NPASS Compound

Structure

CID328763 OpenBabel06191716202D 99101 0 0 1 0 0 0 0 0999 V2000 17.5150 3.2170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6132 6.5016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3785 0.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8541 1.3893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.1861 2.0172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9448 3.2007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4001 1.5014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3125 -0.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4623 5.5678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6387 4.8186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5042 -7.8044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3863 -5.1555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7424 -6.6505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2485 -4.5559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0048 -0.6582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.8317 2.5004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9299 5.7850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3492 4.8675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5658 -2.2789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4426 -3.5751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3141 -2.9273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1910 -4.2235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3869 5.1009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6664 0.8039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6664 -0.1863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5904 3.6839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9514 0.8039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4921 -6.1506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4124 3.4179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8056 -3.6287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3895 0.5563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8694 2.7338 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 14.6281 3.9174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7168 0.7848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9958 -0.1653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.7413 4.6177 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9176 3.8685 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3168 -6.8320 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5287 -5.6506 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6300 -2.6028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8089 1.2990 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1267 -3.8997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2088 4.8349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8166 -3.5816 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9514 -0.1863 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.7036 4.3843 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6346 -6.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4501 3.6513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7546 1.0182 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8799 3.6350 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7423 -0.8982 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9459 -2.2782 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6712 -5.1555 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9357 -0.3239 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8817 -1.9543 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9581 -0.3987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0580 3.9011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6292 -4.5539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5255 4.1182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0712 0.3016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1589 2.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3544 -1.6766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0392 -4.2362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2525 -6.5082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4922 -1.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9891 0.0471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8089 2.2892 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.2343 3.1519 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.2371 -1.3488 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.0957 4.1345 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1754 -5.4340 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3277 -6.8792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.1711 4.6014 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7224 -2.5958 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4756 1.9683 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5632 4.3517 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1090 0.5350 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1333 -3.2505 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0591 -5.9338 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8089 -0.6814 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5287 -6.6408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8750 -4.5481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9825 3.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0026 -7.5650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7668 2.9347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6414 0.3179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3369 2.9510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5649 -4.8777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8045 3.1682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3502 -0.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1212 2.4515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2120 -1.1815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0015 -4.4697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7062 -7.3883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2988 -0.8237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0832 1.0328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2594 -4.5088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0691 -0.9820 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 9 36 1 0 0 0 0 13 79 1 0 0 0 0 14 97 1 0 0 0 0 15 98 1 0 0 0 0 16 32 1 0 0 0 0 17 43 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 40 2 0 0 0 0 20 22 2 0 0 0 0 20 40 1 0 0 0 0 21 42 2 0 0 0 0 22 42 1 0 0 0 0 23 46 1 0 0 0 0 24 25 1 0 0 0 0 24 41 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 41 1 0 0 0 0 28 47 1 0 0 0 0 28 71 1 0 0 0 0 29 48 1 0 0 0 0 29 70 1 0 0 0 0 30 97 1 0 0 0 0 34 7 1 1 0 0 0 34 35 1 0 0 0 0 34 49 1 0 0 0 0 35 8 1 6 0 0 0 35 56 1 0 0 0 0 36 46 1 0 0 0 0 36 57 1 0 0 0 0 37 10 1 1 0 0 0 37 50 1 0 0 0 0 37 68 1 0 0 0 0 38 11 1 1 0 0 0 38 64 1 0 0 0 0 38 72 1 0 0 0 0 39 12 1 6 0 0 0 39 81 1 0 0 0 0 40 55 1 0 0 0 0 41 67 1 6 0 0 0 42 82 1 0 0 0 0 43 59 1 0 0 0 0 43 73 1 0 0 0 0 44 30 1 6 0 0 0 44 58 1 0 0 0 0 44 74 1 0 0 0 0 45 27 1 1 0 0 0 45 66 1 0 0 0 0 45 80 1 0 0 0 0 46 83 1 0 0 0 0 47 72 2 3 0 0 0 47 84 1 0 0 0 0 48 73 2 3 0 0 0 48 85 1 0 0 0 0 49 60 1 1 0 0 0 49 75 1 0 0 0 0 50 61 1 6 0 0 0 50 76 1 0 0 0 0 51 54 1 0 0 0 0 51 62 1 0 0 0 0 51 77 1 1 0 0 0 52 55 1 6 0 0 0 52 65 1 0 0 0 0 52 78 1 0 0 0 0 53 39 1 1 0 0 0 53 63 1 0 0 0 0 53 79 1 0 0 0 0 54 31 1 6 0 0 0 54 99 1 0 0 0 0 55 98 1 1 0 0 0 56 69 2 0 0 0 0 56 86 1 0 0 0 0 57 70 2 3 0 0 0 57 87 1 0 0 0 0 58 71 2 3 0 0 0 58 88 1 0 0 0 0 59 76 2 3 0 0 0 59 89 1 0 0 0 0 60 77 2 3 0 0 0 60 90 1 0 0 0 0 61 75 2 3 0 0 0 61 91 1 0 0 0 0 62 74 2 3 0 0 0 62 92 1 0 0 0 0 63 78 2 3 0 0 0 63 93 1 0 0 0 0 64 79 1 0 0 0 0 64 94 2 0 0 0 0 65 80 1 0 0 0 0 65 95 2 0 0 0 0 66 96 2 0 0 0 0 66 99 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1415.71
Volume:	1399.513
LogP:	1.005
LogD:	0.792
LogS:	-1.192
# Rotatable Bonds:	29
TPSA:	499.01
# H-Bond Aceptor:	32
# H-Bond Donor:	16
# Rings:	3
# Heavy Atoms:	33

MedChem Properties

QED Drug-Likeness Score:	0.016
Synthetic Accessibility Score:	7.386
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:	-4.631
MDCK Permeability:	0.000514118408318609
Pgp-inhibitor:	0.367
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.729

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.79
Plasma Protein Binding (PPB):	44.653682708740234%
Volume Distribution (VD):	0.623
Pgp-substrate:	26.96274757385254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.031
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	1.883
Half-life (T1/2):	0.881

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:	0.023
Skin Sensitization:	0.307
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC328763

Natural Product ID:	NPC328763
*Common Name:**	Mirabamide H
IUPAC Name:	(2R,3S,4S)-4-[[(2S,3S)-3-amino-2-[[(Z)-2-[[2-[[(4Z,6E)-3-hydroxy-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 H
Standard InCHIKey:	JTGKDTRWYWFPLP-HEIJXINOSA-N
Standard InCHI:	InChI=1S/C66H102ClN13O19/c1-16-32(5)26-33(6)18-23-46(83)36(9)57(87)70-29-48(85)73-43(17-2)59(89)76-50(37(10)68)61(91)75-49(34(7)35(8)56(69)86)60(90)77-51-54(31(3)4)99-66(96)45-27-41(67)24-25-80(45)65(95)52(55(98-15)40-19-21-42(82)22-20-40)78-63(93)53(39(12)81)79(13)64(94)38(11)72-47(84)28-71-58(88)44(30-97-14)74-62(51)92/h17-23,26,31-32,34-39,41,44-46,49-55,81-83H,16,24-25,27-30,68H2,1-15H3,(H2,69,86)(H,70,87)(H,71,88)(H,72,84)(H,73,85)(H,74,92)(H,75,91)(H,76,89)(H,77,90)(H,78,93)/b23-18-,33-26+,43-17-/t32?,34-,35+,36?,37-,38-,39+,41-,44+,45-,46?,49-,50-,51+,52+,53-,54+,55+/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
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689429
PubChem CID:	51041989
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	=	42.0	nM	PMID[479475]

☑ 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 NPC328763 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	213
0.1-0.2	1092
0.2-0.3	4609
0.3-0.4	12274
0.4-0.5	12150
0.5-0.6	11291
0.6-0.7	800
0.7-0.8	234
0.8-0.85	21
0.85-0.9	8
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC323662
0.9043	High Similarity	NPC326333
0.8947	High Similarity	NPC326027
0.8602	High Similarity	NPC477552
0.8602	High Similarity	NPC477550
0.8539	High Similarity	NPC194671
0.8539	High Similarity	NPC269750
0.8511	High Similarity	NPC477551
0.8409	Intermediate Similarity	NPC46009
0.84	Intermediate Similarity	NPC209463
0.8371	Intermediate Similarity	NPC279871
0.8315	Intermediate Similarity	NPC306804
0.8268	Intermediate Similarity	NPC158277
0.8202	Intermediate Similarity	NPC475123
0.8202	Intermediate Similarity	NPC475204
0.8054	Intermediate Similarity	NPC294951
0.8043	Intermediate Similarity	NPC473404
0.8022	Intermediate Similarity	NPC50016
0.8011	Intermediate Similarity	NPC137627
0.8011	Intermediate Similarity	NPC248670
0.8011	Intermediate Similarity	NPC273755
0.7989	Intermediate Similarity	NPC294516
0.7989	Intermediate Similarity	NPC107938
0.7967	Intermediate Similarity	NPC473402
0.7967	Intermediate Similarity	NPC476227
0.7967	Intermediate Similarity	NPC155506
0.7967	Intermediate Similarity	NPC159767
0.7967	Intermediate Similarity	NPC471165
0.7957	Intermediate Similarity	NPC471050
0.7957	Intermediate Similarity	NPC471048
0.7957	Intermediate Similarity	NPC471049
0.7956	Intermediate Similarity	NPC230611
0.7937	Intermediate Similarity	NPC61332
0.7937	Intermediate Similarity	NPC473305
0.7937	Intermediate Similarity	NPC163961
0.7937	Intermediate Similarity	NPC240130
0.7935	Intermediate Similarity	NPC45037
0.7917	Intermediate Similarity	NPC473371
0.7914	Intermediate Similarity	NPC299806
0.7901	Intermediate Similarity	NPC40234
0.7802	Intermediate Similarity	NPC196091
0.7789	Intermediate Similarity	NPC102959
0.7778	Intermediate Similarity	NPC63931
0.7772	Intermediate Similarity	NPC26108
0.7755	Intermediate Similarity	NPC469443
0.7749	Intermediate Similarity	NPC60516
0.7742	Intermediate Similarity	NPC475421
0.772	Intermediate Similarity	NPC302715
0.7708	Intermediate Similarity	NPC248822
0.7708	Intermediate Similarity	NPC477526
0.7705	Intermediate Similarity	NPC473693
0.7705	Intermediate Similarity	NPC471568
0.7676	Intermediate Similarity	NPC473354
0.7661	Intermediate Similarity	NPC469360
0.7632	Intermediate Similarity	NPC315542
0.7629	Intermediate Similarity	NPC314083
0.7619	Intermediate Similarity	NPC167763
0.7619	Intermediate Similarity	NPC470112
0.7619	Intermediate Similarity	NPC470903
0.7612	Intermediate Similarity	NPC220060
0.7612	Intermediate Similarity	NPC194699
0.7612	Intermediate Similarity	NPC219350
0.7611	Intermediate Similarity	NPC469243
0.7584	Intermediate Similarity	NPC244509
0.7584	Intermediate Similarity	NPC473580
0.7582	Intermediate Similarity	NPC472923
0.7568	Intermediate Similarity	NPC328494
0.7566	Intermediate Similarity	NPC476321
0.7558	Intermediate Similarity	NPC91953
0.7556	Intermediate Similarity	NPC244336
0.7541	Intermediate Similarity	NPC61004
0.7538	Intermediate Similarity	NPC65714
0.7529	Intermediate Similarity	NPC81026
0.7528	Intermediate Similarity	NPC470902
0.7526	Intermediate Similarity	NPC471526
0.7526	Intermediate Similarity	NPC473378
0.7526	Intermediate Similarity	NPC473407
0.7514	Intermediate Similarity	NPC475544
0.75	Intermediate Similarity	NPC473502
0.75	Intermediate Similarity	NPC197921
0.7488	Intermediate Similarity	NPC469444
0.7487	Intermediate Similarity	NPC477462
0.7487	Intermediate Similarity	NPC473450
0.7486	Intermediate Similarity	NPC223207
0.7476	Intermediate Similarity	NPC25539
0.7474	Intermediate Similarity	NPC477637
0.7473	Intermediate Similarity	NPC89831
0.7472	Intermediate Similarity	NPC473341
0.7471	Intermediate Similarity	NPC266741
0.7463	Intermediate Similarity	NPC469445
0.7463	Intermediate Similarity	NPC469442
0.7463	Intermediate Similarity	NPC277306
0.7459	Intermediate Similarity	NPC186617
0.7458	Intermediate Similarity	NPC475168
0.7458	Intermediate Similarity	NPC7817
0.7446	Intermediate Similarity	NPC290755
0.7446	Intermediate Similarity	NPC471771
0.7446	Intermediate Similarity	NPC304074
0.7424	Intermediate Similarity	NPC471592
0.7419	Intermediate Similarity	NPC274198
0.7419	Intermediate Similarity	NPC198254
0.7405	Intermediate Similarity	NPC328649
0.7399	Intermediate Similarity	NPC469426
0.7399	Intermediate Similarity	NPC469427
0.7363	Intermediate Similarity	NPC319320
0.7363	Intermediate Similarity	NPC287757
0.736	Intermediate Similarity	NPC473491
0.7351	Intermediate Similarity	NPC254700
0.7333	Intermediate Similarity	NPC39431
0.7326	Intermediate Similarity	NPC276506
0.7323	Intermediate Similarity	NPC184933
0.7323	Intermediate Similarity	NPC59827
0.7282	Intermediate Similarity	NPC94862
0.7278	Intermediate Similarity	NPC262166
0.7278	Intermediate Similarity	NPC56685
0.7263	Intermediate Similarity	NPC324081
0.7263	Intermediate Similarity	NPC196243
0.7236	Intermediate Similarity	NPC477638
0.7236	Intermediate Similarity	NPC477632
0.7233	Intermediate Similarity	NPC478005
0.7222	Intermediate Similarity	NPC233702
0.7214	Intermediate Similarity	NPC477527
0.7213	Intermediate Similarity	NPC326349
0.7213	Intermediate Similarity	NPC323336
0.7211	Intermediate Similarity	NPC136797
0.7191	Intermediate Similarity	NPC16188
0.7189	Intermediate Similarity	NPC241794
0.7182	Intermediate Similarity	NPC202198
0.7178	Intermediate Similarity	NPC123859
0.7157	Intermediate Similarity	NPC311357
0.7151	Intermediate Similarity	NPC471053
0.7151	Intermediate Similarity	NPC471051
0.7151	Intermediate Similarity	NPC471052
0.7143	Intermediate Similarity	NPC276120
0.7143	Intermediate Similarity	NPC239762
0.7143	Intermediate Similarity	NPC163392
0.7143	Intermediate Similarity	NPC242728
0.7136	Intermediate Similarity	NPC246303
0.7136	Intermediate Similarity	NPC477631
0.7129	Intermediate Similarity	NPC50548
0.7128	Intermediate Similarity	NPC302597
0.7121	Intermediate Similarity	NPC477636
0.7121	Intermediate Similarity	NPC283207
0.7114	Intermediate Similarity	NPC477639
0.7107	Intermediate Similarity	NPC4910
0.7104	Intermediate Similarity	NPC476268
0.7103	Intermediate Similarity	NPC478007
0.7095	Intermediate Similarity	NPC135121
0.709	Intermediate Similarity	NPC280022
0.709	Intermediate Similarity	NPC129486
0.7079	Intermediate Similarity	NPC144314
0.7079	Intermediate Similarity	NPC477217
0.7079	Intermediate Similarity	NPC201244
0.7068	Intermediate Similarity	NPC475532
0.7062	Intermediate Similarity	NPC153554
0.7056	Intermediate Similarity	NPC9373
0.7049	Intermediate Similarity	NPC476742
0.7037	Intermediate Similarity	NPC478008
0.7031	Intermediate Similarity	NPC17698
0.7031	Intermediate Similarity	NPC165285
0.703	Intermediate Similarity	NPC149962
0.7029	Intermediate Similarity	NPC6570
0.702	Intermediate Similarity	NPC329731
0.7017	Intermediate Similarity	NPC2501
0.7011	Intermediate Similarity	NPC476741
0.701	Intermediate Similarity	NPC97526
0.701	Intermediate Similarity	NPC119652
0.7005	Intermediate Similarity	NPC138083
0.6995	Remote Similarity	NPC261934
0.6995	Remote Similarity	NPC122590
0.6995	Remote Similarity	NPC5194
0.6994	Remote Similarity	NPC326966
0.6994	Remote Similarity	NPC246079
0.6989	Remote Similarity	NPC62104
0.6989	Remote Similarity	NPC1390
0.6978	Remote Similarity	NPC476743
0.6968	Remote Similarity	NPC289776
0.6968	Remote Similarity	NPC191863
0.6968	Remote Similarity	NPC133470
0.6959	Remote Similarity	NPC319766
0.6952	Remote Similarity	NPC471527
0.695	Remote Similarity	NPC64140
0.695	Remote Similarity	NPC29531
0.695	Remote Similarity	NPC174122
0.6944	Remote Similarity	NPC314358
0.694	Remote Similarity	NPC476744
0.6935	Remote Similarity	NPC197743
0.6935	Remote Similarity	NPC56635
0.6935	Remote Similarity	NPC297145
0.6919	Remote Similarity	NPC296712
0.691	Remote Similarity	NPC476989
0.69	Remote Similarity	NPC234069
0.6898	Remote Similarity	NPC313804
0.6898	Remote Similarity	NPC315804
0.6897	Remote Similarity	NPC257390
0.6897	Remote Similarity	NPC471563
0.6889	Remote Similarity	NPC313867
0.6889	Remote Similarity	NPC316008
0.6888	Remote Similarity	NPC32064
0.6879	Remote Similarity	NPC325651

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 NPC328763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	130
0.1-0.2	428
0.2-0.3	797
0.3-0.4	1846
0.4-0.5	3023
0.5-0.6	2514
0.6-0.7	402
0.7-0.8	10
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
0.7558	Intermediate Similarity	NPD7978	Discontinued
0.7403	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7608	Discontinued
0.7278	Intermediate Similarity	NPD7131	Phase 3
0.7264	Intermediate Similarity	NPD7811	Phase 3
0.7264	Intermediate Similarity	NPD7810	Phase 3
0.7181	Intermediate Similarity	NPD7485	Phase 3
0.7181	Intermediate Similarity	NPD7484	Phase 3
0.7166	Intermediate Similarity	NPD8303	Discontinued
0.7135	Intermediate Similarity	NPD3136	Phase 2
0.7119	Intermediate Similarity	NPD6681	Discovery
0.7021	Intermediate Similarity	NPD8031	Discontinued
0.7005	Intermediate Similarity	NPD6851	Approved
0.7005	Intermediate Similarity	NPD6853	Approved
0.6989	Remote Similarity	NPD8019	Approved
0.6919	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD7523	Phase 3
0.6898	Remote Similarity	NPD7495	Discontinued
0.6897	Remote Similarity	NPD6312	Discontinued
0.6839	Remote Similarity	NPD5137	Approved
0.6816	Remote Similarity	NPD7450	Phase 2
0.6802	Remote Similarity	NPD6297	Approved
0.6796	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7972	Discontinued
0.6766	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD1968	Approved
0.6758	Remote Similarity	NPD3400	Discontinued
0.6758	Remote Similarity	NPD1967	Approved
0.6757	Remote Similarity	NPD7303	Discontinued
0.6755	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8162	Phase 2
0.6742	Remote Similarity	NPD8172	Phase 2
0.6742	Remote Similarity	NPD8173	Phase 2
0.6739	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5356	Approved
0.672	Remote Similarity	NPD5355	Approved
0.6718	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4652	Approved
0.6683	Remote Similarity	NPD7565	Approved
0.6667	Remote Similarity	NPD7613	Discontinued
0.6667	Remote Similarity	NPD5745	Approved
0.6651	Remote Similarity	NPD6905	Phase 2
0.6649	Remote Similarity	NPD2888	Approved
0.6649	Remote Similarity	NPD2890	Approved
0.6649	Remote Similarity	NPD2889	Approved
0.6649	Remote Similarity	NPD2017	Approved
0.6633	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2240	Approved
0.663	Remote Similarity	NPD2239	Approved
0.662	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD3536	Discontinued
0.6613	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.66	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6863	Phase 2
0.6583	Remote Similarity	NPD5484	Approved
0.6583	Remote Similarity	NPD5485	Approved
0.658	Remote Similarity	NPD2098	Approved
0.6578	Remote Similarity	NPD6390	Discontinued
0.6575	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3263	Phase 3
0.6556	Remote Similarity	NPD3054	Approved
0.6556	Remote Similarity	NPD3052	Approved
0.6554	Remote Similarity	NPD5746	Approved
0.6545	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD8323	Discontinued
0.6537	Remote Similarity	NPD7617	Discontinued
0.6524	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD3553	Approved
0.6519	Remote Similarity	NPD3554	Approved
0.6519	Remote Similarity	NPD3555	Approved
0.6519	Remote Similarity	NPD3552	Approved
0.651	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5773	Approved
0.651	Remote Similarity	NPD5772	Approved
0.651	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2613	Approved
0.6495	Remote Similarity	NPD5219	Approved
0.6495	Remote Similarity	NPD5218	Approved
0.6493	Remote Similarity	NPD6519	Phase 2
0.6489	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2575	Approved
0.6486	Remote Similarity	NPD6676	Phase 2
0.648	Remote Similarity	NPD3088	Approved
0.648	Remote Similarity	NPD2566	Approved
0.648	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.648	Remote Similarity	NPD2571	Approved
0.648	Remote Similarity	NPD2570	Approved
0.648	Remote Similarity	NPD4745	Approved
0.648	Remote Similarity	NPD3616	Approved
0.648	Remote Similarity	NPD3089	Approved
0.648	Remote Similarity	NPD2573	Approved
0.648	Remote Similarity	NPD3090	Approved
0.648	Remote Similarity	NPD4746	Phase 3
0.648	Remote Similarity	NPD3614	Approved
0.648	Remote Similarity	NPD2574	Discontinued
0.648	Remote Similarity	NPD3615	Approved
0.648	Remote Similarity	NPD3087	Approved
0.6477	Remote Similarity	NPD7318	Phase 3
0.6477	Remote Similarity	NPD2097	Approved
0.6471	Remote Similarity	NPD6088	Approved
0.6468	Remote Similarity	NPD3879	Approved
0.6467	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD9570	Approved
0.6444	Remote Similarity	NPD6346	Approved
0.6437	Remote Similarity	NPD2561	Approved
0.6437	Remote Similarity	NPD2562	Approved
0.6436	Remote Similarity	NPD6419	Discontinued
0.6429	Remote Similarity	NPD6295	Approved
0.6429	Remote Similarity	NPD8356	Approved
0.6429	Remote Similarity	NPD6294	Approved
0.6429	Remote Similarity	NPD6852	Discontinued
0.6425	Remote Similarity	NPD6504	Approved
0.6425	Remote Similarity	NPD6505	Approved
0.6422	Remote Similarity	NPD3878	Approved
0.6422	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4103	Phase 2
0.6418	Remote Similarity	NPD5557	Phase 1
0.6409	Remote Similarity	NPD4684	Phase 3
0.6409	Remote Similarity	NPD4685	Phase 3
0.6409	Remote Similarity	NPD4686	Approved
0.6406	Remote Similarity	NPD6677	Suspended
0.6404	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6689	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4659	Approved
0.6398	Remote Similarity	NPD5481	Discontinued
0.6396	Remote Similarity	NPD6107	Approved
0.6393	Remote Similarity	NPD7827	Phase 1
0.6392	Remote Similarity	NPD3556	Approved
0.6392	Remote Similarity	NPD3558	Approved
0.6392	Remote Similarity	NPD3560	Approved
0.6392	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD3557	Approved
0.639	Remote Similarity	NPD3153	Approved
0.639	Remote Similarity	NPD3154	Approved
0.6388	Remote Similarity	NPD8430	Approved
0.6388	Remote Similarity	NPD4086	Phase 1
0.6387	Remote Similarity	NPD6056	Approved
0.6387	Remote Similarity	NPD3455	Phase 2
0.6387	Remote Similarity	NPD6057	Approved
0.6382	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7317	Phase 3
0.6369	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6042	Phase 2
0.6368	Remote Similarity	NPD5313	Approved
0.6368	Remote Similarity	NPD42	Phase 2
0.6368	Remote Similarity	NPD5312	Approved
0.6368	Remote Similarity	NPD6874	Approved
0.6364	Remote Similarity	NPD2517	Approved
0.6359	Remote Similarity	NPD1725	Approved
0.6359	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD2891	Approved
0.6354	Remote Similarity	NPD8417	Discontinued
0.6354	Remote Similarity	NPD6623	Phase 3
0.6351	Remote Similarity	NPD6034	Phase 2
0.6349	Remote Similarity	NPD3157	Approved
0.6349	Remote Similarity	NPD3158	Phase 1
0.6344	Remote Similarity	NPD8491	Approved
0.6341	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6045	Phase 3
0.6335	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1330	Phase 2
0.6333	Remote Similarity	NPD4360	Phase 2
0.6333	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4363	Phase 3
0.633	Remote Similarity	NPD6666	Approved
0.633	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6667	Approved
0.6329	Remote Similarity	NPD8025	Phase 2
0.6329	Remote Similarity	NPD4157	Discontinued
0.6327	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD8076	Discontinued
0.6321	Remote Similarity	NPD6072	Discontinued
0.6319	Remote Similarity	NPD555	Phase 2
0.6318	Remote Similarity	NPD3909	Discontinued
0.6316	Remote Similarity	NPD5291	Approved
0.6316	Remote Similarity	NPD5292	Approved
0.6316	Remote Similarity	NPD8469	Approved
0.6316	Remote Similarity	NPD8059	Phase 3
0.6316	Remote Similarity	NPD9568	Approved
0.6316	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD2516	Approved
0.6311	Remote Similarity	NPD6967	Phase 2
0.6311	Remote Similarity	NPD8366	Approved
0.6311	Remote Similarity	NPD6796	Discontinued
0.6308	Remote Similarity	NPD5967	Approved
0.6307	Remote Similarity	NPD4677	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