NPASS Compound

Structure

CID323662 OpenBabel06191716172D 100102 0 0 1 0 0 0 0 0999 V2000 15.0622 0.5997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6139 -6.5022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3788 -0.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8542 -1.3894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7330 1.7996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4916 0.6160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4008 -1.5016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3130 0.8820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6390 -4.8190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5043 7.8051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3868 5.1560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3377 -0.5222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7428 6.6511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2490 4.5563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0054 0.6582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3788 1.3164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9305 -5.7855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8960 -1.0509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5664 2.2791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4431 3.5754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3148 2.9276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1916 4.2239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9336 -1.2844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6668 -0.8039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6668 0.1864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1374 0.1327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9515 -0.8039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4923 6.1512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4133 -3.4182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8060 3.6290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3896 -0.5563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4164 1.0829 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.1750 -0.1008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7174 -0.7849 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9964 0.1653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9180 -3.8689 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3169 6.8327 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5292 5.6511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6306 2.6030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8092 -1.2991 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1274 3.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2095 -4.8353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8168 3.5819 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9515 0.1864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2503 -0.5677 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6347 6.6464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4509 -3.6517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7550 -1.0183 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8804 -3.6354 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7425 0.8983 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9463 2.2784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6715 5.1560 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9358 0.3239 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8821 1.9545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9588 0.3988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6294 4.5543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5261 -4.1186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0716 -0.3016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1594 -2.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3547 1.6767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0396 4.2366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2527 6.5088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4925 1.3982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9892 -0.0471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0089 -1.7513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2879 -0.8012 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.8092 -2.2894 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.2346 -3.1522 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.2378 1.3490 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1756 5.4345 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.6923 -2.4680 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3277 6.8798 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.1719 -4.6019 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7227 2.5961 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4760 -1.9685 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5638 -4.3521 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1093 -0.5351 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1337 3.2508 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0594 5.9344 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8092 0.6815 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5292 6.6414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8758 4.5485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5293 0.3825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0027 7.5657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7675 -2.9350 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6421 -0.3179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5653 4.8782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8051 -3.1685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3506 0.6486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1218 -2.4517 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2123 1.1816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0020 4.4701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7065 7.3890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2992 0.8238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0833 -1.0329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0465 -1.9848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0544 0.1612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2598 4.5092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0696 0.9821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 31 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 12 66 1 0 0 0 0 13 79 1 0 0 0 0 14 98 1 0 0 0 0 15 99 1 0 0 0 0 16 32 1 0 0 0 0 17 42 2 0 0 0 0 18 23 2 0 0 0 0 18 33 1 0 0 0 0 19 21 1 0 0 0 0 19 39 2 0 0 0 0 20 22 2 0 0 0 0 20 39 1 0 0 0 0 21 41 2 0 0 0 0 22 41 1 0 0 0 0 23 45 1 0 0 0 0 24 25 1 0 0 0 0 24 40 1 0 0 0 0 25 80 1 0 0 0 0 26 32 1 0 0 0 0 26 33 2 0 0 0 0 27 40 1 0 0 0 0 28 46 1 0 0 0 0 28 70 1 0 0 0 0 29 47 1 0 0 0 0 29 71 1 0 0 0 0 30 98 1 0 0 0 0 34 7 1 6 0 0 0 34 35 1 0 0 0 0 34 48 1 0 0 0 0 35 8 1 1 0 0 0 35 55 1 0 0 0 0 36 9 1 6 0 0 0 36 49 1 0 0 0 0 36 68 1 0 0 0 0 37 10 1 6 0 0 0 37 62 1 0 0 0 0 37 72 1 0 0 0 0 38 11 1 1 0 0 0 38 81 1 0 0 0 0 39 54 1 0 0 0 0 40 67 1 1 0 0 0 41 82 1 0 0 0 0 42 57 1 0 0 0 0 42 73 1 0 0 0 0 43 30 1 1 0 0 0 43 56 1 0 0 0 0 43 74 1 0 0 0 0 44 27 1 6 0 0 0 44 64 1 0 0 0 0 44 80 1 0 0 0 0 45 66 1 0 0 0 0 45 83 1 0 0 0 0 46 72 2 3 0 0 0 46 84 1 0 0 0 0 47 73 2 3 0 0 0 47 85 1 0 0 0 0 48 58 1 6 0 0 0 48 75 1 0 0 0 0 49 59 1 1 0 0 0 49 76 1 0 0 0 0 50 53 1 0 0 0 0 50 60 1 0 0 0 0 50 77 1 6 0 0 0 51 54 1 1 0 0 0 51 63 1 0 0 0 0 51 78 1 0 0 0 0 52 38 1 6 0 0 0 52 61 1 0 0 0 0 52 79 1 0 0 0 0 53 31 1 1 0 0 0 53100 1 0 0 0 0 54 99 1 6 0 0 0 55 69 2 0 0 0 0 55 86 1 0 0 0 0 56 70 2 3 0 0 0 56 87 1 0 0 0 0 57 76 2 3 0 0 0 57 88 1 0 0 0 0 58 77 2 3 0 0 0 58 89 1 0 0 0 0 59 75 2 3 0 0 0 59 90 1 0 0 0 0 60 74 2 3 0 0 0 60 91 1 0 0 0 0 61 78 2 3 0 0 0 61 92 1 0 0 0 0 62 79 1 0 0 0 0 62 93 2 0 0 0 0 63 80 1 0 0 0 0 63 94 2 0 0 0 0 64 95 2 0 0 0 0 64100 1 0 0 0 0 65 66 1 0 0 0 0 65 71 2 3 0 0 0 65 96 1 0 0 0 0 66 97 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1431.71
Volume:	1408.303
LogP:	0.886
LogD:	0.663
LogS:	-1.318
# Rotatable Bonds:	29
TPSA:	519.24
# H-Bond Aceptor:	33
# H-Bond Donor:	17
# Rings:	3
# Heavy Atoms:	34

MedChem Properties

QED Drug-Likeness Score:	0.016
Synthetic Accessibility Score:	7.492
Fsp3:	0.621
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.627
MDCK Permeability:	0.0006853797822259367
Pgp-inhibitor:	0.268
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.044
30% Bioavailability (F30%):	0.852

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.213
Plasma Protein Binding (PPB):	45.42157745361328%
Volume Distribution (VD):	0.641
Pgp-substrate:	31.030071258544922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.03
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	1.637
Half-life (T1/2):	0.884

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.369
Carcinogencity:	0.043
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC323662

Natural Product ID:	NPC323662
*Common Name:**	Mirabamide G
IUPAC Name:	(2R,3S,4S)-4-[[(2S,3S)-3-amino-2-[[(Z)-2-[[2-[[(4Z,6E)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienoyl]amino]acetyl]amino]but-2-enoyl]amino]butanoyl]amino]-N'-[(3R,6S,9S,15R,18R,19R,22S,24S)-24-chloro-6-[(1R)-1-hydroxyethyl]-3-[(R)-(4-hydroxyphenyl)-methoxymethyl]-15-(methoxymethyl)-7,9-dimethyl-2,5,8,11,14,17,21-heptaoxo-19-propan-2-yl-20-oxa-1,4,7,10,13,16-hexazabicyclo[20.4.0]hexacosan-18-yl]-2,3-dimethylpentanediamide
Synonyms:	Mirabamide G
Standard InCHIKey:	CHRQWEAARHYJPF-NAQDZKCESA-N
Standard InCHI:	InChI=1S/C66H102ClN13O20/c1-16-32(5)26-33(6)18-23-45(83)66(12,97)65(96)71-29-47(85)73-42(17-2)57(88)76-49(36(9)68)59(90)75-48(34(7)35(8)55(69)86)58(89)77-50-53(31(3)4)100-64(95)44-27-40(67)24-25-80(44)63(94)51(54(99-15)39-19-21-41(82)22-20-39)78-61(92)52(38(11)81)79(13)62(93)37(10)72-46(84)28-70-56(87)43(30-98-14)74-60(50)91/h17-23,26,31-32,34-38,40,43-45,48-54,81-83,97H,16,24-25,27-30,68H2,1-15H3,(H2,69,86)(H,70,87)(H,71,96)(H,72,84)(H,73,85)(H,74,91)(H,75,90)(H,76,88)(H,77,89)(H,78,92)/b23-18-,33-26+,42-17-/t32?,34-,35+,36-,37-,38+,40-,43+,44-,45?,48-,49-,50+,51+,52-,53+,54+,66?/m0/s1
SMILES:	CCC(C)C=C(C)C=CC(C(C)(C(=O)NCC(=O)NC(=CC)C(=O)NC(C(C)N)C(=O)NC(C(C)C(C)C(=O)N)C(=O)NC1C(OC(=O)C2CC(CCN2C(=O)C(NC(=O)C(N(C(=O)C(NC(=O)CNC(=O)C(NC1=O)COC)C)C)C(C)O)C(C3=CC=C(C=C3)O)OC)Cl)C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689428
PubChem CID:	51041988
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11171	Stelletta clavosa	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21280591]
NPO11171	Stelletta clavosa	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	68.0	nM	PMID[469017]

☑ 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 NPC323662 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	223
0.1-0.2	1109
0.2-0.3	4532
0.3-0.4	12195
0.4-0.5	12230
0.5-0.6	11374
0.6-0.7	781
0.7-0.8	218
0.8-0.85	21
0.85-0.9	8
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC328763
0.9158	High Similarity	NPC326027
0.9053	High Similarity	NPC326333
0.8717	High Similarity	NPC477552
0.8717	High Similarity	NPC477550
0.8624	High Similarity	NPC477551
0.8523	High Similarity	NPC209463
0.8352	Intermediate Similarity	NPC269750
0.8352	Intermediate Similarity	NPC194671
0.8222	Intermediate Similarity	NPC46009
0.8187	Intermediate Similarity	NPC279871
0.8172	Intermediate Similarity	NPC294951
0.8142	Intermediate Similarity	NPC50016
0.8132	Intermediate Similarity	NPC248670
0.8132	Intermediate Similarity	NPC306804
0.8132	Intermediate Similarity	NPC273755
0.8087	Intermediate Similarity	NPC158277
0.8087	Intermediate Similarity	NPC471165
0.8075	Intermediate Similarity	NPC471048
0.8075	Intermediate Similarity	NPC471049
0.8075	Intermediate Similarity	NPC471050
0.8054	Intermediate Similarity	NPC45037
0.8053	Intermediate Similarity	NPC473305
0.8053	Intermediate Similarity	NPC163961
0.8031	Intermediate Similarity	NPC473371
0.8022	Intermediate Similarity	NPC475123
0.8022	Intermediate Similarity	NPC475204
0.7923	Intermediate Similarity	NPC196091
0.7906	Intermediate Similarity	NPC102959
0.7901	Intermediate Similarity	NPC63931
0.7892	Intermediate Similarity	NPC26108
0.7872	Intermediate Similarity	NPC473404
0.7868	Intermediate Similarity	NPC469443
0.7865	Intermediate Similarity	NPC60516
0.7838	Intermediate Similarity	NPC137627
0.7835	Intermediate Similarity	NPC302715
0.7826	Intermediate Similarity	NPC471568
0.7826	Intermediate Similarity	NPC473693
0.7814	Intermediate Similarity	NPC107938
0.7814	Intermediate Similarity	NPC294516
0.7796	Intermediate Similarity	NPC155506
0.7796	Intermediate Similarity	NPC159767
0.7796	Intermediate Similarity	NPC473354
0.7796	Intermediate Similarity	NPC476227
0.7796	Intermediate Similarity	NPC473402
0.7784	Intermediate Similarity	NPC230611
0.7772	Intermediate Similarity	NPC240130
0.7772	Intermediate Similarity	NPC61332
0.7749	Intermediate Similarity	NPC299806
0.773	Intermediate Similarity	NPC40234
0.7723	Intermediate Similarity	NPC220060
0.7723	Intermediate Similarity	NPC219350
0.7723	Intermediate Similarity	NPC194699
0.7684	Intermediate Similarity	NPC476321
0.7656	Intermediate Similarity	NPC315542
0.7653	Intermediate Similarity	NPC65714
0.7644	Intermediate Similarity	NPC471526
0.7641	Intermediate Similarity	NPC473407
0.7641	Intermediate Similarity	NPC473378
0.7606	Intermediate Similarity	NPC477462
0.7598	Intermediate Similarity	NPC469444
0.7594	Intermediate Similarity	NPC89831
0.7594	Intermediate Similarity	NPC328494
0.7585	Intermediate Similarity	NPC25539
0.7581	Intermediate Similarity	NPC186617
0.7579	Intermediate Similarity	NPC475421
0.7573	Intermediate Similarity	NPC469442
0.7573	Intermediate Similarity	NPC277306
0.7573	Intermediate Similarity	NPC469445
0.7551	Intermediate Similarity	NPC248822
0.7551	Intermediate Similarity	NPC477526
0.7538	Intermediate Similarity	NPC471592
0.7486	Intermediate Similarity	NPC469360
0.7475	Intermediate Similarity	NPC314083
0.7461	Intermediate Similarity	NPC470903
0.7461	Intermediate Similarity	NPC470112
0.7461	Intermediate Similarity	NPC167763
0.7459	Intermediate Similarity	NPC470902
0.7446	Intermediate Similarity	NPC469243
0.7419	Intermediate Similarity	NPC472923
0.7418	Intermediate Similarity	NPC244509
0.7418	Intermediate Similarity	NPC473580
0.7398	Intermediate Similarity	NPC94862
0.7391	Intermediate Similarity	NPC244336
0.7386	Intermediate Similarity	NPC91953
0.738	Intermediate Similarity	NPC61004
0.736	Intermediate Similarity	NPC81026
0.7351	Intermediate Similarity	NPC475544
0.734	Intermediate Similarity	NPC473502
0.734	Intermediate Similarity	NPC473450
0.733	Intermediate Similarity	NPC197921
0.7326	Intermediate Similarity	NPC223207
0.732	Intermediate Similarity	NPC477637
0.7308	Intermediate Similarity	NPC473341
0.7303	Intermediate Similarity	NPC266741
0.7293	Intermediate Similarity	NPC475168
0.7293	Intermediate Similarity	NPC7817
0.7287	Intermediate Similarity	NPC471771
0.7287	Intermediate Similarity	NPC304074
0.7287	Intermediate Similarity	NPC290755
0.7273	Intermediate Similarity	NPC471052
0.7273	Intermediate Similarity	NPC471051
0.7273	Intermediate Similarity	NPC471053
0.7263	Intermediate Similarity	NPC198254
0.7263	Intermediate Similarity	NPC274198
0.726	Intermediate Similarity	NPC478005
0.7249	Intermediate Similarity	NPC328649
0.7232	Intermediate Similarity	NPC469427
0.7232	Intermediate Similarity	NPC469426
0.7228	Intermediate Similarity	NPC476268
0.7222	Intermediate Similarity	NPC135121
0.7211	Intermediate Similarity	NPC280022
0.7207	Intermediate Similarity	NPC201244
0.7207	Intermediate Similarity	NPC477217
0.7206	Intermediate Similarity	NPC123859
0.7204	Intermediate Similarity	NPC287757
0.7204	Intermediate Similarity	NPC319320
0.7198	Intermediate Similarity	NPC473491
0.7196	Intermediate Similarity	NPC254700
0.7184	Intermediate Similarity	NPC311357
0.7178	Intermediate Similarity	NPC184933
0.7178	Intermediate Similarity	NPC59827
0.7174	Intermediate Similarity	NPC39431
0.7173	Intermediate Similarity	NPC276506
0.7172	Intermediate Similarity	NPC276120
0.7171	Intermediate Similarity	NPC242728
0.7159	Intermediate Similarity	NPC6570
0.7157	Intermediate Similarity	NPC50548
0.7143	Intermediate Similarity	NPC2501
0.7135	Intermediate Similarity	NPC476741
0.713	Intermediate Similarity	NPC478007
0.7128	Intermediate Similarity	NPC119652
0.7128	Intermediate Similarity	NPC97526
0.712	Intermediate Similarity	NPC122590
0.712	Intermediate Similarity	NPC262166
0.712	Intermediate Similarity	NPC56685
0.7113	Intermediate Similarity	NPC196243
0.7112	Intermediate Similarity	NPC62104
0.7112	Intermediate Similarity	NPC1390
0.7108	Intermediate Similarity	NPC144314
0.7104	Intermediate Similarity	NPC324081
0.7094	Intermediate Similarity	NPC477638
0.7094	Intermediate Similarity	NPC477632
0.7081	Intermediate Similarity	NPC476742
0.7074	Intermediate Similarity	NPC471527
0.7073	Intermediate Similarity	NPC477527
0.7065	Intermediate Similarity	NPC476744
0.7065	Intermediate Similarity	NPC233702
0.7064	Intermediate Similarity	NPC478008
0.7062	Intermediate Similarity	NPC136797
0.7059	Intermediate Similarity	NPC297145
0.7059	Intermediate Similarity	NPC56635
0.7059	Intermediate Similarity	NPC326349
0.7059	Intermediate Similarity	NPC149962
0.7059	Intermediate Similarity	NPC197743
0.7059	Intermediate Similarity	NPC323336
0.7037	Intermediate Similarity	NPC241794
0.7035	Intermediate Similarity	NPC138083
0.7033	Intermediate Similarity	NPC16188
0.7027	Intermediate Similarity	NPC202198
0.7011	Intermediate Similarity	NPC476743
0.7	Intermediate Similarity	NPC246303
0.7	Intermediate Similarity	NPC176226
0.6995	Remote Similarity	NPC477631
0.6983	Remote Similarity	NPC307357
0.6983	Remote Similarity	NPC268841
0.6983	Remote Similarity	NPC239762
0.6983	Remote Similarity	NPC476259
0.6983	Remote Similarity	NPC163392
0.6983	Remote Similarity	NPC46098
0.698	Remote Similarity	NPC64140
0.698	Remote Similarity	NPC29531
0.698	Remote Similarity	NPC283207
0.698	Remote Similarity	NPC51047
0.698	Remote Similarity	NPC477636
0.698	Remote Similarity	NPC174122
0.6979	Remote Similarity	NPC302597
0.6979	Remote Similarity	NPC63040
0.6976	Remote Similarity	NPC477639
0.6966	Remote Similarity	NPC64205
0.6966	Remote Similarity	NPC127741
0.6965	Remote Similarity	NPC4910
0.6963	Remote Similarity	NPC22883
0.6963	Remote Similarity	NPC5719
0.6963	Remote Similarity	NPC210377
0.6963	Remote Similarity	NPC217804
0.6961	Remote Similarity	NPC52748
0.6943	Remote Similarity	NPC129486
0.6931	Remote Similarity	NPC234069
0.6927	Remote Similarity	NPC15068
0.6923	Remote Similarity	NPC475532
0.6919	Remote Similarity	NPC32064
0.6919	Remote Similarity	NPC170302
0.6919	Remote Similarity	NPC475409
0.6919	Remote Similarity	NPC475564
0.6919	Remote Similarity	NPC153554
0.6902	Remote Similarity	NPC9373
0.6895	Remote Similarity	NPC476194
0.6888	Remote Similarity	NPC17698
0.6888	Remote Similarity	NPC165285

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 NPC323662 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	413
0.2-0.3	820
0.3-0.4	1985
0.4-0.5	3024
0.5-0.6	2424
0.6-0.7	345
0.7-0.8	5
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
0.7386	Intermediate Similarity	NPD7978	Discontinued
0.7354	Intermediate Similarity	NPD7608	Discontinued
0.7243	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7811	Phase 3
0.7122	Intermediate Similarity	NPD7810	Phase 3
0.712	Intermediate Similarity	NPD7131	Phase 3
0.7031	Intermediate Similarity	NPD7484	Phase 3
0.7031	Intermediate Similarity	NPD7485	Phase 3
0.7016	Intermediate Similarity	NPD8303	Discontinued
0.6971	Remote Similarity	NPD3136	Phase 2
0.6963	Remote Similarity	NPD8031	Discontinued
0.6961	Remote Similarity	NPD6681	Discovery
0.695	Remote Similarity	NPD6851	Approved
0.695	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6853	Approved
0.6895	Remote Similarity	NPD7972	Discontinued
0.6875	Remote Similarity	NPD7565	Approved
0.6872	Remote Similarity	NPD5137	Approved
0.6842	Remote Similarity	NPD8019	Approved
0.6763	Remote Similarity	NPD6312	Discontinued
0.6755	Remote Similarity	NPD7523	Phase 3
0.6754	Remote Similarity	NPD7495	Discontinued
0.675	Remote Similarity	NPD6297	Approved
0.6667	Remote Similarity	NPD2240	Approved
0.6667	Remote Similarity	NPD7450	Phase 2
0.6667	Remote Similarity	NPD2239	Approved
0.6649	Remote Similarity	NPD3536	Discontinued
0.6649	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.662	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6863	Phase 2
0.662	Remote Similarity	NPD8162	Phase 2
0.6615	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7303	Discontinued
0.6613	Remote Similarity	NPD3400	Discontinued
0.6613	Remote Similarity	NPD1967	Approved
0.6613	Remote Similarity	NPD1968	Approved
0.6613	Remote Similarity	NPD2575	Approved
0.6611	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD8173	Phase 2
0.6593	Remote Similarity	NPD8172	Phase 2
0.6584	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.658	Remote Similarity	NPD5355	Approved
0.658	Remote Similarity	NPD5356	Approved
0.6566	Remote Similarity	NPD4652	Approved
0.6552	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5218	Approved
0.6531	Remote Similarity	NPD5219	Approved
0.6528	Remote Similarity	NPD6905	Phase 2
0.6528	Remote Similarity	NPD6072	Discontinued
0.6526	Remote Similarity	NPD7613	Discontinued
0.6524	Remote Similarity	NPD6676	Phase 2
0.652	Remote Similarity	NPD3263	Phase 3
0.652	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5745	Approved
0.6515	Remote Similarity	NPD2017	Approved
0.6515	Remote Similarity	NPD2889	Approved
0.6515	Remote Similarity	NPD2890	Approved
0.6515	Remote Similarity	NPD2888	Approved
0.6498	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4086	Phase 1
0.6491	Remote Similarity	NPD8059	Phase 3
0.6491	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD8323	Discontinued
0.6486	Remote Similarity	NPD9570	Approved
0.6477	Remote Similarity	NPD8417	Discontinued
0.6474	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6419	Discontinued
0.6471	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5773	Approved
0.6462	Remote Similarity	NPD6034	Phase 2
0.6462	Remote Similarity	NPD5772	Approved
0.6456	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5484	Approved
0.6453	Remote Similarity	NPD5485	Approved
0.6447	Remote Similarity	NPD2098	Approved
0.6443	Remote Similarity	NPD6677	Suspended
0.644	Remote Similarity	NPD6390	Discontinued
0.6439	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7827	Phase 1
0.6425	Remote Similarity	NPD3455	Phase 2
0.6425	Remote Similarity	NPD3153	Approved
0.6425	Remote Similarity	NPD3879	Approved
0.6425	Remote Similarity	NPD3154	Approved
0.6416	Remote Similarity	NPD6796	Discontinued
0.6413	Remote Similarity	NPD3052	Approved
0.6413	Remote Similarity	NPD3054	Approved
0.6411	Remote Similarity	NPD7617	Discontinued
0.6409	Remote Similarity	NPD5746	Approved
0.6408	Remote Similarity	NPD5035	Approved
0.6393	Remote Similarity	NPD7585	Approved
0.6388	Remote Similarity	NPD8356	Approved
0.638	Remote Similarity	NPD3878	Approved
0.6378	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD3552	Approved
0.6378	Remote Similarity	NPD3554	Approved
0.6378	Remote Similarity	NPD6852	Discontinued
0.6378	Remote Similarity	NPD3553	Approved
0.6378	Remote Similarity	NPD3555	Approved
0.6372	Remote Similarity	NPD6519	Phase 2
0.6369	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD4103	Phase 2
0.6368	Remote Similarity	NPD7930	Approved
0.6364	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD555	Phase 2
0.6354	Remote Similarity	NPD2613	Approved
0.6354	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.635	Remote Similarity	NPD6107	Approved
0.6348	Remote Similarity	NPD8430	Approved
0.6347	Remote Similarity	NPD7583	Approved
0.6345	Remote Similarity	NPD2097	Approved
0.6345	Remote Similarity	NPD7318	Phase 3
0.634	Remote Similarity	NPD6057	Approved
0.634	Remote Similarity	NPD6056	Approved
0.6339	Remote Similarity	NPD3090	Approved
0.6339	Remote Similarity	NPD3087	Approved
0.6339	Remote Similarity	NPD2573	Approved
0.6339	Remote Similarity	NPD3615	Approved
0.6339	Remote Similarity	NPD1423	Approved
0.6339	Remote Similarity	NPD3614	Approved
0.6339	Remote Similarity	NPD2566	Approved
0.6339	Remote Similarity	NPD4745	Approved
0.6339	Remote Similarity	NPD3616	Approved
0.6339	Remote Similarity	NPD4746	Phase 3
0.6339	Remote Similarity	NPD3089	Approved
0.6339	Remote Similarity	NPD2574	Discontinued
0.6339	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD2570	Approved
0.6339	Remote Similarity	NPD2571	Approved
0.6339	Remote Similarity	NPD3088	Approved
0.6338	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD6088	Approved
0.6335	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7891	Discontinued
0.633	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD5313	Approved
0.6324	Remote Similarity	NPD5312	Approved
0.6316	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7282	Approved
0.6304	Remote Similarity	NPD6346	Approved
0.6303	Remote Similarity	NPD6505	Approved
0.6303	Remote Similarity	NPD6504	Approved
0.6302	Remote Similarity	NPD3985	Discontinued
0.63	Remote Similarity	NPD4666	Phase 3
0.6293	Remote Similarity	NPD5557	Phase 1
0.6292	Remote Similarity	NPD2561	Approved
0.6292	Remote Similarity	NPD2562	Approved
0.6291	Remote Similarity	NPD7256	Discontinued
0.629	Remote Similarity	NPD6295	Approved
0.629	Remote Similarity	NPD6294	Approved
0.6286	Remote Similarity	NPD4157	Discontinued
0.6283	Remote Similarity	NPD3122	Phase 3
0.628	Remote Similarity	NPD5028	Approved
0.628	Remote Similarity	NPD36	Approved
0.628	Remote Similarity	NPD4955	Approved
0.628	Remote Similarity	NPD4954	Approved
0.628	Remote Similarity	NPD5026	Approved
0.628	Remote Similarity	NPD5034	Approved
0.6276	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7584	Approved
0.627	Remote Similarity	NPD4684	Phase 3
0.627	Remote Similarity	NPD4686	Approved
0.627	Remote Similarity	NPD4685	Phase 3
0.6269	Remote Similarity	NPD6689	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD3557	Approved
0.6263	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD3558	Approved
0.6263	Remote Similarity	NPD3560	Approved
0.6263	Remote Similarity	NPD5481	Discontinued
0.6263	Remote Similarity	NPD3556	Approved
0.6257	Remote Similarity	NPD4659	Approved
0.6256	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7281	Phase 3
0.625	Remote Similarity	NPD5709	Phase 3
0.625	Remote Similarity	NPD259	Phase 1
0.625	Remote Similarity	NPD6874	Approved
0.625	Remote Similarity	NPD7280	Phase 3
0.625	Remote Similarity	NPD6315	Phase 2
0.6245	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7317	Phase 3
0.6244	Remote Similarity	NPD6042	Phase 2
0.6244	Remote Similarity	NPD42	Phase 2
0.6239	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5038	Approved
0.6238	Remote Similarity	NPD5037	Approved
0.6238	Remote Similarity	NPD2517	Approved
0.6238	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD8491	Approved
0.6233	Remote Similarity	NPD7801	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data