NPASS Compound

Structure

CID53534 OpenBabel06191715392D 34 39 0 0 0 0 0 0 0 0999 V2000 -2.1630 1.8084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4626 -3.4774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8558 -0.0328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1127 0.6363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5181 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6479 -1.0109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6791 -1.9383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1616 0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5179 -0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6794 0.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5646 1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6968 -3.1470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1091 -3.9561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5180 -1.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6968 -1.3200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2901 -2.2335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8394 -1.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9537 -0.6508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6792 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6661 2.3261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6787 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6788 -1.9389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8393 -1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8392 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2956 -2.1290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8395 -0.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2922 -2.9380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1145 -3.8515 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5182 -0.4850 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0877 -1.1508 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 3.5514 2.7201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6786 0.9693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6787 -2.9079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 33 1 0 0 0 0 2 34 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 15 2 0 0 0 0 7 17 1 0 0 0 0 8 18 2 0 0 0 0 9 21 2 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 28 1 0 0 0 0 14 22 1 0 0 0 0 14 29 2 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 25 2 0 0 0 0 17 23 1 0 0 0 0 17 24 2 0 0 0 0 18 30 1 0 0 0 0 19 26 2 0 0 0 0 19 29 1 0 0 0 0 20 27 1 0 0 0 0 20 32 2 0 0 0 0 21 24 1 0 0 0 0 21 33 1 0 0 0 0 22 23 2 0 0 0 0 22 34 1 0 0 0 0 23 26 1 0 0 0 0 24 31 1 0 0 0 0 25 27 1 0 0 0 0 25 30 1 0 0 0 0 26 31 1 0 0 0 0 27 28 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.17
Volume:	460.293
LogP:	4.714
LogD:	3.755
LogS:	-6.146
# Rotatable Bonds:	6
TPSA:	92.89
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	2.87
Fsp3:	0.148
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.295
MDCK Permeability:	9.286857675760984e-06
Pgp-inhibitor:	0.93
Pgp-substrate:	0.281
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.089

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	94.83328247070312%
Volume Distribution (VD):	0.919
Pgp-substrate:	3.874763011932373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.179
CYP2C9-inhibitor:	0.958
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.878
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.855
CYP3A4-substrate:	0.673

ADMET: Excretion

Clearance (CL):	3.897
Half-life (T1/2):	0.259

ADMET: Toxicity

hERG Blockers:	0.329
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.724
Rat Oral Acute Toxicity:	0.988
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.569
Carcinogencity:	0.505
Eye Corrosion:	0.003
Eye Irritation:	0.055
Respiratory Toxicity:	0.992

Download Data

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

Natural Product: NPC53534

Natural Product ID:	NPC53534
*Common Name:**	Beta-Carboline-1-Yl-4,8-Dimethoxy-Beta-Carboline-1-Ylethyl Ketone
IUPAC Name:	3-(4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-1-(9H-pyrido[3,4-b]indol-1-yl)propan-1-one
Synonyms:
Standard InCHIKey:	MSRXRROCBIUJCG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H22N4O3/c1-33-21-9-5-7-17-23-22(34-2)14-29-19(26(23)31-24(17)21)10-11-20(32)27-25-16(12-13-28-27)15-6-3-4-8-18(15)30-25/h3-9,12-14,30-31H,10-11H2,1-2H3
SMILES:	COc1cccc2c1[nH]c1c2c(OC)cnc1CCC(=O)c1nccc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229722
PubChem CID:	5315686
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
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(99)00216-2]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	seeds and root bark	Henan, China	n.a.	PMID[26295746]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	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
EC50	2
Others	6

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	EC50	=	78000.0	nM	PMID[528276]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	EC50	=	131000.0	nM	PMID[528276]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	68.3	%	PMID[528276]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	45.5	%	PMID[528276]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	64.8	%	PMID[528276]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	28.9	%	PMID[528276]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	52.4	%	PMID[528276]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	39.4	%	PMID[528276]

☑ 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 NPC53534 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	674
0.1-0.2	4063
0.2-0.3	13142
0.3-0.4	9068
0.4-0.5	11305
0.5-0.6	2167
0.6-0.7	1842
0.7-0.8	401
0.8-0.85	22
0.85-0.9	10
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9654	High Similarity	NPC152620
0.8899	High Similarity	NPC469554
0.8899	High Similarity	NPC101543
0.8874	High Similarity	NPC148889
0.8788	High Similarity	NPC101350
0.8771	High Similarity	NPC26543
0.8745	High Similarity	NPC235685
0.8554	High Similarity	NPC258048
0.8494	Intermediate Similarity	NPC91868
0.8494	Intermediate Similarity	NPC63971
0.8448	Intermediate Similarity	NPC260434
0.8428	Intermediate Similarity	NPC122436
0.8362	Intermediate Similarity	NPC314954
0.834	Intermediate Similarity	NPC182222
0.8311	Intermediate Similarity	NPC26679
0.8259	Intermediate Similarity	NPC185782
0.8178	Intermediate Similarity	NPC207686
0.8178	Intermediate Similarity	NPC473186
0.8178	Intermediate Similarity	NPC196718
0.8109	Intermediate Similarity	NPC39370
0.8101	Intermediate Similarity	NPC102593
0.806	Intermediate Similarity	NPC323969
0.8043	Intermediate Similarity	NPC8022
0.8043	Intermediate Similarity	NPC470799
0.8042	Intermediate Similarity	NPC15801
0.8036	Intermediate Similarity	NPC476138
0.8036	Intermediate Similarity	NPC245816
0.8034	Intermediate Similarity	NPC229893
0.8008	Intermediate Similarity	NPC165964
0.7992	Intermediate Similarity	NPC141053
0.7974	Intermediate Similarity	NPC266249
0.794	Intermediate Similarity	NPC288987
0.7904	Intermediate Similarity	NPC167860
0.7904	Intermediate Similarity	NPC123839
0.7904	Intermediate Similarity	NPC123976
0.7902	Intermediate Similarity	NPC19872
0.7886	Intermediate Similarity	NPC178858
0.7879	Intermediate Similarity	NPC476287
0.7875	Intermediate Similarity	NPC49547
0.7872	Intermediate Similarity	NPC60621
0.7857	Intermediate Similarity	NPC478078
0.7842	Intermediate Similarity	NPC329631
0.7835	Intermediate Similarity	NPC118940
0.7811	Intermediate Similarity	NPC36405
0.7795	Intermediate Similarity	NPC196449
0.7795	Intermediate Similarity	NPC314222
0.7787	Intermediate Similarity	NPC213530
0.7787	Intermediate Similarity	NPC193267
0.7782	Intermediate Similarity	NPC74575
0.7778	Intermediate Similarity	NPC27041
0.7764	Intermediate Similarity	NPC216612
0.7746	Intermediate Similarity	NPC240384
0.7741	Intermediate Similarity	NPC470018
0.7717	Intermediate Similarity	NPC74619
0.7708	Intermediate Similarity	NPC257851
0.7702	Intermediate Similarity	NPC208522
0.7702	Intermediate Similarity	NPC305984
0.7692	Intermediate Similarity	NPC473312
0.7686	Intermediate Similarity	NPC132539
0.7682	Intermediate Similarity	NPC94157
0.7679	Intermediate Similarity	NPC276657
0.7676	Intermediate Similarity	NPC194740
0.7665	Intermediate Similarity	NPC176538
0.7657	Intermediate Similarity	NPC322482
0.7639	Intermediate Similarity	NPC187501
0.7638	Intermediate Similarity	NPC478083
0.759	Intermediate Similarity	NPC142385
0.7586	Intermediate Similarity	NPC287208
0.7574	Intermediate Similarity	NPC39500
0.7565	Intermediate Similarity	NPC317701
0.7565	Intermediate Similarity	NPC475774
0.7563	Intermediate Similarity	NPC208084
0.7562	Intermediate Similarity	NPC157931
0.7561	Intermediate Similarity	NPC477549
0.7555	Intermediate Similarity	NPC232727
0.7542	Intermediate Similarity	NPC477979
0.754	Intermediate Similarity	NPC270515
0.7533	Intermediate Similarity	NPC267928
0.7532	Intermediate Similarity	NPC285558
0.7531	Intermediate Similarity	NPC225279
0.753	Intermediate Similarity	NPC472061
0.7511	Intermediate Similarity	NPC322064
0.75	Intermediate Similarity	NPC161801
0.75	Intermediate Similarity	NPC41679
0.75	Intermediate Similarity	NPC310118
0.749	Intermediate Similarity	NPC78609
0.749	Intermediate Similarity	NPC292958
0.749	Intermediate Similarity	NPC74360
0.748	Intermediate Similarity	NPC137353
0.7479	Intermediate Similarity	NPC304926
0.7479	Intermediate Similarity	NPC476041
0.7479	Intermediate Similarity	NPC21638
0.7478	Intermediate Similarity	NPC326422
0.7469	Intermediate Similarity	NPC144452
0.7462	Intermediate Similarity	NPC132385
0.746	Intermediate Similarity	NPC184680
0.7459	Intermediate Similarity	NPC471762
0.7458	Intermediate Similarity	NPC132642
0.7458	Intermediate Similarity	NPC472099
0.7449	Intermediate Similarity	NPC97902
0.7448	Intermediate Similarity	NPC184408
0.7447	Intermediate Similarity	NPC5145
0.7437	Intermediate Similarity	NPC152768
0.7437	Intermediate Similarity	NPC148183
0.743	Intermediate Similarity	NPC470785
0.7426	Intermediate Similarity	NPC234078
0.7426	Intermediate Similarity	NPC221100
0.7418	Intermediate Similarity	NPC473185
0.7412	Intermediate Similarity	NPC473800
0.741	Intermediate Similarity	NPC72905
0.7398	Intermediate Similarity	NPC477112
0.7398	Intermediate Similarity	NPC474688
0.7398	Intermediate Similarity	NPC267853
0.7391	Intermediate Similarity	NPC476167
0.739	Intermediate Similarity	NPC470022
0.7384	Intermediate Similarity	NPC110182
0.7384	Intermediate Similarity	NPC472098
0.7375	Intermediate Similarity	NPC264285
0.7375	Intermediate Similarity	NPC303658
0.7373	Intermediate Similarity	NPC471304
0.7373	Intermediate Similarity	NPC199667
0.7373	Intermediate Similarity	NPC470020
0.7371	Intermediate Similarity	NPC477066
0.7368	Intermediate Similarity	NPC279189
0.7368	Intermediate Similarity	NPC200553
0.7368	Intermediate Similarity	NPC244897
0.7364	Intermediate Similarity	NPC170114
0.7362	Intermediate Similarity	NPC471891
0.7362	Intermediate Similarity	NPC82548
0.736	Intermediate Similarity	NPC470784
0.7357	Intermediate Similarity	NPC315499
0.7349	Intermediate Similarity	NPC295228
0.7349	Intermediate Similarity	NPC470017
0.7348	Intermediate Similarity	NPC192315
0.7347	Intermediate Similarity	NPC110151
0.7344	Intermediate Similarity	NPC473188
0.7342	Intermediate Similarity	NPC146418
0.7342	Intermediate Similarity	NPC208284
0.7342	Intermediate Similarity	NPC82370
0.7341	Intermediate Similarity	NPC478082
0.7341	Intermediate Similarity	NPC478081
0.7341	Intermediate Similarity	NPC477067
0.7339	Intermediate Similarity	NPC180504
0.7336	Intermediate Similarity	NPC63109
0.7336	Intermediate Similarity	NPC179287
0.7333	Intermediate Similarity	NPC312645
0.7331	Intermediate Similarity	NPC473181
0.7331	Intermediate Similarity	NPC477861
0.7328	Intermediate Similarity	NPC476451
0.7328	Intermediate Similarity	NPC475253
0.7325	Intermediate Similarity	NPC84853
0.7322	Intermediate Similarity	NPC470549
0.7319	Intermediate Similarity	NPC321428
0.7317	Intermediate Similarity	NPC66777
0.7317	Intermediate Similarity	NPC274640
0.7316	Intermediate Similarity	NPC74413
0.7316	Intermediate Similarity	NPC187558
0.7311	Intermediate Similarity	NPC473180
0.7309	Intermediate Similarity	NPC316411
0.7308	Intermediate Similarity	NPC470500
0.7303	Intermediate Similarity	NPC96321
0.7296	Intermediate Similarity	NPC260900
0.7294	Intermediate Similarity	NPC17437
0.7283	Intermediate Similarity	NPC81939
0.728	Intermediate Similarity	NPC236668
0.728	Intermediate Similarity	NPC473187
0.728	Intermediate Similarity	NPC162002
0.728	Intermediate Similarity	NPC89508
0.7277	Intermediate Similarity	NPC300156
0.7277	Intermediate Similarity	NPC45190
0.7277	Intermediate Similarity	NPC472064
0.7276	Intermediate Similarity	NPC192712
0.7273	Intermediate Similarity	NPC171393
0.7273	Intermediate Similarity	NPC295452
0.7273	Intermediate Similarity	NPC473179
0.7265	Intermediate Similarity	NPC223427
0.7258	Intermediate Similarity	NPC315062
0.7257	Intermediate Similarity	NPC174672
0.7257	Intermediate Similarity	NPC174758
0.7256	Intermediate Similarity	NPC473639
0.7255	Intermediate Similarity	NPC475666
0.7254	Intermediate Similarity	NPC16352
0.725	Intermediate Similarity	NPC237740
0.725	Intermediate Similarity	NPC146976
0.7246	Intermediate Similarity	NPC193238
0.7241	Intermediate Similarity	NPC81535
0.724	Intermediate Similarity	NPC174489
0.7238	Intermediate Similarity	NPC264176
0.7234	Intermediate Similarity	NPC475070
0.7234	Intermediate Similarity	NPC472259
0.7231	Intermediate Similarity	NPC469594
0.7218	Intermediate Similarity	NPC326363
0.7218	Intermediate Similarity	NPC24019
0.7216	Intermediate Similarity	NPC472434
0.7214	Intermediate Similarity	NPC207620
0.7209	Intermediate Similarity	NPC67401
0.7208	Intermediate Similarity	NPC469592
0.7208	Intermediate Similarity	NPC227824
0.7208	Intermediate Similarity	NPC471080
0.7202	Intermediate Similarity	NPC269270

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 NPC53534 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	659
0.2-0.3	953
0.3-0.4	1897
0.4-0.5	2614
0.5-0.6	1736
0.6-0.7	847
0.7-0.8	87
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8536	High Similarity	NPD5482	Discontinued
0.8523	High Similarity	NPD5483	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.8305	Intermediate Similarity	NPD3006	Discontinued
0.8289	Intermediate Similarity	NPD4429	Discontinued
0.827	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.8127	Intermediate Similarity	NPD5450	Discontinued
0.7941	Intermediate Similarity	NPD5022	Discontinued
0.7895	Intermediate Similarity	NPD4558	Phase 2
0.7842	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD6242	Discontinued
0.7718	Intermediate Similarity	NPD5479	Discontinued
0.7698	Intermediate Similarity	NPD2311	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7603	Discontinued
0.7615	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7924	Phase 2
0.7577	Intermediate Similarity	NPD7925	Phase 2
0.7564	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD6531	Approved
0.7549	Intermediate Similarity	NPD6530	Approved
0.7544	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD3389	Approved
0.7511	Intermediate Similarity	NPD3393	Approved
0.7511	Intermediate Similarity	NPD3394	Approved
0.751	Intermediate Similarity	NPD4885	Approved
0.751	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6961	Discontinued
0.7479	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6790	Phase 1
0.7436	Intermediate Similarity	NPD2510	Approved
0.7436	Intermediate Similarity	NPD2509	Approved
0.7414	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4442	Phase 2
0.7379	Intermediate Similarity	NPD2951	Discontinued
0.7373	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4368	Phase 2
0.7294	Intermediate Similarity	NPD8358	Approved
0.7287	Intermediate Similarity	NPD1659	Phase 1
0.7287	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD8091	Phase 3
0.7269	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD5559	Phase 2
0.7244	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5632	Approved
0.7218	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7853	Phase 2
0.7206	Intermediate Similarity	NPD7994	Phase 2
0.7201	Intermediate Similarity	NPD5018	Phase 3
0.72	Intermediate Similarity	NPD7558	Phase 2
0.7197	Intermediate Similarity	NPD6456	Discontinued
0.7197	Intermediate Similarity	NPD5416	Discontinued
0.7194	Intermediate Similarity	NPD1927	Discontinued
0.7188	Intermediate Similarity	NPD8100	Phase 3
0.7184	Intermediate Similarity	NPD1856	Discontinued
0.7178	Intermediate Similarity	NPD5293	Phase 2
0.7178	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1038	Approved
0.7174	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7803	Approved
0.7169	Intermediate Similarity	NPD6231	Phase 3
0.7165	Intermediate Similarity	NPD8049	Phase 2
0.7161	Intermediate Similarity	NPD4795	Phase 2
0.7149	Intermediate Similarity	NPD4952	Phase 3
0.7149	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7148	Intermediate Similarity	NPD8349	Phase 1
0.7148	Intermediate Similarity	NPD6228	Discontinued
0.7148	Intermediate Similarity	NPD7708	Approved
0.7143	Intermediate Similarity	NPD5658	Approved
0.7137	Intermediate Similarity	NPD3945	Discontinued
0.7132	Intermediate Similarity	NPD6172	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7956	Approved
0.711	Intermediate Similarity	NPD7955	Approved
0.7105	Intermediate Similarity	NPD3343	Phase 3
0.7104	Intermediate Similarity	NPD8101	Phase 3
0.7102	Intermediate Similarity	NPD1996	Discontinued
0.7097	Intermediate Similarity	NPD7426	Phase 1
0.7092	Intermediate Similarity	NPD3746	Discontinued
0.7088	Intermediate Similarity	NPD1480	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5116	Phase 1
0.7071	Intermediate Similarity	NPD7665	Phase 2
0.7071	Intermediate Similarity	NPD7666	Phase 3
0.7068	Intermediate Similarity	NPD3259	Approved
0.7064	Intermediate Similarity	NPD1740	Approved
0.7064	Intermediate Similarity	NPD1739	Approved
0.7063	Intermediate Similarity	NPD4373	Phase 2
0.7063	Intermediate Similarity	NPD5459	Phase 2
0.7063	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7404	Approved
0.7059	Intermediate Similarity	NPD7198	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5850	Phase 3
0.7028	Intermediate Similarity	NPD8289	Discontinued
0.7028	Intermediate Similarity	NPD5640	Discontinued
0.7028	Intermediate Similarity	NPD3263	Phase 3
0.7023	Intermediate Similarity	NPD8463	Approved
0.7021	Intermediate Similarity	NPD3825	Phase 3
0.702	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6568	Discontinued
0.7019	Intermediate Similarity	NPD5867	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD4039	Approved
0.7017	Intermediate Similarity	NPD4033	Approved
0.7017	Intermediate Similarity	NPD4122	Approved
0.7017	Intermediate Similarity	NPD4035	Approved
0.7017	Intermediate Similarity	NPD4037	Approved
0.7017	Intermediate Similarity	NPD4034	Approved
0.7017	Intermediate Similarity	NPD4038	Approved
0.7017	Intermediate Similarity	NPD32	Approved
0.7017	Intermediate Similarity	NPD4036	Approved
0.7017	Intermediate Similarity	NPD31	Approved
0.7008	Intermediate Similarity	NPD5612	Discontinued
0.7	Intermediate Similarity	NPD4845	Discontinued
0.6996	Remote Similarity	NPD8247	Approved
0.6996	Remote Similarity	NPD8246	Approved
0.6992	Remote Similarity	NPD3402	Phase 1
0.6988	Remote Similarity	NPD5488	Discontinued
0.6987	Remote Similarity	NPD7001	Phase 3
0.6985	Remote Similarity	NPD3811	Discontinued
0.6983	Remote Similarity	NPD7470	Discontinued
0.6983	Remote Similarity	NPD5475	Discontinued
0.6981	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.698	Remote Similarity	NPD946	Discontinued
0.6979	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7067	Approved
0.6977	Remote Similarity	NPD7068	Approved
0.6972	Remote Similarity	NPD7176	Clinical (unspecified phase)
0.6969	Remote Similarity	NPD6963	Approved
0.6969	Remote Similarity	NPD6964	Approved
0.6949	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6968	Phase 2
0.6944	Remote Similarity	NPD5924	Discontinued
0.6944	Remote Similarity	NPD6969	Phase 2
0.6941	Remote Similarity	NPD5891	Approved
0.6939	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD6716	Phase 1
0.6932	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3781	Phase 2
0.6929	Remote Similarity	NPD4850	Phase 1
0.6923	Remote Similarity	NPD6770	Approved
0.692	Remote Similarity	NPD4501	Approved
0.692	Remote Similarity	NPD4500	Approved
0.692	Remote Similarity	NPD484	Approved
0.692	Remote Similarity	NPD7859	Phase 2
0.692	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3507	Phase 2
0.6914	Remote Similarity	NPD4502	Phase 2
0.6914	Remote Similarity	NPD8284	Discontinued
0.6911	Remote Similarity	NPD4989	Phase 2
0.6908	Remote Similarity	NPD8356	Approved
0.6908	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3986	Discontinued
0.6894	Remote Similarity	NPD3477	Phase 2
0.6894	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5532	Phase 2
0.689	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6999	Discontinued
0.6878	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4548	Discontinued
0.6877	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5426	Phase 3
0.6875	Remote Similarity	NPD3947	Discontinued
0.6865	Remote Similarity	NPD6165	Phase 2
0.6865	Remote Similarity	NPD8430	Approved
0.6865	Remote Similarity	NPD6164	Phase 2
0.6863	Remote Similarity	NPD6494	Phase 2
0.686	Remote Similarity	NPD2187	Approved
0.686	Remote Similarity	NPD7467	Discontinued
0.686	Remote Similarity	NPD2189	Approved
0.6855	Remote Similarity	NPD7194	Discontinued
0.6851	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD5066	Phase 2
0.6844	Remote Similarity	NPD5067	Phase 2
0.684	Remote Similarity	NPD6209	Approved
0.6838	Remote Similarity	NPD4372	Phase 1
0.6838	Remote Similarity	NPD8364	Approved
0.6838	Remote Similarity	NPD6569	Phase 2
0.6838	Remote Similarity	NPD8363	Approved
0.6834	Remote Similarity	NPD7417	Discontinued
0.6832	Remote Similarity	NPD6276	Discontinued
0.6825	Remote Similarity	NPD5499	Approved
0.6823	Remote Similarity	NPD7181	Phase 3
0.6818	Remote Similarity	NPD1392	Approved
0.6818	Remote Similarity	NPD7222	Phase 2
0.6816	Remote Similarity	NPD3816	Phase 1
0.6816	Remote Similarity	NPD3815	Phase 1
0.6815	Remote Similarity	NPD7395	Discontinued
0.6815	Remote Similarity	NPD3354	Phase 2
0.6813	Remote Similarity	NPD7408	Phase 2
0.6809	Remote Similarity	NPD4454	Phase 2
0.6806	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5644	Phase 1
0.6805	Remote Similarity	NPD5901	Discontinued
0.6805	Remote Similarity	NPD8442	Discontinued
0.6803	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4881	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