NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	212.09
Volume:	222.7
LogP:	2.037
LogD:	2.474
LogS:	-2.528
# Rotatable Bonds:	2
TPSA:	37.91
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	2.215
Fsp3:	0.154
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:	-4.734
MDCK Permeability:	1.957429230969865e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.091
30% Bioavailability (F30%):	0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.914
Plasma Protein Binding (PPB):	81.28595733642578%
Volume Distribution (VD):	1.483
Pgp-substrate:	16.181161880493164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.654
CYP2C19-substrate:	0.527
CYP2C9-inhibitor:	0.199
CYP2C9-substrate:	0.474
CYP2D6-inhibitor:	0.59
CYP2D6-substrate:	0.77
CYP3A4-inhibitor:	0.489
CYP3A4-substrate:	0.455

ADMET: Excretion

Clearance (CL):	3.962
Half-life (T1/2):	0.57

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.877
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.751
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.808
Skin Sensitization:	0.672
Carcinogencity:	0.531
Eye Corrosion:	0.02
Eye Irritation:	0.917
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC284678

Natural Product ID:	NPC284678
*Common Name:**	1-Methoxymethyl-Beta-Carboline
IUPAC Name:	1-(methoxymethyl)-9H-pyrido[3,4-b]indole
Synonyms:
Standard InCHIKey:	OELXEULZDKMFCS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H12N2O/c1-16-8-12-13-10(6-7-14-12)9-4-2-3-5-11(9)15-13/h2-7,15H,8H2,1H3
SMILES:	COCc1c2c(ccn1)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3400671
PubChem CID:	5382686
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19659728]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28368118]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667820]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6626	Pteris spinulosa	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12026	Papaver radicatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2505	Pachycereus pringlei	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11072	Geigeria schinzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20383	Stenocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6014	Goniothalamus undulatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9375	Medium grandiflorum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14280	Helichrysum angustifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3576	Bersama swinnyi	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13494	Prosopis kuntzei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13798	Cheilanthes marantae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22888	Lophiostoma vaginatispora	Species	Lophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12890	Ophryosporus charua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8640	Nemuaron humboldtii	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8820	Lophocereus marginatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12577	Pinus glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8220	Russula sardonia	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1418	Boletinus paluster	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12988	Blainvillea latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13692	Leontice kiangnanensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2084	Acinetobacter calcoaceticus	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	27.4	%	PMID[488800]

☑ 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 NPC284678 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	594
0.1-0.2	4523
0.2-0.3	13159
0.3-0.4	16775
0.4-0.5	3523
0.5-0.6	1760
0.6-0.7	1696
0.7-0.8	619
0.8-0.85	35
0.85-0.9	11
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9345	High Similarity	NPC48938
0.8994	High Similarity	NPC19872
0.8763	High Similarity	NPC123839
0.8757	High Similarity	NPC266249
0.8743	High Similarity	NPC476138
0.8743	High Similarity	NPC245816
0.8659	High Similarity	NPC198673
0.8634	High Similarity	NPC232727
0.8587	High Similarity	NPC473761
0.8579	High Similarity	NPC176538
0.8571	High Similarity	NPC118940
0.847	Intermediate Similarity	NPC168911
0.847	Intermediate Similarity	NPC239954
0.8466	Intermediate Similarity	NPC179787
0.8466	Intermediate Similarity	NPC201380
0.8415	Intermediate Similarity	NPC267928
0.8415	Intermediate Similarity	NPC321911
0.8413	Intermediate Similarity	NPC185782
0.8405	Intermediate Similarity	NPC63545
0.8396	Intermediate Similarity	NPC470500
0.8396	Intermediate Similarity	NPC470505
0.8377	Intermediate Similarity	NPC26679
0.8354	Intermediate Similarity	NPC469811
0.8353	Intermediate Similarity	NPC102423
0.8343	Intermediate Similarity	NPC131718
0.8324	Intermediate Similarity	NPC476167
0.8305	Intermediate Similarity	NPC314394
0.8272	Intermediate Similarity	NPC167860
0.8272	Intermediate Similarity	NPC123976
0.827	Intermediate Similarity	NPC192315
0.8238	Intermediate Similarity	NPC476287
0.8225	Intermediate Similarity	NPC236711
0.8197	Intermediate Similarity	NPC324149
0.8177	Intermediate Similarity	NPC5145
0.8172	Intermediate Similarity	NPC212213
0.8171	Intermediate Similarity	NPC313791
0.8155	Intermediate Similarity	NPC325903
0.8154	Intermediate Similarity	NPC470799
0.8154	Intermediate Similarity	NPC8022
0.8035	Intermediate Similarity	NPC311276
0.8033	Intermediate Similarity	NPC296527
0.803	Intermediate Similarity	NPC292958
0.801	Intermediate Similarity	NPC477979
0.801	Intermediate Similarity	NPC285558
0.7989	Intermediate Similarity	NPC76748
0.7979	Intermediate Similarity	NPC287208
0.7977	Intermediate Similarity	NPC282231
0.7965	Intermediate Similarity	NPC230869
0.7953	Intermediate Similarity	NPC469785
0.7953	Intermediate Similarity	NPC141353
0.7951	Intermediate Similarity	NPC469554
0.7946	Intermediate Similarity	NPC92111
0.7943	Intermediate Similarity	NPC54988
0.7941	Intermediate Similarity	NPC469765
0.7941	Intermediate Similarity	NPC469786
0.7941	Intermediate Similarity	NPC469763
0.7941	Intermediate Similarity	NPC25008
0.7941	Intermediate Similarity	NPC73952
0.7941	Intermediate Similarity	NPC469760
0.7941	Intermediate Similarity	NPC259644
0.794	Intermediate Similarity	NPC213530
0.794	Intermediate Similarity	NPC193267
0.7919	Intermediate Similarity	NPC122141
0.7919	Intermediate Similarity	NPC470204
0.7919	Intermediate Similarity	NPC279918
0.7917	Intermediate Similarity	NPC475070
0.7907	Intermediate Similarity	NPC469762
0.7904	Intermediate Similarity	NPC159856
0.7902	Intermediate Similarity	NPC260434
0.7895	Intermediate Similarity	NPC70922
0.7895	Intermediate Similarity	NPC211572
0.7895	Intermediate Similarity	NPC80597
0.7895	Intermediate Similarity	NPC75540
0.7895	Intermediate Similarity	NPC212376
0.7892	Intermediate Similarity	NPC314954
0.7892	Intermediate Similarity	NPC190296
0.7879	Intermediate Similarity	NPC115611
0.7877	Intermediate Similarity	NPC134586
0.7874	Intermediate Similarity	NPC470203
0.7864	Intermediate Similarity	NPC101543
0.7861	Intermediate Similarity	NPC60621
0.7861	Intermediate Similarity	NPC307963
0.7861	Intermediate Similarity	NPC310118
0.7849	Intermediate Similarity	NPC138370
0.7841	Intermediate Similarity	NPC49954
0.7841	Intermediate Similarity	NPC474561
0.7833	Intermediate Similarity	NPC211997
0.7829	Intermediate Similarity	NPC317105
0.7826	Intermediate Similarity	NPC62749
0.7824	Intermediate Similarity	NPC105818
0.7824	Intermediate Similarity	NPC24678
0.7824	Intermediate Similarity	NPC132539
0.7811	Intermediate Similarity	NPC470111
0.7809	Intermediate Similarity	NPC470498
0.7805	Intermediate Similarity	NPC84911
0.7801	Intermediate Similarity	NPC121772
0.7798	Intermediate Similarity	NPC314372
0.7797	Intermediate Similarity	NPC201700
0.7797	Intermediate Similarity	NPC63751
0.7789	Intermediate Similarity	NPC265576
0.7788	Intermediate Similarity	NPC182222
0.7784	Intermediate Similarity	NPC274229
0.7783	Intermediate Similarity	NPC122436
0.7778	Intermediate Similarity	NPC13880
0.7778	Intermediate Similarity	NPC224764
0.7778	Intermediate Similarity	NPC251090
0.7772	Intermediate Similarity	NPC15102
0.7772	Intermediate Similarity	NPC470502
0.7766	Intermediate Similarity	NPC84853
0.776	Intermediate Similarity	NPC102755
0.7759	Intermediate Similarity	NPC92796
0.7759	Intermediate Similarity	NPC135141
0.7756	Intermediate Similarity	NPC110151
0.7744	Intermediate Similarity	NPC261195
0.7744	Intermediate Similarity	NPC96102
0.7744	Intermediate Similarity	NPC29886
0.774	Intermediate Similarity	NPC160105
0.7734	Intermediate Similarity	NPC470501
0.7717	Intermediate Similarity	NPC204717
0.7711	Intermediate Similarity	NPC110126
0.7711	Intermediate Similarity	NPC73767
0.7709	Intermediate Similarity	NPC82331
0.7705	Intermediate Similarity	NPC191415
0.7701	Intermediate Similarity	NPC95783
0.77	Intermediate Similarity	NPC36405
0.77	Intermediate Similarity	NPC472027
0.77	Intermediate Similarity	NPC251936
0.7697	Intermediate Similarity	NPC105127
0.7696	Intermediate Similarity	NPC470503
0.7692	Intermediate Similarity	NPC42979
0.7688	Intermediate Similarity	NPC89508
0.7688	Intermediate Similarity	NPC473757
0.7683	Intermediate Similarity	NPC198988
0.7677	Intermediate Similarity	NPC208284
0.7676	Intermediate Similarity	NPC188387
0.7676	Intermediate Similarity	NPC163421
0.7676	Intermediate Similarity	NPC314002
0.7667	Intermediate Similarity	NPC314603
0.7665	Intermediate Similarity	NPC469767
0.7665	Intermediate Similarity	NPC469761
0.7665	Intermediate Similarity	NPC469768
0.7665	Intermediate Similarity	NPC174758
0.7665	Intermediate Similarity	NPC469779
0.7665	Intermediate Similarity	NPC469784
0.7665	Intermediate Similarity	NPC469783
0.7665	Intermediate Similarity	NPC469780
0.7663	Intermediate Similarity	NPC220765
0.7654	Intermediate Similarity	NPC97343
0.7647	Intermediate Similarity	NPC288838
0.7637	Intermediate Similarity	NPC59269
0.7637	Intermediate Similarity	NPC151939
0.7636	Intermediate Similarity	NPC325252
0.7634	Intermediate Similarity	NPC171171
0.7629	Intermediate Similarity	NPC57398
0.7627	Intermediate Similarity	NPC478184
0.7627	Intermediate Similarity	NPC40779
0.7627	Intermediate Similarity	NPC194640
0.7622	Intermediate Similarity	NPC284559
0.7622	Intermediate Similarity	NPC84478
0.7619	Intermediate Similarity	NPC469766
0.7617	Intermediate Similarity	NPC315957
0.7617	Intermediate Similarity	NPC470497
0.7616	Intermediate Similarity	NPC53947
0.7614	Intermediate Similarity	NPC82548
0.7609	Intermediate Similarity	NPC233936
0.7604	Intermediate Similarity	NPC470499
0.7602	Intermediate Similarity	NPC471957
0.76	Intermediate Similarity	NPC234078
0.76	Intermediate Similarity	NPC221100
0.7598	Intermediate Similarity	NPC317430
0.7596	Intermediate Similarity	NPC12649
0.7594	Intermediate Similarity	NPC46580
0.759	Intermediate Similarity	NPC165599
0.7588	Intermediate Similarity	NPC470440
0.7582	Intermediate Similarity	NPC150048
0.7582	Intermediate Similarity	NPC203754
0.7582	Intermediate Similarity	NPC474958
0.7582	Intermediate Similarity	NPC280852
0.7581	Intermediate Similarity	NPC280290
0.7581	Intermediate Similarity	NPC473189
0.7576	Intermediate Similarity	NPC174672
0.7574	Intermediate Similarity	NPC312645
0.7572	Intermediate Similarity	NPC470233
0.7571	Intermediate Similarity	NPC225018
0.7569	Intermediate Similarity	NPC472123
0.7568	Intermediate Similarity	NPC176127
0.7568	Intermediate Similarity	NPC163055
0.756	Intermediate Similarity	NPC279081
0.7557	Intermediate Similarity	NPC293487
0.7554	Intermediate Similarity	NPC469896
0.7553	Intermediate Similarity	NPC242928
0.7552	Intermediate Similarity	NPC141454
0.7542	Intermediate Similarity	NPC49217
0.7541	Intermediate Similarity	NPC248454
0.7541	Intermediate Similarity	NPC145885
0.7541	Intermediate Similarity	NPC84827
0.7541	Intermediate Similarity	NPC14113
0.754	Intermediate Similarity	NPC94752
0.7538	Intermediate Similarity	NPC193761
0.7528	Intermediate Similarity	NPC478182

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 NPC284678 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	677
0.2-0.3	783
0.3-0.4	1567
0.4-0.5	2608
0.5-0.6	1949
0.6-0.7	1114
0.7-0.8	151
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8229	Intermediate Similarity	NPD5065	Approved
0.8225	Intermediate Similarity	NPD2582	Approved
0.8225	Intermediate Similarity	NPD2581	Approved
0.8053	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD5913	Phase 3
0.7946	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD706	Phase 1
0.7876	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD1038	Approved
0.7831	Intermediate Similarity	NPD1722	Approved
0.7797	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD3825	Phase 3
0.7747	Intermediate Similarity	NPD6595	Phase 3
0.7744	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD2144	Approved
0.7727	Intermediate Similarity	NPD3330	Phase 1
0.7725	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD786	Approved
0.7704	Intermediate Similarity	NPD2510	Approved
0.7704	Intermediate Similarity	NPD2509	Approved
0.7701	Intermediate Similarity	NPD6281	Approved
0.7677	Intermediate Similarity	NPD5067	Phase 2
0.7677	Intermediate Similarity	NPD7470	Discontinued
0.7677	Intermediate Similarity	NPD5066	Phase 2
0.7676	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2076	Approved
0.7667	Intermediate Similarity	NPD2077	Approved
0.7654	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD4795	Phase 2
0.763	Intermediate Similarity	NPD2837	Discontinued
0.7617	Intermediate Similarity	NPD1739	Approved
0.7617	Intermediate Similarity	NPD1740	Approved
0.7609	Intermediate Similarity	NPD3038	Discontinued
0.7586	Intermediate Similarity	NPD3402	Phase 1
0.7581	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5596	Phase 2
0.7556	Intermediate Similarity	NPD1325	Approved
0.7556	Intermediate Similarity	NPD1326	Approved
0.7543	Intermediate Similarity	NPD1274	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD424	Approved
0.7542	Intermediate Similarity	NPD425	Approved
0.7535	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD9705	Discontinued
0.7514	Intermediate Similarity	NPD112	Approved
0.7513	Intermediate Similarity	NPD8063	Discontinued
0.75	Intermediate Similarity	NPD4886	Phase 2
0.75	Intermediate Similarity	NPD4079	Approved
0.75	Intermediate Similarity	NPD4076	Approved
0.75	Intermediate Similarity	NPD5475	Discontinued
0.7487	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD1392	Approved
0.7473	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2882	Phase 1
0.7464	Intermediate Similarity	NPD5559	Phase 2
0.7461	Intermediate Similarity	NPD7948	Phase 1
0.7461	Intermediate Similarity	NPD5003	Discontinued
0.746	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5255	Approved
0.7457	Intermediate Similarity	NPD3100	Discontinued
0.7457	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD3505	Approved
0.7446	Intermediate Similarity	NPD3506	Approved
0.7443	Intermediate Similarity	NPD5482	Discontinued
0.7438	Intermediate Similarity	NPD5612	Discontinued
0.7438	Intermediate Similarity	NPD3393	Approved
0.7438	Intermediate Similarity	NPD3394	Approved
0.7438	Intermediate Similarity	NPD3389	Approved
0.7435	Intermediate Similarity	NPD3404	Approved
0.7432	Intermediate Similarity	NPD482	Approved
0.743	Intermediate Similarity	NPD5138	Approved
0.743	Intermediate Similarity	NPD5140	Approved
0.7415	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3835	Phase 3
0.7414	Intermediate Similarity	NPD3833	Phase 3
0.7407	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5862	Discovery
0.7399	Intermediate Similarity	NPD4703	Approved
0.7399	Intermediate Similarity	NPD4702	Approved
0.7396	Intermediate Similarity	NPD802	Phase 2
0.7389	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD4548	Discontinued
0.7379	Intermediate Similarity	NPD1996	Discontinued
0.7374	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD2189	Approved
0.735	Intermediate Similarity	NPD2187	Approved
0.735	Intermediate Similarity	NPD5658	Approved
0.7344	Intermediate Similarity	NPD6569	Phase 2
0.7337	Intermediate Similarity	NPD6492	Phase 2
0.7333	Intermediate Similarity	NPD715	Phase 3
0.7333	Intermediate Similarity	NPD3323	Discontinued
0.732	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3477	Phase 2
0.7318	Intermediate Similarity	NPD687	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD8431	Approved
0.7314	Intermediate Similarity	NPD2172	Phase 1
0.7314	Intermediate Similarity	NPD4462	Approved
0.7314	Intermediate Similarity	NPD4463	Approved
0.731	Intermediate Similarity	NPD1592	Phase 3
0.7297	Intermediate Similarity	NPD2382	Approved
0.7297	Intermediate Similarity	NPD2381	Approved
0.7297	Intermediate Similarity	NPD2380	Approved
0.7296	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7603	Discontinued
0.7273	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6158	Phase 2
0.7267	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD4612	Discontinued
0.7258	Intermediate Similarity	NPD4181	Approved
0.725	Intermediate Similarity	NPD3003	Approved
0.7243	Intermediate Similarity	NPD7558	Phase 2
0.7241	Intermediate Similarity	NPD3939	Suspended
0.724	Intermediate Similarity	NPD2565	Phase 2
0.724	Intermediate Similarity	NPD3321	Discontinued
0.724	Intermediate Similarity	NPD2564	Approved
0.7228	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1741	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD2640	Approved
0.7213	Intermediate Similarity	NPD2641	Approved
0.7206	Intermediate Similarity	NPD8093	Discontinued
0.7204	Intermediate Similarity	NPD5100	Phase 3
0.72	Intermediate Similarity	NPD4547	Phase 3
0.72	Intermediate Similarity	NPD1661	Suspended
0.7198	Intermediate Similarity	NPD2915	Discontinued
0.7196	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD2092	Phase 2
0.7196	Intermediate Similarity	NPD2095	Phase 2
0.7196	Intermediate Similarity	NPD2094	Phase 2
0.7189	Intermediate Similarity	NPD750	Phase 2
0.7183	Intermediate Similarity	NPD6968	Phase 2
0.7183	Intermediate Similarity	NPD6969	Phase 2
0.7181	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD5256	Discontinued
0.7172	Intermediate Similarity	NPD484	Approved
0.7168	Intermediate Similarity	NPD2006	Phase 2
0.7165	Intermediate Similarity	NPD4372	Phase 1
0.7164	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7404	Approved
0.7159	Intermediate Similarity	NPD2430	Phase 2
0.7158	Intermediate Similarity	NPD2096	Phase 2
0.7158	Intermediate Similarity	NPD2091	Phase 2
0.7151	Intermediate Similarity	NPD4128	Approved
0.7151	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD9690	Approved
0.715	Intermediate Similarity	NPD8072	Approved
0.7143	Intermediate Similarity	NPD4203	Approved
0.7143	Intermediate Similarity	NPD4204	Approved
0.7143	Intermediate Similarity	NPD1895	Discontinued
0.7143	Intermediate Similarity	NPD7867	Phase 1
0.7135	Intermediate Similarity	NPD1034	Phase 3
0.7135	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6242	Discontinued
0.7127	Intermediate Similarity	NPD1403	Approved
0.7127	Intermediate Similarity	NPD1404	Approved
0.7126	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3813	Approved
0.7121	Intermediate Similarity	NPD1768	Approved
0.7121	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4640	Approved
0.712	Intermediate Similarity	NPD4639	Approved
0.712	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4638	Approved
0.7115	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4036	Approved
0.7114	Intermediate Similarity	NPD4033	Approved
0.7114	Intermediate Similarity	NPD4122	Approved
0.7114	Intermediate Similarity	NPD4037	Approved
0.7114	Intermediate Similarity	NPD8272	Phase 2
0.7114	Intermediate Similarity	NPD31	Approved
0.7114	Intermediate Similarity	NPD4034	Approved
0.7114	Intermediate Similarity	NPD4038	Approved
0.7114	Intermediate Similarity	NPD5901	Discontinued
0.7114	Intermediate Similarity	NPD32	Approved
0.7114	Intermediate Similarity	NPD4039	Approved
0.7114	Intermediate Similarity	NPD4035	Approved
0.7112	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD925	Approved
0.7104	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD926	Approved
0.7095	Intermediate Similarity	NPD976	Approved
0.7095	Intermediate Similarity	NPD977	Approved
0.7095	Intermediate Similarity	NPD975	Approved
0.7088	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4919	Phase 3
0.7083	Intermediate Similarity	NPD4920	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