NPASS Compound

Structure

CID216507 OpenBabel06191716002D 98110 0 0 1 0 0 0 0 0999 V2000 -7.6883 -5.8126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8361 -8.1289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2677 -7.4867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2643 -0.1702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1496 -1.4445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0252 1.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6043 -6.9262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9057 -6.4453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4453 -6.2365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3561 -6.2154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0593 -5.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7236 -1.6319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6874 -5.6867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4878 -4.7443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7953 -2.8726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3639 -3.1520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5513 -5.6998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8206 -3.2678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8702 -2.5627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6455 -4.5368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3988 0.8920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6275 -6.0820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0524 -7.5454 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0424 -6.5359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4174 -0.6574 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3214 -5.7463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6482 -4.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2045 -4.9017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4714 -2.2142 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7102 -3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1548 -4.1859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9012 -2.0306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7041 -6.2104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1269 -4.4138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4572 -5.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5635 -5.1037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5690 -2.1217 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8870 -5.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1658 -6.5750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7531 -5.8655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7414 -4.4138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6567 -4.5752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5803 -2.8993 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9186 -4.7324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5864 -3.6331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1262 -4.0733 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5720 -0.1676 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8639 -7.0300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0940 -4.4552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4341 -1.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2246 -6.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1581 -3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6437 -6.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4356 -5.4350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9197 -2.5090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4327 -5.4350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5748 -4.2411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9486 -2.5090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4885 -4.2702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0230 -4.6924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7251 -0.6549 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1610 -7.7087 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.3303 -5.4032 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9671 -2.0306 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8176 -3.4807 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1152 -5.8655 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2201 -4.9423 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.3848 -4.7874 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3969 -2.2142 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2456 -4.2303 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7025 -6.5750 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1642 -6.2104 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3120 -3.3641 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3703 0.7884 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9730 -5.3594 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1553 -7.9324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3120 -5.7317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8031 -7.2993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7968 -3.7765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4341 -0.9913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5588 -7.3693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8041 -3.7085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3095 -7.3693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2574 -4.8730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9989 -4.7403 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7434 -6.1866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8936 -6.2557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9103 -4.2916 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1862 -5.2938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8014 -3.6064 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 2.4159 -1.6345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5676 -3.0988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9170 -5.3121 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -4.8754 -2.3059 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.7984 -5.0473 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -6.8441 -3.3019 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -1.3939 -2.8019 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 22 2 0 0 0 0 3 24 1 0 0 0 0 6 74 1 0 0 0 0 7 87 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 26 1 0 0 0 0 10 35 2 0 0 0 0 11 27 2 0 0 0 0 11 36 1 0 0 0 0 12 37 1 0 0 0 0 12 61 1 0 0 0 0 13 26 1 0 0 0 0 13 89 1 0 0 0 0 14 28 1 0 0 0 0 14 88 1 0 0 0 0 15 90 1 0 0 0 0 16 30 2 0 0 0 0 16 95 1 0 0 0 0 17 33 2 0 0 0 0 17 94 1 0 0 0 0 18 31 2 0 0 0 0 18 97 1 0 0 0 0 19 32 2 0 0 0 0 19 98 1 0 0 0 0 20 34 2 0 0 0 0 20 96 1 0 0 0 0 21 74 1 0 0 0 0 21 91 1 0 0 0 0 22 48 1 0 0 0 0 22 63 1 0 0 0 0 23 2 1 6 0 0 0 23 76 1 0 0 0 0 24 40 2 0 0 0 0 24 87 1 0 0 0 0 25 4 1 6 0 0 0 25 47 1 0 0 0 0 25 92 1 0 0 0 0 26 38 2 0 0 0 0 27 41 1 0 0 0 0 27 54 1 0 0 0 0 28 38 1 0 0 0 0 28 44 2 0 0 0 0 29 15 1 6 0 0 0 29 55 1 0 0 0 0 29 64 1 0 0 0 0 30 41 1 0 0 0 0 30 65 1 0 0 0 0 31 49 1 0 0 0 0 31 68 1 0 0 0 0 32 50 1 0 0 0 0 32 69 1 0 0 0 0 33 51 1 0 0 0 0 33 66 1 0 0 0 0 34 52 1 0 0 0 0 34 67 1 0 0 0 0 35 38 1 0 0 0 0 35 75 1 0 0 0 0 36 42 2 0 0 0 0 36 77 1 0 0 0 0 37 92 1 0 0 0 0 37 93 1 1 0 0 0 39 23 1 6 0 0 0 39 53 1 0 0 0 0 39 71 1 0 0 0 0 40 56 1 0 0 0 0 40 72 1 0 0 0 0 41 70 2 0 0 0 0 42 57 1 0 0 0 0 42 70 1 0 0 0 0 43 45 1 0 0 0 0 43 58 1 1 0 0 0 43 73 1 0 0 0 0 44 59 1 0 0 0 0 44 75 1 0 0 0 0 45 46 1 0 0 0 0 45 88 1 1 0 0 0 46 60 1 0 0 0 0 46 93 1 6 0 0 0 47 61 1 6 0 0 0 47 74 1 0 0 0 0 48 62 2 0 0 0 0 48 78 1 0 0 0 0 49 63 2 3 0 0 0 49 79 1 0 0 0 0 50 64 2 3 0 0 0 50 80 1 0 0 0 0 51 71 2 3 0 0 0 51 81 1 0 0 0 0 52 73 2 3 0 0 0 52 82 1 0 0 0 0 53 72 2 3 0 0 0 53 83 1 0 0 0 0 54 66 2 0 0 0 0 54 94 1 0 0 0 0 55 65 2 0 0 0 0 55 95 1 0 0 0 0 56 67 2 0 0 0 0 56 96 1 0 0 0 0 57 68 2 0 0 0 0 57 97 1 0 0 0 0 58 69 2 0 0 0 0 58 98 1 0 0 0 0 59 84 2 0 0 0 0 59 90 1 0 0 0 0 60 85 2 0 0 0 0 60 89 1 0 0 0 0 61 5 1 1 0 0 0 61 91 1 0 0 0 0 75 86 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1434.27
Volume:	1285.917
LogP:	4.177
LogD:	2.195
LogS:	-3.236
# Rotatable Bonds:	8
TPSA:	438.02
# H-Bond Aceptor:	32
# H-Bond Donor:	10
# Rings:	13
# Heavy Atoms:	37

MedChem Properties

QED Drug-Likeness Score:	0.028
Synthetic Accessibility Score:	8.359
Fsp3:	0.344
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:	-6.037
MDCK Permeability:	2.8993732485105284e-05
Pgp-inhibitor:	0.51
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.896
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	97.89104461669922%
Volume Distribution (VD):	0.893
Pgp-substrate:	2.2770209312438965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.471
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.029
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.213
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	-0.18
Half-life (T1/2):	0.062

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.999
Drug-inuced Liver Injury (DILI):	0.999
AMES Toxicity:	0.159
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.019
Carcinogencity:	0.135
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.709

Download Data

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

Natural Product: NPC216507

Natural Product ID:	NPC216507
*Common Name:**	Thiazomycin
IUPAC Name:	n.a.
Synonyms:	Thiazomycin
Standard InCHIKey:	GYOHFSLEKIIJMU-UMNFMQIXSA-N
Standard InCHI:	InChI=1S/C61H58N14O18S5/c1-22(48(62)78)63-49(79)31-18-97-57(68-31)42-36(77)11-27-41(70-42)30-16-95-55(65-30)29-15-90-59(84)44-28-14-88-45(46(60(85)89-13-26-9-8-10-35(38(26)28)75(44)86)93-37-12-61(5)47(25(4)92-37)74(6)21-91-61)43(58-69-32(19-98-58)50(80)64-29)73-52(82)34-20-96-56(67-34)40(24(3)87-7)72-53(83)39(23(2)76)71-51(81)33-17-94-54(27)66-33/h8-11,16-20,23,25,29,37,39,43,45-47,76-77,86H,1,12-15,21H2,2-7H3,(H2,62,78)(H,63,79)(H,64,80)(H,71,81)(H,72,83)(H,73,82)/b40-24+/t23-,25+,29+,37+,39+,43+,45+,46+,47-,61+/m1/s1
SMILES:	CO/C(=C1/N=C(O)[C@@H](N=C(O)c2csc(n2)c2cc(O)c(nc2c2csc(n2)[C@H]2N=C(c3nc([C@@H](N=C(c4nc1sc4)O)[C@@H]1OCc4c(C(=O)OC2)n(c2c4c(COC(=O)[C@H]1O[C@@H]1O[C@@H](C)[C@@H]4[C@@](C1)(C)OCN4C)ccc2)O)sc3)O)c1scc(n1)C(=NC(=C)C(=N)O)O)[C@H](O)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506017
PubChem CID:	NA
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:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0001189] N-acyl-alpha amino acids and derivatives

*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
NPO30090	Amycolatopsis fastidiosa	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17917239]
NPO30090	Amycolatopsis fastidiosa	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19334707]

☑ 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
MIC	23

Activity Type	# Activity
Organism	23

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	0.004	ug.mL-1	PMID[570192]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	0.064	ug.mL-1	PMID[570192]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.016	ug.mL-1	PMID[570192]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.032	ug.mL-1	PMID[570192]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	>	32.0	ug.mL-1	PMID[570192]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32.0	ug.mL-1	PMID[570192]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	32.0	ug.mL-1	PMID[570192]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.003	ug.mL-1	PMID[570193]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.006	ug.mL-1	PMID[570193]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.05	ug.mL-1	PMID[570193]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.01	ug.mL-1	PMID[570193]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	0.02	ug.mL-1	PMID[570193]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	0.03	ug.mL-1	PMID[570193]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	0.02	ug.mL-1	PMID[570193]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	0.01	ug.mL-1	PMID[570193]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	0.002	ug.mL-1	PMID[570193]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	0.01	ug.mL-1	PMID[570193]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	0.003	ug.mL-1	PMID[570193]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	0.002	ug.mL-1	PMID[570193]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	32.0	ug.mL-1	PMID[570193]

☑ 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 NPC216507 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	591
0.1-0.2	2961
0.2-0.3	11734
0.3-0.4	13993
0.4-0.5	10080
0.5-0.6	2893
0.6-0.7	431
0.7-0.8	8
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9686	High Similarity	NPC115282
0.9583	High Similarity	NPC470901
0.9268	High Similarity	NPC470900
0.8693	High Similarity	NPC197881
0.8057	Intermediate Similarity	NPC75609
0.8057	Intermediate Similarity	NPC140284
0.7793	Intermediate Similarity	NPC315061
0.7608	Intermediate Similarity	NPC315411
0.7534	Intermediate Similarity	NPC313966
0.7534	Intermediate Similarity	NPC314254
0.6902	Remote Similarity	NPC473800
0.6733	Remote Similarity	NPC313587
0.6733	Remote Similarity	NPC315893
0.6733	Remote Similarity	NPC316110
0.6724	Remote Similarity	NPC57453
0.67	Remote Similarity	NPC165964
0.6656	Remote Similarity	NPC472436
0.6623	Remote Similarity	NPC152620
0.6621	Remote Similarity	NPC477516
0.6557	Remote Similarity	NPC472435
0.6535	Remote Similarity	NPC478030
0.6533	Remote Similarity	NPC291609
0.6517	Remote Similarity	NPC478141
0.6515	Remote Similarity	NPC258048
0.6511	Remote Similarity	NPC472842
0.65	Remote Similarity	NPC124300
0.649	Remote Similarity	NPC310618
0.6472	Remote Similarity	NPC472846
0.6456	Remote Similarity	NPC478012
0.6456	Remote Similarity	NPC478011
0.6438	Remote Similarity	NPC196449
0.6438	Remote Similarity	NPC314222
0.6435	Remote Similarity	NPC314176
0.6429	Remote Similarity	NPC53534
0.6413	Remote Similarity	NPC207620
0.6403	Remote Similarity	NPC472434
0.6401	Remote Similarity	NPC312645
0.64	Remote Similarity	NPC470785
0.64	Remote Similarity	NPC470784
0.6395	Remote Similarity	NPC279589
0.6394	Remote Similarity	NPC169716
0.639	Remote Similarity	NPC314056
0.6378	Remote Similarity	NPC477633
0.6375	Remote Similarity	NPC45048
0.6367	Remote Similarity	NPC184680
0.6367	Remote Similarity	NPC15801
0.6364	Remote Similarity	NPC237901
0.6364	Remote Similarity	NPC195788
0.6361	Remote Similarity	NPC107836
0.6361	Remote Similarity	NPC473639
0.6355	Remote Similarity	NPC182222
0.6346	Remote Similarity	NPC474183
0.6336	Remote Similarity	NPC315499
0.6331	Remote Similarity	NPC153400
0.6329	Remote Similarity	NPC478013
0.6327	Remote Similarity	NPC475271
0.6317	Remote Similarity	NPC227824
0.6301	Remote Similarity	NPC471303
0.6298	Remote Similarity	NPC89508
0.6294	Remote Similarity	NPC215837
0.6291	Remote Similarity	NPC478029
0.6288	Remote Similarity	NPC475196
0.6286	Remote Similarity	NPC88923
0.6286	Remote Similarity	NPC315634
0.6286	Remote Similarity	NPC100734
0.6285	Remote Similarity	NPC260909
0.6267	Remote Similarity	NPC314270
0.6262	Remote Similarity	NPC191489
0.6258	Remote Similarity	NPC101312
0.6246	Remote Similarity	NPC94428
0.6246	Remote Similarity	NPC263937
0.623	Remote Similarity	NPC284685
0.6225	Remote Similarity	NPC478028
0.6197	Remote Similarity	NPC475844
0.6195	Remote Similarity	NPC478009
0.6195	Remote Similarity	NPC478010
0.6192	Remote Similarity	NPC472845
0.619	Remote Similarity	NPC52254
0.6181	Remote Similarity	NPC91868
0.6181	Remote Similarity	NPC63971
0.6177	Remote Similarity	NPC79386
0.6169	Remote Similarity	NPC178858
0.6164	Remote Similarity	NPC477590
0.6164	Remote Similarity	NPC477588
0.6164	Remote Similarity	NPC477586
0.6164	Remote Similarity	NPC477585
0.6164	Remote Similarity	NPC471979
0.6164	Remote Similarity	NPC315467
0.6156	Remote Similarity	NPC316224
0.6156	Remote Similarity	NPC82070
0.6154	Remote Similarity	NPC329982
0.6151	Remote Similarity	NPC251036
0.6151	Remote Similarity	NPC244856
0.6146	Remote Similarity	NPC469858
0.6146	Remote Similarity	NPC474701
0.6141	Remote Similarity	NPC14812
0.6138	Remote Similarity	NPC314834
0.6136	Remote Similarity	NPC313804
0.6136	Remote Similarity	NPC315804
0.6133	Remote Similarity	NPC33949
0.6127	Remote Similarity	NPC478006
0.6117	Remote Similarity	NPC469734
0.6109	Remote Similarity	NPC274842
0.6103	Remote Similarity	NPC14877
0.6103	Remote Similarity	NPC145178
0.6103	Remote Similarity	NPC475350
0.6102	Remote Similarity	NPC131273
0.6102	Remote Similarity	NPC473441
0.6102	Remote Similarity	NPC314882
0.6098	Remote Similarity	NPC477587
0.6098	Remote Similarity	NPC477589
0.6097	Remote Similarity	NPC471891
0.6091	Remote Similarity	NPC99891
0.6091	Remote Similarity	NPC148889
0.609	Remote Similarity	NPC244741
0.6088	Remote Similarity	NPC476114
0.6083	Remote Similarity	NPC478080
0.608	Remote Similarity	NPC194740
0.6075	Remote Similarity	NPC236424
0.6075	Remote Similarity	NPC306644
0.6074	Remote Similarity	NPC472789
0.6069	Remote Similarity	NPC471978
0.6059	Remote Similarity	NPC472207
0.6054	Remote Similarity	NPC477979
0.6054	Remote Similarity	NPC51388
0.6053	Remote Similarity	NPC323198
0.6053	Remote Similarity	NPC323752
0.6047	Remote Similarity	NPC186351
0.6047	Remote Similarity	NPC469594
0.6046	Remote Similarity	NPC285343
0.6045	Remote Similarity	NPC161801
0.6045	Remote Similarity	NPC218388
0.6042	Remote Similarity	NPC165599
0.6041	Remote Similarity	NPC472098
0.6034	Remote Similarity	NPC315545
0.6034	Remote Similarity	NPC314297
0.6026	Remote Similarity	NPC274640
0.6025	Remote Similarity	NPC129897
0.602	Remote Similarity	NPC469554
0.6019	Remote Similarity	NPC473312
0.6019	Remote Similarity	NPC1203
0.6019	Remote Similarity	NPC328928
0.6013	Remote Similarity	NPC58209
0.6013	Remote Similarity	NPC478083
0.6007	Remote Similarity	NPC128115
0.6006	Remote Similarity	NPC26543
0.6006	Remote Similarity	NPC89549
0.6006	Remote Similarity	NPC473833
0.6006	Remote Similarity	NPC41501
0.6	Remote Similarity	NPC314855
0.6	Remote Similarity	NPC208364
0.6	Remote Similarity	NPC220852
0.6	Remote Similarity	NPC313796
0.6	Remote Similarity	NPC141053
0.6	Remote Similarity	NPC472286
0.6	Remote Similarity	NPC472287
0.6	Remote Similarity	NPC315638
0.6	Remote Similarity	NPC313345
0.5993	Remote Similarity	NPC472061
0.5987	Remote Similarity	NPC260434
0.5987	Remote Similarity	NPC81175
0.5987	Remote Similarity	NPC474688
0.5982	Remote Similarity	NPC477634
0.598	Remote Similarity	NPC325976
0.598	Remote Similarity	NPC21638
0.598	Remote Similarity	NPC36405
0.598	Remote Similarity	NPC475619
0.5975	Remote Similarity	NPC150447
0.5974	Remote Similarity	NPC301501
0.5974	Remote Similarity	NPC101350
0.5973	Remote Similarity	NPC475609
0.5967	Remote Similarity	NPC321592
0.5967	Remote Similarity	NPC132329
0.5967	Remote Similarity	NPC54803
0.5966	Remote Similarity	NPC74562
0.5966	Remote Similarity	NPC317752
0.5966	Remote Similarity	NPC316181
0.5966	Remote Similarity	NPC314648
0.5966	Remote Similarity	NPC151781
0.5962	Remote Similarity	NPC13603
0.5955	Remote Similarity	NPC477861
0.5955	Remote Similarity	NPC477635
0.5955	Remote Similarity	NPC477630
0.5949	Remote Similarity	NPC188400
0.5948	Remote Similarity	NPC473105
0.5947	Remote Similarity	NPC229893
0.5945	Remote Similarity	NPC172355
0.5942	Remote Similarity	NPC28945
0.5942	Remote Similarity	NPC235685
0.5941	Remote Similarity	NPC244536
0.5939	Remote Similarity	NPC469589
0.5937	Remote Similarity	NPC67401
0.5934	Remote Similarity	NPC14288
0.5932	Remote Similarity	NPC318299
0.5932	Remote Similarity	NPC118940
0.5931	Remote Similarity	NPC53255
0.5931	Remote Similarity	NPC317572
0.5931	Remote Similarity	NPC475301
0.5931	Remote Similarity	NPC326930
0.5931	Remote Similarity	NPC478045

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 NPC216507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	641
0.2-0.3	1183
0.3-0.4	2637
0.4-0.5	2971
0.5-0.6	1271
0.6-0.7	165
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6862	Remote Similarity	NPD3074	Discontinued
0.6858	Remote Similarity	NPD3328	Phase 2
0.6656	Remote Similarity	NPD8284	Discontinued
0.6645	Remote Similarity	NPD7769	Phase 3
0.6623	Remote Similarity	NPD6456	Discontinued
0.6615	Remote Similarity	NPD8253	Phase 3
0.6582	Remote Similarity	NPD8107	Approved
0.6579	Remote Similarity	NPD8370	Discontinued
0.6574	Remote Similarity	NPD8489	Phase 1
0.6571	Remote Similarity	NPD8108	Approved
0.653	Remote Similarity	NPD7181	Phase 3
0.6509	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5482	Discontinued
0.6478	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8255	Phase 2
0.6426	Remote Similarity	NPD6475	Phase 2
0.6424	Remote Similarity	NPD8421	Discontinued
0.6413	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6627	Discontinued
0.6391	Remote Similarity	NPD7770	Phase 3
0.6373	Remote Similarity	NPD8101	Phase 3
0.6364	Remote Similarity	NPD8466	Approved
0.6364	Remote Similarity	NPD8465	Approved
0.6364	Remote Similarity	NPD8467	Approved
0.6361	Remote Similarity	NPD6276	Discontinued
0.6352	Remote Similarity	NPD8061	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5857	Phase 3
0.6307	Remote Similarity	NPD6205	Discontinued
0.6302	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7803	Approved
0.6286	Remote Similarity	NPD5450	Discontinued
0.6285	Remote Similarity	NPD8459	Approved
0.6285	Remote Similarity	NPD8425	Approved
0.6285	Remote Similarity	NPD8460	Approved
0.6285	Remote Similarity	NPD8426	Approved
0.6283	Remote Similarity	NPD6716	Phase 1
0.6275	Remote Similarity	NPD8100	Phase 3
0.6271	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD6023	Discontinued
0.6262	Remote Similarity	NPD8428	Approved
0.6262	Remote Similarity	NPD7708	Approved
0.6262	Remote Similarity	NPD8429	Approved
0.6262	Remote Similarity	NPD8427	Approved
0.625	Remote Similarity	NPD8349	Phase 1
0.623	Remote Similarity	NPD7956	Approved
0.623	Remote Similarity	NPD7955	Approved
0.6221	Remote Similarity	NPD5488	Discontinued
0.6206	Remote Similarity	NPD8463	Approved
0.6189	Remote Similarity	NPD7921	Approved
0.6186	Remote Similarity	NPD8246	Approved
0.6186	Remote Similarity	NPD8247	Approved
0.6176	Remote Similarity	NPD8364	Approved
0.6176	Remote Similarity	NPD8357	Approved
0.6176	Remote Similarity	NPD8363	Approved
0.6149	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5050	Approved
0.6146	Remote Similarity	NPD7688	Phase 1
0.6144	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.6137	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD8102	Discontinued
0.6128	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.612	Remote Similarity	NPD3263	Phase 3
0.6117	Remote Similarity	NPD5817	Discontinued
0.6113	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6113	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4373	Phase 2
0.61	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD7924	Phase 2
0.6094	Remote Similarity	NPD5506	Approved
0.6094	Remote Similarity	NPD7925	Phase 2
0.6094	Remote Similarity	NPD5507	Approved
0.6093	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.609	Remote Similarity	NPD7403	Phase 1
0.6082	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD7796	Approved
0.6073	Remote Similarity	NPD7797	Approved
0.606	Remote Similarity	NPD4952	Phase 3
0.6057	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD6756	Phase 1
0.6047	Remote Similarity	NPD8430	Approved
0.6046	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD7417	Discontinued
0.6037	Remote Similarity	NPD5922	Phase 3
0.6032	Remote Similarity	NPD4438	Approved
0.602	Remote Similarity	NPD3746	Discontinued
0.602	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.602	Remote Similarity	NPD8356	Approved
0.6013	Remote Similarity	NPD8468	Phase 2
0.6013	Remote Similarity	NPD7853	Phase 2
0.6007	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6006	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4897	Phase 2
0.6	Remote Similarity	NPD7655	Discontinued
0.6	Remote Similarity	NPD4884	Discovery
0.5993	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD8096	Phase 3
0.5986	Remote Similarity	NPD8097	Phase 3
0.598	Remote Similarity	NPD6246	Approved
0.598	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.598	Remote Similarity	NPD2951	Discontinued
0.5974	Remote Similarity	NPD7398	Approved
0.5974	Remote Similarity	NPD7397	Approved
0.5968	Remote Similarity	NPD8116	Phase 3
0.5968	Remote Similarity	NPD8117	Approved
0.5967	Remote Similarity	NPD4885	Approved
0.5964	Remote Similarity	NPD1955	Discontinued
0.5962	Remote Similarity	NPD8359	Phase 2
0.5961	Remote Similarity	NPD3006	Discontinued
0.596	Remote Similarity	NPD5640	Discontinued
0.5956	Remote Similarity	NPD6531	Approved
0.5956	Remote Similarity	NPD6530	Approved
0.5955	Remote Similarity	NPD3986	Discontinued
0.5951	Remote Similarity	NPD7691	Clinical (unspecified phase)
0.5945	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4086	Phase 1
0.5941	Remote Similarity	NPD6978	Phase 2
0.5928	Remote Similarity	NPD8329	Phase 3
0.5927	Remote Similarity	NPD3925	Approved
0.5927	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7496	Phase 2
0.5926	Remote Similarity	NPD8160	Phase 2
0.5924	Remote Similarity	NPD8324	Phase 2
0.592	Remote Similarity	NPD6974	Phase 3
0.5914	Remote Similarity	NPD6995	Phase 1
0.5906	Remote Similarity	NPD8326	Phase 3
0.5906	Remote Similarity	NPD8325	Phase 3
0.5906	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD7873	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5479	Discontinued
0.59	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.589	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6558	Phase 1
0.5882	Remote Similarity	NPD7806	Phase 2
0.5875	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7928	Approved
0.5873	Remote Similarity	NPD7929	Approved
0.5872	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.587	Remote Similarity	NPD5461	Discontinued
0.5867	Remote Similarity	NPD6455	Phase 3
0.5867	Remote Similarity	NPD6770	Approved
0.5863	Remote Similarity	NPD7031	Phase 1
0.586	Remote Similarity	NPD8375	Approved
0.5856	Remote Similarity	NPD8098	Approved
0.5855	Remote Similarity	NPD7711	Discontinued
0.5855	Remote Similarity	NPD7603	Discontinued
0.5852	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD8016	Phase 3
0.5852	Remote Similarity	NPD4561	Discontinued
0.5852	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5532	Phase 2
0.5847	Remote Similarity	NPD5850	Phase 3
0.5845	Remote Similarity	NPD4502	Phase 2
0.5844	Remote Similarity	NPD8461	Discontinued
0.5844	Remote Similarity	NPD7790	Approved
0.5844	Remote Similarity	NPD7951	Approved
0.5844	Remote Similarity	NPD7950	Approved
0.5844	Remote Similarity	NPD7953	Approved
0.5844	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD7791	Approved
0.5844	Remote Similarity	NPD7952	Approved
0.5844	Remote Similarity	NPD7789	Approved
0.5843	Remote Similarity	NPD7553	Discontinued
0.5841	Remote Similarity	NPD8358	Approved
0.5839	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD4368	Phase 2
0.5839	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD3488	Phase 1
0.5833	Remote Similarity	NPD5632	Approved
0.5831	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.5831	Remote Similarity	NPD6962	Phase 2
0.5825	Remote Similarity	NPD5452	Phase 2
0.5824	Remote Similarity	NPD8524	Approved
0.5823	Remote Similarity	NPD4369	Phase 2
0.5823	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD8525	Approved
0.5818	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5459	Phase 2
0.5809	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.5803	Remote Similarity	NPD8289	Discontinued
0.5798	Remote Similarity	NPD8374	Phase 3
0.5798	Remote Similarity	NPD5022	Discontinued
0.5795	Remote Similarity	NPD7180	Phase 3
0.5794	Remote Similarity	NPD7772	Phase 3
0.5791	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD7731	Approved
0.5784	Remote Similarity	NPD7730	Approved
0.5781	Remote Similarity	NPD7395	Discontinued
0.5779	Remote Similarity	NPD5003	Discontinued
0.5778	Remote Similarity	NPD7967	Discontinued
0.5776	Remote Similarity	NPD3801	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