NPASS Compound

Structure

CID99760 OpenBabel06191715442D 21 24 0 0 1 0 0 0 0 0999 V2000 1.4690 -3.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0686 -2.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4718 0.3867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4069 -1.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8186 -0.1911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6003 -0.5005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1007 -0.6346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1187 -2.7341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8186 -1.8106 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8668 -1.5013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8668 -1.5013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7335 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8668 -0.5004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7335 -2.0018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8668 -0.5004 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6003 -1.5014 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7335 -2.9850 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4518 -1.9930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7344 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 9 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 16 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 17 1 0 0 0 0 8 17 1 0 0 0 0 8 20 1 0 0 0 0 10 9 1 1 0 0 0 10 12 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 6 0 0 0 13 7 1 1 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 18 2 0 0 0 0 16 3 1 1 0 0 0 16 21 1 0 0 0 0 17 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.15
Volume:	295.614
LogP:	2.786
LogD:	2.816
LogS:	-4.163
# Rotatable Bonds:	1
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.752
Synthetic Accessibility Score:	5.763
Fsp3:	0.706
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.794
MDCK Permeability:	1.5225627976178657e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.047
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.447
Plasma Protein Binding (PPB):	67.4312744140625%
Volume Distribution (VD):	1.635
Pgp-substrate:	30.441490173339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.65
CYP2C19-inhibitor:	0.118
CYP2C19-substrate:	0.818
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.083
CYP3A4-substrate:	0.591

ADMET: Excretion

Clearance (CL):	3.872
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.791
Drug-inuced Liver Injury (DILI):	0.817
AMES Toxicity:	0.518
Rat Oral Acute Toxicity:	0.213
Maximum Recommended Daily Dose:	0.766
Skin Sensitization:	0.372
Carcinogencity:	0.71
Eye Corrosion:	0.005
Eye Irritation:	0.137
Respiratory Toxicity:	0.423

Download Data

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

Natural Product: NPC99760

Natural Product ID:	NPC99760
*Common Name:**	PDDUOBCTLLRRFF-AWKHGQQRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PDDUOBCTLLRRFF-AWKHGQQRSA-N
Standard InCHI:	InChI=1S/C17H22O4/c1-9(2)10-4-5-16(3)12(10)6-11-14(21-16)13-7-17(19,8-20-13)15(11)18/h10,12-13,19H,1,4-8H2,2-3H3/t10-,12-,13-,16+,17+/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@]2(C)[C@H]1CC1=C([C@@H]3C[C@@](CO3)(C1=O)O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3752158
PubChem CID:	50905842
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO17605	Adenaria floribunda	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043429]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22209460]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24253739]
NPO40151	Guignardia sp.	Species	Phyllostictaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26577190]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29328	Genista tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29328	Genista tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28860	Saprosma scortechinii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29328	Genista tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29291	Diplopappus fruticosus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17605	Adenaria floribunda	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29527	Stemonoporus affinis	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28860	Saprosma scortechinii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29448	Centaurea thessala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12447	Plagiochila yokogurensis	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29077	Marsupella emarginata	Species	Gymnomitriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29197	Mimosa hostilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29342	Astraeus hygrometricus	Species	Astraeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22440	Arctanthemum arcticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29186	Nardosmia laevigata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28580	Tetragonia tetragonioides	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29122	Scyphiphora hydrophyllacea	Species	Rubiaceae	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
MIC	4
Others	1

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC=>80	>	200.0	ug ml-1	PMID[452528]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[452528]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[452528]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[452528]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.5	ug.mL-1	PMID[452528]

☑ 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 NPC99760 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	230
0.1-0.2	1382
0.2-0.3	4873
0.3-0.4	8942
0.4-0.5	15192
0.5-0.6	7584
0.6-0.7	3906
0.7-0.8	570
0.8-0.85	8
0.85-0.9	2
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC101018
0.8785	High Similarity	NPC471400
0.8302	Intermediate Similarity	NPC471401
0.8276	Intermediate Similarity	NPC472000
0.8276	Intermediate Similarity	NPC471999
0.812	Intermediate Similarity	NPC472001
0.8113	Intermediate Similarity	NPC470541
0.8056	Intermediate Similarity	NPC70369
0.8	Intermediate Similarity	NPC54739
0.8	Intermediate Similarity	NPC91408
0.7944	Intermediate Similarity	NPC306908
0.7881	Intermediate Similarity	NPC472004
0.7798	Intermediate Similarity	NPC181645
0.7797	Intermediate Similarity	NPC476107
0.7788	Intermediate Similarity	NPC77089
0.7778	Intermediate Similarity	NPC35717
0.7768	Intermediate Similarity	NPC204884
0.7759	Intermediate Similarity	NPC326542
0.775	Intermediate Similarity	NPC269642
0.775	Intermediate Similarity	NPC222688
0.7748	Intermediate Similarity	NPC294259
0.7739	Intermediate Similarity	NPC207251
0.7731	Intermediate Similarity	NPC474585
0.7724	Intermediate Similarity	NPC476091
0.7724	Intermediate Similarity	NPC476078
0.7667	Intermediate Similarity	NPC46570
0.7664	Intermediate Similarity	NPC279313
0.7661	Intermediate Similarity	NPC231529
0.7658	Intermediate Similarity	NPC475945
0.7658	Intermediate Similarity	NPC475871
0.7647	Intermediate Similarity	NPC475041
0.7642	Intermediate Similarity	NPC61275
0.7636	Intermediate Similarity	NPC474742
0.7632	Intermediate Similarity	NPC38154
0.7632	Intermediate Similarity	NPC470257
0.7619	Intermediate Similarity	NPC469464
0.7611	Intermediate Similarity	NPC26617
0.7607	Intermediate Similarity	NPC247069
0.7607	Intermediate Similarity	NPC178289
0.7603	Intermediate Similarity	NPC107493
0.76	Intermediate Similarity	NPC475389
0.76	Intermediate Similarity	NPC473838
0.7589	Intermediate Similarity	NPC100487
0.7589	Intermediate Similarity	NPC474741
0.7586	Intermediate Similarity	NPC471933
0.7583	Intermediate Similarity	NPC142882
0.7568	Intermediate Similarity	NPC474747
0.7568	Intermediate Similarity	NPC149371
0.7565	Intermediate Similarity	NPC206595
0.7563	Intermediate Similarity	NPC153440
0.7563	Intermediate Similarity	NPC475372
0.7561	Intermediate Similarity	NPC217901
0.7547	Intermediate Similarity	NPC146852
0.7544	Intermediate Similarity	NPC117604
0.7542	Intermediate Similarity	NPC190286
0.7541	Intermediate Similarity	NPC471392
0.7523	Intermediate Similarity	NPC20078
0.7523	Intermediate Similarity	NPC473574
0.7523	Intermediate Similarity	NPC20066
0.7523	Intermediate Similarity	NPC239895
0.7522	Intermediate Similarity	NPC471332
0.7522	Intermediate Similarity	NPC471333
0.7522	Intermediate Similarity	NPC190867
0.7521	Intermediate Similarity	NPC73300
0.7521	Intermediate Similarity	NPC108721
0.7521	Intermediate Similarity	NPC317210
0.752	Intermediate Similarity	NPC221414
0.752	Intermediate Similarity	NPC162495
0.75	Intermediate Similarity	NPC470882
0.75	Intermediate Similarity	NPC42673
0.75	Intermediate Similarity	NPC230513
0.75	Intermediate Similarity	NPC5292
0.75	Intermediate Similarity	NPC19028
0.75	Intermediate Similarity	NPC163228
0.75	Intermediate Similarity	NPC270850
0.75	Intermediate Similarity	NPC305260
0.75	Intermediate Similarity	NPC475273
0.75	Intermediate Similarity	NPC312536
0.75	Intermediate Similarity	NPC168849
0.75	Intermediate Similarity	NPC9674
0.748	Intermediate Similarity	NPC24651
0.748	Intermediate Similarity	NPC8369
0.7479	Intermediate Similarity	NPC239273
0.7477	Intermediate Similarity	NPC128733
0.7477	Intermediate Similarity	NPC9878
0.7477	Intermediate Similarity	NPC46998
0.7477	Intermediate Similarity	NPC110443
0.7477	Intermediate Similarity	NPC133907
0.7477	Intermediate Similarity	NPC185141
0.7477	Intermediate Similarity	NPC47880
0.746	Intermediate Similarity	NPC475314
0.746	Intermediate Similarity	NPC251564
0.746	Intermediate Similarity	NPC475606
0.746	Intermediate Similarity	NPC477189
0.7459	Intermediate Similarity	NPC170538
0.7459	Intermediate Similarity	NPC312833
0.7456	Intermediate Similarity	NPC43285
0.7456	Intermediate Similarity	NPC58370
0.7455	Intermediate Similarity	NPC212465
0.7455	Intermediate Similarity	NPC177232
0.7455	Intermediate Similarity	NPC300584
0.7438	Intermediate Similarity	NPC143755
0.7438	Intermediate Similarity	NPC79579
0.7438	Intermediate Similarity	NPC109973
0.7438	Intermediate Similarity	NPC478051
0.7429	Intermediate Similarity	NPC228415
0.7429	Intermediate Similarity	NPC87189
0.7419	Intermediate Similarity	NPC293112
0.7419	Intermediate Similarity	NPC473635
0.7417	Intermediate Similarity	NPC257457
0.7417	Intermediate Similarity	NPC475401
0.7417	Intermediate Similarity	NPC311554
0.7414	Intermediate Similarity	NPC5103
0.7407	Intermediate Similarity	NPC477241
0.7402	Intermediate Similarity	NPC475139
0.7402	Intermediate Similarity	NPC474508
0.7402	Intermediate Similarity	NPC473485
0.7402	Intermediate Similarity	NPC180902
0.7398	Intermediate Similarity	NPC265557
0.7398	Intermediate Similarity	NPC11895
0.7398	Intermediate Similarity	NPC473979
0.7398	Intermediate Similarity	NPC91693
0.7398	Intermediate Similarity	NPC473802
0.7398	Intermediate Similarity	NPC469789
0.7398	Intermediate Similarity	NPC105926
0.7398	Intermediate Similarity	NPC18945
0.7395	Intermediate Similarity	NPC49492
0.7395	Intermediate Similarity	NPC138372
0.7395	Intermediate Similarity	NPC266728
0.7395	Intermediate Similarity	NPC106228
0.7395	Intermediate Similarity	NPC478216
0.7395	Intermediate Similarity	NPC207217
0.7391	Intermediate Similarity	NPC217201
0.7391	Intermediate Similarity	NPC29827
0.7391	Intermediate Similarity	NPC10150
0.7383	Intermediate Similarity	NPC144629
0.7377	Intermediate Similarity	NPC310511
0.7373	Intermediate Similarity	NPC194100
0.7373	Intermediate Similarity	NPC312017
0.7373	Intermediate Similarity	NPC478212
0.7373	Intermediate Similarity	NPC9848
0.7368	Intermediate Similarity	NPC243998
0.7368	Intermediate Similarity	NPC223450
0.7368	Intermediate Similarity	NPC470975
0.7368	Intermediate Similarity	NPC54737
0.7368	Intermediate Similarity	NPC103088
0.7368	Intermediate Similarity	NPC470979
0.7364	Intermediate Similarity	NPC27105
0.7364	Intermediate Similarity	NPC474313
0.7364	Intermediate Similarity	NPC69385
0.736	Intermediate Similarity	NPC287423
0.736	Intermediate Similarity	NPC473253
0.736	Intermediate Similarity	NPC473265
0.736	Intermediate Similarity	NPC476008
0.7355	Intermediate Similarity	NPC477092
0.735	Intermediate Similarity	NPC179798
0.735	Intermediate Similarity	NPC304180
0.7345	Intermediate Similarity	NPC320154
0.7345	Intermediate Similarity	NPC168575
0.7345	Intermediate Similarity	NPC475873
0.7345	Intermediate Similarity	NPC474775
0.7345	Intermediate Similarity	NPC117185
0.7345	Intermediate Similarity	NPC123505
0.7344	Intermediate Similarity	NPC88668
0.7339	Intermediate Similarity	NPC469790
0.7339	Intermediate Similarity	NPC172154
0.7339	Intermediate Similarity	NPC473255
0.7339	Intermediate Similarity	NPC473919
0.7339	Intermediate Similarity	NPC473709
0.7339	Intermediate Similarity	NPC475900
0.7339	Intermediate Similarity	NPC476729
0.7339	Intermediate Similarity	NPC81736
0.7339	Intermediate Similarity	NPC67584
0.7333	Intermediate Similarity	NPC122033
0.7333	Intermediate Similarity	NPC98249
0.7333	Intermediate Similarity	NPC478204
0.7333	Intermediate Similarity	NPC470854
0.7333	Intermediate Similarity	NPC287343
0.7333	Intermediate Similarity	NPC469684
0.7333	Intermediate Similarity	NPC477116
0.7333	Intermediate Similarity	NPC475305
0.7333	Intermediate Similarity	NPC471145
0.7333	Intermediate Similarity	NPC53396
0.7333	Intermediate Similarity	NPC474654
0.7333	Intermediate Similarity	NPC27999
0.7333	Intermediate Similarity	NPC471146
0.7333	Intermediate Similarity	NPC97908
0.7333	Intermediate Similarity	NPC473656
0.7328	Intermediate Similarity	NPC11710
0.7328	Intermediate Similarity	NPC187876
0.7328	Intermediate Similarity	NPC214644
0.7328	Intermediate Similarity	NPC471934
0.7323	Intermediate Similarity	NPC213634
0.7323	Intermediate Similarity	NPC279478
0.7323	Intermediate Similarity	NPC241935
0.7321	Intermediate Similarity	NPC474339
0.7321	Intermediate Similarity	NPC171759
0.7321	Intermediate Similarity	NPC477950
0.7321	Intermediate Similarity	NPC472753
0.7321	Intermediate Similarity	NPC150923

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 NPC99760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	1923
0.2-0.3	3852
0.3-0.4	2114
0.4-0.5	662
0.5-0.6	233
0.6-0.7	137
0.7-0.8	4
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
0.7611	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6053	Discontinued
0.7407	Intermediate Similarity	NPD5282	Discontinued
0.7295	Intermediate Similarity	NPD6059	Approved
0.7295	Intermediate Similarity	NPD6054	Approved
0.7236	Intermediate Similarity	NPD6015	Approved
0.7236	Intermediate Similarity	NPD6016	Approved
0.7177	Intermediate Similarity	NPD6370	Approved
0.7177	Intermediate Similarity	NPD5988	Approved
0.7154	Intermediate Similarity	NPD6319	Approved
0.7119	Intermediate Similarity	NPD4634	Approved
0.7063	Intermediate Similarity	NPD7492	Approved
0.7054	Intermediate Similarity	NPD4755	Approved
0.7049	Intermediate Similarity	NPD7115	Discovery
0.7008	Intermediate Similarity	NPD6616	Approved
0.6975	Remote Similarity	NPD6371	Approved
0.6957	Remote Similarity	NPD5211	Phase 2
0.6953	Remote Similarity	NPD7078	Approved
0.6953	Remote Similarity	NPD8293	Discontinued
0.6949	Remote Similarity	NPD7320	Approved
0.6942	Remote Similarity	NPD4632	Approved
0.693	Remote Similarity	NPD4700	Approved
0.693	Remote Similarity	NPD5285	Approved
0.693	Remote Similarity	NPD5286	Approved
0.693	Remote Similarity	NPD4696	Approved
0.6923	Remote Similarity	NPD6402	Approved
0.6923	Remote Similarity	NPD7128	Approved
0.6923	Remote Similarity	NPD5739	Approved
0.6923	Remote Similarity	NPD6675	Approved
0.6923	Remote Similarity	NPD6008	Approved
0.6899	Remote Similarity	NPD7736	Approved
0.6891	Remote Similarity	NPD6372	Approved
0.6891	Remote Similarity	NPD6373	Approved
0.6864	Remote Similarity	NPD5697	Approved
0.6864	Remote Similarity	NPD5701	Approved
0.686	Remote Similarity	NPD8297	Approved
0.6846	Remote Similarity	NPD7319	Approved
0.6838	Remote Similarity	NPD5141	Approved
0.681	Remote Similarity	NPD5224	Approved
0.681	Remote Similarity	NPD5225	Approved
0.681	Remote Similarity	NPD5226	Approved
0.681	Remote Similarity	NPD4633	Approved
0.6807	Remote Similarity	NPD6899	Approved
0.6807	Remote Similarity	NPD6881	Approved
0.6777	Remote Similarity	NPD6649	Approved
0.6777	Remote Similarity	NPD6650	Approved
0.6769	Remote Similarity	NPD6033	Approved
0.6752	Remote Similarity	NPD5174	Approved
0.6752	Remote Similarity	NPD5175	Approved
0.675	Remote Similarity	NPD6014	Approved
0.675	Remote Similarity	NPD6013	Approved
0.675	Remote Similarity	NPD6012	Approved
0.6744	Remote Similarity	NPD7507	Approved
0.6727	Remote Similarity	NPD4753	Phase 2
0.6726	Remote Similarity	NPD5695	Phase 3
0.6726	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5223	Approved
0.6698	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4225	Approved
0.6696	Remote Similarity	NPD5696	Approved
0.6694	Remote Similarity	NPD6883	Approved
0.6694	Remote Similarity	NPD7290	Approved
0.6694	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6011	Approved
0.664	Remote Similarity	NPD6009	Approved
0.6639	Remote Similarity	NPD4767	Approved
0.6639	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD4768	Approved
0.6639	Remote Similarity	NPD8130	Phase 1
0.6639	Remote Similarity	NPD6869	Approved
0.6639	Remote Similarity	NPD6847	Approved
0.6636	Remote Similarity	NPD6110	Phase 1
0.6612	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4754	Approved
0.6609	Remote Similarity	NPD6084	Phase 2
0.6609	Remote Similarity	NPD6083	Phase 2
0.6585	Remote Similarity	NPD6882	Approved
0.6583	Remote Similarity	NPD6412	Phase 2
0.6579	Remote Similarity	NPD5210	Approved
0.6579	Remote Similarity	NPD4629	Approved
0.6562	Remote Similarity	NPD8513	Phase 3
0.6562	Remote Similarity	NPD5983	Phase 2
0.6557	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4729	Approved
0.6529	Remote Similarity	NPD4730	Approved
0.6529	Remote Similarity	NPD5128	Approved
0.6522	Remote Similarity	NPD4697	Phase 3
0.6518	Remote Similarity	NPD46	Approved
0.6518	Remote Similarity	NPD6698	Approved
0.6518	Remote Similarity	NPD5785	Approved
0.6504	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD7604	Phase 2
0.646	Remote Similarity	NPD5693	Phase 1
0.6455	Remote Similarity	NPD4249	Approved
0.6455	Remote Similarity	NPD5786	Approved
0.6444	Remote Similarity	NPD6845	Suspended
0.6434	Remote Similarity	NPD7503	Approved
0.6434	Remote Similarity	NPD8516	Approved
0.6434	Remote Similarity	NPD8517	Approved
0.6434	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8515	Approved
0.6429	Remote Similarity	NPD6274	Approved
0.6429	Remote Similarity	NPD1695	Approved
0.6423	Remote Similarity	NPD5249	Phase 3
0.6423	Remote Similarity	NPD5248	Approved
0.6423	Remote Similarity	NPD5247	Approved
0.6423	Remote Similarity	NPD5250	Approved
0.6423	Remote Similarity	NPD5251	Approved
0.6422	Remote Similarity	NPD4197	Approved
0.6418	Remote Similarity	NPD5956	Approved
0.6406	Remote Similarity	NPD7516	Approved
0.6404	Remote Similarity	NPD5778	Approved
0.6404	Remote Similarity	NPD5779	Approved
0.6404	Remote Similarity	NPD4202	Approved
0.6396	Remote Similarity	NPD4250	Approved
0.6396	Remote Similarity	NPD4251	Approved
0.6379	Remote Similarity	NPD5222	Approved
0.6379	Remote Similarity	NPD5221	Approved
0.6379	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5215	Approved
0.6371	Remote Similarity	NPD5217	Approved
0.6371	Remote Similarity	NPD5216	Approved
0.637	Remote Similarity	NPD7260	Phase 2
0.6364	Remote Similarity	NPD5329	Approved
0.6364	Remote Similarity	NPD5363	Approved
0.6364	Remote Similarity	NPD6336	Discontinued
0.6328	Remote Similarity	NPD7327	Approved
0.6328	Remote Similarity	NPD7328	Approved
0.6325	Remote Similarity	NPD5173	Approved
0.6316	Remote Similarity	NPD7983	Approved
0.6311	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4694	Approved
0.6306	Remote Similarity	NPD5280	Approved
0.6306	Remote Similarity	NPD5690	Phase 2
0.6306	Remote Similarity	NPD5279	Phase 3
0.6306	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD1700	Approved
0.6296	Remote Similarity	NPD5369	Approved
0.6293	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.629	Remote Similarity	NPD5169	Approved
0.629	Remote Similarity	NPD5135	Approved
0.629	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5328	Approved
0.6279	Remote Similarity	NPD7100	Approved
0.6279	Remote Similarity	NPD7101	Approved
0.6279	Remote Similarity	NPD4522	Approved
0.6273	Remote Similarity	NPD3133	Approved
0.6273	Remote Similarity	NPD3666	Approved
0.6273	Remote Similarity	NPD3665	Phase 1
0.6271	Remote Similarity	NPD7638	Approved
0.6261	Remote Similarity	NPD6399	Phase 3
0.626	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD6317	Approved
0.624	Remote Similarity	NPD5127	Approved
0.6239	Remote Similarity	NPD4269	Approved
0.6239	Remote Similarity	NPD4223	Phase 3
0.6239	Remote Similarity	NPD4270	Approved
0.6239	Remote Similarity	NPD6435	Approved
0.6239	Remote Similarity	NPD4221	Approved
0.6218	Remote Similarity	NPD7639	Approved
0.6218	Remote Similarity	NPD7640	Approved
0.6216	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD8328	Phase 3
0.6202	Remote Similarity	NPD6313	Approved
0.6202	Remote Similarity	NPD6314	Approved
0.6202	Remote Similarity	NPD6335	Approved
0.6194	Remote Similarity	NPD8074	Phase 3
0.6183	Remote Similarity	NPD8033	Approved
0.6183	Remote Similarity	NPD6908	Approved
0.6183	Remote Similarity	NPD6909	Approved
0.6182	Remote Similarity	NPD5362	Discontinued
0.6174	Remote Similarity	NPD5284	Approved
0.6174	Remote Similarity	NPD5281	Approved
0.6174	Remote Similarity	NPD6079	Approved
0.6167	Remote Similarity	NPD5344	Discontinued
0.6161	Remote Similarity	NPD3618	Phase 1
0.614	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6080	Approved
0.614	Remote Similarity	NPD6904	Approved
0.614	Remote Similarity	NPD6673	Approved
0.614	Remote Similarity	NPD6101	Approved
0.6107	Remote Similarity	NPD8377	Approved
0.6107	Remote Similarity	NPD8294	Approved
0.6094	Remote Similarity	NPD5167	Approved
0.6087	Remote Similarity	NPD5207	Approved
0.6087	Remote Similarity	NPD5692	Phase 3
0.6071	Remote Similarity	NPD1694	Approved
0.6068	Remote Similarity	NPD6001	Approved
0.6061	Remote Similarity	NPD8380	Approved
0.6061	Remote Similarity	NPD8378	Approved
0.6061	Remote Similarity	NPD8296	Approved
0.6061	Remote Similarity	NPD8379	Approved
0.6061	Remote Similarity	NPD8335	Approved
0.6061	Remote Similarity	NPD6921	Approved
0.6055	Remote Similarity	NPD4252	Approved
0.6055	Remote Similarity	NPD5368	Approved
0.6055	Remote Similarity	NPD4695	Discontinued

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