166	Approved
0.6913	Remote Similarity	NPD3165	Approved
0.6913	Remote Similarity	NPD3167	Approved
0.6913	Remote Similarity	NPD3164	Approved
0.6903	Remote Similarity	NPD2030	Discontinued
0.6899	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7212	Phase 2
0.6899	Remote Similarity	NPD7213	Phase 3
0.6887	Remote Similarity	NPD1613	Approved
0.6887	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3156	Discontinued
0.6879	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2122	Discontinued
0.6871	Remote Similarity	NPD1794	Approved
0.6863	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4536	Approved
0.6863	Remote Similarity	NPD4538	Approved
0.6859	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6674	Discontinued
0.6859	Remote Similarity	NPD5289	Phase 2
0.6853	Remote Similarity	NPD6382	Discontinued
0.6852	Remote Similarity	NPD6502	Phase 2
0.6849	Remote Similarity	NPD1669	Approved
0.6849	Remote Similarity	NPD6583	Phase 3
0.6849	Remote Similarity	NPD6582	Phase 2
0.6842	Remote Similarity	NPD654	Phase 3
0.6835	Remote Similarity	NPD3122	Phase 3
0.6835	Remote Similarity	NPD6666	Approved
0.6835	Remote Similarity	NPD6667	Approved
0.6829	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3705	Approved
0.6821	Remote Similarity	NPD5745	Approved
0.6818	Remote Similarity	NPD6380	Phase 1
0.6818	Remote Similarity	NPD3152	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4772	Phase 2
0.681	Remote Similarity	NPD4773	Phase 2
0.6805	Remote Similarity	NPD2216	Approved
0.6805	Remote Similarity	NPD2215	Approved
0.68	Remote Similarity	NPD5163	Phase 2
0.68	Remote Similarity	NPD3027	Phase 3
0.6795	Remote Similarity	NPD2424	Discontinued
0.6795	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1774	Approved
0.679	Remote Similarity	NPD4005	Discontinued
0.6788	Remote Similarity	NPD6063	Approved
0.6779	Remote Similarity	NPD1712	Approved
0.6779	Remote Similarity	NPD4993	Discontinued
0.6774	Remote Similarity	NPD2239	Approved
0.6774	Remote Similarity	NPD2240	Approved
0.6772	Remote Similarity	NPD5160	Discontinued
0.6761	Remote Similarity	NPD3596	Phase 2
0.6757	Remote Similarity	NPD4098	Discontinued
0.6757	Remote Similarity	NPD6669	Phase 2
0.6752	Remote Similarity	NPD5061	Approved
0.6752	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5062	Approved
0.675	Remote Similarity	NPD7447	Phase 1
0.6747	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD2428	Approved
0.6735	Remote Similarity	NPD2429	Approved
0.6733	Remote Similarity	NPD596	Approved
0.6733	Remote Similarity	NPD600	Approved
0.6731	Remote Similarity	NPD7266	Discontinued
0.673	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4003	Phase 3
0.6727	Remote Similarity	NPD8455	Phase 2
0.6727	Remote Similarity	NPD7972	Discontinued
0.6726	Remote Similarity	NPD2904	Discontinued
0.6726	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5677	Discontinued
0.6726	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD5150	Phase 2
0.6716	Remote Similarity	NPD291	Approved
0.6715	Remote Similarity	NPD1358	Approved
0.6711	Remote Similarity	NPD6584	Phase 3
0.6711	Remote Similarity	NPD4062	Phase 3
0.6711	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6233	Phase 2
0.6711	Remote Similarity	NPD3691	Phase 2
0.6711	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3690	Phase 2
0.6711	Remote Similarity	NPD2990	Approved
0.6711	Remote Similarity	NPD2987	Approved
0.671	Remote Similarity	NPD5588	Approved
0.671	Remote Similarity	NPD5960	Phase 3
0.6707	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD8031	Discontinued
0.669	Remote Similarity	NPD2556	Approved
0.669	Remote Similarity	NPD2554	Approved
0.6689	Remote Similarity	NPD8651	Approved
0.6689	Remote Similarity	NPD5746	Approved
0.6689	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD2157	Approved
0.6688	Remote Similarity	NPD2492	Phase 1
0.6687	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1548	Phase 1
0.6667	Remote Similarity	NPD3823	Discontinued
0.6667	Remote Similarity	NPD6032	Approved
0.6667	Remote Similarity	NPD3382	Approved
0.6667	Remote Similarity	NPD3383	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