NPASS Compound

Structure

CID136951 OpenBabel06191715492D 24 25 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 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 0.8660 3.5000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 10 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 17 1 0 0 0 0 8 17 2 0 0 0 0 8 24 2 0 0 0 0 9 1 1 1 0 0 0 9 13 1 0 0 0 0 9 21 1 0 0 0 0 10 18 2 0 0 0 0 10 22 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 6 0 0 0 14 15 1 0 0 0 0 14 20 1 1 0 0 0 15 16 1 0 0 0 0 15 22 1 1 0 0 0 16 21 1 0 0 0 0 16 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.09
Volume:	334.608
LogP:	2.487
LogD:	1.127
LogS:	-3.51
# Rotatable Bonds:	6
TPSA:	97.58
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.464
Synthetic Accessibility Score:	3.934
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:	-5.533
MDCK Permeability:	4.9584166845306754e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.079
Human Intestinal Absorption (HIA):	0.542
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.18
Plasma Protein Binding (PPB):	19.09572982788086%
Volume Distribution (VD):	0.832
Pgp-substrate:	71.96665954589844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.228
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.353
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.2
CYP2D6-inhibitor:	0.625
CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	2.914
Half-life (T1/2):	0.607

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.294
Drug-inuced Liver Injury (DILI):	0.909
AMES Toxicity:	0.564
Rat Oral Acute Toxicity:	0.223
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.703
Carcinogencity:	0.137
Eye Corrosion:	0.025
Eye Irritation:	0.131
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC136951

Natural Product ID:	NPC136951
*Common Name:**	4-[(2'-O-Acetyl-Alpha-L-Rhamnosyloxy)Benzyl]Isothiocyanate
IUPAC Name:	[(2S,3R,4R,5R,6S)-4,5-dihydroxy-2-[4-(isothiocyanatomethyl)phenoxy]-6-methyloxan-3-yl] acetate
Synonyms:
Standard InCHIKey:	NHFOSXIOFJJQTP-FSDJSFAOSA-N
Standard InCHI:	InChI=1S/C16H19NO6S/c1-9-13(19)14(20)15(22-10(2)18)16(21-9)23-12-5-3-11(4-6-12)7-17-8-24/h3-6,9,13-16,19-20H,7H2,1-2H3/t9-,13-,14+,15+,16-/m0/s1
SMILES:	S=C=NCc1ccc(cc1)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223891
PubChem CID:	46933086
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]
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]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO3905	Medinilla magnifica	Species	Melastomataceae	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]
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]
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]

☑ 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	=	1670.0	nM	PMID[476740]

☑ 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 NPC136951 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	164
0.1-0.2	1098
0.2-0.3	4346
0.3-0.4	11814
0.4-0.5	7223
0.5-0.6	11420
0.6-0.7	6087
0.7-0.8	514
0.8-0.85	21
0.85-0.9	1
0.9-0.95	2
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC97004
1.0	High Similarity	NPC161155
0.9781	High Similarity	NPC97282
0.963	High Similarity	NPC36434
0.9416	High Similarity	NPC298821
0.9348	High Similarity	NPC123761
0.8477	Intermediate Similarity	NPC305700
0.8477	Intermediate Similarity	NPC10221
0.8477	Intermediate Similarity	NPC197741
0.8477	Intermediate Similarity	NPC187028
0.8477	Intermediate Similarity	NPC140915
0.8477	Intermediate Similarity	NPC18249
0.8357	Intermediate Similarity	NPC295970
0.8299	Intermediate Similarity	NPC178466
0.8299	Intermediate Similarity	NPC63628
0.8288	Intermediate Similarity	NPC195814
0.8235	Intermediate Similarity	NPC469412
0.8235	Intermediate Similarity	NPC198734
0.8214	Intermediate Similarity	NPC198798
0.8212	Intermediate Similarity	NPC114659
0.8212	Intermediate Similarity	NPC139699
0.8162	Intermediate Similarity	NPC60589
0.8162	Intermediate Similarity	NPC469708
0.8102	Intermediate Similarity	NPC269242
0.8069	Intermediate Similarity	NPC471029
0.8067	Intermediate Similarity	NPC313414
0.8	Intermediate Similarity	NPC287429
0.7986	Intermediate Similarity	NPC476142
0.7959	Intermediate Similarity	NPC37468
0.7905	Intermediate Similarity	NPC124149
0.7902	Intermediate Similarity	NPC146540
0.7902	Intermediate Similarity	NPC302378
0.7852	Intermediate Similarity	NPC100389
0.7847	Intermediate Similarity	NPC26653
0.7847	Intermediate Similarity	NPC270849
0.7847	Intermediate Similarity	NPC248355
0.7838	Intermediate Similarity	NPC166180
0.7826	Intermediate Similarity	NPC14950
0.7823	Intermediate Similarity	NPC34456
0.7793	Intermediate Similarity	NPC472024
0.7793	Intermediate Similarity	NPC80600
0.7786	Intermediate Similarity	NPC226712
0.777	Intermediate Similarity	NPC55040
0.777	Intermediate Similarity	NPC185778
0.773	Intermediate Similarity	NPC52097
0.7724	Intermediate Similarity	NPC166040
0.7718	Intermediate Similarity	NPC186418
0.7718	Intermediate Similarity	NPC157554
0.7718	Intermediate Similarity	NPC103409
0.7697	Intermediate Similarity	NPC157816
0.7692	Intermediate Similarity	NPC470510
0.7687	Intermediate Similarity	NPC162093
0.7687	Intermediate Similarity	NPC269421
0.7682	Intermediate Similarity	NPC202700
0.7671	Intermediate Similarity	NPC474491
0.766	Intermediate Similarity	NPC11724
0.7647	Intermediate Similarity	NPC469367
0.7647	Intermediate Similarity	NPC478239
0.7639	Intermediate Similarity	NPC471157
0.7635	Intermediate Similarity	NPC25821
0.7635	Intermediate Similarity	NPC49074
0.7635	Intermediate Similarity	NPC115022
0.7635	Intermediate Similarity	NPC294166
0.7632	Intermediate Similarity	NPC186406
0.7632	Intermediate Similarity	NPC215512
0.7632	Intermediate Similarity	NPC476442
0.7632	Intermediate Similarity	NPC80098
0.7619	Intermediate Similarity	NPC121376
0.7619	Intermediate Similarity	NPC9912
0.7616	Intermediate Similarity	NPC226005
0.7609	Intermediate Similarity	NPC175771
0.7603	Intermediate Similarity	NPC97326
0.7603	Intermediate Similarity	NPC307110
0.76	Intermediate Similarity	NPC294470
0.7597	Intermediate Similarity	NPC471028
0.7591	Intermediate Similarity	NPC313193
0.7589	Intermediate Similarity	NPC476872
0.7586	Intermediate Similarity	NPC156692
0.7586	Intermediate Similarity	NPC173150
0.7586	Intermediate Similarity	NPC471882
0.7586	Intermediate Similarity	NPC35288
0.7586	Intermediate Similarity	NPC45224
0.7586	Intermediate Similarity	NPC471881
0.7586	Intermediate Similarity	NPC106677
0.7584	Intermediate Similarity	NPC187194
0.7582	Intermediate Similarity	NPC145319
0.7569	Intermediate Similarity	NPC83218
0.7569	Intermediate Similarity	NPC126991
0.7569	Intermediate Similarity	NPC12308
0.7568	Intermediate Similarity	NPC303422
0.7568	Intermediate Similarity	NPC165686
0.7568	Intermediate Similarity	NPC26080
0.7568	Intermediate Similarity	NPC85799
0.7566	Intermediate Similarity	NPC210478
0.7564	Intermediate Similarity	NPC470935
0.7564	Intermediate Similarity	NPC471032
0.7552	Intermediate Similarity	NPC212176
0.7548	Intermediate Similarity	NPC226722
0.7548	Intermediate Similarity	NPC85624
0.7533	Intermediate Similarity	NPC470236
0.7533	Intermediate Similarity	NPC238243
0.7533	Intermediate Similarity	NPC212729
0.7517	Intermediate Similarity	NPC69513
0.7517	Intermediate Similarity	NPC215833
0.7517	Intermediate Similarity	NPC252114
0.7517	Intermediate Similarity	NPC233559
0.7516	Intermediate Similarity	NPC79908
0.75	Intermediate Similarity	NPC115144
0.75	Intermediate Similarity	NPC62101
0.75	Intermediate Similarity	NPC49353
0.75	Intermediate Similarity	NPC225384
0.75	Intermediate Similarity	NPC248307
0.75	Intermediate Similarity	NPC277857
0.75	Intermediate Similarity	NPC95733
0.75	Intermediate Similarity	NPC291153
0.75	Intermediate Similarity	NPC470392
0.75	Intermediate Similarity	NPC74320
0.75	Intermediate Similarity	NPC107120
0.75	Intermediate Similarity	NPC246869
0.75	Intermediate Similarity	NPC476865
0.75	Intermediate Similarity	NPC138777
0.75	Intermediate Similarity	NPC101503
0.75	Intermediate Similarity	NPC65942
0.75	Intermediate Similarity	NPC199928
0.7484	Intermediate Similarity	NPC232228
0.7484	Intermediate Similarity	NPC292443
0.7484	Intermediate Similarity	NPC476867
0.7483	Intermediate Similarity	NPC164857
0.7483	Intermediate Similarity	NPC218003
0.7483	Intermediate Similarity	NPC40664
0.7483	Intermediate Similarity	NPC197723
0.7483	Intermediate Similarity	NPC3293
0.7483	Intermediate Similarity	NPC165482
0.7483	Intermediate Similarity	NPC253595
0.7483	Intermediate Similarity	NPC138350
0.7482	Intermediate Similarity	NPC148055
0.7468	Intermediate Similarity	NPC140502
0.7467	Intermediate Similarity	NPC476411
0.7467	Intermediate Similarity	NPC251981
0.7467	Intermediate Similarity	NPC130496
0.7467	Intermediate Similarity	NPC48863
0.7467	Intermediate Similarity	NPC188555
0.7467	Intermediate Similarity	NPC13745
0.7466	Intermediate Similarity	NPC288416
0.7455	Intermediate Similarity	NPC198741
0.7452	Intermediate Similarity	NPC471764
0.7452	Intermediate Similarity	NPC175275
0.7452	Intermediate Similarity	NPC87950
0.7452	Intermediate Similarity	NPC97240
0.7452	Intermediate Similarity	NPC296377
0.745	Intermediate Similarity	NPC299144
0.745	Intermediate Similarity	NPC252833
0.7448	Intermediate Similarity	NPC29477
0.7436	Intermediate Similarity	NPC476869
0.7436	Intermediate Similarity	NPC476864
0.7436	Intermediate Similarity	NPC476866
0.7436	Intermediate Similarity	NPC476868
0.7434	Intermediate Similarity	NPC87777
0.7434	Intermediate Similarity	NPC138738
0.7434	Intermediate Similarity	NPC470413
0.7434	Intermediate Similarity	NPC262328
0.7432	Intermediate Similarity	NPC262606
0.7419	Intermediate Similarity	NPC302286
0.7419	Intermediate Similarity	NPC475213
0.7419	Intermediate Similarity	NPC237872
0.7419	Intermediate Similarity	NPC152796
0.7419	Intermediate Similarity	NPC263397
0.7419	Intermediate Similarity	NPC242756
0.7419	Intermediate Similarity	NPC88754
0.7419	Intermediate Similarity	NPC116104
0.7417	Intermediate Similarity	NPC79957
0.7415	Intermediate Similarity	NPC40377
0.7415	Intermediate Similarity	NPC225307
0.7415	Intermediate Similarity	NPC198487
0.7405	Intermediate Similarity	NPC96294
0.7405	Intermediate Similarity	NPC95990
0.7405	Intermediate Similarity	NPC478237
0.7405	Intermediate Similarity	NPC93924
0.7405	Intermediate Similarity	NPC182119
0.7405	Intermediate Similarity	NPC169510
0.7405	Intermediate Similarity	NPC220282
0.74	Intermediate Similarity	NPC469449
0.74	Intermediate Similarity	NPC132895
0.74	Intermediate Similarity	NPC6836
0.7397	Intermediate Similarity	NPC61181
0.7394	Intermediate Similarity	NPC263835
0.7389	Intermediate Similarity	NPC476743
0.7386	Intermediate Similarity	NPC212770
0.7386	Intermediate Similarity	NPC98777
0.7383	Intermediate Similarity	NPC254819
0.7383	Intermediate Similarity	NPC235294
0.7383	Intermediate Similarity	NPC46137
0.7383	Intermediate Similarity	NPC29734
0.7383	Intermediate Similarity	NPC281798
0.7375	Intermediate Similarity	NPC270811
0.7375	Intermediate Similarity	NPC471073
0.7372	Intermediate Similarity	NPC478240
0.7372	Intermediate Similarity	NPC110063
0.7372	Intermediate Similarity	NPC297342
0.7368	Intermediate Similarity	NPC203230

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 NPC136951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	117
0.1-0.2	547
0.2-0.3	1090
0.3-0.4	2407
0.4-0.5	2584
0.5-0.6	1635
0.6-0.7	742
0.7-0.8	28
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7786	Intermediate Similarity	NPD1091	Approved
0.7733	Intermediate Similarity	NPD3656	Approved
0.7552	Intermediate Similarity	NPD3685	Discontinued
0.75	Intermediate Similarity	NPD1375	Discontinued
0.75	Intermediate Similarity	NPD3536	Discontinued
0.75	Intermediate Similarity	NPD4123	Phase 3
0.7468	Intermediate Similarity	NPD3687	Approved
0.7468	Intermediate Similarity	NPD3686	Approved
0.7391	Intermediate Similarity	NPD4433	Discontinued
0.7375	Intermediate Similarity	NPD4675	Approved
0.7375	Intermediate Similarity	NPD4678	Approved
0.7356	Intermediate Similarity	NPD6843	Phase 3
0.7356	Intermediate Similarity	NPD6842	Approved
0.7356	Intermediate Similarity	NPD6841	Approved
0.7342	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1048	Approved
0.729	Intermediate Similarity	NPD1652	Phase 2
0.7248	Intermediate Similarity	NPD3180	Approved
0.7248	Intermediate Similarity	NPD3179	Approved
0.7226	Intermediate Similarity	NPD2030	Discontinued
0.72	Intermediate Similarity	NPD3145	Approved
0.72	Intermediate Similarity	NPD3144	Approved
0.717	Intermediate Similarity	NPD4739	Approved
0.716	Intermediate Similarity	NPD6502	Phase 2
0.7152	Intermediate Similarity	NPD6667	Approved
0.7152	Intermediate Similarity	NPD5745	Approved
0.7152	Intermediate Similarity	NPD7477	Discontinued
0.7152	Intermediate Similarity	NPD6666	Approved
0.7152	Intermediate Similarity	NPD2674	Phase 3
0.7143	Intermediate Similarity	NPD1653	Approved
0.7143	Intermediate Similarity	NPD4108	Discontinued
0.7134	Intermediate Similarity	NPD5772	Approved
0.7134	Intermediate Similarity	NPD5773	Approved
0.7133	Intermediate Similarity	NPD5163	Phase 2
0.7115	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7153	Discontinued
0.7108	Intermediate Similarity	NPD5604	Discontinued
0.7097	Intermediate Similarity	NPD2239	Approved
0.7097	Intermediate Similarity	NPD2240	Approved
0.707	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7007	Discovery
0.7051	Intermediate Similarity	NPD7266	Discontinued
0.7044	Intermediate Similarity	NPD5295	Discontinued
0.7044	Intermediate Similarity	NPD5756	Phase 2
0.7039	Intermediate Similarity	NPD4062	Phase 3
0.7039	Intermediate Similarity	NPD6233	Phase 2
0.7037	Intermediate Similarity	NPD4003	Phase 3
0.7032	Intermediate Similarity	NPD3693	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2977	Approved
0.703	Intermediate Similarity	NPD2978	Approved
0.703	Intermediate Similarity	NPD8455	Phase 2
0.703	Intermediate Similarity	NPD7972	Discontinued
0.7029	Intermediate Similarity	NPD2684	Approved
0.7024	Intermediate Similarity	NPD5677	Discontinued
0.702	Intermediate Similarity	NPD5746	Approved
0.7013	Intermediate Similarity	NPD3054	Approved
0.7013	Intermediate Similarity	NPD3052	Approved
0.7012	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2563	Approved
0.6988	Remote Similarity	NPD2560	Approved
0.6987	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2161	Phase 2
0.6987	Remote Similarity	NPD6032	Approved
0.698	Remote Similarity	NPD3567	Approved
0.698	Remote Similarity	NPD3568	Approved
0.6974	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7097	Phase 1
0.6966	Remote Similarity	NPD2594	Approved
0.6966	Remote Similarity	NPD2595	Approved
0.6962	Remote Similarity	NPD6364	Approved
0.6962	Remote Similarity	NPD4162	Approved
0.6962	Remote Similarity	NPD44	Approved
0.6959	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1358	Approved
0.6957	Remote Similarity	NPD290	Approved
0.6954	Remote Similarity	NPD2614	Approved
0.695	Remote Similarity	NPD7843	Approved
0.6948	Remote Similarity	NPD4340	Discontinued
0.6943	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD776	Approved
0.6937	Remote Similarity	NPD5058	Phase 3
0.6933	Remote Similarity	NPD558	Phase 2
0.6928	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4666	Phase 3
0.6918	Remote Similarity	NPD6331	Phase 2
0.6914	Remote Similarity	NPD52	Approved
0.6914	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7526	Approved
0.6914	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2653	Approved
0.6899	Remote Similarity	NPD2424	Discontinued
0.6892	Remote Similarity	NPD2235	Phase 2
0.6892	Remote Similarity	NPD2231	Phase 2
0.6883	Remote Similarity	NPD2238	Phase 2
0.6875	Remote Similarity	NPD2677	Approved
0.6867	Remote Similarity	NPD1819	Approved
0.6867	Remote Similarity	NPD1820	Approved
0.6867	Remote Similarity	NPD1817	Approved
0.6867	Remote Similarity	NPD1818	Approved
0.6867	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5709	Phase 3
0.6863	Remote Similarity	NPD6798	Discontinued
0.6863	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2458	Approved
0.6855	Remote Similarity	NPD2460	Phase 3
0.6855	Remote Similarity	NPD4236	Phase 3
0.6855	Remote Similarity	NPD2459	Approved
0.6855	Remote Similarity	NPD3060	Approved
0.6855	Remote Similarity	NPD4237	Approved
0.6852	Remote Similarity	NPD6419	Discontinued
0.6846	Remote Similarity	NPD4129	Approved
0.6845	Remote Similarity	NPD6669	Phase 2
0.6842	Remote Similarity	NPD7315	Approved
0.6842	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6071	Discontinued
0.6835	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD821	Approved
0.6826	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7583	Approved
0.6824	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2904	Discontinued
0.6824	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD839	Approved
0.6818	Remote Similarity	NPD840	Approved
0.6818	Remote Similarity	NPD1423	Approved
0.6813	Remote Similarity	NPD4628	Phase 3
0.681	Remote Similarity	NPD6390	Discontinued
0.6807	Remote Similarity	NPD6072	Discontinued
0.6806	Remote Similarity	NPD7157	Approved
0.6805	Remote Similarity	NPD8031	Discontinued
0.6803	Remote Similarity	NPD2667	Approved
0.6803	Remote Similarity	NPD2668	Approved
0.68	Remote Similarity	NPD5557	Phase 1
0.6797	Remote Similarity	NPD3167	Approved
0.6797	Remote Similarity	NPD3165	Approved
0.6797	Remote Similarity	NPD3166	Approved
0.6797	Remote Similarity	NPD3164	Approved
0.6795	Remote Similarity	NPD2492	Phase 1
0.679	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7212	Phase 2
0.679	Remote Similarity	NPD7213	Phase 3
0.6789	Remote Similarity	NPD7585	Approved
0.6788	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3909	Discontinued
0.6774	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3156	Discontinued
0.677	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD2122	Discontinued
0.6766	Remote Similarity	NPD5355	Approved
0.6766	Remote Similarity	NPD5356	Approved
0.6766	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3134	Approved
0.6761	Remote Similarity	NPD3823	Discontinued
0.6757	Remote Similarity	NPD3847	Discontinued
0.6752	Remote Similarity	NPD4538	Approved
0.6752	Remote Similarity	NPD4536	Approved
0.6752	Remote Similarity	NPD696	Discontinued
0.6752	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6674	Discontinued
0.675	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5289	Phase 2
0.6748	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7773	Phase 2
0.6738	Remote Similarity	NPD556	Approved
0.6735	Remote Similarity	NPD6382	Discontinued
0.6735	Remote Similarity	NPD1357	Approved
0.6733	Remote Similarity	NPD6583	Phase 3
0.6733	Remote Similarity	NPD6582	Phase 2
0.6731	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6355	Discontinued
0.6731	Remote Similarity	NPD5124	Phase 1
0.6728	Remote Similarity	NPD3122	Phase 3
0.6727	Remote Similarity	NPD4210	Discontinued
0.6726	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7039	Approved
0.6723	Remote Similarity	NPD7038	Approved
0.6723	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5535	Approved
0.6711	Remote Similarity	NPD3705	Approved
0.6711	Remote Similarity	NPD422	Phase 1
0.671	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6380	Phase 1
0.6709	Remote Similarity	NPD3152	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4773	Phase 2
0.6707	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4772	Phase 2
0.6706	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2388	Discontinued
0.6705	Remote Similarity	NPD2216	Approved
0.6705	Remote Similarity	NPD2215	Approved
0.6688	Remote Similarity	NPD3027	Phase 3
0.6688	Remote Similarity	NPD6653	Approved
0.6687	Remote Similarity	NPD4005	Discontinued
0.6687	Remote Similarity	NPD5811	Approved
0.6686	Remote Similarity	NPD6063	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