NPASS Compound

Structure

CID255447 OpenBabel06191716062D 61 65 0 0 1 0 0 0 0 0999 V2000 1.9153 5.0495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4153 4.1835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2460 -4.1835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4967 -1.2503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6122 0.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9787 5.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9509 -0.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7462 0.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6122 1.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7199 4.4766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2716 6.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0849 -0.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9509 -1.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4604 0.6966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8801 0.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7462 2.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7539 4.2178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3057 5.8908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2188 -0.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0849 -2.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7721 1.4220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9833 -0.1822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0141 2.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0809 4.6660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3528 -2.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8392 -3.7001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4153 4.1835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7460 -3.3174 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5308 -0.9914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8801 1.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0468 4.9249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2188 -1.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1481 1.9153 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8221 3.7001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5132 -1.9153 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1305 0.9914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9153 -3.3174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9153 3.3174 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8221 -3.7001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1481 -1.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5308 0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7460 3.3174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5132 1.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8392 3.7001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 -0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8306 -3.8306 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.5393 -2.7087 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.6613 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1220 -2.7087 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.5393 2.7087 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8306 3.8306 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1220 2.7087 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 1.4153 -4.1835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0809 -4.6660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0141 -2.4153 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4967 1.2503 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2460 4.1835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3528 2.4153 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5804 4.6660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8354 -1.2503 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 14 21 1 0 0 0 0 14 22 1 0 0 0 0 15 30 2 0 0 0 0 16 30 1 0 0 0 0 17 31 2 0 0 0 0 18 31 1 0 0 0 0 19 32 2 0 0 0 0 20 32 1 0 0 0 0 22 53 1 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 37 1 0 0 0 0 26 46 1 0 0 0 0 28 3 1 1 0 0 0 28 39 1 0 0 0 0 28 47 1 0 0 0 0 29 4 1 1 0 0 0 29 40 1 0 0 0 0 29 48 1 0 0 0 0 33 23 1 1 0 0 0 33 41 1 0 0 0 0 33 50 1 0 0 0 0 34 24 1 1 0 0 0 34 42 1 0 0 0 0 34 51 1 0 0 0 0 35 25 1 1 0 0 0 35 45 1 0 0 0 0 35 49 1 0 0 0 0 36 21 1 1 0 0 0 36 43 1 0 0 0 0 36 53 1 0 0 0 0 37 49 2 3 0 0 0 37 54 1 0 0 0 0 38 27 1 1 0 0 0 38 44 1 0 0 0 0 38 52 1 0 0 0 0 39 46 2 3 0 0 0 39 55 1 0 0 0 0 40 47 2 3 0 0 0 40 56 1 0 0 0 0 41 48 2 3 0 0 0 41 57 1 0 0 0 0 42 50 2 3 0 0 0 42 58 1 0 0 0 0 43 52 2 3 0 0 0 43 59 1 0 0 0 0 44 51 2 3 0 0 0 44 60 1 0 0 0 0 45 53 1 0 0 0 0 45 61 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	836.42
Volume:	857.57
LogP:	3.267
LogD:	2.473
LogS:	-3.349
# Rotatable Bonds:	7
TPSA:	234.48
# H-Bond Aceptor:	16
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.187
Synthetic Accessibility Score:	5.726
Fsp3:	0.422
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.872
MDCK Permeability:	5.9663951105903834e-05
Pgp-inhibitor:	0.725
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.734
20% Bioavailability (F20%):	0.611
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	47.95697784423828%
Volume Distribution (VD):	0.776
Pgp-substrate:	34.291873931884766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.038
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.12
CYP2D6-inhibitor:	0.309
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.139
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	1.239
Half-life (T1/2):	0.778

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.589
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.218
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC255447

Natural Product ID:	NPC255447
*Common Name:**	Microtoenin B
IUPAC Name:	(3S,9S,12S,15S,18S,21S,24S)-3,15,18-tribenzyl-9,12-dimethyl-21-propan-2-yl-1,4,7,10,13,16,19,22-octazabicyclo[22.3.0]heptacosane-2,5,8,11,14,17,20,23-octone
Synonyms:	microtoenin B
Standard InCHIKey:	OQEDQPROIDLGAM-SRZLETEKSA-N
Standard InCHI:	InChI=1S/C45H56N8O8/c1-27(2)38-44(60)51-34(24-31-17-10-6-11-18-31)42(58)50-33(23-30-15-8-5-9-16-30)41(57)48-29(4)40(56)47-28(3)39(55)46-26-37(54)49-35(25-32-19-12-7-13-20-32)45(61)53-22-14-21-36(53)43(59)52-38/h5-13,15-20,27-29,33-36,38H,14,21-26H2,1-4H3,(H,46,55)(H,47,56)(H,48,57)(H,49,54)(H,50,58)(H,51,60)(H,52,59)/t28-,29-,33-,34-,35-,36-,38-/m0/s1
SMILES:	OC1=N[C@@H](Cc2ccccc2)C(=O)N2CCC[C@H]2C(=N[C@@H](C(C)C)C(=N[C@H](C(=N[C@H](C(=N[C@H](C(=N[C@H](C(=NC1)O)C)O)C)O)Cc1ccccc1)O)Cc1ccccc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502053
PubChem CID:	11434381
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO21245	Microtoena prainiana	Species	Lamiaceae	Eukaryota	stems	n.a.	n.a.	PMID[15217277]
NPO21245	Microtoena prainiana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21245	Microtoena prainiana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100.0	ug.mL-1	PMID[534805]

☑ 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 NPC255447 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	160
0.1-0.2	843
0.2-0.3	4240
0.3-0.4	19598
0.4-0.5	14411
0.5-0.6	2483
0.6-0.7	565
0.7-0.8	307
0.8-0.85	59
0.85-0.9	23
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9516	High Similarity	NPC473322
0.9206	High Similarity	NPC111428
0.918	High Similarity	NPC200964
0.9016	High Similarity	NPC470546
0.8984	High Similarity	NPC200589
0.8934	High Similarity	NPC470545
0.8852	High Similarity	NPC470544
0.881	High Similarity	NPC6975
0.8692	High Similarity	NPC300315
0.8651	High Similarity	NPC202521
0.8626	High Similarity	NPC130309
0.8571	High Similarity	NPC476990
0.8548	High Similarity	NPC285926
0.8548	High Similarity	NPC14672
0.8548	High Similarity	NPC315276
0.8516	High Similarity	NPC46427
0.8496	Intermediate Similarity	NPC287401
0.8478	Intermediate Similarity	NPC209509
0.8438	Intermediate Similarity	NPC252878
0.8406	Intermediate Similarity	NPC476978
0.8387	Intermediate Similarity	NPC33742
0.8385	Intermediate Similarity	NPC101719
0.838	Intermediate Similarity	NPC233702
0.8359	Intermediate Similarity	NPC71684
0.8357	Intermediate Similarity	NPC16188
0.8356	Intermediate Similarity	NPC473003
0.8333	Intermediate Similarity	NPC161069
0.8322	Intermediate Similarity	NPC202198
0.8322	Intermediate Similarity	NPC122590
0.8308	Intermediate Similarity	NPC222466
0.8296	Intermediate Similarity	NPC248283
0.8248	Intermediate Similarity	NPC132636
0.8214	Intermediate Similarity	NPC5620
0.8207	Intermediate Similarity	NPC469903
0.8175	Intermediate Similarity	NPC471265
0.8175	Intermediate Similarity	NPC471264
0.816	Intermediate Similarity	NPC35850
0.816	Intermediate Similarity	NPC276949
0.8156	Intermediate Similarity	NPC262077
0.812	Intermediate Similarity	NPC319766
0.8116	Intermediate Similarity	NPC92784
0.8116	Intermediate Similarity	NPC98424
0.8116	Intermediate Similarity	NPC470884
0.8116	Intermediate Similarity	NPC476133
0.8116	Intermediate Similarity	NPC178662
0.8112	Intermediate Similarity	NPC2501
0.811	Intermediate Similarity	NPC239357
0.8099	Intermediate Similarity	NPC138775
0.8092	Intermediate Similarity	NPC175726
0.8092	Intermediate Similarity	NPC474082
0.8079	Intermediate Similarity	NPC328649
0.8079	Intermediate Similarity	NPC141957
0.8029	Intermediate Similarity	NPC141050
0.8026	Intermediate Similarity	NPC469904
0.8014	Intermediate Similarity	NPC473002
0.8014	Intermediate Similarity	NPC52748
0.8	Intermediate Similarity	NPC269398
0.8	Intermediate Similarity	NPC263493
0.8	Intermediate Similarity	NPC476989
0.7987	Intermediate Similarity	NPC469902
0.7986	Intermediate Similarity	NPC129666
0.7958	Intermediate Similarity	NPC316008
0.7958	Intermediate Similarity	NPC322878
0.7958	Intermediate Similarity	NPC313867
0.7933	Intermediate Similarity	NPC241794
0.7929	Intermediate Similarity	NPC239762
0.7929	Intermediate Similarity	NPC163392
0.7914	Intermediate Similarity	NPC127741
0.7902	Intermediate Similarity	NPC314358
0.7895	Intermediate Similarity	NPC22746
0.7887	Intermediate Similarity	NPC314388
0.7887	Intermediate Similarity	NPC315283
0.7857	Intermediate Similarity	NPC89489
0.7821	Intermediate Similarity	NPC136797
0.7808	Intermediate Similarity	NPC473491
0.7793	Intermediate Similarity	NPC471821
0.7793	Intermediate Similarity	NPC471820
0.7793	Intermediate Similarity	NPC105717
0.7755	Intermediate Similarity	NPC162104
0.774	Intermediate Similarity	NPC254798
0.7733	Intermediate Similarity	NPC297145
0.7733	Intermediate Similarity	NPC197743
0.7724	Intermediate Similarity	NPC329761
0.7724	Intermediate Similarity	NPC225648
0.7722	Intermediate Similarity	NPC473001
0.7721	Intermediate Similarity	NPC89923
0.7721	Intermediate Similarity	NPC152850
0.7721	Intermediate Similarity	NPC239990
0.7721	Intermediate Similarity	NPC71933
0.7721	Intermediate Similarity	NPC105114
0.771	Intermediate Similarity	NPC220698
0.7708	Intermediate Similarity	NPC315266
0.7703	Intermediate Similarity	NPC261934
0.7703	Intermediate Similarity	NPC56685
0.7703	Intermediate Similarity	NPC5194
0.7692	Intermediate Similarity	NPC197682
0.7692	Intermediate Similarity	NPC77905
0.7692	Intermediate Similarity	NPC139326
0.7687	Intermediate Similarity	NPC475168
0.7687	Intermediate Similarity	NPC7817
0.7676	Intermediate Similarity	NPC476259
0.7671	Intermediate Similarity	NPC240848
0.7647	Intermediate Similarity	NPC136453
0.7643	Intermediate Similarity	NPC137627
0.7622	Intermediate Similarity	NPC168113
0.7619	Intermediate Similarity	NPC283783
0.7616	Intermediate Similarity	NPC324850
0.7606	Intermediate Similarity	NPC313694
0.7606	Intermediate Similarity	NPC242159
0.7603	Intermediate Similarity	NPC145113
0.7595	Intermediate Similarity	NPC317725
0.7595	Intermediate Similarity	NPC326407
0.7586	Intermediate Similarity	NPC471680
0.7584	Intermediate Similarity	NPC286551
0.7584	Intermediate Similarity	NPC262166
0.7569	Intermediate Similarity	NPC176226
0.7566	Intermediate Similarity	NPC244336
0.7554	Intermediate Similarity	NPC157311
0.7552	Intermediate Similarity	NPC307357
0.7552	Intermediate Similarity	NPC268841
0.7552	Intermediate Similarity	NPC46098
0.7548	Intermediate Similarity	NPC61004
0.7535	Intermediate Similarity	NPC68865
0.7533	Intermediate Similarity	NPC470902
0.7532	Intermediate Similarity	NPC471051
0.7532	Intermediate Similarity	NPC471052
0.7532	Intermediate Similarity	NPC471053
0.752	Intermediate Similarity	NPC473418
0.7519	Intermediate Similarity	NPC474584
0.7518	Intermediate Similarity	NPC477937
0.7516	Intermediate Similarity	NPC471527
0.75	Intermediate Similarity	NPC302597
0.75	Intermediate Similarity	NPC44805
0.75	Intermediate Similarity	NPC8761
0.7484	Intermediate Similarity	NPC26108
0.7484	Intermediate Similarity	NPC223207
0.7484	Intermediate Similarity	NPC477462
0.7483	Intermediate Similarity	NPC311658
0.7468	Intermediate Similarity	NPC89831
0.7467	Intermediate Similarity	NPC473341
0.7451	Intermediate Similarity	NPC469898
0.7445	Intermediate Similarity	NPC47667
0.7438	Intermediate Similarity	NPC196243
0.7436	Intermediate Similarity	NPC471771
0.7436	Intermediate Similarity	NPC290755
0.7436	Intermediate Similarity	NPC304074
0.7421	Intermediate Similarity	NPC475532
0.7403	Intermediate Similarity	NPC469901
0.7379	Intermediate Similarity	NPC469426
0.7379	Intermediate Similarity	NPC469427
0.7377	Intermediate Similarity	NPC473501
0.7377	Intermediate Similarity	NPC475439
0.7375	Intermediate Similarity	NPC165285
0.7375	Intermediate Similarity	NPC159767
0.7375	Intermediate Similarity	NPC155506
0.7372	Intermediate Similarity	NPC63931
0.7368	Intermediate Similarity	NPC169328
0.7368	Intermediate Similarity	NPC244509
0.7365	Intermediate Similarity	NPC135121
0.7364	Intermediate Similarity	NPC319579
0.7358	Intermediate Similarity	NPC230611
0.7347	Intermediate Similarity	NPC477217
0.7347	Intermediate Similarity	NPC201244
0.7323	Intermediate Similarity	NPC45033
0.7313	Intermediate Similarity	NPC310467
0.7312	Intermediate Similarity	NPC306804
0.7297	Intermediate Similarity	NPC314114
0.7296	Intermediate Similarity	NPC198254
0.7296	Intermediate Similarity	NPC274198
0.7295	Intermediate Similarity	NPC25565
0.729	Intermediate Similarity	NPC469243
0.7286	Intermediate Similarity	NPC469666
0.7273	Intermediate Similarity	NPC326349
0.7273	Intermediate Similarity	NPC323336
0.7267	Intermediate Similarity	NPC473402
0.7267	Intermediate Similarity	NPC164608
0.7267	Intermediate Similarity	NPC317362
0.7267	Intermediate Similarity	NPC318930
0.7267	Intermediate Similarity	NPC279871
0.7267	Intermediate Similarity	NPC471165
0.7255	Intermediate Similarity	NPC476268
0.7254	Intermediate Similarity	NPC246079
0.7254	Intermediate Similarity	NPC246913
0.7239	Intermediate Similarity	NPC97526
0.7239	Intermediate Similarity	NPC119652
0.7233	Intermediate Similarity	NPC129486
0.7233	Intermediate Similarity	NPC280022
0.7226	Intermediate Similarity	NPC62104
0.7226	Intermediate Similarity	NPC319320
0.7226	Intermediate Similarity	NPC1390
0.7226	Intermediate Similarity	NPC287757
0.7222	Intermediate Similarity	NPC273907
0.7222	Intermediate Similarity	NPC474811
0.7222	Intermediate Similarity	NPC475598
0.7222	Intermediate Similarity	NPC90194
0.7222	Intermediate Similarity	NPC9687
0.7222	Intermediate Similarity	NPC118099
0.7222	Intermediate Similarity	NPC79465
0.7222	Intermediate Similarity	NPC474855
0.7222	Intermediate Similarity	NPC474787

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 NPC255447 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	121
0.1-0.2	367
0.2-0.3	690
0.3-0.4	1805
0.4-0.5	3784
0.5-0.6	1869
0.6-0.7	410
0.7-0.8	93
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8682	High Similarity	NPD5339	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD8173	Phase 2
0.8444	Intermediate Similarity	NPD8172	Phase 2
0.8321	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD8643	Discontinued
0.8235	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD8323	Discontinued
0.8134	Intermediate Similarity	NPD4125	Approved
0.8092	Intermediate Similarity	NPD2584	Suspended
0.8085	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD7720	Phase 2
0.8045	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD8416	Discontinued
0.7887	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD5263	Approved
0.782	Intermediate Similarity	NPD3072	Approved
0.782	Intermediate Similarity	NPD3073	Approved
0.782	Intermediate Similarity	NPD3071	Approved
0.7817	Intermediate Similarity	NPD8076	Discontinued
0.7793	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4762	Approved
0.7744	Intermediate Similarity	NPD4761	Approved
0.7737	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6901	Phase 3
0.7724	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD6792	Phase 3
0.766	Intermediate Similarity	NPD6073	Approved
0.7651	Intermediate Similarity	NPD8315	Phase 1
0.763	Intermediate Similarity	NPD4677	Discontinued
0.7612	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4676	Approved
0.7591	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD4175	Approved
0.7536	Intermediate Similarity	NPD5759	Approved
0.7536	Intermediate Similarity	NPD4177	Approved
0.7519	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7613	Discontinued
0.75	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5725	Approved
0.7386	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5581	Approved
0.7365	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD3644	Approved
0.7364	Intermediate Similarity	NPD3642	Approved
0.7364	Intermediate Similarity	NPD3643	Approved
0.7338	Intermediate Similarity	NPD7011	Discontinued
0.7308	Intermediate Similarity	NPD8351	Phase 2
0.7286	Intermediate Similarity	NPD3626	Phase 3
0.7286	Intermediate Similarity	NPD3040	Approved
0.7273	Intermediate Similarity	NPD8265	Approved
0.7273	Intermediate Similarity	NPD6623	Phase 3
0.7254	Intermediate Similarity	NPD1330	Phase 2
0.7254	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3908	Approved
0.7215	Intermediate Similarity	NPD8303	Discontinued
0.7211	Intermediate Similarity	NPD2022	Approved
0.7208	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5747	Discontinued
0.7203	Intermediate Similarity	NPD941	Approved
0.7203	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3598	Phase 3
0.7194	Intermediate Similarity	NPD5578	Approved
0.7194	Intermediate Similarity	NPD3125	Approved
0.7194	Intermediate Similarity	NPD2031	Discontinued
0.7194	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7130	Phase 3
0.7185	Intermediate Similarity	NPD6343	Approved
0.7185	Intermediate Similarity	NPD6345	Approved
0.7183	Intermediate Similarity	NPD2046	Approved
0.7183	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2047	Approved
0.7183	Intermediate Similarity	NPD2043	Approved
0.7183	Intermediate Similarity	NPD21	Approved
0.7183	Intermediate Similarity	NPD2044	Approved
0.7183	Intermediate Similarity	NPD2051	Approved
0.7183	Intermediate Similarity	NPD2048	Approved
0.7183	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2045	Approved
0.7178	Intermediate Similarity	NPD8362	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7679	Phase 2
0.7163	Intermediate Similarity	NPD7828	Discontinued
0.7162	Intermediate Similarity	NPD2436	Approved
0.7162	Intermediate Similarity	NPD2437	Approved
0.7153	Intermediate Similarity	NPD5323	Approved
0.7143	Intermediate Similarity	NPD7512	Approved
0.7143	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7511	Approved
0.7143	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7450	Phase 2
0.7134	Intermediate Similarity	NPD7771	Discontinued
0.7133	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4126	Approved
0.7123	Intermediate Similarity	NPD6295	Approved
0.7123	Intermediate Similarity	NPD6852	Discontinued
0.7123	Intermediate Similarity	NPD6294	Approved
0.7117	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD999	Phase 2
0.7097	Intermediate Similarity	NPD8417	Discontinued
0.7095	Intermediate Similarity	NPD2088	Approved
0.7095	Intermediate Similarity	NPD2087	Approved
0.7092	Intermediate Similarity	NPD4151	Approved
0.7083	Intermediate Similarity	NPD7086	Phase 2
0.7071	Intermediate Similarity	NPD5367	Discontinued
0.7063	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5613	Approved
0.7039	Intermediate Similarity	NPD8165	Discontinued
0.7039	Intermediate Similarity	NPD6088	Approved
0.7039	Intermediate Similarity	NPD5614	Approved
0.7034	Intermediate Similarity	NPD4153	Approved
0.7014	Intermediate Similarity	NPD5299	Approved
0.6993	Remote Similarity	NPD4432	Discontinued
0.6992	Remote Similarity	NPD480	Approved
0.6986	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5991	Approved
0.6985	Remote Similarity	NPD5990	Approved
0.6972	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7599	Phase 2
0.6939	Remote Similarity	NPD5004	Approved
0.6939	Remote Similarity	NPD7510	Approved
0.6928	Remote Similarity	NPD3988	Approved
0.6928	Remote Similarity	NPD3987	Approved
0.6918	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7600	Phase 2
0.6918	Remote Similarity	NPD5296	Approved
0.6903	Remote Similarity	NPD7131	Phase 3
0.6899	Remote Similarity	NPD8019	Approved
0.6894	Remote Similarity	NPD3581	Discontinued
0.689	Remote Similarity	NPD7965	Phase 2
0.689	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3551	Approved
0.6887	Remote Similarity	NPD5265	Approved
0.6887	Remote Similarity	NPD5264	Approved
0.6884	Remote Similarity	NPD5981	Approved
0.6875	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7522	Discontinued
0.6859	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3588	Discontinued
0.6849	Remote Similarity	NPD8118	Discontinued
0.6846	Remote Similarity	NPD3480	Approved
0.6842	Remote Similarity	NPD6676	Phase 2
0.6842	Remote Similarity	NPD1967	Approved
0.6842	Remote Similarity	NPD1968	Approved
0.6839	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1348	Approved
0.6831	Remote Similarity	NPD6325	Discontinued
0.6828	Remote Similarity	NPD4794	Discontinued
0.6824	Remote Similarity	NPD8125	Discontinued
0.6824	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8240	Discontinued
0.6821	Remote Similarity	NPD6681	Discovery
0.6797	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD8352	Phase 1
0.6788	Remote Similarity	NPD8124	Phase 3
0.6788	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3123	Discovery
0.6783	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD747	Discontinued
0.6731	Remote Similarity	NPD5229	Approved
0.6731	Remote Similarity	NPD7303	Discontinued
0.6731	Remote Similarity	NPD5230	Approved
0.6726	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5717	Approved
0.6718	Remote Similarity	NPD1018	Approved
0.6714	Remote Similarity	NPD6806	Phase 1
0.6714	Remote Similarity	NPD7342	Discontinued
0.6707	Remote Similarity	NPD7485	Phase 3
0.6707	Remote Similarity	NPD7484	Phase 3
0.6705	Remote Similarity	NPD7944	Discontinued
0.6691	Remote Similarity	NPD998	Approved
0.6691	Remote Similarity	NPD2218	Phase 2
0.6691	Remote Similarity	NPD2217	Approved
0.669	Remote Similarity	NPD6408	Phase 1
0.6687	Remote Similarity	NPD8630	Approved
0.6667	Remote Similarity	NPD5024	Approved
0.6667	Remote Similarity	NPD4214	Discontinued
0.6667	Remote Similarity	NPD4621	Approved
0.6667	Remote Similarity	NPD7617	Discontinued
0.6667	Remote Similarity	NPD5187	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4619	Approved
0.6667	Remote Similarity	NPD4682	Phase 2
0.6667	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1344	Phase 2
0.6646	Remote Similarity	NPD4566	Approved
0.6646	Remote Similarity	NPD4648	Approved
0.6646	Remote Similarity	NPD4567	Approved
0.6646	Remote Similarity	NPD4646	Approved
0.6646	Remote Similarity	NPD4647	Approved
0.6641	Remote Similarity	NPD466	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