NPASS Compound

Structure

CID229893 OpenBabel06191716022D 27 31 0 0 0 0 0 0 0 0999 V2000 3.2452 -3.5389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3847 -3.9080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9434 -4.4678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5383 -4.3967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3848 -2.9313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5916 -2.8130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9880 -4.6709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6923 -3.9083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6924 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0558 -3.0161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5386 -2.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6362 -3.0161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6925 -0.9769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3344 -3.9450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6922 -2.9311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8465 0.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 -1.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 -1.4652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8465 1.4654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3576 -3.9450 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 -2.4428 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 1.6919 -0.9768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8232 1.4654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3581 2.3113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 6 1 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 11 2 0 0 0 0 6 12 2 0 0 0 0 7 15 2 0 0 0 0 8 16 2 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 24 2 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 21 26 1 0 0 0 0 21 27 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.1
Volume:	356.713
LogP:	4.124
LogD:	2.726
LogS:	-3.57
# Rotatable Bonds:	3
TPSA:	98.84
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	2.431
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.359
MDCK Permeability:	5.031100954511203e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	99.30221557617188%
Volume Distribution (VD):	0.448
Pgp-substrate:	1.311584234237671%

ADMET: Metabolism

CYP1A2-inhibitor:	0.91
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.147
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.437
CYP2C9-substrate:	0.118
CYP2D6-inhibitor:	0.667
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.401
CYP3A4-substrate:	0.059

ADMET: Excretion

Clearance (CL):	1.198
Half-life (T1/2):	0.483

ADMET: Toxicity

hERG Blockers:	0.102
Human Hepatotoxicity (H-HT):	0.951
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.652
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.19
Carcinogencity:	0.252
Eye Corrosion:	0.003
Eye Irritation:	0.217
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC229893

Natural Product ID:	NPC229893
*Common Name:**	1-(1H-Indole-3-Carbonyl)-9H-Pyrido[3,4-B]Indole-3-Carboxylic Acid
IUPAC Name:	1-(1H-indole-3-carbonyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid
Synonyms:
Standard InCHIKey:	XAJFCGSSMHQTIO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H13N3O3/c25-20(14-10-22-15-7-3-1-6-12(14)15)19-18-13(9-17(24-19)21(26)27)11-5-2-4-8-16(11)23-18/h1-10,22-23H,(H,26,27)
SMILES:	c1ccc2c(c1)c(c[nH]2)C(=O)c1c2c(cc(C(=O)O)n1)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1910719
PubChem CID:	56649543
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
NPO2794	Salvia clevelandii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190465]
NPO929	Corydalis scouleri	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26081757]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[27169184]
NPO41092	Burkholderia sp. NBF227	Strain	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[30826506]
NPO929	Corydalis scouleri	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5990	Frangula alnus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO929	Corydalis scouleri	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9156	Cystophora congesta	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11502	Polystichum aculeatum	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5990	Frangula alnus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10797	Nerine corusca	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23765.1	Cotoneaster salicifolius var. henryanus	Varieties	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5500	Protea eximia	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO929	Corydalis scouleri	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2794	Salvia clevelandii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3130	Ainsliaea acerifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14184	Scoliodon walbeehmi	Species	Carcharhinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	7
Others	6

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	23450.0	nM	PMID[554409]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	16900.0	nM	PMID[554409]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	4.89	%	PMID[554409]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	17.68	%	PMID[554409]
NPT515	Cell Line	SGC-7901	Homo sapiens	GI	=	62.97	%	PMID[554410]
NPT65	Cell Line	HepG2	Homo sapiens	GI	=	78.4	%	PMID[554410]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	=	67690.0	nM	PMID[554410]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	51820.0	nM	PMID[554410]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24780.0	nM	PMID[554409]
NPT2	Others	Unspecified		GI	=	72.17	%	PMID[554410]
NPT2	Others	Unspecified		GI	=	71.95	%	PMID[554410]
NPT2	Others	Unspecified		IC50	=	48750.0	nM	PMID[554410]
NPT2	Others	Unspecified		IC50	=	41880.0	nM	PMID[554410]

☑ 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 NPC229893 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	506
0.1-0.2	3111
0.2-0.3	13591
0.3-0.4	17333
0.4-0.5	3732
0.5-0.6	1800
0.6-0.7	1969
0.7-0.8	589
0.8-0.85	49
0.85-0.9	13
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9059	High Similarity	NPC82370
0.892	High Similarity	NPC207686
0.8756	High Similarity	NPC57398
0.8693	High Similarity	NPC141454
0.8647	High Similarity	NPC118940
0.8636	High Similarity	NPC326422
0.8571	High Similarity	NPC27041
0.8565	High Similarity	NPC178858
0.8544	High Similarity	NPC266249
0.8529	High Similarity	NPC165599
0.8524	High Similarity	NPC36405
0.8515	High Similarity	NPC74619
0.8488	Intermediate Similarity	NPC132539
0.8465	Intermediate Similarity	NPC474916
0.8462	Intermediate Similarity	NPC123839
0.8439	Intermediate Similarity	NPC317701
0.8416	Intermediate Similarity	NPC235685
0.8406	Intermediate Similarity	NPC244741
0.8378	Intermediate Similarity	NPC101350
0.8364	Intermediate Similarity	NPC276657
0.831	Intermediate Similarity	NPC472285
0.8284	Intermediate Similarity	NPC131887
0.8252	Intermediate Similarity	NPC471944
0.8251	Intermediate Similarity	NPC15801
0.8246	Intermediate Similarity	NPC63971
0.8246	Intermediate Similarity	NPC91868
0.8241	Intermediate Similarity	NPC62749
0.8235	Intermediate Similarity	NPC227582
0.8227	Intermediate Similarity	NPC202812
0.82	Intermediate Similarity	NPC278434
0.8195	Intermediate Similarity	NPC67288
0.8178	Intermediate Similarity	NPC322064
0.8169	Intermediate Similarity	NPC89508
0.8159	Intermediate Similarity	NPC321708
0.8155	Intermediate Similarity	NPC258048
0.814	Intermediate Similarity	NPC312645
0.8131	Intermediate Similarity	NPC477979
0.8119	Intermediate Similarity	NPC83111
0.8116	Intermediate Similarity	NPC252338
0.8108	Intermediate Similarity	NPC260434
0.808	Intermediate Similarity	NPC182222
0.8079	Intermediate Similarity	NPC476460
0.8072	Intermediate Similarity	NPC200553
0.8072	Intermediate Similarity	NPC279189
0.804	Intermediate Similarity	NPC191415
0.8034	Intermediate Similarity	NPC53534
0.8027	Intermediate Similarity	NPC267853
0.8	Intermediate Similarity	NPC174489
0.8	Intermediate Similarity	NPC304203
0.7991	Intermediate Similarity	NPC244897
0.798	Intermediate Similarity	NPC284775
0.7973	Intermediate Similarity	NPC192712
0.7965	Intermediate Similarity	NPC162002
0.7953	Intermediate Similarity	NPC110182
0.7941	Intermediate Similarity	NPC154339
0.7941	Intermediate Similarity	NPC324091
0.7936	Intermediate Similarity	NPC264285
0.793	Intermediate Similarity	NPC26641
0.7924	Intermediate Similarity	NPC63109
0.7923	Intermediate Similarity	NPC79356
0.7923	Intermediate Similarity	NPC102592
0.792	Intermediate Similarity	NPC316411
0.7919	Intermediate Similarity	NPC122436
0.7895	Intermediate Similarity	NPC74413
0.7892	Intermediate Similarity	NPC221873
0.7889	Intermediate Similarity	NPC217372
0.7889	Intermediate Similarity	NPC183662
0.7889	Intermediate Similarity	NPC111275
0.7889	Intermediate Similarity	NPC15573
0.7877	Intermediate Similarity	NPC472259
0.787	Intermediate Similarity	NPC171393
0.787	Intermediate Similarity	NPC295452
0.7867	Intermediate Similarity	NPC260900
0.7867	Intermediate Similarity	NPC315062
0.786	Intermediate Similarity	NPC37152
0.785	Intermediate Similarity	NPC126709
0.785	Intermediate Similarity	NPC283219
0.785	Intermediate Similarity	NPC219336
0.785	Intermediate Similarity	NPC248041
0.785	Intermediate Similarity	NPC55772
0.7841	Intermediate Similarity	NPC97902
0.7833	Intermediate Similarity	NPC152620
0.7826	Intermediate Similarity	NPC267343
0.7822	Intermediate Similarity	NPC102755
0.7822	Intermediate Similarity	NPC48938
0.7821	Intermediate Similarity	NPC165964
0.7816	Intermediate Similarity	NPC138370
0.7812	Intermediate Similarity	NPC476491
0.7803	Intermediate Similarity	NPC476818
0.7798	Intermediate Similarity	NPC478157
0.7793	Intermediate Similarity	NPC16352
0.7789	Intermediate Similarity	NPC203468
0.7789	Intermediate Similarity	NPC110500
0.7789	Intermediate Similarity	NPC149155
0.7788	Intermediate Similarity	NPC471194
0.7788	Intermediate Similarity	NPC471193
0.7783	Intermediate Similarity	NPC476073
0.7783	Intermediate Similarity	NPC207851
0.7773	Intermediate Similarity	NPC213308
0.7773	Intermediate Similarity	NPC473310
0.7767	Intermediate Similarity	NPC116555
0.7757	Intermediate Similarity	NPC175602
0.7752	Intermediate Similarity	NPC31700
0.775	Intermediate Similarity	NPC267885
0.7748	Intermediate Similarity	NPC60621
0.7746	Intermediate Similarity	NPC476098
0.7725	Intermediate Similarity	NPC81535
0.7721	Intermediate Similarity	NPC270918
0.7717	Intermediate Similarity	NPC474412
0.7714	Intermediate Similarity	NPC167710
0.7706	Intermediate Similarity	NPC219087
0.7703	Intermediate Similarity	NPC323969
0.7699	Intermediate Similarity	NPC33949
0.7696	Intermediate Similarity	NPC5145
0.7696	Intermediate Similarity	NPC104712
0.7692	Intermediate Similarity	NPC324149
0.7689	Intermediate Similarity	NPC45459
0.7689	Intermediate Similarity	NPC315491
0.7677	Intermediate Similarity	NPC78020
0.7672	Intermediate Similarity	NPC148889
0.7662	Intermediate Similarity	NPC151635
0.7661	Intermediate Similarity	NPC72956
0.7659	Intermediate Similarity	NPC15102
0.7658	Intermediate Similarity	NPC269270
0.7652	Intermediate Similarity	NPC57453
0.765	Intermediate Similarity	NPC61038
0.765	Intermediate Similarity	NPC478158
0.7639	Intermediate Similarity	NPC183777
0.7628	Intermediate Similarity	NPC470500
0.7626	Intermediate Similarity	NPC6865
0.7626	Intermediate Similarity	NPC153980
0.7624	Intermediate Similarity	NPC145885
0.7624	Intermediate Similarity	NPC14113
0.7624	Intermediate Similarity	NPC84827
0.7623	Intermediate Similarity	NPC14686
0.7621	Intermediate Similarity	NPC235684
0.7617	Intermediate Similarity	NPC193761
0.7617	Intermediate Similarity	NPC328318
0.7617	Intermediate Similarity	NPC328596
0.761	Intermediate Similarity	NPC477003
0.7604	Intermediate Similarity	NPC171787
0.7602	Intermediate Similarity	NPC471192
0.7593	Intermediate Similarity	NPC472064
0.7586	Intermediate Similarity	NPC41679
0.7585	Intermediate Similarity	NPC17059
0.7578	Intermediate Similarity	NPC74360
0.7576	Intermediate Similarity	NPC477549
0.7568	Intermediate Similarity	NPC267811
0.7565	Intermediate Similarity	NPC70155
0.7562	Intermediate Similarity	NPC252572
0.7559	Intermediate Similarity	NPC237414
0.7557	Intermediate Similarity	NPC237740
0.7549	Intermediate Similarity	NPC469896
0.7546	Intermediate Similarity	NPC475070
0.7546	Intermediate Similarity	NPC470505
0.7546	Intermediate Similarity	NPC314648
0.7538	Intermediate Similarity	NPC41717
0.7537	Intermediate Similarity	NPC59269
0.7536	Intermediate Similarity	NPC315555
0.7534	Intermediate Similarity	NPC309845
0.7533	Intermediate Similarity	NPC24370
0.7533	Intermediate Similarity	NPC319232
0.7512	Intermediate Similarity	NPC472065
0.7512	Intermediate Similarity	NPC192315
0.7512	Intermediate Similarity	NPC317373
0.7511	Intermediate Similarity	NPC207866
0.7511	Intermediate Similarity	NPC234078
0.7511	Intermediate Similarity	NPC221100
0.7511	Intermediate Similarity	NPC282247
0.7511	Intermediate Similarity	NPC317752
0.751	Intermediate Similarity	NPC77101
0.75	Intermediate Similarity	NPC472116
0.75	Intermediate Similarity	NPC128244
0.7489	Intermediate Similarity	NPC472070
0.7489	Intermediate Similarity	NPC473312
0.7489	Intermediate Similarity	NPC304926
0.7489	Intermediate Similarity	NPC476041
0.7488	Intermediate Similarity	NPC81802
0.7488	Intermediate Similarity	NPC472210
0.7488	Intermediate Similarity	NPC247735
0.7488	Intermediate Similarity	NPC133003
0.7488	Intermediate Similarity	NPC472295
0.7488	Intermediate Similarity	NPC269886
0.7477	Intermediate Similarity	NPC476167
0.7477	Intermediate Similarity	NPC284338
0.7477	Intermediate Similarity	NPC293917
0.7476	Intermediate Similarity	NPC243058
0.7467	Intermediate Similarity	NPC272174
0.7466	Intermediate Similarity	NPC75634
0.7466	Intermediate Similarity	NPC318299
0.7465	Intermediate Similarity	NPC327592
0.7465	Intermediate Similarity	NPC473376
0.7458	Intermediate Similarity	NPC471536
0.7455	Intermediate Similarity	NPC281049
0.7454	Intermediate Similarity	NPC472069
0.7454	Intermediate Similarity	NPC472063
0.7454	Intermediate Similarity	NPC472062
0.7452	Intermediate Similarity	NPC160381
0.7451	Intermediate Similarity	NPC219848
0.7446	Intermediate Similarity	NPC196718

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 NPC229893 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	618
0.2-0.3	882
0.3-0.4	1930
0.4-0.5	2460
0.5-0.6	1890
0.6-0.7	944
0.7-0.8	160
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
0.8398	Intermediate Similarity	NPD5901	Discontinued
0.8019	Intermediate Similarity	NPD2510	Approved
0.8019	Intermediate Similarity	NPD2509	Approved
0.8	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD5426	Phase 3
0.7957	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3178	Discontinued
0.7926	Intermediate Similarity	NPD3393	Approved
0.7926	Intermediate Similarity	NPD3394	Approved
0.7926	Intermediate Similarity	NPD3389	Approved
0.786	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7470	Discontinued
0.7821	Intermediate Similarity	NPD5482	Discontinued
0.781	Intermediate Similarity	NPD6999	Discontinued
0.781	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD482	Approved
0.7778	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD7666	Phase 3
0.7767	Intermediate Similarity	NPD7665	Phase 2
0.775	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD6987	Phase 1
0.7696	Intermediate Similarity	NPD2096	Phase 2
0.7696	Intermediate Similarity	NPD2091	Phase 2
0.7689	Intermediate Similarity	NPD484	Approved
0.767	Intermediate Similarity	NPD4948	Discontinued
0.7647	Intermediate Similarity	NPD2094	Phase 2
0.7647	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2095	Phase 2
0.7647	Intermediate Similarity	NPD2092	Phase 2
0.7593	Intermediate Similarity	NPD7001	Phase 3
0.7593	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD6164	Phase 2
0.7577	Intermediate Similarity	NPD4845	Discontinued
0.7577	Intermediate Similarity	NPD6165	Phase 2
0.757	Intermediate Similarity	NPD5017	Discontinued
0.7565	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2336	Approved
0.7558	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3947	Discontinued
0.7546	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1996	Discontinued
0.7536	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD7603	Discontinued
0.7525	Intermediate Similarity	NPD5065	Approved
0.7523	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6173	Approved
0.7512	Intermediate Similarity	NPD2008	Discontinued
0.7512	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5475	Discontinued
0.7477	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD750	Phase 2
0.7466	Intermediate Similarity	NPD8096	Phase 3
0.7466	Intermediate Similarity	NPD2411	Approved
0.7466	Intermediate Similarity	NPD8097	Phase 3
0.7445	Intermediate Similarity	NPD6753	Phase 1
0.7445	Intermediate Similarity	NPD6752	Phase 1
0.7439	Intermediate Similarity	NPD5450	Discontinued
0.7431	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD6530	Approved
0.7418	Intermediate Similarity	NPD6531	Approved
0.7418	Intermediate Similarity	NPD2307	Discontinued
0.7404	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5003	Discontinued
0.7379	Intermediate Similarity	NPD6595	Phase 3
0.7371	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7359	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6665	Discontinued
0.7354	Intermediate Similarity	NPD3795	Approved
0.7354	Intermediate Similarity	NPD3794	Approved
0.7354	Intermediate Similarity	NPD3243	Approved
0.7339	Intermediate Similarity	NPD4886	Phase 2
0.7319	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD6242	Discontinued
0.7313	Intermediate Similarity	NPD5827	Discontinued
0.7309	Intermediate Similarity	NPD8093	Discontinued
0.7309	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7948	Phase 1
0.7291	Intermediate Similarity	NPD1575	Approved
0.7291	Intermediate Similarity	NPD1573	Approved
0.7285	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD3006	Discontinued
0.7273	Intermediate Similarity	NPD6178	Phase 3
0.7269	Intermediate Similarity	NPD6770	Approved
0.7269	Intermediate Similarity	NPD7404	Approved
0.7256	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD1600	Suspended
0.7251	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2844	Phase 3
0.723	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8289	Discontinued
0.7225	Intermediate Similarity	NPD4429	Discontinued
0.7222	Intermediate Similarity	NPD3746	Discontinued
0.722	Intermediate Similarity	NPD4051	Discontinued
0.722	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD3222	Phase 2
0.7212	Intermediate Similarity	NPD6452	Discontinued
0.7212	Intermediate Similarity	NPD6733	Discontinued
0.7209	Intermediate Similarity	NPD7618	Phase 3
0.7209	Intermediate Similarity	NPD7619	Phase 3
0.7198	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4558	Phase 2
0.719	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2813	Phase 3
0.7179	Intermediate Similarity	NPD7688	Phase 1
0.7176	Intermediate Similarity	NPD4848	Phase 1
0.7171	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3905	Phase 3
0.7156	Intermediate Similarity	NPD4852	Phase 2
0.7156	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7878	Phase 2
0.7149	Intermediate Similarity	NPD8098	Approved
0.7149	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD5479	Discontinued
0.713	Intermediate Similarity	NPD2442	Approved
0.713	Intermediate Similarity	NPD2443	Approved
0.7129	Intermediate Similarity	NPD2481	Approved
0.7129	Intermediate Similarity	NPD2479	Phase 3
0.7123	Intermediate Similarity	NPD4601	Approved
0.7123	Intermediate Similarity	NPD4600	Approved
0.7123	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7951	Approved
0.7119	Intermediate Similarity	NPD7789	Approved
0.7119	Intermediate Similarity	NPD7790	Approved
0.7119	Intermediate Similarity	NPD7952	Approved
0.7119	Intermediate Similarity	NPD7791	Approved
0.7119	Intermediate Similarity	NPD7950	Approved
0.7119	Intermediate Similarity	NPD7953	Approved
0.7109	Intermediate Similarity	NPD1096	Discontinued
0.7108	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6995	Phase 1
0.7093	Intermediate Similarity	NPD7970	Approved
0.7093	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3280	Approved
0.7083	Intermediate Similarity	NPD460	Discontinued
0.7072	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5022	Discontinued
0.7061	Intermediate Similarity	NPD8160	Phase 2
0.7059	Intermediate Similarity	NPD8073	Approved
0.7059	Intermediate Similarity	NPD2879	Approved
0.7059	Intermediate Similarity	NPD2881	Approved
0.7054	Intermediate Similarity	NPD6376	Discontinued
0.7054	Intermediate Similarity	NPD7860	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7731	Approved
0.7051	Intermediate Similarity	NPD7730	Approved
0.7048	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8094	Discontinued
0.7042	Intermediate Similarity	NPD706	Phase 1
0.704	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7957	Phase 1
0.7039	Intermediate Similarity	NPD7271	Approved
0.7037	Intermediate Similarity	NPD4922	Phase 2
0.7037	Intermediate Similarity	NPD4376	Phase 3
0.7035	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5416	Discontinued
0.7027	Intermediate Similarity	NPD6176	Phase 1
0.7026	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4499	Approved
0.7023	Intermediate Similarity	NPD2564	Approved
0.7023	Intermediate Similarity	NPD2565	Phase 2
0.7022	Intermediate Similarity	NPD4506	Discontinued
0.7021	Intermediate Similarity	NPD1571	Phase 2
0.7021	Intermediate Similarity	NPD7780	Approved
0.7021	Intermediate Similarity	NPD7781	Approved
0.7019	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD1631	Approved
0.7009	Intermediate Similarity	NPD7711	Discontinued
0.7008	Intermediate Similarity	NPD8349	Phase 1
0.7004	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD3959	Phase 2
0.6996	Remote Similarity	NPD3962	Phase 2
0.6992	Remote Similarity	NPD7824	Approved
0.6987	Remote Similarity	NPD5891	Approved
0.6982	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7994	Phase 2
0.6978	Remote Similarity	NPD6459	Phase 2
0.6977	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7415	Suspended

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