NPASS Compound

Structure

NPC469427 OpenBabel07101719132D 54 55 0 0 1 0 0 0 0 0999 V2000 -4.2841 5.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2739 4.5706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2785 -0.0718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0331 1.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5250 -3.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8997 1.2847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0363 6.5410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8224 -1.2216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2584 0.1740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3111 6.3999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3078 5.5889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0239 -1.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4657 2.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6301 2.1866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4657 3.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7944 2.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6301 4.1164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8941 -3.3996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1232 4.5989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3903 4.9582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2253 0.8916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8151 -3.6876 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.9960 1.6231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0895 5.5776 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9285 -0.2626 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7944 3.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2875 4.1164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6831 -2.4580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6128 4.3868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3644 1.3273 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8920 -0.2094 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0261 -4.6292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1810 2.5701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6259 3.2128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1479 5.3666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9212 5.0596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7859 0.1537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7929 0.5498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9470 -4.9172 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.3162 -5.2827 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.0485 3.5258 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6524 2.2482 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5136 0.7874 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0485 5.4714 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6741 4.8613 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1030 -1.1510 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2378 -2.1700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1456 2.5435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5729 3.3978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2152 6.2605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4710 5.8526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2912 -0.6683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4658 -0.1418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 9 43 1 0 0 0 0 10 44 1 0 0 0 0 11 45 1 0 0 0 0 12 46 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 26 2 0 0 0 0 17 26 1 0 0 0 0 18 22 1 0 0 0 0 18 28 1 0 0 0 0 19 26 1 0 0 0 0 22 32 1 0 0 0 0 23 6 1 1 0 0 0 23 33 1 0 0 0 0 23 43 1 0 0 0 0 24 7 1 1 0 0 0 24 35 1 0 0 0 0 24 44 1 0 0 0 0 25 8 1 6 0 0 0 25 31 1 0 0 0 0 25 54 1 0 0 0 0 27 19 1 6 0 0 0 27 34 1 0 0 0 0 27 45 1 0 0 0 0 28 46 1 0 0 0 0 28 47 2 0 0 0 0 29 20 1 6 0 0 0 29 36 1 0 0 0 0 29 41 1 0 0 0 0 30 21 1 1 0 0 0 30 38 1 0 0 0 0 30 42 1 0 0 0 0 31 37 1 0 0 0 0 31 46 1 6 0 0 0 32 39 1 0 0 0 0 32 40 1 0 0 0 0 33 41 2 3 0 0 0 33 48 1 0 0 0 0 34 42 2 3 0 0 0 34 49 1 0 0 0 0 35 45 1 0 0 0 0 35 50 2 0 0 0 0 36 44 1 0 0 0 0 36 51 2 0 0 0 0 37 43 1 0 0 0 0 37 52 2 0 0 0 0 38 53 2 0 0 0 0 38 54 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	796.37
Volume:	789.051
LogP:	3.313
LogD:	2.174
LogS:	-3.812
# Rotatable Bonds:	9
TPSA:	165.74
# H-Bond Aceptor:	14
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.3
Synthetic Accessibility Score:	5.648
Fsp3:	0.658
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.451
MDCK Permeability:	4.3616644688881934e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.46
Human Intestinal Absorption (HIA):	0.684
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.162
Plasma Protein Binding (PPB):	88.26171112060547%
Volume Distribution (VD):	0.827
Pgp-substrate:	4.126687049865723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.825
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.836
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	7.048
Half-life (T1/2):	0.416

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.969
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.194
Maximum Recommended Daily Dose:	0.087
Skin Sensitization:	0.02
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.053

Download Data

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

Natural Product: NPC469427

Natural Product ID:	NPC469427
*Common Name:**	Itralamide B
IUPAC Name:	N-[(3S,6R,9S,12R,15S,18S,19R)-6-benzyl-7,9,10,15,16,19-hexamethyl-2,5,8,11,14,17-hexaoxo-3,12-di(propan-2-yl)-1-oxa-4,7,10,13,16-pentazacyclononadec-18-yl]-4,4-dichloro-N,3-dimethylbutanamide
Synonyms:
Standard InCHIKey:	SZZBMDKRUBNFQR-ONAOHADISA-N
Standard InCHI:	InChI=1S/C38H58Cl2N6O8/c1-20(2)29-36(51)44(10)24(7)35(50)45(11)27(19-26-16-14-13-15-17-26)34(49)42-30(21(3)4)38(53)54-25(8)31(37(52)43(9)23(6)33(48)41-29)46(12)28(47)18-22(5)32(39)40/h13-17,20-25,27,29-32H,18-19H2,1-12H3,(H,41,48)(H,42,49)/t22?,23-,24-,25+,27+,29+,30-,31-/m0/s1
SMILES:	ClC(C(CC(=O)N([C@H]1[C@@H](C)OC(=O)[C@@H](N=C(O)[C@@H](Cc2ccccc2)N(C)C(=O)[C@@H](N(C(=O)[C@H](N=C([C@@H](N(C1=O)C)C)O)C(C)C)C)C)C(C)C)C)C)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078518
PubChem CID:	44479476
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10514329]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10654420]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10691708]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	palauan	n.a.	PMID[10691729]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10843570]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10924172]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10978206]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076571]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076573]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076574]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11277744]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11389621]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11430000]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473443]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11922791]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762816]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[12828459]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14575437]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1517734]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[16643028]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125217]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17441769]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18444683]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Singapore	n.a.	PMID[19093843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19489598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	eastern Caribbean	n.a.	PMID[19739598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19839606]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20030365]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	panamanian	n.a.	PMID[20158242]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Floridian	n.a.	PMID[20166701]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20936843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21138309]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2128518]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21341718]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21539315]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21806011]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21999614]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22035372]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29792428]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3924698]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[7623050]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[8699186]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9584405]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599278]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599279]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9784156]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	6000.0	nM	PMID[510912]

☑ 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 NPC469427 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	124
0.1-0.2	752
0.2-0.3	4954
0.3-0.4	22127
0.4-0.5	12494
0.5-0.6	1519
0.6-0.7	466
0.7-0.8	234
0.8-0.85	24
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469426
0.8582	High Similarity	NPC319766
0.8511	High Similarity	NPC176226
0.838	Intermediate Similarity	NPC139326
0.8369	Intermediate Similarity	NPC476259
0.8369	Intermediate Similarity	NPC239762
0.8369	Intermediate Similarity	NPC163392
0.8357	Intermediate Similarity	NPC471265
0.8357	Intermediate Similarity	NPC471264
0.8357	Intermediate Similarity	NPC127741
0.8357	Intermediate Similarity	NPC68865
0.831	Intermediate Similarity	NPC168113
0.831	Intermediate Similarity	NPC269398
0.831	Intermediate Similarity	NPC263493
0.8264	Intermediate Similarity	NPC316008
0.8264	Intermediate Similarity	NPC313867
0.8252	Intermediate Similarity	NPC197682
0.8239	Intermediate Similarity	NPC307357
0.8239	Intermediate Similarity	NPC46098
0.8239	Intermediate Similarity	NPC268841
0.8207	Intermediate Similarity	NPC314358
0.8194	Intermediate Similarity	NPC315283
0.8194	Intermediate Similarity	NPC314388
0.8169	Intermediate Similarity	NPC178662
0.8169	Intermediate Similarity	NPC476133
0.8169	Intermediate Similarity	NPC92784
0.8169	Intermediate Similarity	NPC470884
0.8169	Intermediate Similarity	NPC98424
0.8143	Intermediate Similarity	NPC287401
0.8138	Intermediate Similarity	NPC209509
0.8138	Intermediate Similarity	NPC5620
0.8125	Intermediate Similarity	NPC161069
0.8071	Intermediate Similarity	NPC246079
0.8069	Intermediate Similarity	NPC476978
0.8027	Intermediate Similarity	NPC145113
0.7973	Intermediate Similarity	NPC105717
0.7933	Intermediate Similarity	NPC162104
0.7926	Intermediate Similarity	NPC45777
0.7926	Intermediate Similarity	NPC477061
0.7919	Intermediate Similarity	NPC129666
0.791	Intermediate Similarity	NPC470546
0.7905	Intermediate Similarity	NPC135121
0.7905	Intermediate Similarity	NPC225648
0.7905	Intermediate Similarity	NPC329761
0.7905	Intermediate Similarity	NPC138775
0.7895	Intermediate Similarity	NPC470544
0.7891	Intermediate Similarity	NPC201244
0.7891	Intermediate Similarity	NPC477217
0.7883	Intermediate Similarity	NPC46427
0.7836	Intermediate Similarity	NPC470545
0.7836	Intermediate Similarity	NPC169328
0.7823	Intermediate Similarity	NPC52748
0.781	Intermediate Similarity	NPC252878
0.78	Intermediate Similarity	NPC2501
0.7778	Intermediate Similarity	NPC237420
0.7778	Intermediate Similarity	NPC310467
0.7763	Intermediate Similarity	NPC286551
0.7763	Intermediate Similarity	NPC473341
0.7754	Intermediate Similarity	NPC6975
0.7748	Intermediate Similarity	NPC7817
0.7748	Intermediate Similarity	NPC475168
0.7746	Intermediate Similarity	NPC130309
0.7737	Intermediate Similarity	NPC202521
0.7733	Intermediate Similarity	NPC240848
0.7733	Intermediate Similarity	NPC471820
0.7733	Intermediate Similarity	NPC471821
0.7718	Intermediate Similarity	NPC262077
0.7708	Intermediate Similarity	NPC248283
0.7677	Intermediate Similarity	NPC197743
0.7677	Intermediate Similarity	NPC297145
0.7673	Intermediate Similarity	NPC209463
0.7664	Intermediate Similarity	NPC476990
0.7651	Intermediate Similarity	NPC315266
0.7647	Intermediate Similarity	NPC122590
0.7643	Intermediate Similarity	NPC101719
0.763	Intermediate Similarity	NPC239357
0.76	Intermediate Similarity	NPC81026
0.7597	Intermediate Similarity	NPC470902
0.7571	Intermediate Similarity	NPC22746
0.7571	Intermediate Similarity	NPC222466
0.7551	Intermediate Similarity	NPC132636
0.7536	Intermediate Similarity	NPC478014
0.7536	Intermediate Similarity	NPC200964
0.7536	Intermediate Similarity	NPC478015
0.7536	Intermediate Similarity	NPC478016
0.7535	Intermediate Similarity	NPC89923
0.7535	Intermediate Similarity	NPC152850
0.7535	Intermediate Similarity	NPC105114
0.7535	Intermediate Similarity	NPC71933
0.7535	Intermediate Similarity	NPC239990
0.7533	Intermediate Similarity	NPC322878
0.7533	Intermediate Similarity	NPC266741
0.7516	Intermediate Similarity	NPC62104
0.7516	Intermediate Similarity	NPC1390
0.7483	Intermediate Similarity	NPC473322
0.7482	Intermediate Similarity	NPC71684
0.7468	Intermediate Similarity	NPC471527
0.7465	Intermediate Similarity	NPC136453
0.7431	Intermediate Similarity	NPC300315
0.7399	Intermediate Similarity	NPC328763
0.7379	Intermediate Similarity	NPC157311
0.7379	Intermediate Similarity	NPC255447
0.7375	Intermediate Similarity	NPC471052
0.7375	Intermediate Similarity	NPC471051
0.7375	Intermediate Similarity	NPC471053
0.7362	Intermediate Similarity	NPC473693
0.7362	Intermediate Similarity	NPC471568
0.7333	Intermediate Similarity	NPC273814
0.7329	Intermediate Similarity	NPC5719
0.7329	Intermediate Similarity	NPC22883
0.7329	Intermediate Similarity	NPC217804
0.7329	Intermediate Similarity	NPC8761
0.7329	Intermediate Similarity	NPC44805
0.7329	Intermediate Similarity	NPC210377
0.7329	Intermediate Similarity	NPC472923
0.7286	Intermediate Similarity	NPC80150
0.7286	Intermediate Similarity	NPC190663
0.7284	Intermediate Similarity	NPC15068
0.7279	Intermediate Similarity	NPC35850
0.7279	Intermediate Similarity	NPC276949
0.7273	Intermediate Similarity	NPC47667
0.7261	Intermediate Similarity	NPC39431
0.7256	Intermediate Similarity	NPC475204
0.7256	Intermediate Similarity	NPC196091
0.7256	Intermediate Similarity	NPC40234
0.7256	Intermediate Similarity	NPC475123
0.7244	Intermediate Similarity	NPC300443
0.7241	Intermediate Similarity	NPC111428
0.7239	Intermediate Similarity	NPC107938
0.7239	Intermediate Similarity	NPC294516
0.7239	Intermediate Similarity	NPC63040
0.7232	Intermediate Similarity	NPC323662
0.7229	Intermediate Similarity	NPC158277
0.7226	Intermediate Similarity	NPC33742
0.7195	Intermediate Similarity	NPC186617
0.7183	Intermediate Similarity	NPC160493
0.7179	Intermediate Similarity	NPC473491
0.7169	Intermediate Similarity	NPC248670
0.7152	Intermediate Similarity	NPC46009
0.7143	Intermediate Similarity	NPC314992
0.7134	Intermediate Similarity	NPC473502
0.7133	Intermediate Similarity	NPC175726
0.7133	Intermediate Similarity	NPC474082
0.7126	Intermediate Similarity	NPC326407
0.7126	Intermediate Similarity	NPC318930
0.7126	Intermediate Similarity	NPC317725
0.7126	Intermediate Similarity	NPC476227
0.7126	Intermediate Similarity	NPC477462
0.7126	Intermediate Similarity	NPC317362
0.7125	Intermediate Similarity	NPC324850
0.7123	Intermediate Similarity	NPC469666
0.7122	Intermediate Similarity	NPC2265
0.7121	Intermediate Similarity	NPC88267
0.7121	Intermediate Similarity	NPC194390
0.7121	Intermediate Similarity	NPC224610
0.7121	Intermediate Similarity	NPC113326
0.7119	Intermediate Similarity	NPC473371
0.7115	Intermediate Similarity	NPC283783
0.7114	Intermediate Similarity	NPC141050
0.7108	Intermediate Similarity	NPC230611
0.7101	Intermediate Similarity	NPC475421
0.7083	Intermediate Similarity	NPC476260
0.7083	Intermediate Similarity	NPC50016
0.7083	Intermediate Similarity	NPC476241
0.708	Intermediate Similarity	NPC474584
0.7075	Intermediate Similarity	NPC200589
0.7066	Intermediate Similarity	NPC137627
0.7066	Intermediate Similarity	NPC273755
0.7066	Intermediate Similarity	NPC306804
0.7059	Intermediate Similarity	NPC77905
0.7037	Intermediate Similarity	NPC469901
0.7034	Intermediate Similarity	NPC476125
0.7034	Intermediate Similarity	NPC476179
0.7024	Intermediate Similarity	NPC471165
0.7024	Intermediate Similarity	NPC473354
0.7024	Intermediate Similarity	NPC473402
0.7024	Intermediate Similarity	NPC159767
0.7024	Intermediate Similarity	NPC155506
0.7024	Intermediate Similarity	NPC26108
0.7024	Intermediate Similarity	NPC279871
0.702	Intermediate Similarity	NPC43755
0.7	Intermediate Similarity	NPC244509
0.6994	Remote Similarity	NPC73655
0.6988	Remote Similarity	NPC473000
0.6981	Remote Similarity	NPC262166
0.6977	Remote Similarity	NPC167763
0.6977	Remote Similarity	NPC470112
0.6977	Remote Similarity	NPC470903
0.6975	Remote Similarity	NPC469898
0.6975	Remote Similarity	NPC24617
0.6933	Remote Similarity	NPC114806
0.6929	Remote Similarity	NPC197470
0.6923	Remote Similarity	NPC475439
0.6923	Remote Similarity	NPC476183
0.6923	Remote Similarity	NPC473501
0.6909	Remote Similarity	NPC63931
0.6908	Remote Similarity	NPC6570
0.6901	Remote Similarity	NPC194671
0.6901	Remote Similarity	NPC45037
0.6901	Remote Similarity	NPC269750

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 NPC469427 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	85
0.1-0.2	341
0.2-0.3	815
0.3-0.4	2561
0.4-0.5	3796
0.5-0.6	1257
0.6-0.7	275
0.7-0.8	18
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8099	Intermediate Similarity	NPD8173	Phase 2
0.8099	Intermediate Similarity	NPD8172	Phase 2
0.7655	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD2584	Suspended
0.755	Intermediate Similarity	NPD8323	Discontinued
0.7466	Intermediate Similarity	NPD8416	Discontinued
0.74	Intermediate Similarity	NPD8076	Discontinued
0.7379	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8265	Approved
0.7343	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4175	Approved
0.7241	Intermediate Similarity	NPD4177	Approved
0.72	Intermediate Similarity	NPD6852	Discontinued
0.7181	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8643	Discontinued
0.7143	Intermediate Similarity	NPD1968	Approved
0.7143	Intermediate Similarity	NPD1967	Approved
0.7143	Intermediate Similarity	NPD2218	Phase 2
0.7143	Intermediate Similarity	NPD2217	Approved
0.7133	Intermediate Similarity	NPD5725	Approved
0.7133	Intermediate Similarity	NPD6073	Approved
0.7124	Intermediate Similarity	NPD6681	Discovery
0.7115	Intermediate Similarity	NPD6088	Approved
0.7114	Intermediate Similarity	NPD6623	Phase 3
0.7114	Intermediate Similarity	NPD4153	Approved
0.7095	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6901	Phase 3
0.7075	Intermediate Similarity	NPD4125	Approved
0.7055	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD8315	Phase 1
0.7034	Intermediate Similarity	NPD5367	Discontinued
0.7007	Intermediate Similarity	NPD3626	Phase 3
0.7006	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5292	Approved
0.7	Intermediate Similarity	NPD5291	Approved
0.6974	Remote Similarity	NPD6295	Approved
0.6974	Remote Similarity	NPD6294	Approved
0.6972	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4677	Discontinued
0.6959	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8417	Discontinued
0.6948	Remote Similarity	NPD2022	Approved
0.6948	Remote Similarity	NPD4152	Approved
0.6937	Remote Similarity	NPD4646	Approved
0.6937	Remote Similarity	NPD4648	Approved
0.6937	Remote Similarity	NPD4647	Approved
0.6933	Remote Similarity	NPD4557	Approved
0.6933	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5747	Discontinued
0.6933	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1348	Approved
0.6928	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3480	Approved
0.6918	Remote Similarity	NPD4731	Phase 3
0.6914	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2045	Approved
0.6913	Remote Similarity	NPD2047	Approved
0.6913	Remote Similarity	NPD21	Approved
0.6913	Remote Similarity	NPD2044	Approved
0.6913	Remote Similarity	NPD2051	Approved
0.6913	Remote Similarity	NPD2046	Approved
0.6913	Remote Similarity	NPD2048	Approved
0.6913	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2043	Approved
0.6903	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3073	Approved
0.6897	Remote Similarity	NPD3071	Approved
0.6897	Remote Similarity	NPD3072	Approved
0.6887	Remote Similarity	NPD5296	Approved
0.6864	Remote Similarity	NPD8124	Phase 3
0.6864	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2088	Approved
0.6839	Remote Similarity	NPD2087	Approved
0.6828	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4761	Approved
0.6828	Remote Similarity	NPD4762	Approved
0.6824	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5230	Approved
0.6813	Remote Similarity	NPD5229	Approved
0.681	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7342	Discontinued
0.6803	Remote Similarity	NPD3125	Approved
0.68	Remote Similarity	NPD4738	Phase 2
0.6797	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2436	Approved
0.6795	Remote Similarity	NPD2437	Approved
0.6779	Remote Similarity	NPD3040	Approved
0.6776	Remote Similarity	NPD5323	Approved
0.6765	Remote Similarity	NPD7130	Phase 3
0.6747	Remote Similarity	NPD8351	Phase 2
0.6733	Remote Similarity	NPD2613	Approved
0.6733	Remote Similarity	NPD5263	Approved
0.6733	Remote Similarity	NPD4676	Approved
0.6731	Remote Similarity	NPD7978	Discontinued
0.6731	Remote Similarity	NPD7720	Phase 2
0.673	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7599	Phase 2
0.6712	Remote Similarity	NPD4215	Approved
0.6712	Remote Similarity	NPD2608	Approved
0.6712	Remote Similarity	NPD2612	Approved
0.6712	Remote Similarity	NPD4216	Approved
0.6712	Remote Similarity	NPD4217	Approved
0.6712	Remote Similarity	NPD3132	Approved
0.6712	Remote Similarity	NPD4218	Approved
0.6712	Remote Similarity	NPD2611	Approved
0.6712	Remote Similarity	NPD3131	Approved
0.6712	Remote Similarity	NPD2610	Approved
0.6712	Remote Similarity	NPD2609	Approved
0.6711	Remote Similarity	NPD3614	Approved
0.6711	Remote Similarity	NPD3088	Approved
0.6711	Remote Similarity	NPD3087	Approved
0.6711	Remote Similarity	NPD2571	Approved
0.6711	Remote Similarity	NPD2570	Approved
0.6711	Remote Similarity	NPD2573	Approved
0.6711	Remote Similarity	NPD3615	Approved
0.6711	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3089	Approved
0.6711	Remote Similarity	NPD2574	Discontinued
0.6711	Remote Similarity	NPD4745	Approved
0.6711	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4746	Phase 3
0.6711	Remote Similarity	NPD2566	Approved
0.6711	Remote Similarity	NPD3616	Approved
0.6711	Remote Similarity	NPD3090	Approved
0.671	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7613	Discontinued
0.6708	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3642	Approved
0.6691	Remote Similarity	NPD3644	Approved
0.6691	Remote Similarity	NPD3643	Approved
0.6689	Remote Similarity	NPD2031	Discontinued
0.6687	Remote Similarity	NPD3987	Approved
0.6687	Remote Similarity	NPD5613	Approved
0.6687	Remote Similarity	NPD7600	Phase 2
0.6687	Remote Similarity	NPD3988	Approved
0.6687	Remote Similarity	NPD5614	Approved
0.6687	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7485	Phase 3
0.6686	Remote Similarity	NPD7484	Phase 3
0.6667	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5309	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7814	Approved
0.6667	Remote Similarity	NPD7965	Phase 2
0.6667	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5982	Phase 2
0.6646	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2891	Approved
0.6646	Remote Similarity	NPD5264	Approved
0.6646	Remote Similarity	NPD5265	Approved
0.6645	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5299	Approved
0.6645	Remote Similarity	NPD1330	Phase 2
0.6645	Remote Similarity	NPD5581	Approved
0.6626	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4684	Phase 3
0.6623	Remote Similarity	NPD3577	Discontinued
0.6623	Remote Similarity	NPD4686	Approved
0.6623	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4685	Phase 3
0.6621	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD5981	Approved
0.6604	Remote Similarity	NPD6676	Phase 2
0.66	Remote Similarity	NPD3588	Discontinued
0.6597	Remote Similarity	NPD7522	Discontinued
0.6587	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4794	Discontinued
0.6573	Remote Similarity	NPD7508	Discontinued
0.6568	Remote Similarity	NPD8303	Discontinued
0.6564	Remote Similarity	NPD7131	Phase 3
0.6561	Remote Similarity	NPD7512	Approved
0.6561	Remote Similarity	NPD7511	Approved
0.6554	Remote Similarity	NPD5335	Discontinued
0.6549	Remote Similarity	NPD2650	Approved
0.6549	Remote Similarity	NPD2652	Approved
0.6531	Remote Similarity	NPD7813	Approved
0.6531	Remote Similarity	NPD7815	Approved
0.6528	Remote Similarity	NPD3123	Discovery
0.6522	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7105	Phase 1
0.6503	Remote Similarity	NPD3820	Approved
0.6503	Remote Similarity	NPD3821	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3822	Approved
0.6494	Remote Similarity	NPD8118	Discontinued
0.6494	Remote Similarity	NPD5745	Approved
0.6491	Remote Similarity	NPD6303	Approved
0.6491	Remote Similarity	NPD6304	Approved
0.649	Remote Similarity	NPD4151	Approved
0.6486	Remote Similarity	NPD3603	Phase 3
0.6486	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD1582	Approved
0.6481	Remote Similarity	NPD2014	Approved
0.6481	Remote Similarity	NPD2016	Approved
0.6481	Remote Similarity	NPD2013	Approved
0.6481	Remote Similarity	NPD1581	Approved
0.6478	Remote Similarity	NPD5341	Clinical (unspecified phase)

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