NPASS Compound

Structure

CID315061 OpenBabel06191716132D 89 95 0 0 1 0 0 0 0 0999 V2000 0.3248 -2.6197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8177 3.5758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9463 4.2665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0803 3.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4822 1.2665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6264 -3.9463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4759 -2.8785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5923 4.2829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8854 -1.1276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3920 -4.2879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3946 3.2125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6855 2.0727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6412 -2.8785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1443 0.5838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6162 0.3113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4907 4.0241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0997 1.5060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0473 -0.5407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5248 4.2829 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -12.8123 3.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0803 2.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3482 0.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3676 -2.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7688 -2.1714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6264 4.0241 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8892 -1.2147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3049 -3.2917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3010 2.7899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6724 0.3113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3483 -2.1714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6162 -0.2335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7495 3.0582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5392 -0.7701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7688 2.2492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3676 3.0582 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5778 -0.7701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7495 -2.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3483 2.2492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6724 -0.2335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6783 4.2665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9463 2.2665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2142 1.2665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8796 -2.7940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4822 -0.7335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7256 -1.2821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3514 2.5994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8310 3.1528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2861 -3.0750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9980 1.8318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1190 -1.7540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7656 -2.5216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2375 2.8718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5392 0.8479 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5778 0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4446 0.3113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6783 5.2665 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -12.8123 2.7665 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.2142 2.2665 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.3482 -0.2335 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8310 -3.0750 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.3514 -2.5216 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.1443 -0.5060 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9980 -1.7540 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2861 3.1528 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.6824 1.8424 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4446 -0.2335 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.8796 2.8718 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.3915 -1.2821 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2375 -2.7940 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7656 2.5994 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7256 1.3599 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2660 5.2489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9193 4.7312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.5444 3.7665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.9463 1.2665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0803 0.7665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3022 -3.7003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4822 -1.7335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1807 -1.7047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9250 3.4186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9181 4.1490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1989 -4.0712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1789 2.4054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4267 1.1067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6598 -1.7067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8130 -3.0623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7456 3.1012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5997 0.6400 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 4 21 2 0 0 0 0 5 22 2 0 0 0 0 6 23 2 0 0 0 0 7 24 2 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 84 1 0 0 0 0 13 30 2 0 0 0 0 14 15 2 0 0 0 0 14 29 1 0 0 0 0 15 31 1 0 0 0 0 16 19 1 0 0 0 0 16 32 2 0 0 0 0 17 34 2 0 0 0 0 17 88 1 0 0 0 0 18 33 2 0 0 0 0 18 89 1 0 0 0 0 19 72 1 0 0 0 0 20 40 1 0 0 0 0 20 57 1 0 0 0 0 21 41 1 0 0 0 0 21 58 1 0 0 0 0 22 42 1 0 0 0 0 22 59 1 0 0 0 0 23 43 1 0 0 0 0 23 60 1 0 0 0 0 24 50 1 0 0 0 0 24 61 1 0 0 0 0 25 8 1 1 0 0 0 25 73 1 0 0 0 0 26 36 2 0 0 0 0 26 85 1 0 0 0 0 27 37 2 0 0 0 0 27 86 1 0 0 0 0 28 38 2 0 0 0 0 28 87 1 0 0 0 0 29 39 2 0 0 0 0 29 54 1 0 0 0 0 30 51 1 0 0 0 0 30 63 1 0 0 0 0 31 44 1 0 0 0 0 31 62 2 0 0 0 0 32 52 1 0 0 0 0 32 64 1 0 0 0 0 33 45 1 0 0 0 0 33 66 1 0 0 0 0 34 46 1 0 0 0 0 34 65 1 0 0 0 0 35 25 1 1 0 0 0 35 47 1 0 0 0 0 35 67 1 0 0 0 0 36 39 1 0 0 0 0 36 68 1 0 0 0 0 37 48 1 0 0 0 0 37 69 1 0 0 0 0 38 49 1 0 0 0 0 38 70 1 0 0 0 0 39 62 1 0 0 0 0 40 56 2 0 0 0 0 40 74 1 0 0 0 0 41 57 2 3 0 0 0 41 75 1 0 0 0 0 42 58 2 3 0 0 0 42 76 1 0 0 0 0 43 61 2 3 0 0 0 43 77 1 0 0 0 0 44 59 1 0 0 0 0 44 78 2 0 0 0 0 45 63 2 3 0 0 0 45 79 1 0 0 0 0 46 67 2 3 0 0 0 46 80 1 0 0 0 0 47 64 2 3 0 0 0 47 81 1 0 0 0 0 48 60 2 3 0 0 0 48 82 1 0 0 0 0 49 71 2 3 0 0 0 49 83 1 0 0 0 0 50 68 2 0 0 0 0 50 85 1 0 0 0 0 51 69 2 0 0 0 0 51 86 1 0 0 0 0 52 70 2 0 0 0 0 52 87 1 0 0 0 0 53 55 1 0 0 0 0 53 71 1 0 0 0 0 53 84 1 1 0 0 0 54 65 2 0 0 0 0 54 88 1 0 0 0 0 55 66 2 0 0 0 0 55 89 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1258.33
Volume:	1174.457
LogP:	1.455
LogD:	1.295
LogS:	-2.418
# Rotatable Bonds:	11
TPSA:	488.89
# H-Bond Aceptor:	32
# H-Bond Donor:	13
# Rings:	7
# Heavy Atoms:	34

MedChem Properties

QED Drug-Likeness Score:	0.048
Synthetic Accessibility Score:	7.906
Fsp3:	0.2
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:	-6.32
MDCK Permeability:	1.16E-05
Pgp-inhibitor:	0.999
Pgp-substrate:	1
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.842
30% Bioavailability (F30%):	0.488

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	85.70%
Volume Distribution (VD):	0.499
Pgp-substrate:	9.54%

ADMET: Metabolism

CYP1A2-inhibitor:	0.394
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.016
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0
CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.043

ADMET: Excretion

Clearance (CL):	0.628
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	1
Drug-inuced Liver Injury (DILI):	1
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.274
Skin Sensitization:	0.616
Carcinogencity:	0.945
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.992

Download Data

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

Natural Product: NPC315061

Natural Product ID:	NPC315061
*Common Name:**	Methylsulfomycin I
IUPAC Name:	n.a.
Synonyms:	Methylsulfomycin I
Standard InCHIKey:	AGPXPIZWMMLJPG-QJBUXTFLSA-N
Standard InCHI:	InChI=1S/C55H54N16O16S2/c1-13-30-51-69-37(27(10)86-51)48(82)60-23(6)43(77)61-24(7)50-68-36(26(9)85-50)39-29(14-15-31(62-39)44(78)59-22(5)42(76)58-21(4)41(75)57-20(3)40(56)74)54-65-34(17-88-54)46(80)67-35(25(8)73)47(81)64-32(16-19(2)72)52-70-38(28(11)87-52)49(83)71-53(84-12)55-66-33(18-89-55)45(79)63-30/h13-19,25,35,53,72-73H,3-7H2,1-2,8-12H3,(H2,56,74)(H,57,75)(H,58,76)(H,59,78)(H,60,82)(H,61,77)(H,63,79)(H,64,81)(H,67,80)(H,71,83)/b30-13-,32-16+/t19?,25-,35+,53+/m1/s1
SMILES:	C/C=C/1N=C(O)c2csc(n2)[C@H](OC)N=C(O)c2nc(oc2C)/C(=CC(O)C)/N=C(O)[C@@H](N=C(c2nc(c3c(c4nc(C(=C)N=C(C(=C)N=C(c5nc1oc5C)O)O)oc4C)nc(cc3)C(=O)NC(=C)C(=NC(=C)C(=NC(=C)C(=N)O)O)O)sc2)O)[C@H](O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444458
PubChem CID:	44575355
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
NPO40612	Streptomyces sp. HIL Y-9420704	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10579874]

☑ 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	2
Others	8

Activity Type	# Activity
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.06	ug.mL-1	PMID[490729]
NPT1605	Organism	Enterococcus	Enterococcus	MIC	=	0.06	ug.mL-1	PMID[490729]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	FC	=	6.2	n.a.	PMID[490729]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	FC	=	6.2	n.a.	PMID[490729]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	FC	=	12.4	n.a.	PMID[490729]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	FC	=	12.4	n.a.	PMID[490729]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	FC	=	800.0	n.a.	PMID[490729]
NPT5905	Organism	Echinococcus equinus	Echinococcus equinus	FC	=	800.0	n.a.	PMID[490729]

☑ 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 NPC315061 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	483
0.1-0.2	4348
0.2-0.3	13395
0.3-0.4	14787
0.4-0.5	6681
0.5-0.6	2772
0.6-0.7	214
0.7-0.8	14
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC315411
0.8075	Intermediate Similarity	NPC140284
0.8075	Intermediate Similarity	NPC75609
0.8028	Intermediate Similarity	NPC470900
0.7793	Intermediate Similarity	NPC216507
0.7793	Intermediate Similarity	NPC470901
0.7767	Intermediate Similarity	NPC115282
0.775	Intermediate Similarity	NPC197881
0.7455	Intermediate Similarity	NPC313966
0.7455	Intermediate Similarity	NPC314254
0.7117	Intermediate Similarity	NPC478030
0.7038	Intermediate Similarity	NPC49195
0.6931	Remote Similarity	NPC165964
0.6914	Remote Similarity	NPC475196
0.6844	Remote Similarity	NPC258048
0.6825	Remote Similarity	NPC477588
0.6825	Remote Similarity	NPC477586
0.6825	Remote Similarity	NPC477585
0.6825	Remote Similarity	NPC477590
0.6752	Remote Similarity	NPC477587
0.6752	Remote Similarity	NPC477589
0.6728	Remote Similarity	NPC477516
0.6726	Remote Similarity	NPC313587
0.6726	Remote Similarity	NPC315893
0.6726	Remote Similarity	NPC316110
0.6693	Remote Similarity	NPC315872
0.6633	Remote Similarity	NPC314222
0.6633	Remote Similarity	NPC196449
0.663	Remote Similarity	NPC476830
0.6619	Remote Similarity	NPC161801
0.6617	Remote Similarity	NPC478141
0.6606	Remote Similarity	NPC168135
0.6606	Remote Similarity	NPC477218
0.6606	Remote Similarity	NPC196718
0.6606	Remote Similarity	NPC322800
0.6593	Remote Similarity	NPC476831
0.6593	Remote Similarity	NPC476827
0.6593	Remote Similarity	NPC476826
0.6581	Remote Similarity	NPC325683
0.6569	Remote Similarity	NPC177432
0.6569	Remote Similarity	NPC299035
0.6568	Remote Similarity	NPC477219
0.6552	Remote Similarity	NPC152620
0.6545	Remote Similarity	NPC102593
0.6544	Remote Similarity	NPC37924
0.652	Remote Similarity	NPC476828
0.6487	Remote Similarity	NPC178664
0.6458	Remote Similarity	NPC53534
0.6436	Remote Similarity	NPC194740
0.6421	Remote Similarity	NPC63971
0.6421	Remote Similarity	NPC91868
0.6421	Remote Similarity	NPC323969
0.64	Remote Similarity	NPC476832
0.637	Remote Similarity	NPC101350
0.637	Remote Similarity	NPC478029
0.637	Remote Similarity	NPC312645
0.6358	Remote Similarity	NPC315499
0.635	Remote Similarity	NPC314633
0.6335	Remote Similarity	NPC235685
0.6312	Remote Similarity	NPC470784
0.631	Remote Similarity	NPC79386
0.6299	Remote Similarity	NPC478028
0.6296	Remote Similarity	NPC477979
0.6292	Remote Similarity	NPC475350
0.6292	Remote Similarity	NPC14877
0.6292	Remote Similarity	NPC145178
0.6291	Remote Similarity	NPC205372
0.6283	Remote Similarity	NPC251036
0.6277	Remote Similarity	NPC184680
0.6259	Remote Similarity	NPC89508
0.6254	Remote Similarity	NPC470785
0.6246	Remote Similarity	NPC472436
0.6237	Remote Similarity	NPC58209
0.6235	Remote Similarity	NPC96016
0.6228	Remote Similarity	NPC141053
0.6227	Remote Similarity	NPC131885
0.6226	Remote Similarity	NPC138562
0.6224	Remote Similarity	NPC316224
0.6221	Remote Similarity	NPC473639
0.6214	Remote Similarity	NPC260434
0.6213	Remote Similarity	NPC322064
0.6211	Remote Similarity	NPC148889
0.6209	Remote Similarity	NPC97746
0.6208	Remote Similarity	NPC269367
0.6204	Remote Similarity	NPC315804
0.6204	Remote Similarity	NPC313804
0.6197	Remote Similarity	NPC474183
0.6173	Remote Similarity	NPC122436
0.6172	Remote Similarity	NPC26543
0.6172	Remote Similarity	NPC49051
0.6167	Remote Similarity	NPC75179
0.6167	Remote Similarity	NPC291609
0.6165	Remote Similarity	NPC186351
0.6151	Remote Similarity	NPC67401
0.6149	Remote Similarity	NPC215837
0.6148	Remote Similarity	NPC182222
0.6145	Remote Similarity	NPC288987
0.6143	Remote Similarity	NPC472435
0.6142	Remote Similarity	NPC132539
0.6141	Remote Similarity	NPC314056
0.6132	Remote Similarity	NPC124300
0.6129	Remote Similarity	NPC153467
0.6127	Remote Similarity	NPC207620
0.6125	Remote Similarity	NPC310618
0.6117	Remote Similarity	NPC16066
0.6113	Remote Similarity	NPC329631
0.6111	Remote Similarity	NPC160100
0.6109	Remote Similarity	NPC303658
0.6109	Remote Similarity	NPC309919
0.6108	Remote Similarity	NPC169716
0.6107	Remote Similarity	NPC140296
0.6106	Remote Similarity	NPC478011
0.6106	Remote Similarity	NPC478012
0.6105	Remote Similarity	NPC165599
0.6105	Remote Similarity	NPC240384
0.6105	Remote Similarity	NPC15801
0.6099	Remote Similarity	NPC469858
0.6095	Remote Similarity	NPC85702
0.609	Remote Similarity	NPC472434
0.6087	Remote Similarity	NPC298436
0.6086	Remote Similarity	NPC314176
0.6084	Remote Similarity	NPC477633
0.6082	Remote Similarity	NPC472259
0.608	Remote Similarity	NPC478013
0.6076	Remote Similarity	NPC166712
0.6075	Remote Similarity	NPC18487
0.6075	Remote Similarity	NPC153400
0.607	Remote Similarity	NPC57453
0.6069	Remote Similarity	NPC72715
0.6066	Remote Similarity	NPC146418
0.6062	Remote Similarity	NPC238242
0.6059	Remote Similarity	NPC472286
0.6059	Remote Similarity	NPC472287
0.6057	Remote Similarity	NPC229893
0.6056	Remote Similarity	NPC63279
0.6055	Remote Similarity	NPC188400
0.6054	Remote Similarity	NPC244543
0.6051	Remote Similarity	NPC235866
0.6045	Remote Similarity	NPC317572
0.6042	Remote Similarity	NPC119006
0.6041	Remote Similarity	NPC473800
0.6037	Remote Similarity	NPC244741
0.6035	Remote Similarity	NPC34770
0.6035	Remote Similarity	NPC475619
0.6035	Remote Similarity	NPC297642
0.6031	Remote Similarity	NPC165538
0.6022	Remote Similarity	NPC257511
0.6016	Remote Similarity	NPC34319
0.6014	Remote Similarity	NPC473187
0.6014	Remote Similarity	NPC305984
0.6	Remote Similarity	NPC208364
0.6	Remote Similarity	NPC329982
0.6	Remote Similarity	NPC161242
0.5986	Remote Similarity	NPC14812
0.5985	Remote Similarity	NPC473493
0.5979	Remote Similarity	NPC122886
0.5978	Remote Similarity	NPC321428
0.5972	Remote Similarity	NPC314954
0.5972	Remote Similarity	NPC471762
0.5971	Remote Similarity	NPC123839
0.5966	Remote Similarity	NPC189079
0.5965	Remote Similarity	NPC207686
0.5963	Remote Similarity	NPC473239
0.596	Remote Similarity	NPC471979
0.596	Remote Similarity	NPC227824
0.5958	Remote Similarity	NPC35042
0.5954	Remote Similarity	NPC122427
0.5954	Remote Similarity	NPC329961
0.5953	Remote Similarity	NPC25316
0.5953	Remote Similarity	NPC263485
0.5953	Remote Similarity	NPC229160
0.5953	Remote Similarity	NPC41982
0.5953	Remote Similarity	NPC249662
0.5941	Remote Similarity	NPC315638
0.5941	Remote Similarity	NPC313345
0.5941	Remote Similarity	NPC314855
0.5941	Remote Similarity	NPC313796
0.594	Remote Similarity	NPC63109
0.5938	Remote Similarity	NPC476080
0.5938	Remote Similarity	NPC475534
0.5935	Remote Similarity	NPC314270
0.5935	Remote Similarity	NPC260909
0.5934	Remote Similarity	NPC107077
0.5934	Remote Similarity	NPC223791
0.5932	Remote Similarity	NPC133609
0.5932	Remote Similarity	NPC473188
0.593	Remote Similarity	NPC217176
0.593	Remote Similarity	NPC14288
0.5927	Remote Similarity	NPC118940
0.5926	Remote Similarity	NPC75498
0.5923	Remote Similarity	NPC39370
0.5923	Remote Similarity	NPC325976
0.5922	Remote Similarity	NPC472789
0.5921	Remote Similarity	NPC36405
0.592	Remote Similarity	NPC74619
0.5919	Remote Similarity	NPC315545
0.5919	Remote Similarity	NPC316403
0.5919	Remote Similarity	NPC314297
0.5918	Remote Similarity	NPC173250
0.5915	Remote Similarity	NPC66777

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 NPC315061 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	697
0.2-0.3	1116
0.3-0.4	2408
0.4-0.5	3114
0.5-0.6	1419
0.6-0.7	136
0.7-0.8	4
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
0.7296	Intermediate Similarity	NPD3328	Phase 2
0.7116	Intermediate Similarity	NPD3074	Discontinued
0.7094	Intermediate Similarity	NPD4898	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5817	Discontinued
0.7057	Intermediate Similarity	NPD8284	Discontinued
0.7	Intermediate Similarity	NPD7416	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6475	Phase 2
0.6777	Remote Similarity	NPD7853	Phase 2
0.6762	Remote Similarity	NPD5857	Phase 3
0.6742	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD8107	Approved
0.6728	Remote Similarity	NPD7031	Phase 1
0.6724	Remote Similarity	NPD8108	Approved
0.6716	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD6444	Clinical (unspecified phase)
0.6679	Remote Similarity	NPD2951	Discontinued
0.6679	Remote Similarity	NPD6205	Discontinued
0.6601	Remote Similarity	NPD8253	Phase 3
0.66	Remote Similarity	NPD1955	Discontinued
0.6596	Remote Similarity	NPD4369	Phase 2
0.6585	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5461	Discontinued
0.657	Remote Similarity	NPD3488	Phase 1
0.6566	Remote Similarity	NPD3945	Discontinued
0.6561	Remote Similarity	NPD1480	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD4569	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6627	Discontinued
0.6516	Remote Similarity	NPD8255	Phase 2
0.6506	Remote Similarity	NPD6974	Phase 3
0.6481	Remote Similarity	NPD8246	Approved
0.6481	Remote Similarity	NPD8247	Approved
0.6475	Remote Similarity	NPD3250	Phase 1
0.6452	Remote Similarity	NPD4368	Phase 2
0.6448	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD8061	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD3507	Phase 2
0.6421	Remote Similarity	NPD7180	Phase 3
0.6393	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6756	Phase 1
0.6382	Remote Similarity	NPD4884	Discovery
0.637	Remote Similarity	NPD1976	Approved
0.6364	Remote Similarity	NPD5922	Phase 3
0.6364	Remote Similarity	NPD4887	Discontinued
0.6357	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5479	Discontinued
0.6348	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6342	Remote Similarity	NPD7053	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD946	Discontinued
0.6335	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8117	Approved
0.6303	Remote Similarity	NPD8116	Phase 3
0.6302	Remote Similarity	NPD7403	Phase 1
0.63	Remote Similarity	NPD5850	Phase 3
0.6296	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD5924	Discontinued
0.629	Remote Similarity	NPD1927	Discontinued
0.629	Remote Similarity	NPD2893	Phase 3
0.6286	Remote Similarity	NPD4850	Phase 1
0.6284	Remote Similarity	NPD6023	Discontinued
0.6273	Remote Similarity	NPD8160	Phase 2
0.6272	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.627	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6255	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2779	Approved
0.625	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD5416	Discontinued
0.6237	Remote Similarity	NPD5022	Discontinued
0.6236	Remote Similarity	NPD5293	Phase 2
0.6232	Remote Similarity	NPD6173	Approved
0.6228	Remote Similarity	NPD8101	Phase 3
0.6228	Remote Similarity	NPD5482	Discontinued
0.622	Remote Similarity	NPD5532	Phase 2
0.6208	Remote Similarity	NPD7924	Phase 2
0.6208	Remote Similarity	NPD7925	Phase 2
0.6208	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6206	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7681	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD1936	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD8102	Discontinued
0.6194	Remote Similarity	NPD3351	Approved
0.6187	Remote Similarity	NPD3263	Phase 3
0.6185	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD8430	Approved
0.6164	Remote Similarity	NPD8463	Approved
0.6162	Remote Similarity	NPD8097	Phase 3
0.6162	Remote Similarity	NPD8096	Phase 3
0.6157	Remote Similarity	NPD3350	Approved
0.6151	Remote Similarity	NPD6246	Approved
0.6148	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD3392	Approved
0.6146	Remote Similarity	NPD7226	Phase 3
0.6146	Remote Similarity	NPD5749	Phase 2
0.6146	Remote Similarity	NPD7227	Phase 3
0.6143	Remote Similarity	NPD4438	Approved
0.6138	Remote Similarity	NPD8324	Phase 2
0.6137	Remote Similarity	NPD6209	Approved
0.6137	Remote Similarity	NPD8356	Approved
0.6136	Remote Similarity	NPD2778	Approved
0.6134	Remote Similarity	NPD8489	Phase 1
0.6132	Remote Similarity	NPD6716	Phase 1
0.6129	Remote Similarity	NPD8289	Discontinued
0.6126	Remote Similarity	NPD1224	Phase 2
0.6126	Remote Similarity	NPD1225	Phase 2
0.6125	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD8100	Phase 3
0.6118	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD8525	Approved
0.6117	Remote Similarity	NPD1638	Discovery
0.6113	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD7994	Phase 2
0.6103	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD6276	Discontinued
0.6099	Remote Similarity	NPD1867	Approved
0.6098	Remote Similarity	NPD7872	Phase 2
0.6084	Remote Similarity	NPD6825	Phase 1
0.6071	Remote Similarity	NPD5640	Discontinued
0.6069	Remote Similarity	NPD6397	Phase 3
0.6069	Remote Similarity	NPD5750	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD1659	Phase 1
0.6062	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.606	Remote Similarity	NPD5459	Phase 2
0.6059	Remote Similarity	NPD4130	Phase 3
0.6058	Remote Similarity	NPD8349	Phase 1
0.6056	Remote Similarity	NPD4373	Phase 2
0.6051	Remote Similarity	NPD5632	Approved
0.6051	Remote Similarity	NPD4429	Discontinued
0.6048	Remote Similarity	NPD7214	Phase 3
0.6048	Remote Similarity	NPD6450	Phase 2
0.6045	Remote Similarity	NPD6324	Phase 1
0.6042	Remote Similarity	NPD1505	Phase 2
0.6038	Remote Similarity	NPD772	Phase 3
0.6033	Remote Similarity	NPD5450	Discontinued
0.6032	Remote Similarity	NPD6558	Phase 1
0.6031	Remote Similarity	NPD1745	Approved
0.6028	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6021	Remote Similarity	NPD4322	Discontinued
0.6019	Remote Similarity	NPD7929	Approved
0.6019	Remote Similarity	NPD7928	Approved
0.6014	Remote Similarity	NPD8359	Phase 2
0.6007	Remote Similarity	NPD5116	Phase 1
0.6007	Remote Similarity	NPD7215	Phase 2
0.6007	Remote Similarity	NPD4952	Phase 3
0.6007	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6007	Remote Similarity	NPD3986	Discontinued
0.6	Remote Similarity	NPD4679	Discontinued
0.6	Remote Similarity	NPD3264	Phase 3
0.5993	Remote Similarity	NPD7941	Phase 3
0.5993	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD5509	Phase 1
0.5986	Remote Similarity	NPD5273	Approved
0.5986	Remote Similarity	NPD5271	Approved
0.5985	Remote Similarity	NPD5866	Approved
0.5985	Remote Similarity	NPD5452	Phase 2
0.5979	Remote Similarity	NPD3756	Phase 1
0.5979	Remote Similarity	NPD7921	Approved
0.5978	Remote Similarity	NPD8322	Phase 2
0.5974	Remote Similarity	NPD7181	Phase 3
0.5966	Remote Similarity	NPD7022	Phase 2
0.5963	Remote Similarity	NPD8098	Approved
0.5958	Remote Similarity	NPD3006	Discontinued
0.5957	Remote Similarity	NPD7711	Discontinued
0.595	Remote Similarity	NPD8479	Phase 2
0.595	Remote Similarity	NPD3308	Approved
0.5948	Remote Similarity	NPD7316	Discontinued
0.5948	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD2783	Phase 2
0.5946	Remote Similarity	NPD3844	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD8403	Phase 1
0.5938	Remote Similarity	NPD8421	Discontinued
0.5935	Remote Similarity	NPD8460	Approved
0.5935	Remote Similarity	NPD7878	Phase 2
0.5935	Remote Similarity	NPD8459	Approved
0.593	Remote Similarity	NPD1466	Phase 3
0.593	Remote Similarity	NPD1467	Approved
0.5927	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.5925	Remote Similarity	NPD5047	Clinical (unspecified phase)
0.5925	Remote Similarity	NPD7176	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD8363	Approved
0.5921	Remote Similarity	NPD8364	Approved
0.5918	Remote Similarity	NPD7946	Pre-registration
0.5914	Remote Similarity	NPD3307	Approved
0.5914	Remote Similarity	NPD3875	Discontinued
0.5911	Remote Similarity	NPD7727	Phase 2
0.5909	Remote Similarity	NPD8465	Approved
0.5909	Remote Similarity	NPD8466	Approved
0.5909	Remote Similarity	NPD6153	Approved
0.5909	Remote Similarity	NPD7664	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