NPASS Compound

Structure

NPC470951 OpenBabel07101718222D 75 80 0 0 0 0 0 0 0 0999 V2000 -6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 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 -6.0622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 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 -8.6603 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 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 -11.2583 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 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 -10.3923 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 -10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 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 -9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 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 -11.2583 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 -11.2583 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -4.0000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -5.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -1.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -6.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -4.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 4 2 0 0 0 0 1 25 1 0 0 0 0 2 5 2 0 0 0 0 2 26 1 0 0 0 0 3 6 2 0 0 0 0 3 27 1 0 0 0 0 4 42 1 0 0 0 0 5 43 1 0 0 0 0 6 44 1 0 0 0 0 7 10 1 0 0 0 0 7 25 1 0 0 0 0 8 11 1 0 0 0 0 8 26 1 0 0 0 0 9 12 1 0 0 0 0 9 27 1 0 0 0 0 10 58 1 0 0 0 0 11 59 1 0 0 0 0 12 60 1 0 0 0 0 13 28 2 0 0 0 0 13 31 1 0 0 0 0 14 29 2 0 0 0 0 14 32 1 0 0 0 0 15 25 2 0 0 0 0 15 33 1 0 0 0 0 16 26 2 0 0 0 0 16 34 1 0 0 0 0 17 27 2 0 0 0 0 17 35 1 0 0 0 0 18 28 1 0 0 0 0 18 36 2 0 0 0 0 19 29 1 0 0 0 0 19 37 2 0 0 0 0 20 30 2 0 0 0 0 20 38 1 0 0 0 0 21 28 1 0 0 0 0 21 39 1 0 0 0 0 22 29 1 0 0 0 0 22 40 1 0 0 0 0 23 30 1 0 0 0 0 23 41 1 0 0 0 0 24 30 1 0 0 0 0 24 45 2 0 0 0 0 31 32 1 0 0 0 0 31 46 2 0 0 0 0 32 47 2 0 0 0 0 33 42 2 0 0 0 0 33 52 1 0 0 0 0 34 43 2 0 0 0 0 34 53 1 0 0 0 0 35 44 2 0 0 0 0 35 54 1 0 0 0 0 36 46 1 0 0 0 0 36 55 1 0 0 0 0 37 47 1 0 0 0 0 37 56 1 0 0 0 0 38 48 2 0 0 0 0 38 57 1 0 0 0 0 39 49 1 0 0 0 0 39 61 2 0 0 0 0 40 50 1 0 0 0 0 40 62 2 0 0 0 0 41 51 1 0 0 0 0 41 63 2 0 0 0 0 42 64 1 0 0 0 0 43 65 1 0 0 0 0 44 75 1 0 0 0 0 45 48 1 0 0 0 0 45 75 1 0 0 0 0 46 66 1 0 0 0 0 47 67 1 0 0 0 0 48 68 1 0 0 0 0 49 58 2 3 0 0 0 49 69 1 0 0 0 0 50 60 2 3 0 0 0 50 70 1 0 0 0 0 51 59 2 3 0 0 0 51 71 1 0 0 0 0 61 72 1 0 0 0 0 62 73 1 0 0 0 0 63 74 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.27
Volume:	468.991
LogP:	3.806
LogD:	3.471
LogS:	-5.068
# Rotatable Bonds:	1
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	6.552
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.233
MDCK Permeability:	1.066313598130364e-05
Pgp-inhibitor:	0.221
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.06
30% Bioavailability (F30%):	0.942

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.825
Plasma Protein Binding (PPB):	83.73265075683594%
Volume Distribution (VD):	1.132
Pgp-substrate:	10.877388954162598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.385
CYP2C19-inhibitor:	0.3
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.463
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.265
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.726

ADMET: Excretion

Clearance (CL):	9.392
Half-life (T1/2):	0.278

ADMET: Toxicity

hERG Blockers:	0.977
Human Hepatotoxicity (H-HT):	0.508
Drug-inuced Liver Injury (DILI):	0.842
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.748
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.938
Carcinogencity:	0.629
Eye Corrosion:	0.036
Eye Irritation:	0.056
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC470951

Natural Product ID:	NPC470951
*Common Name:**	Sesquibastadin 1
IUPAC Name:	(2E)-3-[3-bromo-5-[3-bromo-5-[(2E)-3-[2-[3-bromo-4-[3-bromo-5-[(2E)-3-[2-(3-bromo-4-hydroxyphenyl)ethylamino]-2-hydroxyimino-3-oxopropyl]-2-hydroxyphenoxy]phenyl]ethylamino]-2-hydroxyimino-3-oxopropyl]-2-hydroxyphenyl]-4-hydroxyphenyl]-N-[2-(3-bromo-4-hydroxyphenyl)ethyl]-2-hydroxyiminopropanamide
Synonyms:	Sesquibastadin 1
Standard InCHIKey:	VRWFLNVDDMVVDA-OFMCOEKFSA-N
Standard InCHI:	InChI=1S/C51H44Br6N6O12/c52-33-15-25(1-4-42(33)64)7-10-58-49(69)39(61-72)21-28-13-31(46(66)36(55)18-28)32-14-29(19-37(56)47(32)67)22-40(62-73)50(70)60-12-9-27-3-6-44(35(54)17-27)75-45-24-30(20-38(57)48(45)68)23-41(63-74)51(71)59-11-8-26-2-5-43(65)34(53)16-26/h1-6,13-20,24,64-68,72-74H,7-12,21-23H2,(H,58,69)(H,59,71)(H,60,70)/b61-39+,62-40+,63-41+
SMILES:	O/N=C(/C(=NCCc1ccc(c(c1)Br)Oc1cc(C/C(=NO)/C(=NCCc2ccc(c(c2)Br)O)O)cc(c1O)Br)O)Cc1cc(Br)c(c(c1)c1cc(C/C(=NO)/C(=NCCc2ccc(c(c2)Br)O)O)cc(c1O)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333163
PubChem CID:	71524406
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers [CHEMONTID:0001845] Bromodiphenyl ethers

*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
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[2089117]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23249297]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Bismarck archipelago	n.a.	PMID[7623047]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[8904842]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988595]
NPO16920	Ianthella basta	Species	Ianthellidae	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	22

Activity Type	# Activity
Individual Protein	20
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1660	Individual Protein	NUAK family SNF1-like kinase 1	Homo sapiens	IC50	=	1700.0	nM	PMID[476018]
NPT1432	Individual Protein	Serine/threonine-protein kinase Aurora-A	Homo sapiens	IC50	=	2600.0	nM	PMID[476018]
NPT1433	Individual Protein	Serine/threonine-protein kinase Aurora-B	Homo sapiens	IC50	=	2300.0	nM	PMID[476018]
NPT1434	Individual Protein	Serine/threonine-protein kinase B-raf	Homo sapiens	IC50	=	1700.0	nM	PMID[476018]
NPT2571	Individual Protein	Mitogen-activated protein kinase kinase kinase 8	Homo sapiens	IC50	=	1300.0	nM	PMID[476018]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	=	600.0	nM	PMID[476018]
NPT2572	Individual Protein	Ephrin type-B receptor 4	Homo sapiens	IC50	=	3400.0	nM	PMID[476018]
NPT286	Individual Protein	Receptor protein-tyrosine kinase erbB-2	Homo sapiens	IC50	=	2100.0	nM	PMID[476018]
NPT1650	Individual Protein	Tyrosine-protein kinase receptor FLT3	Homo sapiens	IC50	=	1400.0	nM	PMID[476018]
NPT1438	Individual Protein	Insulin-like growth factor I receptor	Homo sapiens	IC50	=	1000.0	nM	PMID[476018]
NPT1436	Individual Protein	Focal adhesion kinase 1	Homo sapiens	IC50	=	3500.0	nM	PMID[476018]
NPT2574	Individual Protein	Insulin receptor	Homo sapiens	IC50	=	1400.0	nM	PMID[476018]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	=	800.0	nM	PMID[476018]
NPT2575	Individual Protein	Platelet-derived growth factor receptor beta	Homo sapiens	IC50	=	4000.0	nM	PMID[476018]
NPT1702	Individual Protein	Serine/threonine-protein kinase PLK4	Homo sapiens	IC50	=	700.0	nM	PMID[476018]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	=	700.0	nM	PMID[476018]
NPT2576	Individual Protein	Tyrosine-protein kinase TIE-2	Homo sapiens	IC50	=	600.0	nM	PMID[476018]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	IC50	=	600.0	nM	PMID[476018]
NPT2573	Individual Protein	Vascular endothelial growth factor receptor 3	Homo sapiens	IC50	=	1600.0	nM	PMID[476018]
NPT3814	Protein Complex	Cyclin-dependent kinase 2/cyclin A	Homo sapiens	IC50	=	6500.0	nM	PMID[476018]
NPT1560	Protein Complex	Cyclin-dependent kinase 4/cyclin D1	Homo sapiens	IC50	=	1400.0	nM	PMID[476018]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	IC50	=	6400.0	nM	PMID[476018]

☑ 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 NPC470951 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	472
0.1-0.2	2409
0.2-0.3	11910
0.3-0.4	7307
0.4-0.5	7949
0.5-0.6	10464
0.6-0.7	2097
0.7-0.8	58
0.8-0.85	7
0.85-0.9	16
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC225130
0.9231	High Similarity	NPC469979
0.9176	High Similarity	NPC126128
0.9176	High Similarity	NPC473462
0.9176	High Similarity	NPC110454
0.9176	High Similarity	NPC207819
0.9176	High Similarity	NPC298981
0.9123	High Similarity	NPC290534
0.9118	High Similarity	NPC226001
0.9017	High Similarity	NPC301941
0.9017	High Similarity	NPC214188
0.9017	High Similarity	NPC74618
0.8864	High Similarity	NPC49172
0.8814	High Similarity	NPC144823
0.88	High Similarity	NPC475283
0.88	High Similarity	NPC152205
0.8764	High Similarity	NPC82741
0.8764	High Similarity	NPC141405
0.8764	High Similarity	NPC473409
0.8743	High Similarity	NPC475396
0.8708	High Similarity	NPC471591
0.8603	High Similarity	NPC473892
0.8603	High Similarity	NPC475658
0.8525	High Similarity	NPC469721
0.8523	High Similarity	NPC475615
0.8449	Intermediate Similarity	NPC156055
0.8443	Intermediate Similarity	NPC475432
0.8432	Intermediate Similarity	NPC469731
0.8246	Intermediate Similarity	NPC473738
0.7943	Intermediate Similarity	NPC123848
0.7877	Intermediate Similarity	NPC90984
0.7692	Intermediate Similarity	NPC474128
0.7647	Intermediate Similarity	NPC222039
0.7647	Intermediate Similarity	NPC100478
0.7525	Intermediate Similarity	NPC254581
0.7514	Intermediate Similarity	NPC179250
0.7514	Intermediate Similarity	NPC50380
0.7443	Intermediate Similarity	NPC258222
0.7416	Intermediate Similarity	NPC275027
0.7414	Intermediate Similarity	NPC5462
0.7401	Intermediate Similarity	NPC7398
0.7333	Intermediate Similarity	NPC107602
0.7305	Intermediate Similarity	NPC474091
0.7278	Intermediate Similarity	NPC156311
0.7191	Intermediate Similarity	NPC470935
0.7191	Intermediate Similarity	NPC471032
0.7167	Intermediate Similarity	NPC127402
0.716	Intermediate Similarity	NPC475735
0.716	Intermediate Similarity	NPC114102
0.7135	Intermediate Similarity	NPC88896
0.7126	Intermediate Similarity	NPC156854
0.7126	Intermediate Similarity	NPC134431
0.7107	Intermediate Similarity	NPC41122
0.7107	Intermediate Similarity	NPC318805
0.7101	Intermediate Similarity	NPC210655
0.7081	Intermediate Similarity	NPC38980
0.7076	Intermediate Similarity	NPC73656
0.7072	Intermediate Similarity	NPC52475
0.7056	Intermediate Similarity	NPC109968
0.7039	Intermediate Similarity	NPC115144
0.7039	Intermediate Similarity	NPC277857
0.7033	Intermediate Similarity	NPC18614
0.7021	Intermediate Similarity	NPC268503
0.7021	Intermediate Similarity	NPC42549
0.7021	Intermediate Similarity	NPC256012
0.7021	Intermediate Similarity	NPC250846
0.7021	Intermediate Similarity	NPC317272
0.7021	Intermediate Similarity	NPC240841
0.7018	Intermediate Similarity	NPC214869
0.7006	Intermediate Similarity	NPC135349
0.7005	Intermediate Similarity	NPC22115
0.7005	Intermediate Similarity	NPC275680
0.7	Intermediate Similarity	NPC35961
0.7	Intermediate Similarity	NPC195749
0.7	Intermediate Similarity	NPC262297
0.7	Intermediate Similarity	NPC52029
0.6994	Remote Similarity	NPC141023
0.6978	Remote Similarity	NPC477612
0.6965	Remote Similarity	NPC234318
0.6959	Remote Similarity	NPC473724
0.695	Remote Similarity	NPC30182
0.695	Remote Similarity	NPC85381
0.695	Remote Similarity	NPC478092
0.695	Remote Similarity	NPC478091
0.695	Remote Similarity	NPC473589
0.6944	Remote Similarity	NPC95652
0.6944	Remote Similarity	NPC150714
0.6941	Remote Similarity	NPC155838
0.6936	Remote Similarity	NPC71888
0.6936	Remote Similarity	NPC303993
0.6936	Remote Similarity	NPC120114
0.6923	Remote Similarity	NPC304630
0.6923	Remote Similarity	NPC47672
0.6923	Remote Similarity	NPC17837
0.6919	Remote Similarity	NPC157333
0.6914	Remote Similarity	NPC213471
0.691	Remote Similarity	NPC78530
0.6904	Remote Similarity	NPC95426
0.6904	Remote Similarity	NPC302245
0.6904	Remote Similarity	NPC16357
0.6902	Remote Similarity	NPC233926
0.6902	Remote Similarity	NPC279406
0.6902	Remote Similarity	NPC226809
0.69	Remote Similarity	NPC478093
0.6893	Remote Similarity	NPC61783
0.6893	Remote Similarity	NPC20520
0.6888	Remote Similarity	NPC30779
0.6882	Remote Similarity	NPC186898
0.6882	Remote Similarity	NPC251571
0.6879	Remote Similarity	NPC189482
0.6875	Remote Similarity	NPC108434
0.6875	Remote Similarity	NPC231371
0.6875	Remote Similarity	NPC475215
0.6869	Remote Similarity	NPC139783
0.6869	Remote Similarity	NPC65312
0.6865	Remote Similarity	NPC224161
0.6864	Remote Similarity	NPC28476
0.6864	Remote Similarity	NPC133407
0.6857	Remote Similarity	NPC309667
0.6856	Remote Similarity	NPC32064
0.6854	Remote Similarity	NPC470372
0.6851	Remote Similarity	NPC126291
0.6839	Remote Similarity	NPC474051
0.6837	Remote Similarity	NPC286119
0.6836	Remote Similarity	NPC477837
0.6836	Remote Similarity	NPC477838
0.6831	Remote Similarity	NPC321657
0.6831	Remote Similarity	NPC211561
0.6831	Remote Similarity	NPC318373
0.6831	Remote Similarity	NPC476969
0.6828	Remote Similarity	NPC46335
0.6818	Remote Similarity	NPC204848
0.6818	Remote Similarity	NPC41473
0.6818	Remote Similarity	NPC312770
0.6818	Remote Similarity	NPC160607
0.6818	Remote Similarity	NPC14600
0.6813	Remote Similarity	NPC202742
0.6813	Remote Similarity	NPC263940
0.6813	Remote Similarity	NPC108811
0.6813	Remote Similarity	NPC76412
0.6813	Remote Similarity	NPC82917
0.6813	Remote Similarity	NPC58190
0.6813	Remote Similarity	NPC204770
0.6813	Remote Similarity	NPC70409
0.6813	Remote Similarity	NPC18185
0.6813	Remote Similarity	NPC170103
0.6813	Remote Similarity	NPC294558
0.6813	Remote Similarity	NPC236202
0.6813	Remote Similarity	NPC262911
0.6811	Remote Similarity	NPC56635
0.6802	Remote Similarity	NPC90998
0.6802	Remote Similarity	NPC222661
0.6802	Remote Similarity	NPC181796
0.6802	Remote Similarity	NPC279228
0.6802	Remote Similarity	NPC42663
0.6802	Remote Similarity	NPC8836
0.6802	Remote Similarity	NPC285931
0.6802	Remote Similarity	NPC182052
0.6802	Remote Similarity	NPC7715
0.6802	Remote Similarity	NPC258657
0.6802	Remote Similarity	NPC290005
0.6802	Remote Similarity	NPC49075
0.6802	Remote Similarity	NPC251735
0.6802	Remote Similarity	NPC271013
0.6802	Remote Similarity	NPC290582
0.6802	Remote Similarity	NPC311973
0.6802	Remote Similarity	NPC229373
0.6802	Remote Similarity	NPC328155
0.6802	Remote Similarity	NPC217748
0.6802	Remote Similarity	NPC223690
0.6802	Remote Similarity	NPC239824
0.6802	Remote Similarity	NPC15414
0.6802	Remote Similarity	NPC185639
0.6802	Remote Similarity	NPC54654
0.6802	Remote Similarity	NPC104196
0.68	Remote Similarity	NPC66840
0.68	Remote Similarity	NPC256307
0.68	Remote Similarity	NPC206900
0.6791	Remote Similarity	NPC202104
0.6791	Remote Similarity	NPC206736
0.6791	Remote Similarity	NPC195766
0.6784	Remote Similarity	NPC124626
0.6784	Remote Similarity	NPC153990
0.6784	Remote Similarity	NPC116465
0.6784	Remote Similarity	NPC212237
0.6782	Remote Similarity	NPC313737
0.6782	Remote Similarity	NPC303144
0.6782	Remote Similarity	NPC6854
0.6782	Remote Similarity	NPC285078
0.678	Remote Similarity	NPC299583
0.678	Remote Similarity	NPC48956
0.6776	Remote Similarity	NPC281549
0.6776	Remote Similarity	NPC20757
0.6776	Remote Similarity	NPC227516
0.6774	Remote Similarity	NPC115203
0.6768	Remote Similarity	NPC254441
0.6768	Remote Similarity	NPC167116
0.6768	Remote Similarity	NPC274716
0.6761	Remote Similarity	NPC474587
0.6761	Remote Similarity	NPC475132

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 NPC470951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	933
0.2-0.3	1445
0.3-0.4	2862
0.4-0.5	2236
0.5-0.6	1251
0.6-0.7	173
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7065	Intermediate Similarity	NPD8095	Phase 1
0.7006	Intermediate Similarity	NPD6331	Phase 2
0.691	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4010	Discontinued
0.6802	Remote Similarity	NPD8053	Approved
0.6802	Remote Similarity	NPD8054	Approved
0.6724	Remote Similarity	NPD7477	Discontinued
0.6724	Remote Similarity	NPD2674	Phase 3
0.6721	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8070	Approved
0.6686	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD6072	Discontinued
0.663	Remote Similarity	NPD52	Approved
0.663	Remote Similarity	NPD7526	Approved
0.663	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD2161	Phase 2
0.6576	Remote Similarity	NPD4123	Phase 3
0.6571	Remote Similarity	NPD3145	Approved
0.6571	Remote Similarity	NPD3144	Approved
0.655	Remote Similarity	NPD1669	Approved
0.6545	Remote Similarity	NPD7833	Phase 2
0.6545	Remote Similarity	NPD7831	Phase 2
0.6545	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2802	Phase 3
0.6519	Remote Similarity	NPD7153	Discontinued
0.6508	Remote Similarity	NPD5722	Discontinued
0.6492	Remote Similarity	NPD7773	Phase 2
0.6474	Remote Similarity	NPD5772	Approved
0.6474	Remote Similarity	NPD5773	Approved
0.6455	Remote Similarity	NPD7438	Suspended
0.6453	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7906	Approved
0.6447	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD8251	Approved
0.6447	Remote Similarity	NPD8252	Approved
0.6447	Remote Similarity	NPD8099	Discontinued
0.6444	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2157	Approved
0.6417	Remote Similarity	NPD2122	Discontinued
0.6414	Remote Similarity	NPD8156	Discontinued
0.6402	Remote Similarity	NPD4678	Approved
0.6402	Remote Similarity	NPD4675	Approved
0.6398	Remote Similarity	NPD7019	Approved
0.6398	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD7020	Approved
0.6398	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD3778	Approved
0.6368	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD4005	Discontinued
0.6348	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD27	Approved
0.6345	Remote Similarity	NPD2489	Approved
0.6343	Remote Similarity	NPD6584	Phase 3
0.6339	Remote Similarity	NPD7037	Approved
0.6337	Remote Similarity	NPD7311	Approved
0.6337	Remote Similarity	NPD7313	Approved
0.6337	Remote Similarity	NPD7312	Approved
0.6337	Remote Similarity	NPD7310	Approved
0.6322	Remote Similarity	NPD2922	Phase 1
0.6321	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD1558	Phase 1
0.6307	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD7309	Approved
0.6302	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD5929	Approved
0.6294	Remote Similarity	NPD6687	Approved
0.6294	Remote Similarity	NPD6688	Approved
0.6292	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5111	Phase 2
0.6292	Remote Similarity	NPD5110	Phase 2
0.6292	Remote Similarity	NPD5109	Approved
0.6289	Remote Similarity	NPD4055	Discovery
0.6284	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD1375	Discontinued
0.6264	Remote Similarity	NPD4108	Discontinued
0.6257	Remote Similarity	NPD6087	Phase 1
0.6256	Remote Similarity	NPD4577	Approved
0.6256	Remote Similarity	NPD4578	Approved
0.625	Remote Similarity	NPD4433	Discontinued
0.6244	Remote Similarity	NPD4663	Approved
0.6244	Remote Similarity	NPD3051	Approved
0.6237	Remote Similarity	NPD5241	Discontinued
0.623	Remote Similarity	NPD6502	Phase 2
0.6223	Remote Similarity	NPD4739	Approved
0.6223	Remote Similarity	NPD7447	Phase 1
0.6222	Remote Similarity	NPD1613	Approved
0.6222	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4162	Approved
0.6216	Remote Similarity	NPD5177	Phase 3
0.6215	Remote Similarity	NPD1712	Approved
0.6214	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD2970	Approved
0.6212	Remote Similarity	NPD2969	Approved
0.6209	Remote Similarity	NPD6895	Approved
0.6209	Remote Similarity	NPD6896	Approved
0.6205	Remote Similarity	NPD3453	Discontinued
0.6201	Remote Similarity	NPD5718	Phase 2
0.6176	Remote Similarity	NPD3337	Discontinued
0.6171	Remote Similarity	NPD6582	Phase 2
0.6171	Remote Similarity	NPD6583	Phase 3
0.617	Remote Similarity	NPD2420	Approved
0.617	Remote Similarity	NPD2421	Approved
0.6169	Remote Similarity	NPD4873	Discontinued
0.6162	Remote Similarity	NPD7608	Discontinued
0.616	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD7451	Discontinued
0.615	Remote Similarity	NPD3692	Discontinued
0.615	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD4666	Phase 3
0.6138	Remote Similarity	NPD4584	Approved
0.6138	Remote Similarity	NPD3985	Discontinued
0.6134	Remote Similarity	NPD8455	Phase 2
0.6133	Remote Similarity	NPD4060	Phase 1
0.6129	Remote Similarity	NPD3060	Approved
0.6127	Remote Similarity	NPD7549	Discontinued
0.6117	Remote Similarity	NPD3845	Phase 1
0.6114	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD6184	Discontinued
0.6106	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD2183	Approved
0.6105	Remote Similarity	NPD4319	Phase 2
0.6105	Remote Similarity	NPD6090	Discontinued
0.6105	Remote Similarity	NPD2184	Approved
0.6103	Remote Similarity	NPD6063	Approved
0.6101	Remote Similarity	NPD7671	Approved
0.6101	Remote Similarity	NPD7672	Approved
0.6094	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5709	Phase 3
0.6089	Remote Similarity	NPD42	Phase 2
0.6089	Remote Similarity	NPD6042	Phase 2
0.6085	Remote Similarity	NPD7212	Phase 2
0.6085	Remote Similarity	NPD7213	Phase 3
0.6077	Remote Similarity	NPD4475	Approved
0.6077	Remote Similarity	NPD4474	Approved
0.6075	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.607	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD3296	Phase 1
0.6061	Remote Similarity	NPD6746	Phase 2
0.6056	Remote Similarity	NPD3027	Phase 3
0.6053	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD2977	Approved
0.6051	Remote Similarity	NPD2978	Approved
0.6045	Remote Similarity	NPD5311	Approved
0.6045	Remote Similarity	NPD5310	Approved
0.6043	Remote Similarity	NPD6674	Discontinued
0.6042	Remote Similarity	NPD4003	Phase 3
0.6038	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD2804	Phase 1
0.6033	Remote Similarity	NPD7119	Phase 2
0.6032	Remote Similarity	NPD6666	Approved
0.6032	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6667	Approved
0.6029	Remote Similarity	NPD3823	Discontinued
0.6023	Remote Similarity	NPD2233	Approved
0.6023	Remote Similarity	NPD2232	Approved
0.6023	Remote Similarity	NPD2230	Approved
0.6022	Remote Similarity	NPD7030	Discontinued
0.6021	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.602	Remote Similarity	NPD2296	Approved
0.602	Remote Similarity	NPD2898	Approved
0.6019	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7546	Discontinued
0.6	Remote Similarity	NPD2488	Approved
0.6	Remote Similarity	NPD4908	Phase 1
0.6	Remote Similarity	NPD5283	Phase 1
0.6	Remote Similarity	NPD6071	Discontinued
0.6	Remote Similarity	NPD2490	Approved
0.6	Remote Similarity	NPD8151	Discontinued
0.6	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.599	Remote Similarity	NPD6030	Approved
0.599	Remote Similarity	NPD6031	Approved
0.599	Remote Similarity	NPD7427	Discontinued
0.5989	Remote Similarity	NPD839	Approved
0.5989	Remote Similarity	NPD840	Approved
0.5979	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD2677	Approved
0.5978	Remote Similarity	NPD4097	Suspended
0.5978	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD228	Approved
0.5971	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.597	Remote Similarity	NPD4083	Discontinued
0.597	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD7095	Approved
0.5967	Remote Similarity	NPD1024	Discontinued
0.5961	Remote Similarity	NPD7177	Discontinued
0.596	Remote Similarity	NPD5604	Discontinued
0.5957	Remote Similarity	NPD4236	Phase 3
0.5957	Remote Similarity	NPD4237	Approved

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