NPASS Compound

Structure

CID225400 OpenBabel06191716022D 33 38 0 0 1 0 0 0 0 0999 V2000 -1.9100 3.0522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0277 -0.0136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9100 -1.9478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1198 -2.1485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7760 -1.4478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3767 -2.8177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0439 -1.4478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9119 -1.1704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7760 -0.4478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4256 -2.5086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5541 1.0522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0439 2.5522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0496 -0.2215 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0439 -0.4478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9609 -0.8614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9100 0.0522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2177 -1.5305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6881 1.5522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0439 1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6881 2.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 -1.1350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1779 0.0522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5596 -0.0524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5541 0.0522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1779 3.0522 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3064 0.4476 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9100 1.0522 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1779 1.0522 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3517 -1.0305 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5541 3.0522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1428 -2.0011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6881 -0.4478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4202 0.5522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 14 2 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 10 17 2 0 0 0 0 11 24 1 0 0 0 0 12 1 1 6 0 0 0 12 19 1 0 0 0 0 12 25 1 0 0 0 0 13 2 1 6 0 0 0 13 21 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 11 1 1 0 0 0 18 20 1 0 0 0 0 18 28 1 0 0 0 0 19 27 2 0 0 0 0 19 28 1 0 0 0 0 20 25 2 0 0 0 0 20 30 1 0 0 0 0 21 29 1 0 0 0 0 21 31 2 0 0 0 0 22 28 1 0 0 0 0 22 32 2 0 0 0 0 23 24 1 6 0 0 0 23 26 1 0 0 0 0 23 29 1 0 0 0 0 24 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	445.18
Volume:	436.101
LogP:	0.491
LogD:	1.069
LogS:	-3.029
# Rotatable Bonds:	2
TPSA:	116.56
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	4.363
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.602
MDCK Permeability:	1.4714228200318757e-05
Pgp-inhibitor:	0.185
Pgp-substrate:	0.567
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.279
Plasma Protein Binding (PPB):	63.25926971435547%
Volume Distribution (VD):	1.892
Pgp-substrate:	28.753742218017578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.345
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.117
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.192
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	2.086
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.992
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.52
Carcinogencity:	0.57
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC225400

Natural Product ID:	NPC225400
*Common Name:**	Fumiquinazoline A
IUPAC Name:	(1S,4R)-4-[[(2S,3aS,4S)-4-hydroxy-2-methyl-1-oxo-3,3a-dihydro-2H-imidazo[1,2-a]indol-4-yl]methyl]-1-methyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
Synonyms:
Standard InCHIKey:	DQQCCKFZJNINST-VCPZKGNQSA-N
Standard InCHI:	InChI=1S/C24H23N5O4/c1-12-19-27-16-9-5-3-7-14(16)22(32)28(19)18(20(30)25-12)11-24(33)15-8-4-6-10-17(15)29-21(31)13(2)26-23(24)29/h3-10,12-13,18,23,26,33H,11H2,1-2H3,(H,25,30)/t12-,13-,18+,23-,24-/m0/s1
SMILES:	C[C@@H]1N[C@H]2N(C1=O)c1c([C@@]2(O)C[C@@H]2C(=N[C@H](c3n2c(=O)c2c(n3)cccc2)C)O)cccc1
Synthetic Gene Cluster:	BGC0000355;
ChEMBL Identifier:	CHEMBL2229120
PubChem CID:	11247802
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines

*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
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO24205	Peucedanum terebinthaceum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24205	Peucedanum terebinthaceum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23164	Nepeta aragonensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24205	Peucedanum terebinthaceum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19822	Onoseris gnaphalioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
MIC	8
Others	2

Activity Type	# Activity
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1769	Organism	Mythimna separata	Mythimna separata	AFI	=	45.0	%	PMID[538020]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	39.7	ug.mL-1	PMID[538020]
NPT1203	Organism	Fusarium graminearum	Fusarium graminearum	MIC	=	12.5	ug.mL-1	PMID[538020]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	MIC	=	50.0	ug.mL-1	PMID[538020]
NPT5164	Organism	Fusarium oxysporum f. sp. niveum	Fusarium oxysporum f. sp. niveum	MIC	=	25.0	ug.mL-1	PMID[538020]
NPT2600	Organism	Fusarium solani	Fusarium solani	MIC	=	50.0	ug.mL-1	PMID[538020]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	MIC	=	12.5	ug.mL-1	PMID[538020]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MIC	=	12.5	ug.mL-1	PMID[538020]
NPT2705	Organism	Alternaria solani	Alternaria solani	MIC	=	12.5	ug.mL-1	PMID[538020]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	=	12.5	ug.mL-1	PMID[538020]

☑ 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 NPC225400 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	446
0.1-0.2	2870
0.2-0.3	13669
0.3-0.4	17226
0.4-0.5	3636
0.5-0.6	3011
0.6-0.7	1646
0.7-0.8	122
0.8-0.85	31
0.85-0.9	16
0.9-0.95	11
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9945	High Similarity	NPC470786
0.9945	High Similarity	NPC471155
0.9945	High Similarity	NPC472538
0.9891	High Similarity	NPC270241
0.9568	High Similarity	NPC295548
0.933	High Similarity	NPC248601
0.8942	High Similarity	NPC106118
0.8883	High Similarity	NPC472539
0.8883	High Similarity	NPC472540
0.8883	High Similarity	NPC470787
0.8836	High Similarity	NPC472542
0.8836	High Similarity	NPC472541
0.87	High Similarity	NPC471197
0.8673	High Similarity	NPC285192
0.8657	High Similarity	NPC471198
0.8542	High Similarity	NPC471199
0.8421	Intermediate Similarity	NPC471196
0.8421	Intermediate Similarity	NPC471195
0.8333	Intermediate Similarity	NPC15384
0.8333	Intermediate Similarity	NPC244425
0.7968	Intermediate Similarity	NPC355
0.7937	Intermediate Similarity	NPC475607
0.7927	Intermediate Similarity	NPC307396
0.7895	Intermediate Similarity	NPC474081
0.7884	Intermediate Similarity	NPC475594
0.7884	Intermediate Similarity	NPC470548
0.7853	Intermediate Similarity	NPC474041
0.7853	Intermediate Similarity	NPC475761
0.7817	Intermediate Similarity	NPC276430
0.7784	Intermediate Similarity	NPC68650
0.7755	Intermediate Similarity	NPC473815
0.7754	Intermediate Similarity	NPC471130
0.7701	Intermediate Similarity	NPC189116
0.7647	Intermediate Similarity	NPC88970
0.7634	Intermediate Similarity	NPC154478
0.7619	Intermediate Similarity	NPC471194
0.7619	Intermediate Similarity	NPC6865
0.7619	Intermediate Similarity	NPC471193
0.7619	Intermediate Similarity	NPC153980
0.7585	Intermediate Similarity	NPC471191
0.7571	Intermediate Similarity	NPC72956
0.7527	Intermediate Similarity	NPC84317
0.75	Intermediate Similarity	NPC471663
0.7449	Intermediate Similarity	NPC475685
0.743	Intermediate Similarity	NPC471192
0.7419	Intermediate Similarity	NPC295021
0.7373	Intermediate Similarity	NPC272174
0.7356	Intermediate Similarity	NPC471436
0.7347	Intermediate Similarity	NPC14849
0.7291	Intermediate Similarity	NPC92803
0.7268	Intermediate Similarity	NPC472118
0.7264	Intermediate Similarity	NPC150308
0.7263	Intermediate Similarity	NPC471122
0.726	Intermediate Similarity	NPC474896
0.7245	Intermediate Similarity	NPC328611
0.724	Intermediate Similarity	NPC113056
0.724	Intermediate Similarity	NPC138293
0.7227	Intermediate Similarity	NPC31097
0.7222	Intermediate Similarity	NPC182057
0.7222	Intermediate Similarity	NPC147298
0.7222	Intermediate Similarity	NPC131450
0.7202	Intermediate Similarity	NPC471124
0.7192	Intermediate Similarity	NPC18890
0.7157	Intermediate Similarity	NPC248862
0.7149	Intermediate Similarity	NPC220851
0.7143	Intermediate Similarity	NPC471944
0.7136	Intermediate Similarity	NPC475094
0.7112	Intermediate Similarity	NPC300596
0.7112	Intermediate Similarity	NPC237649
0.7107	Intermediate Similarity	NPC177261
0.7101	Intermediate Similarity	NPC198401
0.709	Intermediate Similarity	NPC117032
0.7049	Intermediate Similarity	NPC207554
0.7042	Intermediate Similarity	NPC477178
0.7042	Intermediate Similarity	NPC254850
0.7042	Intermediate Similarity	NPC477180
0.7042	Intermediate Similarity	NPC477181
0.7035	Intermediate Similarity	NPC471743
0.7023	Intermediate Similarity	NPC71238
0.701	Intermediate Similarity	NPC476231
0.7009	Intermediate Similarity	NPC477174
0.7009	Intermediate Similarity	NPC470490
0.7009	Intermediate Similarity	NPC477173
0.7005	Intermediate Similarity	NPC324445
0.6995	Remote Similarity	NPC477179
0.6977	Remote Similarity	NPC470488
0.6959	Remote Similarity	NPC475359
0.6959	Remote Similarity	NPC191817
0.6944	Remote Similarity	NPC470491
0.6944	Remote Similarity	NPC471945
0.6944	Remote Similarity	NPC475259
0.6944	Remote Similarity	NPC471950
0.6931	Remote Similarity	NPC39822
0.6927	Remote Similarity	NPC473615
0.6927	Remote Similarity	NPC54981
0.6923	Remote Similarity	NPC300299
0.6919	Remote Similarity	NPC43477
0.6916	Remote Similarity	NPC471762
0.6912	Remote Similarity	NPC471946
0.6912	Remote Similarity	NPC471951
0.6898	Remote Similarity	NPC243850
0.6893	Remote Similarity	NPC229484
0.6878	Remote Similarity	NPC254798
0.6878	Remote Similarity	NPC259626
0.6872	Remote Similarity	NPC309531
0.6872	Remote Similarity	NPC472102
0.6872	Remote Similarity	NPC157931
0.686	Remote Similarity	NPC292675
0.685	Remote Similarity	NPC285622
0.6842	Remote Similarity	NPC194740
0.6837	Remote Similarity	NPC472117
0.6829	Remote Similarity	NPC21429
0.6829	Remote Similarity	NPC2933
0.6828	Remote Similarity	NPC2823
0.6821	Remote Similarity	NPC276085
0.682	Remote Similarity	NPC14812
0.6818	Remote Similarity	NPC472115
0.6818	Remote Similarity	NPC214960
0.6818	Remote Similarity	NPC472114
0.6818	Remote Similarity	NPC279527
0.6806	Remote Similarity	NPC473376
0.6786	Remote Similarity	NPC27904
0.678	Remote Similarity	NPC256288
0.6769	Remote Similarity	NPC222029
0.6769	Remote Similarity	NPC66777
0.6766	Remote Similarity	NPC475532
0.6765	Remote Similarity	NPC91179
0.6763	Remote Similarity	NPC141612
0.6763	Remote Similarity	NPC17273
0.6763	Remote Similarity	NPC135601
0.6758	Remote Similarity	NPC207428
0.6757	Remote Similarity	NPC122553
0.6753	Remote Similarity	NPC89987
0.6739	Remote Similarity	NPC326363
0.6733	Remote Similarity	NPC165285
0.6728	Remote Similarity	NPC470489
0.6725	Remote Similarity	NPC257851
0.672	Remote Similarity	NPC136002
0.672	Remote Similarity	NPC83214
0.6701	Remote Similarity	NPC469903
0.6701	Remote Similarity	NPC471132
0.6694	Remote Similarity	NPC314882
0.6684	Remote Similarity	NPC311658
0.6683	Remote Similarity	NPC242269
0.6667	Remote Similarity	NPC97584
0.6667	Remote Similarity	NPC229893
0.6667	Remote Similarity	NPC128582
0.6667	Remote Similarity	NPC477714
0.6653	Remote Similarity	NPC478006
0.6653	Remote Similarity	NPC471536
0.6652	Remote Similarity	NPC147983
0.6652	Remote Similarity	NPC177996
0.6652	Remote Similarity	NPC322064
0.665	Remote Similarity	NPC36495
0.665	Remote Similarity	NPC182131
0.665	Remote Similarity	NPC473003
0.665	Remote Similarity	NPC17698
0.6649	Remote Similarity	NPC471164
0.6638	Remote Similarity	NPC475969
0.6638	Remote Similarity	NPC122886
0.6638	Remote Similarity	NPC475859
0.6637	Remote Similarity	NPC54744
0.6636	Remote Similarity	NPC316282
0.6635	Remote Similarity	NPC203628
0.6632	Remote Similarity	NPC144691
0.6624	Remote Similarity	NPC325976
0.6622	Remote Similarity	NPC477715
0.6619	Remote Similarity	NPC221873
0.6618	Remote Similarity	NPC470317
0.6617	Remote Similarity	NPC129486
0.6612	Remote Similarity	NPC63109
0.6605	Remote Similarity	NPC100863
0.6599	Remote Similarity	NPC104345
0.6595	Remote Similarity	NPC470730
0.6595	Remote Similarity	NPC477175
0.6595	Remote Similarity	NPC316104
0.6595	Remote Similarity	NPC162417
0.6595	Remote Similarity	NPC253476
0.6593	Remote Similarity	NPC303658
0.6591	Remote Similarity	NPC478075
0.6591	Remote Similarity	NPC16249
0.6588	Remote Similarity	NPC5630
0.6585	Remote Similarity	NPC74619
0.6585	Remote Similarity	NPC473001
0.6583	Remote Similarity	NPC289776
0.6583	Remote Similarity	NPC133470
0.6583	Remote Similarity	NPC293458
0.6583	Remote Similarity	NPC191863
0.6571	Remote Similarity	NPC17059
0.6567	Remote Similarity	NPC474877
0.6566	Remote Similarity	NPC469902
0.6565	Remote Similarity	NPC115588
0.6564	Remote Similarity	NPC219397
0.6564	Remote Similarity	NPC473002
0.6561	Remote Similarity	NPC316202
0.6561	Remote Similarity	NPC471574
0.6555	Remote Similarity	NPC133003
0.6553	Remote Similarity	NPC97526
0.6553	Remote Similarity	NPC119652
0.655	Remote Similarity	NPC313757

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 NPC225400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	563
0.2-0.3	850
0.3-0.4	1513
0.4-0.5	2444
0.5-0.6	2152
0.6-0.7	1198
0.7-0.8	203
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
0.8115	Intermediate Similarity	NPD6557	Phase 2
0.8093	Intermediate Similarity	NPD5042	Phase 1
0.7817	Intermediate Similarity	NPD8240	Discontinued
0.7673	Intermediate Similarity	NPD5856	Discontinued
0.7513	Intermediate Similarity	NPD5923	Phase 1
0.75	Intermediate Similarity	NPD3990	Phase 3
0.7474	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD3989	Phase 3
0.7347	Intermediate Similarity	NPD4092	Approved
0.7296	Intermediate Similarity	NPD4091	Approved
0.7245	Intermediate Similarity	NPD3522	Approved
0.7222	Intermediate Similarity	NPD3997	Approved
0.7222	Intermediate Similarity	NPD3999	Approved
0.7222	Intermediate Similarity	NPD3998	Approved
0.7192	Intermediate Similarity	NPD7855	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3996	Approved
0.7172	Intermediate Similarity	NPD3994	Approved
0.7172	Intermediate Similarity	NPD3992	Approved
0.7172	Intermediate Similarity	NPD3995	Approved
0.7172	Intermediate Similarity	NPD3991	Approved
0.7172	Intermediate Similarity	NPD3993	Approved
0.7156	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD2813	Phase 3
0.7143	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7232	Discontinued
0.709	Intermediate Similarity	NPD3248	Phase 1
0.7087	Intermediate Similarity	NPD7570	Approved
0.7087	Intermediate Similarity	NPD7569	Approved
0.7068	Intermediate Similarity	NPD951	Approved
0.7062	Intermediate Similarity	NPD7817	Phase 1
0.7059	Intermediate Similarity	NPD4515	Suspended
0.7043	Intermediate Similarity	NPD6017	Discontinued
0.704	Intermediate Similarity	NPD6753	Phase 1
0.704	Intermediate Similarity	NPD6752	Phase 1
0.7021	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7617	Discontinued
0.6985	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3917	Approved
0.6972	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3918	Approved
0.6944	Remote Similarity	NPD6487	Approved
0.6944	Remote Similarity	NPD6486	Approved
0.6941	Remote Similarity	NPD3780	Phase 2
0.6931	Remote Similarity	NPD979	Approved
0.6927	Remote Similarity	NPD3915	Approved
0.6923	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4412	Phase 2
0.69	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6301	Phase 2
0.6842	Remote Similarity	NPD4942	Approved
0.6842	Remote Similarity	NPD5937	Approved
0.6839	Remote Similarity	NPD7072	Phase 2
0.6837	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4393	Approved
0.6821	Remote Similarity	NPD33	Approved
0.682	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6199	Discontinued
0.6806	Remote Similarity	NPD8115	Approved
0.6806	Remote Similarity	NPD8114	Approved
0.6794	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6260	Discontinued
0.677	Remote Similarity	NPD8311	Discontinued
0.6766	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5445	Approved
0.6761	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD1920	Approved
0.6758	Remote Similarity	NPD1919	Approved
0.6755	Remote Similarity	NPD5024	Approved
0.6755	Remote Similarity	NPD4430	Phase 2
0.6742	Remote Similarity	NPD7225	Discontinued
0.6742	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2791	Discontinued
0.6726	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6164	Phase 2
0.6725	Remote Similarity	NPD6165	Phase 2
0.6719	Remote Similarity	NPD5748	Phase 2
0.6714	Remote Similarity	NPD5515	Phase 2
0.6714	Remote Similarity	NPD5077	Approved
0.6714	Remote Similarity	NPD5076	Approved
0.6713	Remote Similarity	NPD3774	Approved
0.6713	Remote Similarity	NPD3773	Approved
0.6713	Remote Similarity	NPD3775	Approved
0.671	Remote Similarity	NPD7552	Discontinued
0.6696	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6142	Phase 3
0.6684	Remote Similarity	NPD7011	Discontinued
0.6683	Remote Similarity	NPD4329	Approved
0.6683	Remote Similarity	NPD6878	Phase 2
0.6683	Remote Similarity	NPD6879	Phase 2
0.6683	Remote Similarity	NPD4330	Approved
0.6682	Remote Similarity	NPD3802	Phase 3
0.6667	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2369	Discontinued
0.6667	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7727	Phase 2
0.6667	Remote Similarity	NPD4888	Discontinued
0.6667	Remote Similarity	NPD5552	Discontinued
0.6652	Remote Similarity	NPD3353	Approved
0.6651	Remote Similarity	NPD4948	Discontinued
0.6649	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD1524	Phase 1
0.6639	Remote Similarity	NPD4946	Phase 2
0.6635	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD7568	Phase 1
0.6609	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5997	Discontinued
0.6599	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3792	Approved
0.658	Remote Similarity	NPD5942	Approved
0.658	Remote Similarity	NPD7694	Discontinued
0.658	Remote Similarity	NPD5423	Phase 2
0.658	Remote Similarity	NPD5941	Approved
0.6579	Remote Similarity	NPD1625	Approved
0.6578	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD8149	Discontinued
0.6577	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4982	Discontinued
0.6573	Remote Similarity	NPD1059	Phase 2
0.6571	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7599	Phase 2
0.6558	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD7572	Phase 2
0.6553	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD3782	Discontinued
0.6553	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6218	Discontinued
0.6548	Remote Similarity	NPD7091	Discontinued
0.6548	Remote Similarity	NPD7105	Phase 1
0.6547	Remote Similarity	NPD7470	Discontinued
0.654	Remote Similarity	NPD7677	Discontinued
0.6537	Remote Similarity	NPD8289	Discontinued
0.6533	Remote Similarity	NPD5989	Phase 1
0.6533	Remote Similarity	NPD7970	Approved
0.6533	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2790	Discontinued
0.6531	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5194	Approved
0.6528	Remote Similarity	NPD5196	Approved
0.6528	Remote Similarity	NPD5197	Approved
0.6526	Remote Similarity	NPD7786	Discontinued
0.6522	Remote Similarity	NPD6829	Phase 2
0.6522	Remote Similarity	NPD6173	Approved
0.6517	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5807	Phase 2
0.6515	Remote Similarity	NPD212	Discontinued
0.6512	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5840	Discontinued
0.6504	Remote Similarity	NPD6596	Phase 2
0.6502	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5901	Discontinued
0.6498	Remote Similarity	NPD6249	Phase 2
0.6498	Remote Similarity	NPD7308	Discontinued
0.6498	Remote Similarity	NPD5882	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD6248	Phase 2
0.6495	Remote Similarity	NPD4432	Discontinued
0.6495	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD2820	Phase 3
0.6489	Remote Similarity	NPD8094	Discontinued
0.6489	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3243	Approved
0.6488	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5466	Approved
0.6488	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2442	Approved
0.6486	Remote Similarity	NPD2443	Approved
0.6485	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6532	Discontinued
0.6482	Remote Similarity	NPD4514	Approved
0.6481	Remote Similarity	NPD7767	Approved
0.6481	Remote Similarity	NPD1571	Phase 2
0.6477	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3625	Discontinued
0.6473	Remote Similarity	NPD7771	Discontinued
0.6473	Remote Similarity	NPD3959	Phase 2
0.6473	Remote Similarity	NPD7921	Approved
0.6473	Remote Similarity	NPD3962	Phase 2
0.6471	Remote Similarity	NPD3776	Discontinued
0.6471	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD3790	Phase 2
0.6468	Remote Similarity	NPD6805	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data