NPASS Compound

Structure

CID325976 OpenBabel06191716182D 98105 0 0 1 0 0 0 0 0999 V2000 3.0630 2.8164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 4.1036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7132 -1.6826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8942 -3.4052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7811 2.3963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3744 1.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1933 3.2053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7044 -9.6579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3044 -4.7456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2044 -10.5239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4089 -5.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6447 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3799 1.3782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1988 3.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2044 -8.7918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3909 -4.3389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2044 -10.5239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5999 -6.3280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8526 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6973 -7.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4293 -7.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6973 -8.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4293 -8.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9071 -8.4841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9016 -8.5886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6937 1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7572 2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5633 -6.0924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -7.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1970 -3.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 -8.8577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3783 -8.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1037 -5.5848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0140 3.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3065 -2.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5633 -7.0924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 -8.0487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6037 -4.7188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5633 -9.0924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2044 -8.7918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5818 -4.9267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7044 -9.6579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6864 -5.9212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1095 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5003 -7.5706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5493 1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6973 -5.5924 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -6.4014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 -3.7007 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5602 -7.8796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 1.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3083 -9.5022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0955 -9.5268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3119 -2.7007 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3664 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3664 -7.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5547 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -7.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -4.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5547 -7.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1040 -4.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1040 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4858 2.9344 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.3028 -9.6067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0465 -9.2178 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2738 -9.4500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7728 -6.3280 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5493 -7.8796 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.6973 -0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5003 1.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.1095 -6.4014 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -5.5924 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -7.5706 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -2.7007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5602 1.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.3119 -3.7007 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 8.5633 -10.0924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7205 -10.3112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8875 -10.5050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9541 1.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9541 -7.8796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5547 2.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1554 -7.8796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 -4.9879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5547 -8.9841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0551 -4.9879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 -1.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0551 -1.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1554 1.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 38 1 0 0 0 0 2 38 1 0 0 0 0 3 39 1 0 0 0 0 4 39 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 12 28 1 0 0 0 0 13 21 1 0 0 0 0 13 29 1 0 0 0 0 14 40 2 0 0 0 0 15 40 1 0 0 0 0 16 45 2 0 0 0 0 17 46 2 0 0 0 0 18 47 2 0 0 0 0 19 48 2 0 0 0 0 22 24 1 0 0 0 0 22 41 2 0 0 0 0 23 25 2 0 0 0 0 23 41 1 0 0 0 0 24 44 2 0 0 0 0 25 44 1 0 0 0 0 26 27 1 0 0 0 0 27 58 1 0 0 0 0 28 71 1 0 0 0 0 29 85 1 0 0 0 0 30 38 1 0 0 0 0 31 41 1 0 0 0 0 32 40 1 0 0 0 0 33 42 1 0 0 0 0 34 43 1 0 0 0 0 35 59 1 0 0 0 0 36 42 2 0 0 0 0 36 74 1 0 0 0 0 37 43 2 0 0 0 0 37 75 1 0 0 0 0 42 45 1 0 0 0 0 43 46 1 0 0 0 0 44 86 1 0 0 0 0 45 47 1 0 0 0 0 46 48 1 0 0 0 0 47 74 1 0 0 0 0 48 75 1 0 0 0 0 49 20 1 6 0 0 0 49 61 1 0 0 0 0 49 77 1 0 0 0 0 50 26 1 6 0 0 0 50 62 1 0 0 0 0 50 76 1 0 0 0 0 51 30 1 6 0 0 0 51 63 1 0 0 0 0 51 78 1 0 0 0 0 52 31 1 6 0 0 0 52 67 1 0 0 0 0 52 79 1 0 0 0 0 53 33 1 1 0 0 0 53 64 1 0 0 0 0 53 80 1 0 0 0 0 54 34 1 6 0 0 0 54 65 1 0 0 0 0 54 82 1 0 0 0 0 55 35 1 6 0 0 0 55 66 1 0 0 0 0 55 81 1 0 0 0 0 56 32 1 1 0 0 0 56 70 1 0 0 0 0 56 83 1 0 0 0 0 57 21 1 6 0 0 0 57 68 1 0 0 0 0 57 85 1 0 0 0 0 58 72 2 0 0 0 0 58 87 1 0 0 0 0 59 73 2 0 0 0 0 59 88 1 0 0 0 0 60 39 1 6 0 0 0 60 69 1 0 0 0 0 60 84 1 0 0 0 0 61 78 2 3 0 0 0 61 89 1 0 0 0 0 62 79 2 3 0 0 0 62 90 1 0 0 0 0 63 83 2 3 0 0 0 63 91 1 0 0 0 0 64 81 2 3 0 0 0 64 92 1 0 0 0 0 65 80 2 3 0 0 0 65 93 1 0 0 0 0 66 76 2 3 0 0 0 66 94 1 0 0 0 0 67 84 2 3 0 0 0 67 95 1 0 0 0 0 68 82 2 3 0 0 0 68 96 1 0 0 0 0 69 77 2 3 0 0 0 69 97 1 0 0 0 0 70 85 1 0 0 0 0 70 98 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1347.68
Volume:	1361.5
LogP:	1.853
LogD:	1.766
LogS:	-3.196
# Rotatable Bonds:	19
TPSA:	469.14
# H-Bond Aceptor:	28
# H-Bond Donor:	18
# Rings:	8
# Heavy Atoms:	28

MedChem Properties

QED Drug-Likeness Score:	0.027
Synthetic Accessibility Score:	7.568
Fsp3:	0.429
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:	-3.224
MDCK Permeability:	0.00011053230264224112
Pgp-inhibitor:	0.027
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.926
Plasma Protein Binding (PPB):	49.773494720458984%
Volume Distribution (VD):	0.566
Pgp-substrate:	36.07141876220703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.02
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.53
Half-life (T1/2):	0.88

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.611
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.812
Carcinogencity:	0.299
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC325976

Natural Product ID:	NPC325976
*Common Name:**	Tyrocidine C
IUPAC Name:	3-[(3R,6S,9S,12S,15S,18S,21S,24R,27S,30S)-21-(2-amino-2-oxoethyl)-9-(3-aminopropyl)-3-benzyl-15-[(4-hydroxyphenyl)methyl]-24,27-bis(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29-decaoxo-12-propan-2-yl-1,4,7,10,13,16,19,22,25,28-decazabicyclo[28.3.0]tritriacontan-18-yl]propanamide
Synonyms:	Tyrocidine C
Standard InCHIKey:	NJMWWUADORPGGY-AJOXBXEMSA-N
Standard InCHI:	InChI=1S/C70H89N15O13/c1-38(2)30-51-63(91)83-56(32-40-14-6-5-7-15-40)70(98)85-29-13-21-57(85)68(96)82-54(34-43-37-75-48-19-11-9-17-46(43)48)65(93)80-53(33-42-36-74-47-18-10-8-16-45(42)47)64(92)81-55(35-59(73)88)66(94)76-50(26-27-58(72)87)62(90)79-52(31-41-22-24-44(86)25-23-41)67(95)84-60(39(3)4)69(97)77-49(20-12-28-71)61(89)78-51/h5-11,14-19,22-25,36-39,49-57,60,74-75,86H,12-13,20-21,26-35,71H2,1-4H3,(H2,72,87)(H2,73,88)(H,76,94)(H,77,97)(H,78,89)(H,79,90)(H,80,93)(H,81,92)(H,82,96)(H,83,91)(H,84,95)/t49-,50-,51-,52-,53+,54-,55-,56+,57-,60-/m0/s1
SMILES:	NCCC[C@@H]1N=C(O)[C@@H](N=C(O)[C@H](Cc2ccc(cc2)O)N=C(O)[C@H](CCC(=N)O)N=C(O)[C@H](CC(=N)O)N=C(O)[C@H](N=C([C@@H](N=C([C@H]2N(C(=O)[C@H](N=C([C@@H](N=C1O)CC(C)C)O)Cc1ccccc1)CCC2)O)Cc1c[nH]c2c1cccc2)O)Cc1c[nH]c2c1cccc2)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL576465
PubChem CID:	45485349
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
NPO23673	Brevibacillus brevis	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4320358]

☑ 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
Others	7

Activity Type	# Activity
NON-MOLECULAR	1
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	<	50.0	%	PMID[530057]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	Activity	=	1.48	%	PMID[530057]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	Activity	=	66.0	%	PMID[530057]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	T1/2	=	0.52	hr	PMID[530057]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IC50	=	6400.0	nM	PMID[530057]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	ICmax	=	9.0	uM	PMID[530057]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	IC50	=	9500.0	nM	PMID[530057]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	ICmax	=	13.0	uM	PMID[530057]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	IC50	=	7000.0	nM	PMID[530057]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	ICmax	=	11.0	uM	PMID[530057]

☑ 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 NPC325976 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	2500
0.2-0.3	14174
0.3-0.4	14266
0.4-0.5	5952
0.5-0.6	2957
0.6-0.7	1860
0.7-0.8	468
0.8-0.85	35
0.85-0.9	9
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9807	High Similarity	NPC326363
0.9193	High Similarity	NPC153400
0.8756	High Similarity	NPC24370
0.8756	High Similarity	NPC319232
0.8739	High Similarity	NPC28945
0.852	High Similarity	NPC323752
0.8489	Intermediate Similarity	NPC285343
0.8404	Intermediate Similarity	NPC162860
0.8396	Intermediate Similarity	NPC54420
0.8372	Intermediate Similarity	NPC75634
0.8356	Intermediate Similarity	NPC220852
0.8349	Intermediate Similarity	NPC477714
0.8333	Intermediate Similarity	NPC314882
0.8303	Intermediate Similarity	NPC477715
0.8278	Intermediate Similarity	NPC171317
0.827	Intermediate Similarity	NPC478006
0.8265	Intermediate Similarity	NPC264285
0.8233	Intermediate Similarity	NPC477633
0.8211	Intermediate Similarity	NPC478157
0.8182	Intermediate Similarity	NPC478009
0.8153	Intermediate Similarity	NPC473317
0.8148	Intermediate Similarity	NPC107077
0.8148	Intermediate Similarity	NPC223791
0.814	Intermediate Similarity	NPC315467
0.8128	Intermediate Similarity	NPC477635
0.8128	Intermediate Similarity	NPC477630
0.8122	Intermediate Similarity	NPC155143
0.8117	Intermediate Similarity	NPC16352
0.8089	Intermediate Similarity	NPC214142
0.8087	Intermediate Similarity	NPC184225
0.8075	Intermediate Similarity	NPC475506
0.807	Intermediate Similarity	NPC321592
0.807	Intermediate Similarity	NPC54803
0.8068	Intermediate Similarity	NPC213629
0.8066	Intermediate Similarity	NPC100321
0.8062	Intermediate Similarity	NPC95240
0.8062	Intermediate Similarity	NPC223409
0.8053	Intermediate Similarity	NPC124920
0.8053	Intermediate Similarity	NPC304307
0.8053	Intermediate Similarity	NPC34580
0.8053	Intermediate Similarity	NPC118559
0.8053	Intermediate Similarity	NPC261251
0.8044	Intermediate Similarity	NPC125597
0.8037	Intermediate Similarity	NPC110602
0.8037	Intermediate Similarity	NPC75726
0.8037	Intermediate Similarity	NPC31385
0.8033	Intermediate Similarity	NPC478010
0.8019	Intermediate Similarity	NPC473640
0.8018	Intermediate Similarity	NPC100547
0.8017	Intermediate Similarity	NPC477861
0.7982	Intermediate Similarity	NPC322135
0.7982	Intermediate Similarity	NPC478158
0.7974	Intermediate Similarity	NPC41679
0.7965	Intermediate Similarity	NPC478028
0.7948	Intermediate Similarity	NPC14288
0.7937	Intermediate Similarity	NPC281049
0.7931	Intermediate Similarity	NPC15801
0.7909	Intermediate Similarity	NPC320968
0.7897	Intermediate Similarity	NPC478029
0.7897	Intermediate Similarity	NPC293917
0.7892	Intermediate Similarity	NPC304926
0.7892	Intermediate Similarity	NPC476041
0.7885	Intermediate Similarity	NPC94752
0.7879	Intermediate Similarity	NPC284888
0.7879	Intermediate Similarity	NPC323198
0.7878	Intermediate Similarity	NPC314056
0.7871	Intermediate Similarity	NPC478011
0.7867	Intermediate Similarity	NPC99666
0.786	Intermediate Similarity	NPC315491
0.786	Intermediate Similarity	NPC45459
0.786	Intermediate Similarity	NPC191382
0.786	Intermediate Similarity	NPC56109
0.7857	Intermediate Similarity	NPC303658
0.7848	Intermediate Similarity	NPC183407
0.7845	Intermediate Similarity	NPC33064
0.7845	Intermediate Similarity	NPC245055
0.784	Intermediate Similarity	NPC314176
0.7821	Intermediate Similarity	NPC82472
0.7798	Intermediate Similarity	NPC473376
0.7798	Intermediate Similarity	NPC475070
0.7798	Intermediate Similarity	NPC470500
0.7797	Intermediate Similarity	NPC473312
0.7788	Intermediate Similarity	NPC276657
0.7783	Intermediate Similarity	NPC324149
0.7782	Intermediate Similarity	NPC478013
0.7762	Intermediate Similarity	NPC17059
0.7753	Intermediate Similarity	NPC474896
0.7749	Intermediate Similarity	NPC69843
0.7748	Intermediate Similarity	NPC82370
0.7739	Intermediate Similarity	NPC6215
0.7729	Intermediate Similarity	NPC478012
0.7725	Intermediate Similarity	NPC321708
0.7721	Intermediate Similarity	NPC156704
0.7719	Intermediate Similarity	NPC155444
0.7719	Intermediate Similarity	NPC31097
0.7716	Intermediate Similarity	NPC475969
0.7716	Intermediate Similarity	NPC475859
0.7709	Intermediate Similarity	NPC272174
0.7706	Intermediate Similarity	NPC476874
0.7706	Intermediate Similarity	NPC193761
0.7703	Intermediate Similarity	NPC5145
0.7685	Intermediate Similarity	NPC131887
0.7682	Intermediate Similarity	NPC63031
0.7682	Intermediate Similarity	NPC328924
0.7682	Intermediate Similarity	NPC207686
0.7678	Intermediate Similarity	NPC46580
0.7672	Intermediate Similarity	NPC470730
0.7672	Intermediate Similarity	NPC477175
0.7662	Intermediate Similarity	NPC323244
0.7662	Intermediate Similarity	NPC476491
0.766	Intermediate Similarity	NPC477549
0.7658	Intermediate Similarity	NPC476116
0.7657	Intermediate Similarity	NPC78609
0.7655	Intermediate Similarity	NPC27041
0.764	Intermediate Similarity	NPC117980
0.7639	Intermediate Similarity	NPC474877
0.7639	Intermediate Similarity	NPC77555
0.7633	Intermediate Similarity	NPC475746
0.763	Intermediate Similarity	NPC171171
0.7629	Intermediate Similarity	NPC194740
0.7619	Intermediate Similarity	NPC228835
0.7611	Intermediate Similarity	NPC74969
0.7611	Intermediate Similarity	NPC322064
0.7607	Intermediate Similarity	NPC165743
0.7607	Intermediate Similarity	NPC89987
0.7605	Intermediate Similarity	NPC81175
0.76	Intermediate Similarity	NPC54744
0.7597	Intermediate Similarity	NPC470729
0.7597	Intermediate Similarity	NPC477176
0.7595	Intermediate Similarity	NPC470784
0.7591	Intermediate Similarity	NPC476098
0.7588	Intermediate Similarity	NPC269270
0.7583	Intermediate Similarity	NPC15102
0.7583	Intermediate Similarity	NPC314002
0.7578	Intermediate Similarity	NPC61038
0.7577	Intermediate Similarity	NPC305984
0.7576	Intermediate Similarity	NPC476818
0.7574	Intermediate Similarity	NPC63279
0.7573	Intermediate Similarity	NPC171393
0.7573	Intermediate Similarity	NPC295452
0.757	Intermediate Similarity	NPC117244
0.757	Intermediate Similarity	NPC473763
0.7568	Intermediate Similarity	NPC323927
0.7565	Intermediate Similarity	NPC162748
0.7564	Intermediate Similarity	NPC477177
0.7564	Intermediate Similarity	NPC476451
0.756	Intermediate Similarity	NPC271792
0.7559	Intermediate Similarity	NPC477634
0.7558	Intermediate Similarity	NPC227582
0.7555	Intermediate Similarity	NPC14686
0.7554	Intermediate Similarity	NPC33949
0.7553	Intermediate Similarity	NPC184680
0.7552	Intermediate Similarity	NPC178858
0.7544	Intermediate Similarity	NPC473310
0.7542	Intermediate Similarity	NPC477107
0.7542	Intermediate Similarity	NPC477108
0.7542	Intermediate Similarity	NPC297642
0.7542	Intermediate Similarity	NPC477109
0.7536	Intermediate Similarity	NPC204717
0.7534	Intermediate Similarity	NPC213308
0.7534	Intermediate Similarity	NPC252338
0.7523	Intermediate Similarity	NPC175602
0.7523	Intermediate Similarity	NPC306376
0.7522	Intermediate Similarity	NPC477610
0.7521	Intermediate Similarity	NPC470785
0.7521	Intermediate Similarity	NPC471891
0.752	Intermediate Similarity	NPC321939
0.7511	Intermediate Similarity	NPC315804
0.7511	Intermediate Similarity	NPC213530
0.7511	Intermediate Similarity	NPC193267
0.7511	Intermediate Similarity	NPC272549
0.7511	Intermediate Similarity	NPC313804
0.75	Intermediate Similarity	NPC201831
0.75	Intermediate Similarity	NPC17487
0.749	Intermediate Similarity	NPC91868
0.749	Intermediate Similarity	NPC63971
0.7489	Intermediate Similarity	NPC270918
0.7488	Intermediate Similarity	NPC314603
0.7488	Intermediate Similarity	NPC220765
0.7479	Intermediate Similarity	NPC477607
0.7479	Intermediate Similarity	NPC477608
0.7478	Intermediate Similarity	NPC110182
0.7466	Intermediate Similarity	NPC476073
0.7464	Intermediate Similarity	NPC59269
0.7458	Intermediate Similarity	NPC477516
0.7457	Intermediate Similarity	NPC64216
0.7456	Intermediate Similarity	NPC36405
0.7456	Intermediate Similarity	NPC170114
0.7454	Intermediate Similarity	NPC471448
0.7448	Intermediate Similarity	NPC101350
0.7446	Intermediate Similarity	NPC60621
0.7445	Intermediate Similarity	NPC207866
0.7436	Intermediate Similarity	NPC186351
0.7432	Intermediate Similarity	NPC53144
0.7429	Intermediate Similarity	NPC181081
0.7429	Intermediate Similarity	NPC11126
0.7424	Intermediate Similarity	NPC472285
0.7421	Intermediate Similarity	NPC300183
0.7419	Intermediate Similarity	NPC63109
0.7412	Intermediate Similarity	NPC470549

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 NPC325976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	562
0.2-0.3	885
0.3-0.4	1597
0.4-0.5	2706
0.5-0.6	2203
0.6-0.7	848
0.7-0.8	106
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9324	High Similarity	NPD8405	Clinical (unspecified phase)
0.8584	High Similarity	NPD7603	Discontinued
0.8406	Intermediate Similarity	NPD7948	Phase 1
0.8203	Intermediate Similarity	NPD8093	Discontinued
0.814	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD7470	Discontinued
0.8	Intermediate Similarity	NPD8094	Discontinued
0.7972	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7897	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD8349	Phase 1
0.7879	Intermediate Similarity	NPD7790	Approved
0.7879	Intermediate Similarity	NPD7951	Approved
0.7879	Intermediate Similarity	NPD7950	Approved
0.7879	Intermediate Similarity	NPD7791	Approved
0.7879	Intermediate Similarity	NPD7952	Approved
0.7879	Intermediate Similarity	NPD7789	Approved
0.7879	Intermediate Similarity	NPD7953	Approved
0.786	Intermediate Similarity	NPD484	Approved
0.786	Intermediate Similarity	NPD7781	Approved
0.786	Intermediate Similarity	NPD7780	Approved
0.7812	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD8284	Discontinued
0.7802	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD7730	Approved
0.7739	Intermediate Similarity	NPD7731	Approved
0.7717	Intermediate Similarity	NPD8272	Phase 2
0.771	Intermediate Similarity	NPD7944	Discontinued
0.7703	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD7824	Approved
0.7652	Intermediate Similarity	NPD7271	Approved
0.765	Intermediate Similarity	NPD8395	Approved
0.765	Intermediate Similarity	NPD8396	Approved
0.7647	Intermediate Similarity	NPD8322	Phase 2
0.7642	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5426	Phase 3
0.7619	Intermediate Similarity	NPD7711	Discontinued
0.7566	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7970	Approved
0.756	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7181	Phase 3
0.7534	Intermediate Similarity	NPD7666	Phase 3
0.7534	Intermediate Similarity	NPD7665	Phase 2
0.7534	Intermediate Similarity	NPD2916	Discontinued
0.7523	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7957	Phase 1
0.7512	Intermediate Similarity	NPD8431	Approved
0.7512	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7558	Phase 2
0.7489	Intermediate Similarity	NPD6999	Discontinued
0.7489	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD8524	Approved
0.7468	Intermediate Similarity	NPD8289	Discontinued
0.7456	Intermediate Similarity	NPD5612	Discontinued
0.7455	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7001	Phase 3
0.7436	Intermediate Similarity	NPD8430	Approved
0.7436	Intermediate Similarity	NPD8292	Phase 2
0.7431	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD8016	Phase 3
0.7417	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8356	Approved
0.7412	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD2094	Phase 2
0.7406	Intermediate Similarity	NPD2095	Phase 2
0.7406	Intermediate Similarity	NPD2092	Phase 2
0.7401	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD6595	Phase 3
0.7391	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7619	Phase 3
0.7385	Intermediate Similarity	NPD7618	Phase 3
0.7384	Intermediate Similarity	NPD4885	Approved
0.7371	Intermediate Similarity	NPD2091	Phase 2
0.7371	Intermediate Similarity	NPD2096	Phase 2
0.7368	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5065	Approved
0.7269	Intermediate Similarity	NPD8247	Approved
0.7269	Intermediate Similarity	NPD8246	Approved
0.726	Intermediate Similarity	NPD802	Phase 2
0.7257	Intermediate Similarity	NPD5559	Phase 2
0.7253	Intermediate Similarity	NPD6242	Discontinued
0.7244	Intermediate Similarity	NPD5901	Discontinued
0.7235	Intermediate Similarity	NPD8525	Approved
0.7232	Intermediate Similarity	NPD8073	Approved
0.7229	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6376	Discontinued
0.7224	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4845	Discontinued
0.7215	Intermediate Similarity	NPD6165	Phase 2
0.7215	Intermediate Similarity	NPD6665	Discontinued
0.7215	Intermediate Similarity	NPD6164	Phase 2
0.7212	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD482	Approved
0.72	Intermediate Similarity	NPD8072	Approved
0.7182	Intermediate Similarity	NPD1038	Approved
0.7177	Intermediate Similarity	NPD5482	Discontinued
0.7173	Intermediate Similarity	NPD7426	Phase 1
0.7172	Intermediate Similarity	NPD7576	Discontinued
0.717	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD8098	Approved
0.7162	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD8363	Approved
0.716	Intermediate Similarity	NPD8364	Approved
0.7156	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6975	Discontinued
0.7148	Intermediate Similarity	NPD8459	Approved
0.7148	Intermediate Similarity	NPD8460	Approved
0.7143	Intermediate Similarity	NPD8091	Phase 3
0.7125	Intermediate Similarity	NPD8106	Phase 2
0.7111	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4511	Phase 1
0.7104	Intermediate Similarity	NPD7689	Approved
0.7104	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD8096	Phase 3
0.71	Intermediate Similarity	NPD3330	Phase 1
0.71	Intermediate Similarity	NPD8097	Phase 3
0.7093	Intermediate Similarity	NPD8115	Approved
0.7093	Intermediate Similarity	NPD8114	Approved
0.7089	Intermediate Similarity	NPD7716	Approved
0.7089	Intermediate Similarity	NPD7717	Approved
0.7085	Intermediate Similarity	NPD7921	Approved
0.7078	Intermediate Similarity	NPD7853	Phase 2
0.7075	Intermediate Similarity	NPD750	Phase 2
0.707	Intermediate Similarity	NPD6456	Discontinued
0.7069	Intermediate Similarity	NPD3243	Approved
0.7064	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD8427	Approved
0.7061	Intermediate Similarity	NPD8429	Approved
0.7061	Intermediate Similarity	NPD8428	Approved
0.7061	Intermediate Similarity	NPD8466	Approved
0.7061	Intermediate Similarity	NPD8467	Approved
0.7061	Intermediate Similarity	NPD8465	Approved
0.7054	Intermediate Similarity	NPD7777	Approved
0.7054	Intermediate Similarity	NPD7778	Approved
0.7054	Intermediate Similarity	NPD53	Approved
0.7052	Intermediate Similarity	NPD7859	Phase 2
0.7042	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3961	Discontinued
0.7031	Intermediate Similarity	NPD7222	Phase 2
0.7027	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD4852	Phase 2
0.7025	Intermediate Similarity	NPD3746	Discontinued
0.7024	Intermediate Similarity	NPD8463	Approved
0.7022	Intermediate Similarity	NPD3814	Phase 1
0.7021	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6531	Approved
0.702	Intermediate Similarity	NPD6530	Approved
0.7009	Intermediate Similarity	NPD7112	Discontinued
0.7	Intermediate Similarity	NPD2510	Approved
0.7	Intermediate Similarity	NPD4558	Phase 2
0.7	Intermediate Similarity	NPD2509	Approved
0.7	Intermediate Similarity	NPD4086	Phase 1
0.6996	Remote Similarity	NPD7415	Suspended
0.6992	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD8403	Phase 1
0.698	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6159	Phase 2
0.6969	Remote Similarity	NPD8255	Phase 2
0.696	Remote Similarity	NPD8358	Approved
0.6957	Remote Similarity	NPD7452	Approved
0.6957	Remote Similarity	NPD7453	Approved
0.6955	Remote Similarity	NPD8425	Approved
0.6955	Remote Similarity	NPD8426	Approved
0.6935	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6664	Approved
0.6929	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7994	Phase 2
0.6929	Remote Similarity	NPD6978	Phase 2
0.6917	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7688	Phase 1
0.691	Remote Similarity	NPD5066	Phase 2
0.691	Remote Similarity	NPD5067	Phase 2
0.6907	Remote Similarity	NPD8256	Approved
0.6907	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD8257	Approved
0.6905	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6995	Phase 1
0.689	Remote Similarity	NPD8370	Discontinued
0.6886	Remote Similarity	NPD7817	Phase 1
0.6883	Remote Similarity	NPD1392	Approved
0.6878	Remote Similarity	NPD7878	Phase 2
0.6872	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.687	Remote Similarity	NPD3006	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data