NPASS Compound

Structure

CID88110 OpenBabel06191715422D 22 25 0 0 0 0 0 0 0 0999 V2000 -3.9487 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4487 -3.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4487 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 -3.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9875 -0.1151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -1.2443 0.5540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 9 12 1 0 0 0 0 9 21 2 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 20 2 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	289.09
Volume:	292.569
LogP:	2.907
LogD:	3.007
LogS:	-5.433
# Rotatable Bonds:	2
TPSA:	78.61
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.557
Synthetic Accessibility Score:	2.369
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.14
MDCK Permeability:	7.373527296294924e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.2
30% Bioavailability (F30%):	0.262

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.745
Plasma Protein Binding (PPB):	97.27033233642578%
Volume Distribution (VD):	0.433
Pgp-substrate:	1.4498897790908813%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.18
CYP2C19-inhibitor:	0.451
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.375
CYP2C9-substrate:	0.804
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.78
CYP3A4-substrate:	0.182

ADMET: Excretion

Clearance (CL):	2.587
Half-life (T1/2):	0.507

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.856
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.496
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.319
Skin Sensitization:	0.558
Carcinogencity:	0.434
Eye Corrosion:	0.005
Eye Irritation:	0.958
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC88110

Natural Product ID:	NPC88110
*Common Name:**	Bouchardatine
IUPAC Name:	2-(4-oxo-1H-quinazolin-2-yl)-1H-indole-3-carbaldehyde
Synonyms:
Standard InCHIKey:	ZDTNFKKWSCJPNF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H11N3O2/c21-9-12-10-5-1-3-7-13(10)18-15(12)16-19-14-8-4-2-6-11(14)17(22)20-16/h1-9,18H,(H,19,20,22)
SMILES:	c1ccc2c(c1)c(C=O)c(c1[nH]c3ccccc3c(=O)n1)[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3596962
PubChem CID:	21576497
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
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	fruit	n.a.	PMID[10820058]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16441086]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	Unripe fruit	n.a.	n.a.	PMID[9644064]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22204	Tylostylis discolor	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3683.1	Pteridium aquilinum subsp. latiusculum	Subspecies	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20117	Leucas lanata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4954	Eleutherococcus divaricatus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22779	Sphagnum magellanicum	Species	Sphagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23009	Udotea flabellum	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22962	Coussarea hydrangeifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29067	Spondias dulcis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10669	Cousinia pterocaulos	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22906	Bouchardatia neurococca	Species	Rutaceae	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	2
Others	19

Activity Type	# Activity
Cell Line	18
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	57.0	%	PMID[490281]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	40.0	%	PMID[490281]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	5.0	%	PMID[490281]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	18.0	%	PMID[490281]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	50.0	%	PMID[490281]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	2.0	%	PMID[490281]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	80.0	%	PMID[490281]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	<	10.0	%	PMID[490281]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	30.0	%	PMID[490281]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	50.0	%	PMID[490281]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	16.7	%	PMID[490282]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	24.1	%	PMID[490282]
NPT520	Cell Line	3T3-L1	Mus musculus	TIME	=	120.0	hr	PMID[490282]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	20.1	%	PMID[490283]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	24.1	%	PMID[490283]
NPT520	Cell Line	3T3-L1	Mus musculus	IC50	>	50000.0	nM	PMID[490283]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[490283]
NPT610	Others	Molecular identity unknown		Inhibition	=	14.8	%	PMID[490282]
NPT610	Others	Molecular identity unknown		Inhibition	=	20.1	%	PMID[490282]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	14.6	%	PMID[490284]

☑ 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 NPC88110 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	825
0.1-0.2	8055
0.2-0.3	16340
0.3-0.4	12337
0.4-0.5	2122
0.5-0.6	2132
0.6-0.7	729
0.7-0.8	138
0.8-0.85	14
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9112	High Similarity	NPC21429
0.8521	High Similarity	NPC471943
0.8373	Intermediate Similarity	NPC76982
0.8305	Intermediate Similarity	NPC133003
0.8289	Intermediate Similarity	NPC471191
0.8258	Intermediate Similarity	NPC141612
0.8258	Intermediate Similarity	NPC135601
0.8258	Intermediate Similarity	NPC17273
0.8218	Intermediate Similarity	NPC151635
0.8208	Intermediate Similarity	NPC252572
0.8129	Intermediate Similarity	NPC42372
0.8093	Intermediate Similarity	NPC471192
0.809	Intermediate Similarity	NPC470205
0.8073	Intermediate Similarity	NPC72956
0.8031	Intermediate Similarity	NPC471194
0.8031	Intermediate Similarity	NPC153980
0.8031	Intermediate Similarity	NPC471193
0.8031	Intermediate Similarity	NPC6865
0.8023	Intermediate Similarity	NPC115232
0.8022	Intermediate Similarity	NPC324091
0.7989	Intermediate Similarity	NPC102755
0.7955	Intermediate Similarity	NPC293216
0.7907	Intermediate Similarity	NPC214106
0.7889	Intermediate Similarity	NPC117027
0.7869	Intermediate Similarity	NPC473666
0.7865	Intermediate Similarity	NPC284775
0.7845	Intermediate Similarity	NPC477003
0.7789	Intermediate Similarity	NPC471944
0.7784	Intermediate Similarity	NPC476460
0.7772	Intermediate Similarity	NPC243850
0.7771	Intermediate Similarity	NPC114637
0.7735	Intermediate Similarity	NPC470677
0.7713	Intermediate Similarity	NPC102592
0.7713	Intermediate Similarity	NPC79356
0.7705	Intermediate Similarity	NPC99939
0.7705	Intermediate Similarity	NPC308931
0.7701	Intermediate Similarity	NPC326422
0.7701	Intermediate Similarity	NPC242116
0.7673	Intermediate Similarity	NPC220851
0.7672	Intermediate Similarity	NPC167710
0.7661	Intermediate Similarity	NPC295021
0.7637	Intermediate Similarity	NPC191415
0.761	Intermediate Similarity	NPC157931
0.761	Intermediate Similarity	NPC257851
0.7606	Intermediate Similarity	NPC304203
0.7581	Intermediate Similarity	NPC221873
0.7576	Intermediate Similarity	NPC470702
0.7576	Intermediate Similarity	NPC473218
0.7573	Intermediate Similarity	NPC66777
0.7573	Intermediate Similarity	NPC471762
0.7566	Intermediate Similarity	NPC19692
0.7566	Intermediate Similarity	NPC220151
0.7557	Intermediate Similarity	NPC21174
0.7557	Intermediate Similarity	NPC271797
0.7554	Intermediate Similarity	NPC110158
0.7538	Intermediate Similarity	NPC470703
0.753	Intermediate Similarity	NPC2823
0.7529	Intermediate Similarity	NPC299594
0.7526	Intermediate Similarity	NPC317701
0.7515	Intermediate Similarity	NPC470440
0.75	Intermediate Similarity	NPC472297
0.75	Intermediate Similarity	NPC472296
0.75	Intermediate Similarity	NPC161861
0.7471	Intermediate Similarity	NPC478186
0.747	Intermediate Similarity	NPC207554
0.7439	Intermediate Similarity	NPC300299
0.7438	Intermediate Similarity	NPC250361
0.7426	Intermediate Similarity	NPC267811
0.7419	Intermediate Similarity	NPC476341
0.7391	Intermediate Similarity	NPC91179
0.7378	Intermediate Similarity	NPC473930
0.7374	Intermediate Similarity	NPC470509
0.7374	Intermediate Similarity	NPC116555
0.7368	Intermediate Similarity	NPC472113
0.7362	Intermediate Similarity	NPC22079
0.736	Intermediate Similarity	NPC271734
0.7356	Intermediate Similarity	NPC281094
0.7354	Intermediate Similarity	NPC154339
0.7353	Intermediate Similarity	NPC242556
0.7348	Intermediate Similarity	NPC6982
0.7346	Intermediate Similarity	NPC473762
0.7344	Intermediate Similarity	NPC472293
0.7337	Intermediate Similarity	NPC114033
0.7337	Intermediate Similarity	NPC58268
0.7337	Intermediate Similarity	NPC101130
0.7337	Intermediate Similarity	NPC129412
0.7337	Intermediate Similarity	NPC11126
0.7337	Intermediate Similarity	NPC277157
0.732	Intermediate Similarity	NPC477004
0.7317	Intermediate Similarity	NPC475450
0.7301	Intermediate Similarity	NPC473587
0.7297	Intermediate Similarity	NPC16659
0.7287	Intermediate Similarity	NPC160381
0.7278	Intermediate Similarity	NPC238499
0.7278	Intermediate Similarity	NPC284635
0.7277	Intermediate Similarity	NPC472292
0.7277	Intermediate Similarity	NPC272458
0.7273	Intermediate Similarity	NPC228835
0.7268	Intermediate Similarity	NPC469529
0.7263	Intermediate Similarity	NPC478184
0.7263	Intermediate Similarity	NPC472112
0.7263	Intermediate Similarity	NPC8104
0.7256	Intermediate Similarity	NPC475428
0.7243	Intermediate Similarity	NPC265710
0.724	Intermediate Similarity	NPC267343
0.7231	Intermediate Similarity	NPC474318
0.7231	Intermediate Similarity	NPC475914
0.7231	Intermediate Similarity	NPC268744
0.7231	Intermediate Similarity	NPC201266
0.7231	Intermediate Similarity	NPC153123
0.7231	Intermediate Similarity	NPC220797
0.7225	Intermediate Similarity	NPC138370
0.7216	Intermediate Similarity	NPC470507
0.7212	Intermediate Similarity	NPC179365
0.7211	Intermediate Similarity	NPC63199
0.7211	Intermediate Similarity	NPC102338
0.7211	Intermediate Similarity	NPC111602
0.7211	Intermediate Similarity	NPC196251
0.7209	Intermediate Similarity	NPC204141
0.7204	Intermediate Similarity	NPC73994
0.7202	Intermediate Similarity	NPC83214
0.7202	Intermediate Similarity	NPC125746
0.7194	Intermediate Similarity	NPC77241
0.7194	Intermediate Similarity	NPC166209
0.7194	Intermediate Similarity	NPC269203
0.7194	Intermediate Similarity	NPC13456
0.7189	Intermediate Similarity	NPC473380
0.7189	Intermediate Similarity	NPC240088
0.7188	Intermediate Similarity	NPC216550
0.7188	Intermediate Similarity	NPC67551
0.7186	Intermediate Similarity	NPC198988
0.7184	Intermediate Similarity	NPC124005
0.7184	Intermediate Similarity	NPC37548
0.7181	Intermediate Similarity	NPC467063
0.7176	Intermediate Similarity	NPC115611
0.7173	Intermediate Similarity	NPC314333
0.7158	Intermediate Similarity	NPC17059
0.7158	Intermediate Similarity	NPC278434
0.7143	Intermediate Similarity	NPC325252
0.7143	Intermediate Similarity	NPC195704
0.7143	Intermediate Similarity	NPC14448
0.7143	Intermediate Similarity	NPC167200
0.7143	Intermediate Similarity	NPC138596
0.7143	Intermediate Similarity	NPC200397
0.7143	Intermediate Similarity	NPC64661
0.7143	Intermediate Similarity	NPC237414
0.7143	Intermediate Similarity	NPC98156
0.7143	Intermediate Similarity	NPC292434
0.7136	Intermediate Similarity	NPC132539
0.7127	Intermediate Similarity	NPC71132
0.7122	Intermediate Similarity	NPC322064
0.7119	Intermediate Similarity	NPC471458
0.7118	Intermediate Similarity	NPC312092
0.7118	Intermediate Similarity	NPC88097
0.7113	Intermediate Similarity	NPC202812
0.7113	Intermediate Similarity	NPC294693
0.7111	Intermediate Similarity	NPC194881
0.7104	Intermediate Similarity	NPC65080
0.7097	Intermediate Similarity	NPC234987
0.7095	Intermediate Similarity	NPC293487
0.7093	Intermediate Similarity	NPC136002
0.7083	Intermediate Similarity	NPC329858
0.7081	Intermediate Similarity	NPC41174
0.7076	Intermediate Similarity	NPC74928
0.7076	Intermediate Similarity	NPC244087
0.7076	Intermediate Similarity	NPC205604
0.7076	Intermediate Similarity	NPC12831
0.7076	Intermediate Similarity	NPC169308
0.7076	Intermediate Similarity	NPC302717
0.7076	Intermediate Similarity	NPC129753
0.7076	Intermediate Similarity	NPC3698
0.7076	Intermediate Similarity	NPC48171
0.7076	Intermediate Similarity	NPC97230
0.7076	Intermediate Similarity	NPC59839
0.7076	Intermediate Similarity	NPC286529
0.7076	Intermediate Similarity	NPC77582
0.7076	Intermediate Similarity	NPC209281
0.7072	Intermediate Similarity	NPC478182
0.7069	Intermediate Similarity	NPC143872
0.7067	Intermediate Similarity	NPC323969
0.7062	Intermediate Similarity	NPC247735
0.7062	Intermediate Similarity	NPC472210
0.7062	Intermediate Similarity	NPC81802
0.7062	Intermediate Similarity	NPC269886
0.7062	Intermediate Similarity	NPC472295
0.7056	Intermediate Similarity	NPC122141
0.7048	Intermediate Similarity	NPC207428
0.7041	Intermediate Similarity	NPC141454
0.7041	Intermediate Similarity	NPC218268
0.7031	Intermediate Similarity	NPC175474
0.7022	Intermediate Similarity	NPC38736
0.7021	Intermediate Similarity	NPC469896
0.7016	Intermediate Similarity	NPC90415
0.7016	Intermediate Similarity	NPC94752
0.701	Intermediate Similarity	NPC47190
0.7005	Intermediate Similarity	NPC183662
0.7005	Intermediate Similarity	NPC217372
0.7005	Intermediate Similarity	NPC131887
0.7005	Intermediate Similarity	NPC28848
0.7005	Intermediate Similarity	NPC15573

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 NPC88110 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	449
0.1-0.2	712
0.2-0.3	1101
0.3-0.4	2476
0.4-0.5	2000
0.5-0.6	1713
0.6-0.7	637
0.7-0.8	58
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7784	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5473	Discontinued
0.7692	Intermediate Similarity	NPD3319	Phase 1
0.7692	Intermediate Similarity	NPD3318	Approved
0.7692	Intermediate Similarity	NPD3320	Approved
0.7641	Intermediate Similarity	NPD2443	Approved
0.7641	Intermediate Similarity	NPD2442	Approved
0.7622	Intermediate Similarity	NPD3246	Discontinued
0.7568	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4922	Phase 2
0.7526	Intermediate Similarity	NPD4848	Phase 1
0.7487	Intermediate Similarity	NPD7657	Approved
0.7487	Intermediate Similarity	NPD7656	Approved
0.746	Intermediate Similarity	NPD1896	Approved
0.7449	Intermediate Similarity	NPD2008	Discontinued
0.7433	Intermediate Similarity	NPD4988	Discontinued
0.7424	Intermediate Similarity	NPD2408	Discontinued
0.741	Intermediate Similarity	NPD1262	Discovery
0.74	Intermediate Similarity	NPD2411	Approved
0.7362	Intermediate Similarity	NPD1920	Approved
0.7362	Intermediate Similarity	NPD1919	Approved
0.735	Intermediate Similarity	NPD4863	Approved
0.7347	Intermediate Similarity	NPD6176	Phase 1
0.7344	Intermediate Similarity	NPD1871	Approved
0.7333	Intermediate Similarity	NPD7817	Phase 1
0.7306	Intermediate Similarity	NPD6664	Approved
0.7287	Intermediate Similarity	NPD4940	Approved
0.7273	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7454	Approved
0.7228	Intermediate Similarity	NPD7455	Approved
0.7228	Intermediate Similarity	NPD4075	Phase 2
0.7225	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2880	Discontinued
0.7209	Intermediate Similarity	NPD1524	Phase 1
0.7202	Intermediate Similarity	NPD7619	Phase 3
0.7202	Intermediate Similarity	NPD7618	Phase 3
0.7181	Intermediate Similarity	NPD7564	Discontinued
0.7174	Intermediate Similarity	NPD4128	Approved
0.7173	Intermediate Similarity	NPD4499	Approved
0.7172	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD1506	Discontinued
0.7143	Intermediate Similarity	NPD4462	Approved
0.7143	Intermediate Similarity	NPD4463	Approved
0.7129	Intermediate Similarity	NPD4051	Discontinued
0.7121	Intermediate Similarity	NPD2879	Approved
0.7121	Intermediate Similarity	NPD2881	Approved
0.7118	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7406	Phase 2
0.7112	Intermediate Similarity	NPD2481	Approved
0.7112	Intermediate Similarity	NPD2479	Phase 3
0.7107	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5809	Phase 3
0.7094	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1982	Phase 1
0.7086	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6828	Phase 2
0.7065	Intermediate Similarity	NPD3905	Phase 3
0.7062	Intermediate Similarity	NPD4348	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8050	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5901	Discontinued
0.7044	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1952	Discontinued
0.7031	Intermediate Similarity	NPD5016	Approved
0.703	Intermediate Similarity	NPD2509	Approved
0.703	Intermediate Similarity	NPD2510	Approved
0.7029	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3868	Phase 1
0.7022	Intermediate Similarity	NPD7072	Phase 2
0.7021	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5199	Approved
0.7019	Intermediate Similarity	NPD5198	Approved
0.7016	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7065	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2214	Approved
0.7	Intermediate Similarity	NPD5001	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2213	Approved
0.6994	Remote Similarity	NPD4047	Discontinued
0.6979	Remote Similarity	NPD3961	Discontinued
0.6979	Remote Similarity	NPD4948	Discontinued
0.697	Remote Similarity	NPD5854	Approved
0.6968	Remote Similarity	NPD3077	Approved
0.6968	Remote Similarity	NPD3079	Approved
0.6968	Remote Similarity	NPD3078	Approved
0.6968	Remote Similarity	NPD3076	Approved
0.6965	Remote Similarity	NPD4299	Phase 1
0.6959	Remote Similarity	NPD1658	Discontinued
0.6954	Remote Similarity	NPD5254	Discontinued
0.6954	Remote Similarity	NPD5446	Phase 2
0.6952	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7175	Phase 1
0.694	Remote Similarity	NPD2915	Discontinued
0.6939	Remote Similarity	NPD5853	Phase 3
0.6939	Remote Similarity	NPD5855	Phase 3
0.6935	Remote Similarity	NPD4501	Approved
0.6935	Remote Similarity	NPD4500	Approved
0.6915	Remote Similarity	NPD4181	Approved
0.691	Remote Similarity	NPD3248	Phase 1
0.6904	Remote Similarity	NPD7027	Phase 3
0.6902	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7727	Phase 2
0.6895	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD460	Discontinued
0.6881	Remote Similarity	NPD8114	Approved
0.6881	Remote Similarity	NPD7207	Approved
0.6881	Remote Similarity	NPD7208	Approved
0.6881	Remote Similarity	NPD7209	Approved
0.6881	Remote Similarity	NPD8115	Approved
0.6878	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3389	Approved
0.6875	Remote Similarity	NPD3394	Approved
0.6875	Remote Similarity	NPD3393	Approved
0.6869	Remote Similarity	NPD6164	Phase 2
0.6869	Remote Similarity	NPD6165	Phase 2
0.6868	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5491	Phase 3
0.6847	Remote Similarity	NPD5489	Phase 1
0.6845	Remote Similarity	NPD5475	Discontinued
0.6842	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5146	Suspended
0.6842	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD3431	Approved
0.6837	Remote Similarity	NPD3430	Approved
0.6831	Remote Similarity	NPD5400	Approved
0.6829	Remote Similarity	NPD1600	Suspended
0.6827	Remote Similarity	NPD5293	Phase 2
0.6825	Remote Similarity	NPD3505	Approved
0.6825	Remote Similarity	NPD3506	Approved
0.6824	Remote Similarity	NPD3385	Approved
0.6821	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6470	Phase 3
0.6809	Remote Similarity	NPD482	Approved
0.6809	Remote Similarity	NPD4883	Approved
0.6805	Remote Similarity	NPD1541	Approved
0.6804	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6249	Phase 2
0.68	Remote Similarity	NPD6248	Phase 2
0.6798	Remote Similarity	NPD3947	Discontinued
0.6798	Remote Similarity	NPD3100	Discontinued
0.6798	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4076	Approved
0.6789	Remote Similarity	NPD4079	Approved
0.6786	Remote Similarity	NPD947	Approved
0.6786	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5003	Discontinued
0.678	Remote Similarity	NPD6459	Phase 2
0.678	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD2837	Discontinued
0.6772	Remote Similarity	NPD5104	Approved
0.6772	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4334	Discontinued
0.6766	Remote Similarity	NPD4600	Approved
0.6766	Remote Similarity	NPD4601	Approved
0.6763	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.676	Remote Similarity	NPD3835	Phase 3
0.676	Remote Similarity	NPD3833	Phase 3
0.6758	Remote Similarity	NPD6142	Phase 3
0.6753	Remote Similarity	NPD6217	Discontinued
0.6753	Remote Similarity	NPD5444	Phase 1
0.675	Remote Similarity	NPD4364	Phase 1
0.675	Remote Similarity	NPD465	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4506	Discontinued
0.6746	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD6242	Discontinued
0.6743	Remote Similarity	NPD1722	Approved
0.6742	Remote Similarity	NPD4942	Approved
0.6736	Remote Similarity	NPD2091	Phase 2
0.6736	Remote Similarity	NPD2096	Phase 2
0.6733	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7878	Phase 2
0.6724	Remote Similarity	NPD786	Approved
0.672	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5426	Phase 3
0.6714	Remote Similarity	NPD4854	Phase 3
0.6702	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6787	Phase 2
0.6699	Remote Similarity	NPD7232	Discontinued
0.6686	Remote Similarity	NPD4880	Discontinued
0.6686	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1683	Approved
0.6684	Remote Similarity	NPD2844	Phase 3
0.6684	Remote Similarity	NPD5021	Discontinued
0.6684	Remote Similarity	NPD1534	Approved
0.6684	Remote Similarity	NPD2092	Phase 2

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