NPASS Compound

Structure

CID25897 OpenBabel06191715352D 26 29 0 0 0 0 0 0 0 0999 V2000 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1222 -5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3902 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3902 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2562 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2562 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 0.9706 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -5.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1222 -4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 6 1 0 0 0 0 4 11 2 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 9 17 2 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 13 25 1 0 0 0 0 14 18 2 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 19 22 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	349.14
Volume:	355.883
LogP:	3.25
LogD:	3.123
LogS:	-3.833
# Rotatable Bonds:	3
TPSA:	83.26
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.529
Synthetic Accessibility Score:	2.818
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.333
MDCK Permeability:	6.674313681287458e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.927
Human Intestinal Absorption (HIA):	0.08
20% Bioavailability (F20%):	0.123
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	92.94160461425781%
Volume Distribution (VD):	0.867
Pgp-substrate:	5.6631951332092285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.236
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.357
CYP2D6-inhibitor:	0.395
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.315
CYP3A4-substrate:	0.435

ADMET: Excretion

Clearance (CL):	8.091
Half-life (T1/2):	0.67

ADMET: Toxicity

hERG Blockers:	0.868
Human Hepatotoxicity (H-HT):	0.988
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.944
Rat Oral Acute Toxicity:	0.721
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.276
Carcinogencity:	0.927
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.883

Download Data

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

Natural Product: NPC25897

Natural Product ID:	NPC25897
*Common Name:**	Kealiinine A
IUPAC Name:	2-amino-6-methoxy-9-(4-methoxyphenyl)-3-methylbenzo[f]benzimidazol-7-ol
Synonyms:
Standard InCHIKey:	LWHVSHIPEZJGGL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19N3O3/c1-23-15-8-12-9-17(26-3)16(24)10-14(12)18(19(15)22-20(23)21)11-4-6-13(25-2)7-5-11/h4-10,24H,1-3H3,(H2,21,22)
SMILES:	Cn1c2cc3cc(c(cc3c(c3ccc(cc3)OC)c2[nH]c1=N)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488196
PubChem CID:	9997944
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002441] Naphthols and derivatives

*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
NPO29509	Leucetta chagosensis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193030]
NPO29509	Leucetta chagosensis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165143]
NPO29509	Leucetta chagosensis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17822294]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17996677]
NPO29473	Amycolatopsis mediterranei	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25256628]
NPO644	Pestalotiopsis theae	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27731995]
NPO29509	Leucetta chagosensis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29648818]
NPO29255	Salvia chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30370766]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29043	Hypoxylon oceanicum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29025	Streptomyces nojiriensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28861	Cladonia graciliformis	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29509	Leucetta chagosensis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28968	Teucrium flavum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29434	Centaurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29255	Salvia chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29238	Heterocondylus vitalbae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17683	Cryptocarya moschata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29473	Amycolatopsis mediterranei	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29124	Argemone squarrosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24421.1	Agave salmiana var. ferox	Varieties	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29065	Hypoxis rooperi	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO644	Pestalotiopsis theae	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29470	Anhalonium fissuratum	n.a.	n.a.	n.a.	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	2
Others	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	23400.0	nM	PMID[479492]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[479493]
NPT176	Organism	Artemia salina	Artemia salina	Activity	=	50.0	%	PMID[479491]

☑ 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 NPC25897 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	782
0.1-0.2	5609
0.2-0.3	12026
0.3-0.4	8836
0.4-0.5	11001
0.5-0.6	3273
0.6-0.7	1032
0.7-0.8	133
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC79213
0.8995	High Similarity	NPC261388
0.8289	Intermediate Similarity	NPC276674
0.8289	Intermediate Similarity	NPC33902
0.8105	Intermediate Similarity	NPC320088
0.7969	Intermediate Similarity	NPC474904
0.7914	Intermediate Similarity	NPC285941
0.776	Intermediate Similarity	NPC249405
0.7732	Intermediate Similarity	NPC477186
0.7696	Intermediate Similarity	NPC207873
0.7696	Intermediate Similarity	NPC190461
0.7696	Intermediate Similarity	NPC100573
0.7656	Intermediate Similarity	NPC311936
0.7644	Intermediate Similarity	NPC287588
0.7617	Intermediate Similarity	NPC119579
0.7602	Intermediate Similarity	NPC312531
0.7577	Intermediate Similarity	NPC28425
0.7576	Intermediate Similarity	NPC78284
0.7526	Intermediate Similarity	NPC179704
0.7512	Intermediate Similarity	NPC17677
0.7487	Intermediate Similarity	NPC24954
0.7475	Intermediate Similarity	NPC212163
0.7474	Intermediate Similarity	NPC215747
0.7474	Intermediate Similarity	NPC192939
0.7473	Intermediate Similarity	NPC13397
0.7461	Intermediate Similarity	NPC265383
0.746	Intermediate Similarity	NPC35627
0.746	Intermediate Similarity	NPC81247
0.746	Intermediate Similarity	NPC476573
0.744	Intermediate Similarity	NPC90185
0.7433	Intermediate Similarity	NPC27410
0.7433	Intermediate Similarity	NPC166014
0.7423	Intermediate Similarity	NPC260118
0.7413	Intermediate Similarity	NPC162653
0.7402	Intermediate Similarity	NPC295676
0.7374	Intermediate Similarity	NPC22928
0.7366	Intermediate Similarity	NPC186063
0.7323	Intermediate Similarity	NPC219170
0.7323	Intermediate Similarity	NPC180253
0.7317	Intermediate Similarity	NPC471489
0.7302	Intermediate Similarity	NPC247251
0.7297	Intermediate Similarity	NPC26601
0.7295	Intermediate Similarity	NPC244606
0.7295	Intermediate Similarity	NPC156728
0.7268	Intermediate Similarity	NPC477020
0.7268	Intermediate Similarity	NPC66341
0.7268	Intermediate Similarity	NPC192135
0.7263	Intermediate Similarity	NPC324144
0.7254	Intermediate Similarity	NPC69712
0.7254	Intermediate Similarity	NPC26240
0.7254	Intermediate Similarity	NPC477562
0.725	Intermediate Similarity	NPC296742
0.725	Intermediate Similarity	NPC112676
0.7243	Intermediate Similarity	NPC277669
0.7243	Intermediate Similarity	NPC76213
0.724	Intermediate Similarity	NPC306555
0.724	Intermediate Similarity	NPC158376
0.724	Intermediate Similarity	NPC298979
0.724	Intermediate Similarity	NPC12053
0.724	Intermediate Similarity	NPC117188
0.724	Intermediate Similarity	NPC145832
0.724	Intermediate Similarity	NPC210140
0.724	Intermediate Similarity	NPC81218
0.724	Intermediate Similarity	NPC205421
0.724	Intermediate Similarity	NPC474931
0.7236	Intermediate Similarity	NPC69213
0.723	Intermediate Similarity	NPC298449
0.7228	Intermediate Similarity	NPC302001
0.7225	Intermediate Similarity	NPC196447
0.7225	Intermediate Similarity	NPC306843
0.7225	Intermediate Similarity	NPC477563
0.7225	Intermediate Similarity	NPC253043
0.7225	Intermediate Similarity	NPC212794
0.7225	Intermediate Similarity	NPC13504
0.7225	Intermediate Similarity	NPC136508
0.7225	Intermediate Similarity	NPC78222
0.7225	Intermediate Similarity	NPC96603
0.7222	Intermediate Similarity	NPC276060
0.7213	Intermediate Similarity	NPC191376
0.7213	Intermediate Similarity	NPC179825
0.7213	Intermediate Similarity	NPC321505
0.72	Intermediate Similarity	NPC224293
0.7186	Intermediate Similarity	NPC135772
0.7178	Intermediate Similarity	NPC294244
0.7175	Intermediate Similarity	NPC473182
0.7174	Intermediate Similarity	NPC476571
0.7174	Intermediate Similarity	NPC24233
0.7174	Intermediate Similarity	NPC428
0.7174	Intermediate Similarity	NPC135538
0.7174	Intermediate Similarity	NPC147390
0.7174	Intermediate Similarity	NPC246587
0.7173	Intermediate Similarity	NPC1229
0.7172	Intermediate Similarity	NPC155442
0.7172	Intermediate Similarity	NPC476574
0.7172	Intermediate Similarity	NPC477561
0.7172	Intermediate Similarity	NPC312918
0.7165	Intermediate Similarity	NPC152212
0.7157	Intermediate Similarity	NPC114364
0.7157	Intermediate Similarity	NPC320223
0.7156	Intermediate Similarity	NPC280272
0.715	Intermediate Similarity	NPC471604
0.715	Intermediate Similarity	NPC85482
0.7143	Intermediate Similarity	NPC199465
0.7143	Intermediate Similarity	NPC128560
0.7143	Intermediate Similarity	NPC229166
0.7135	Intermediate Similarity	NPC207824
0.7135	Intermediate Similarity	NPC134858
0.7135	Intermediate Similarity	NPC219162
0.7135	Intermediate Similarity	NPC60538
0.7122	Intermediate Similarity	NPC161804
0.7121	Intermediate Similarity	NPC474507
0.7113	Intermediate Similarity	NPC477185
0.7107	Intermediate Similarity	NPC148709
0.7107	Intermediate Similarity	NPC173416
0.7107	Intermediate Similarity	NPC476577
0.7104	Intermediate Similarity	NPC185838
0.7092	Intermediate Similarity	NPC477187
0.709	Intermediate Similarity	NPC126519
0.709	Intermediate Similarity	NPC203784
0.709	Intermediate Similarity	NPC170503
0.7087	Intermediate Similarity	NPC23080
0.7087	Intermediate Similarity	NPC193906
0.7083	Intermediate Similarity	NPC233650
0.7077	Intermediate Similarity	NPC118274
0.7077	Intermediate Similarity	NPC168753
0.7074	Intermediate Similarity	NPC477564
0.7074	Intermediate Similarity	NPC2295
0.7062	Intermediate Similarity	NPC193777
0.7059	Intermediate Similarity	NPC326316
0.7059	Intermediate Similarity	NPC81733
0.7056	Intermediate Similarity	NPC119722
0.7056	Intermediate Similarity	NPC477558
0.7043	Intermediate Similarity	NPC477565
0.7043	Intermediate Similarity	NPC103379
0.7041	Intermediate Similarity	NPC239775
0.7033	Intermediate Similarity	NPC199277
0.7033	Intermediate Similarity	NPC135887
0.7031	Intermediate Similarity	NPC60186
0.7027	Intermediate Similarity	NPC253883
0.7027	Intermediate Similarity	NPC95075
0.7027	Intermediate Similarity	NPC90844
0.7024	Intermediate Similarity	NPC29472
0.7023	Intermediate Similarity	NPC266931
0.7016	Intermediate Similarity	NPC230942
0.7016	Intermediate Similarity	NPC315498
0.701	Intermediate Similarity	NPC304659
0.701	Intermediate Similarity	NPC86144
0.7005	Intermediate Similarity	NPC151895
0.7005	Intermediate Similarity	NPC88249
0.7005	Intermediate Similarity	NPC220858
0.7005	Intermediate Similarity	NPC192768
0.7005	Intermediate Similarity	NPC97221
0.7004	Intermediate Similarity	NPC473183
0.7	Intermediate Similarity	NPC147091
0.6995	Remote Similarity	NPC186546
0.6995	Remote Similarity	NPC476576
0.6991	Remote Similarity	NPC473184
0.6989	Remote Similarity	NPC130941
0.6984	Remote Similarity	NPC292003
0.6979	Remote Similarity	NPC249274
0.6979	Remote Similarity	NPC205167
0.6979	Remote Similarity	NPC266753
0.6979	Remote Similarity	NPC232924
0.6979	Remote Similarity	NPC160298
0.6979	Remote Similarity	NPC477559
0.6979	Remote Similarity	NPC306902
0.6974	Remote Similarity	NPC150879
0.6972	Remote Similarity	NPC204446
0.6968	Remote Similarity	NPC52475
0.6965	Remote Similarity	NPC116284
0.6963	Remote Similarity	NPC269449
0.6959	Remote Similarity	NPC284183
0.6959	Remote Similarity	NPC4138
0.6959	Remote Similarity	NPC121275
0.6954	Remote Similarity	NPC475215
0.6954	Remote Similarity	NPC108434
0.6947	Remote Similarity	NPC172765
0.6947	Remote Similarity	NPC127674
0.6947	Remote Similarity	NPC276588
0.6947	Remote Similarity	NPC54379
0.6947	Remote Similarity	NPC469817
0.6947	Remote Similarity	NPC5238
0.6947	Remote Similarity	NPC193949
0.6947	Remote Similarity	NPC39701
0.6947	Remote Similarity	NPC278799
0.6947	Remote Similarity	NPC207757
0.6947	Remote Similarity	NPC204828
0.6947	Remote Similarity	NPC110416
0.6947	Remote Similarity	NPC189266
0.6947	Remote Similarity	NPC295691
0.6947	Remote Similarity	NPC249797
0.6947	Remote Similarity	NPC2413
0.6947	Remote Similarity	NPC184026
0.6935	Remote Similarity	NPC476151
0.6931	Remote Similarity	NPC133011
0.6931	Remote Similarity	NPC82285
0.6931	Remote Similarity	NPC18614
0.6927	Remote Similarity	NPC111485
0.6923	Remote Similarity	NPC317272
0.6923	Remote Similarity	NPC250846

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 NPC25897 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	394
0.1-0.2	727
0.2-0.3	851
0.3-0.4	1822
0.4-0.5	2637
0.5-0.6	2001
0.6-0.7	646
0.7-0.8	71
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
0.7914	Intermediate Similarity	NPD5810	Discontinued
0.77	Intermediate Similarity	NPD6612	Phase 2
0.7592	Intermediate Similarity	NPD7479	Phase 2
0.7451	Intermediate Similarity	NPD3515	Approved
0.7451	Intermediate Similarity	NPD3516	Approved
0.7436	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7032	Approved
0.7344	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4083	Discontinued
0.7313	Intermediate Similarity	NPD6046	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7262	Phase 1
0.7225	Intermediate Similarity	NPD3983	Phase 3
0.7225	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1909	Discontinued
0.7175	Intermediate Similarity	NPD4080	Discontinued
0.7173	Intermediate Similarity	NPD6767	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3301	Approved
0.7103	Intermediate Similarity	NPD4356	Discontinued
0.7094	Intermediate Similarity	NPD3633	Approved
0.7094	Intermediate Similarity	NPD3634	Approved
0.7044	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5641	Discontinued
0.7037	Intermediate Similarity	NPD8149	Discontinued
0.7031	Intermediate Similarity	NPD4796	Discontinued
0.7028	Intermediate Similarity	NPD5658	Approved
0.7026	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3290	Approved
0.7019	Intermediate Similarity	NPD3289	Phase 3
0.7016	Intermediate Similarity	NPD1742	Approved
0.7016	Intermediate Similarity	NPD19	Approved
0.7016	Intermediate Similarity	NPD1743	Approved
0.7015	Intermediate Similarity	NPD6340	Approved
0.7015	Intermediate Similarity	NPD6339	Approved
0.7014	Intermediate Similarity	NPD5530	Phase 1
0.7005	Intermediate Similarity	NPD5600	Discontinued
0.6971	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4859	Phase 1
0.6947	Remote Similarity	NPD7922	Phase 1
0.6919	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD2883	Discontinued
0.6904	Remote Similarity	NPD5938	Phase 3
0.6898	Remote Similarity	NPD7225	Discontinued
0.6882	Remote Similarity	NPD2420	Approved
0.6882	Remote Similarity	NPD2421	Approved
0.6875	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6527	Approved
0.6865	Remote Similarity	NPD5241	Discontinued
0.6833	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3845	Phase 1
0.6828	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4511	Phase 1
0.6816	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3920	Phase 2
0.6798	Remote Similarity	NPD6723	Discontinued
0.6793	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3349	Phase 2
0.678	Remote Similarity	NPD3398	Discontinued
0.6772	Remote Similarity	NPD6030	Approved
0.6772	Remote Similarity	NPD6031	Approved
0.6771	Remote Similarity	NPD1954	Phase 1
0.6766	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6877	Discontinued
0.6744	Remote Similarity	NPD7263	Phase 2
0.6741	Remote Similarity	NPD7278	Phase 2
0.6741	Remote Similarity	NPD7279	Phase 2
0.6736	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3631	Phase 3
0.6731	Remote Similarity	NPD6526	Approved
0.6718	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7831	Phase 2
0.6718	Remote Similarity	NPD7833	Phase 2
0.6714	Remote Similarity	NPD7034	Discontinued
0.6703	Remote Similarity	NPD4597	Approved
0.6703	Remote Similarity	NPD4598	Approved
0.6701	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD2898	Approved
0.6683	Remote Similarity	NPD2489	Approved
0.6683	Remote Similarity	NPD27	Approved
0.6682	Remote Similarity	NPD5071	Phase 2
0.6682	Remote Similarity	NPD3804	Discontinued
0.6681	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5560	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7453	Approved
0.6667	Remote Similarity	NPD7222	Phase 2
0.6667	Remote Similarity	NPD7452	Approved
0.6667	Remote Similarity	NPD5582	Discontinued
0.6667	Remote Similarity	NPD2794	Discontinued
0.6667	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7726	Phase 1
0.6651	Remote Similarity	NPD5645	Phase 3
0.6651	Remote Similarity	NPD5150	Phase 2
0.665	Remote Similarity	NPD6037	Discontinued
0.6649	Remote Similarity	NPD6738	Phase 2
0.6649	Remote Similarity	NPD6737	Phase 2
0.6649	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3975	Discontinued
0.6632	Remote Similarity	NPD2468	Approved
0.6632	Remote Similarity	NPD2469	Approved
0.6617	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6357	Discontinued
0.6615	Remote Similarity	NPD6063	Approved
0.6615	Remote Similarity	NPD5599	Discontinued
0.661	Remote Similarity	NPD6230	Discontinued
0.6607	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5930	Phase 3
0.6603	Remote Similarity	NPD3922	Approved
0.6603	Remote Similarity	NPD3921	Approved
0.6603	Remote Similarity	NPD3924	Approved
0.6603	Remote Similarity	NPD3923	Approved
0.6598	Remote Similarity	NPD7298	Approved
0.6591	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD6238	Discontinued
0.6584	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD3051	Approved
0.6583	Remote Similarity	NPD4010	Discontinued
0.6579	Remote Similarity	NPD4584	Approved
0.6579	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7125	Discontinued
0.657	Remote Similarity	NPD4951	Discontinued
0.6564	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6500	Approved
0.6562	Remote Similarity	NPD6501	Approved
0.6558	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD8053	Approved
0.6553	Remote Similarity	NPD8054	Approved
0.6552	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2970	Approved
0.655	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2969	Approved
0.6546	Remote Similarity	NPD2789	Approved
0.6545	Remote Similarity	NPD4502	Phase 2
0.6544	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5902	Approved
0.6532	Remote Similarity	NPD5903	Approved
0.653	Remote Similarity	NPD3592	Approved
0.653	Remote Similarity	NPD3591	Approved
0.6528	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6473	Phase 1
0.6524	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2917	Approved
0.652	Remote Similarity	NPD6297	Approved
0.652	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6320	Approved
0.6515	Remote Similarity	NPD6742	Phase 2
0.6515	Remote Similarity	NPD6743	Phase 2
0.6513	Remote Similarity	NPD5720	Discontinued
0.6511	Remote Similarity	NPD5905	Phase 1
0.6509	Remote Similarity	NPD3964	Approved
0.6509	Remote Similarity	NPD6494	Phase 2
0.6508	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2843	Phase 2
0.6507	Remote Similarity	NPD2845	Phase 2
0.6505	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD5612	Discontinued
0.6502	Remote Similarity	NPD4873	Discontinued
0.6502	Remote Similarity	NPD5562	Approved
0.6502	Remote Similarity	NPD5561	Approved
0.65	Remote Similarity	NPD4166	Phase 2
0.6495	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5617	Suspended
0.6495	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3763	Approved
0.6485	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5718	Phase 2
0.6481	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.648	Remote Similarity	NPD2978	Approved
0.648	Remote Similarity	NPD2977	Approved
0.648	Remote Similarity	NPD6283	Phase 2
0.6479	Remote Similarity	NPD7491	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD4605	Approved
0.6479	Remote Similarity	NPD4604	Approved
0.6474	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD1440	Discontinued
0.6459	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD7906	Approved
0.6459	Remote Similarity	NPD4157	Discontinued
0.6455	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD2674	Phase 3
0.6447	Remote Similarity	NPD3560	Approved
0.6447	Remote Similarity	NPD3556	Approved
0.6447	Remote Similarity	NPD3557	Approved
0.6447	Remote Similarity	NPD3558	Approved
0.6447	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD4017	Approved
0.6436	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4577	Approved
0.6425	Remote Similarity	NPD4578	Approved
0.6422	Remote Similarity	NPD4996	Approved
0.6422	Remote Similarity	NPD4995	Approved
0.6419	Remote Similarity	NPD3541	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