NPASS Compound

Structure

CID319766 OpenBabel06191716152D 98 99 0 0 1 0 0 0 0 0999 V2000 -7.3082 10.4893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9409 8.8770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3082 2.8922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9409 4.5045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3296 0.4111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8985 -0.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3296 12.9704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8985 13.9461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5867 -1.3914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2418 -0.8808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5867 14.7729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2418 14.2623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6604 2.8454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9363 0.0975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0771 -1.2794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0129 1.8956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0129 11.4858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0129 11.4858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3369 13.6199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0129 1.8956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2585 9.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3924 8.5361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2585 10.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5264 9.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3924 10.5361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6604 10.5361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6720 6.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6720 7.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1462 14.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2310 12.3285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1591 9.5005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1591 3.8810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3324 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3324 13.0451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2669 -0.6583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2669 14.0398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7944 3.3454 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2310 1.0530 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1462 -0.9141 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5264 10.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9972 13.3068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7944 10.0361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5509 11.5954 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6720 7.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6720 6.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2282 9.1351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2282 4.2463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7690 1.1626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7690 12.2189 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9721 0.2973 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9721 13.0842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5509 1.7861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9972 0.0747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2282 4.2463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9721 13.0842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2282 9.1351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9972 13.3068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9721 0.2973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7690 1.1626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7690 12.2189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5509 1.7861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7944 10.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5509 11.5954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7944 3.3454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9972 0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5230 5.2019 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.5230 8.1796 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 13.3815 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5230 8.1796 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.5230 5.2019 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9030 12.7189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9030 0.6626 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9030 0.6626 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2310 2.5191 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2310 10.8624 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2310 10.8624 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9030 12.7189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2310 2.5191 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0771 14.6609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9363 13.2840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2060 1.2756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3644 -1.5376 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6692 7.2655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6692 6.1160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1591 3.8810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2669 14.0398 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1591 9.5005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1462 14.2956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2669 -0.6583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3324 0.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3324 13.0451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2310 1.0530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6604 10.5361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2310 12.3285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6604 2.8454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1462 -0.9141 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 4 33 1 0 0 0 0 5 34 1 0 0 0 0 6 34 1 0 0 0 0 7 35 1 0 0 0 0 8 35 1 0 0 0 0 9 36 1 0 0 0 0 10 36 1 0 0 0 0 11 37 1 0 0 0 0 12 37 1 0 0 0 0 16 75 1 0 0 0 0 17 76 1 0 0 0 0 18 77 1 0 0 0 0 19 78 1 0 0 0 0 20 79 1 0 0 0 0 21 80 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 26 2 0 0 0 0 25 41 2 0 0 0 0 26 41 1 0 0 0 0 27 41 1 0 0 0 0 28 45 1 0 0 0 0 28 67 1 0 0 0 0 29 46 1 0 0 0 0 29 68 1 0 0 0 0 30 81 1 0 0 0 0 31 82 1 0 0 0 0 38 13 1 6 0 0 0 38 55 1 0 0 0 0 38 75 1 0 0 0 0 39 14 1 6 0 0 0 39 83 1 0 0 0 0 40 15 1 6 0 0 0 40 84 1 0 0 0 0 42 30 1 1 0 0 0 42 56 1 0 0 0 0 42 69 1 0 0 0 0 43 27 1 6 0 0 0 43 57 1 0 0 0 0 43 76 1 0 0 0 0 44 31 1 1 0 0 0 44 61 1 0 0 0 0 44 77 1 0 0 0 0 45 70 2 3 0 0 0 45 85 1 0 0 0 0 46 71 2 3 0 0 0 46 86 1 0 0 0 0 47 32 1 1 0 0 0 47 63 1 0 0 0 0 47 70 1 0 0 0 0 48 33 1 1 0 0 0 48 65 1 0 0 0 0 48 71 1 0 0 0 0 49 34 1 1 0 0 0 49 62 1 0 0 0 0 49 73 1 0 0 0 0 50 35 1 1 0 0 0 50 64 1 0 0 0 0 50 72 1 0 0 0 0 51 36 1 1 0 0 0 51 66 1 0 0 0 0 51 74 1 0 0 0 0 52 37 1 1 0 0 0 52 58 1 0 0 0 0 52 78 1 0 0 0 0 53 39 1 1 0 0 0 53 60 1 0 0 0 0 53 79 1 0 0 0 0 54 40 1 1 0 0 0 54 59 1 0 0 0 0 54 80 1 0 0 0 0 55 67 2 3 0 0 0 55 87 1 0 0 0 0 56 72 2 3 0 0 0 56 88 1 0 0 0 0 57 68 2 3 0 0 0 57 89 1 0 0 0 0 58 69 2 3 0 0 0 58 90 1 0 0 0 0 59 73 2 3 0 0 0 59 91 1 0 0 0 0 60 74 2 3 0 0 0 60 92 1 0 0 0 0 61 78 1 0 0 0 0 61 93 2 0 0 0 0 62 75 1 0 0 0 0 62 94 2 0 0 0 0 63 77 1 0 0 0 0 63 95 2 0 0 0 0 64 76 1 0 0 0 0 64 96 2 0 0 0 0 65 79 1 0 0 0 0 65 97 2 0 0 0 0 66 80 1 0 0 0 0 66 98 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1386.81
Volume:	1400.337
LogP:	0.653
LogD:	0.227
LogS:	-1.706
# Rotatable Bonds:	12
TPSA:	453.03
# H-Bond Aceptor:	32
# H-Bond Donor:	12
# Rings:	2
# Heavy Atoms:	32

MedChem Properties

QED Drug-Likeness Score:	0.133
Synthetic Accessibility Score:	7.865
Fsp3:	0.697
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:	-4.461
MDCK Permeability:	0.0002721687778830528
Pgp-inhibitor:	0.991
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.085

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.238
Plasma Protein Binding (PPB):	65.56368255615234%
Volume Distribution (VD):	0.767
Pgp-substrate:	26.542896270751953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.068

ADMET: Excretion

Clearance (CL):	1.606
Half-life (T1/2):	0.809

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.999
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.083
Carcinogencity:	0.0
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.806

Download Data

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

Natural Product: NPC319766

Natural Product ID:	NPC319766
*Common Name:**	Verrucamide D
IUPAC Name:	(3S,6S,12R,15S,18S,21S,24S,27S,33R,36S,39S,42S)-33-benzyl-18,24-bis[(1R)-1-hydroxyethyl]-3,39-bis(hydroxymethyl)-1,4,12,13,19,25,34-heptamethyl-6,15,21,27,36,42-hexa(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31,34,37,40-tetradecazacyclodotetracontane-2,5,8,11,14,17,20,23,26,29,32,35,38,41-tetradecone
Synonyms:	Verrucamide D
Standard InCHIKey:	HRWLTBUENCFLGG-RBQVGXDUSA-N
Standard InCHI:	InChI=1S/C66H110N14O18/c1-32(2)47-63(95)77(18)44(31-82)61(93)78(19)52(37(11)12)58(90)69-42(30-81)56(88)72-50(35(7)8)64(96)76(17)43(27-41-25-23-22-24-26-41)57(89)68-29-46(86)71-48(33(3)4)65(97)79(20)53(39(14)83)60(92)74-51(36(9)10)66(98)80(21)54(40(15)84)59(91)73-49(34(5)6)62(94)75(16)38(13)55(87)67-28-45(85)70-47/h22-26,32-40,42-44,47-54,81-84H,27-31H2,1-21H3,(H,67,87)(H,68,89)(H,69,90)(H,70,85)(H,71,86)(H,72,88)(H,73,91)(H,74,92)/t38-,39-,40-,42+,43-,44+,47+,48+,49+,50+,51+,52+,53+,54+/m1/s1
SMILES:	OC[C@@H]1N=C(O)[C@H](C(C)C)N(C)C(=O)[C@H](CO)N(C)C(=O)[C@@H](N=C(O)CN=C(O)[C@@H](C)N(C)C(=O)[C@@H](N=C(O)[C@@H](N(C(=O)[C@@H](N=C([C@@H](N(C(=O)[C@@H](N=C(CN=C([C@H](N(C(=O)[C@@H](N=C1O)C(C)C)C)Cc1ccccc1)O)O)C(C)C)C)[C@H](O)C)O)C(C)C)C)[C@H](O)C)C(C)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784383
PubChem CID:	53355016
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
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075777]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[13678412]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21539317]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
MIC	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	9.09	ug.mL-1	PMID[490810]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	40.0	ug.mL-1	PMID[490810]

☑ 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 NPC319766 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	119
0.1-0.2	674
0.2-0.3	4310
0.3-0.4	20543
0.4-0.5	14279
0.5-0.6	1888
0.6-0.7	526
0.7-0.8	290
0.8-0.85	52
0.85-0.9	15
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9134	High Similarity	NPC287401
0.8931	High Similarity	NPC476259
0.8871	High Similarity	NPC46427
0.879	High Similarity	NPC252878
0.872	High Similarity	NPC6975
0.871	High Similarity	NPC202521
0.8682	High Similarity	NPC130309
0.8657	High Similarity	NPC176226
0.8629	High Similarity	NPC476990
0.8618	High Similarity	NPC470546
0.8607	High Similarity	NPC470544
0.8582	High Similarity	NPC469427
0.8582	High Similarity	NPC469426
0.8537	High Similarity	NPC470545
0.8507	High Similarity	NPC163392
0.8507	High Similarity	NPC239762
0.8444	Intermediate Similarity	NPC168113
0.8382	Intermediate Similarity	NPC197682
0.837	Intermediate Similarity	NPC307357
0.837	Intermediate Similarity	NPC46098
0.837	Intermediate Similarity	NPC268841
0.8358	Intermediate Similarity	NPC68865
0.8321	Intermediate Similarity	NPC476978
0.8306	Intermediate Similarity	NPC239357
0.8295	Intermediate Similarity	NPC101719
0.8248	Intermediate Similarity	NPC139326
0.8222	Intermediate Similarity	NPC471264
0.8222	Intermediate Similarity	NPC471265
0.8222	Intermediate Similarity	NPC127741
0.8217	Intermediate Similarity	NPC22746
0.8217	Intermediate Similarity	NPC222466
0.8209	Intermediate Similarity	NPC248283
0.8201	Intermediate Similarity	NPC314358
0.8189	Intermediate Similarity	NPC200964
0.8182	Intermediate Similarity	NPC300315
0.8175	Intermediate Similarity	NPC269398
0.8175	Intermediate Similarity	NPC263493
0.8156	Intermediate Similarity	NPC2501
0.8129	Intermediate Similarity	NPC5620
0.8129	Intermediate Similarity	NPC316008
0.8129	Intermediate Similarity	NPC313867
0.8125	Intermediate Similarity	NPC71684
0.812	Intermediate Similarity	NPC255447
0.8116	Intermediate Similarity	NPC161069
0.8106	Intermediate Similarity	NPC473322
0.8099	Intermediate Similarity	NPC475168
0.8099	Intermediate Similarity	NPC7817
0.8074	Intermediate Similarity	NPC141050
0.8058	Intermediate Similarity	NPC315283
0.8058	Intermediate Similarity	NPC314388
0.8047	Intermediate Similarity	NPC478015
0.8047	Intermediate Similarity	NPC478014
0.8047	Intermediate Similarity	NPC45777
0.8047	Intermediate Similarity	NPC477061
0.8047	Intermediate Similarity	NPC478016
0.8029	Intermediate Similarity	NPC92784
0.8029	Intermediate Similarity	NPC476133
0.8029	Intermediate Similarity	NPC470884
0.8029	Intermediate Similarity	NPC98424
0.8029	Intermediate Similarity	NPC178662
0.8014	Intermediate Similarity	NPC297145
0.8014	Intermediate Similarity	NPC197743
0.8014	Intermediate Similarity	NPC135121
0.8014	Intermediate Similarity	NPC145113
0.8	Intermediate Similarity	NPC201244
0.8	Intermediate Similarity	NPC315266
0.8	Intermediate Similarity	NPC477217
0.8	Intermediate Similarity	NPC209509
0.7986	Intermediate Similarity	NPC122590
0.7931	Intermediate Similarity	NPC470902
0.7929	Intermediate Similarity	NPC52748
0.7926	Intermediate Similarity	NPC246079
0.792	Intermediate Similarity	NPC276949
0.792	Intermediate Similarity	NPC35850
0.7917	Intermediate Similarity	NPC224610
0.7917	Intermediate Similarity	NPC162104
0.7917	Intermediate Similarity	NPC88267
0.7917	Intermediate Similarity	NPC194390
0.7917	Intermediate Similarity	NPC113326
0.7902	Intermediate Similarity	NPC129666
0.7887	Intermediate Similarity	NPC225648
0.7887	Intermediate Similarity	NPC329761
0.7887	Intermediate Similarity	NPC138775
0.7863	Intermediate Similarity	NPC175726
0.7863	Intermediate Similarity	NPC474082
0.7862	Intermediate Similarity	NPC473341
0.7857	Intermediate Similarity	NPC33742
0.7847	Intermediate Similarity	NPC473491
0.7836	Intermediate Similarity	NPC469666
0.7836	Intermediate Similarity	NPC111428
0.7832	Intermediate Similarity	NPC105717
0.7812	Intermediate Similarity	NPC169328
0.777	Intermediate Similarity	NPC132636
0.7755	Intermediate Similarity	NPC244509
0.7752	Intermediate Similarity	NPC310467
0.7744	Intermediate Similarity	NPC47667
0.774	Intermediate Similarity	NPC262166
0.7718	Intermediate Similarity	NPC62104
0.7718	Intermediate Similarity	NPC1390
0.7718	Intermediate Similarity	NPC469898
0.7708	Intermediate Similarity	NPC471820
0.7708	Intermediate Similarity	NPC471821
0.7667	Intermediate Similarity	NPC471527
0.7647	Intermediate Similarity	NPC200589
0.7622	Intermediate Similarity	NPC322878
0.7619	Intermediate Similarity	NPC286551
0.7616	Intermediate Similarity	NPC73655
0.7615	Intermediate Similarity	NPC237420
0.7606	Intermediate Similarity	NPC77905
0.76	Intermediate Similarity	NPC244336
0.7586	Intermediate Similarity	NPC240848
0.7569	Intermediate Similarity	NPC262077
0.7563	Intermediate Similarity	NPC473501
0.7563	Intermediate Similarity	NPC475439
0.755	Intermediate Similarity	NPC469901
0.7533	Intermediate Similarity	NPC324850
0.7532	Intermediate Similarity	NPC63040
0.7516	Intermediate Similarity	NPC217804
0.7516	Intermediate Similarity	NPC210377
0.7516	Intermediate Similarity	NPC22883
0.7516	Intermediate Similarity	NPC5719
0.75	Intermediate Similarity	NPC328494
0.7481	Intermediate Similarity	NPC314992
0.7479	Intermediate Similarity	NPC25565
0.7468	Intermediate Similarity	NPC15068
0.7462	Intermediate Similarity	NPC2265
0.7462	Intermediate Similarity	NPC315276
0.7462	Intermediate Similarity	NPC14672
0.7462	Intermediate Similarity	NPC285926
0.7451	Intermediate Similarity	NPC471053
0.7451	Intermediate Similarity	NPC471052
0.7451	Intermediate Similarity	NPC471051
0.7448	Intermediate Similarity	NPC81026
0.7436	Intermediate Similarity	NPC475204
0.7436	Intermediate Similarity	NPC473693
0.7436	Intermediate Similarity	NPC475123
0.7436	Intermediate Similarity	NPC471568
0.7432	Intermediate Similarity	NPC300443
0.7419	Intermediate Similarity	NPC302597
0.7415	Intermediate Similarity	NPC283783
0.7405	Intermediate Similarity	NPC158277
0.7405	Intermediate Similarity	NPC477462
0.7394	Intermediate Similarity	NPC89489
0.7383	Intermediate Similarity	NPC5194
0.7383	Intermediate Similarity	NPC56685
0.7383	Intermediate Similarity	NPC261934
0.7379	Intermediate Similarity	NPC266741
0.7372	Intermediate Similarity	NPC71933
0.7372	Intermediate Similarity	NPC473000
0.7372	Intermediate Similarity	NPC89923
0.7372	Intermediate Similarity	NPC105114
0.7372	Intermediate Similarity	NPC152850
0.7372	Intermediate Similarity	NPC239990
0.7342	Intermediate Similarity	NPC248670
0.7325	Intermediate Similarity	NPC40234
0.7325	Intermediate Similarity	NPC196091
0.7325	Intermediate Similarity	NPC46009
0.7315	Intermediate Similarity	NPC233702
0.7308	Intermediate Similarity	NPC107938
0.7308	Intermediate Similarity	NPC294516
0.7299	Intermediate Similarity	NPC136453
0.7296	Intermediate Similarity	NPC136797
0.7296	Intermediate Similarity	NPC317362
0.7296	Intermediate Similarity	NPC318930
0.7292	Intermediate Similarity	NPC476989
0.729	Intermediate Similarity	NPC472923
0.7287	Intermediate Similarity	NPC273814
0.7287	Intermediate Similarity	NPC474584
0.7286	Intermediate Similarity	NPC325479
0.7279	Intermediate Similarity	NPC16188
0.7278	Intermediate Similarity	NPC230611
0.7267	Intermediate Similarity	NPC202198
0.7261	Intermediate Similarity	NPC186617
0.7252	Intermediate Similarity	NPC188010
0.725	Intermediate Similarity	NPC50016
0.725	Intermediate Similarity	NPC469900
0.7239	Intermediate Similarity	NPC302169
0.7239	Intermediate Similarity	NPC190663
0.7239	Intermediate Similarity	NPC80150
0.7233	Intermediate Similarity	NPC306804
0.7233	Intermediate Similarity	NPC137627
0.7214	Intermediate Similarity	NPC157311
0.7206	Intermediate Similarity	NPC35996
0.7197	Intermediate Similarity	NPC209463
0.7188	Intermediate Similarity	NPC473402
0.7188	Intermediate Similarity	NPC476227
0.7188	Intermediate Similarity	NPC471165
0.7188	Intermediate Similarity	NPC279871
0.7188	Intermediate Similarity	NPC26108
0.7181	Intermediate Similarity	NPC254798
0.7179	Intermediate Similarity	NPC63931
0.7171	Intermediate Similarity	NPC469903
0.7171	Intermediate Similarity	NPC476268
0.7163	Intermediate Similarity	NPC8761
0.7163	Intermediate Similarity	NPC44805
0.716	Intermediate Similarity	NPC475421
0.7143	Intermediate Similarity	NPC24617
0.7143	Intermediate Similarity	NPC254088
0.7143	Intermediate Similarity	NPC471680
0.7134	Intermediate Similarity	NPC254700

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 NPC319766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	97
0.1-0.2	289
0.2-0.3	794
0.3-0.4	2498
0.4-0.5	3688
0.5-0.6	1429
0.6-0.7	318
0.7-0.8	35
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD8172	Phase 2
0.8636	High Similarity	NPD8173	Phase 2
0.8148	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD8416	Discontinued
0.7762	Intermediate Similarity	NPD8323	Discontinued
0.773	Intermediate Similarity	NPD8076	Discontinued
0.7704	Intermediate Similarity	NPD3626	Phase 3
0.763	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8265	Approved
0.7518	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7342	Discontinued
0.75	Intermediate Similarity	NPD7130	Phase 3
0.75	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2218	Phase 2
0.7481	Intermediate Similarity	NPD2217	Approved
0.7465	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD2584	Suspended
0.7417	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7522	Discontinued
0.7394	Intermediate Similarity	NPD6901	Phase 3
0.7376	Intermediate Similarity	NPD8643	Discontinued
0.7361	Intermediate Similarity	NPD7978	Discontinued
0.7324	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4125	Approved
0.7246	Intermediate Similarity	NPD3588	Discontinued
0.7241	Intermediate Similarity	NPD7720	Phase 2
0.7226	Intermediate Similarity	NPD5367	Discontinued
0.7211	Intermediate Similarity	NPD6676	Phase 2
0.7197	Intermediate Similarity	NPD3123	Discovery
0.7192	Intermediate Similarity	NPD6681	Discovery
0.7183	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6852	Discontinued
0.7153	Intermediate Similarity	NPD4677	Discontinued
0.7143	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD8417	Discontinued
0.7123	Intermediate Similarity	NPD2022	Approved
0.7122	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8315	Phase 1
0.7101	Intermediate Similarity	NPD6792	Phase 3
0.7092	Intermediate Similarity	NPD21	Approved
0.7092	Intermediate Similarity	NPD2048	Approved
0.7092	Intermediate Similarity	NPD2043	Approved
0.7092	Intermediate Similarity	NPD2045	Approved
0.7092	Intermediate Similarity	NPD2051	Approved
0.7092	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2044	Approved
0.7092	Intermediate Similarity	NPD2046	Approved
0.7092	Intermediate Similarity	NPD2047	Approved
0.7092	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7613	Discontinued
0.708	Intermediate Similarity	NPD3071	Approved
0.708	Intermediate Similarity	NPD3073	Approved
0.708	Intermediate Similarity	NPD3072	Approved
0.7075	Intermediate Similarity	NPD2437	Approved
0.7075	Intermediate Similarity	NPD2436	Approved
0.7071	Intermediate Similarity	NPD4175	Approved
0.7071	Intermediate Similarity	NPD4177	Approved
0.7042	Intermediate Similarity	NPD7908	Discontinued
0.7007	Intermediate Similarity	NPD2087	Approved
0.7007	Intermediate Similarity	NPD4152	Approved
0.7007	Intermediate Similarity	NPD2088	Approved
0.7007	Intermediate Similarity	NPD4762	Approved
0.7007	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4761	Approved
0.6992	Remote Similarity	NPD7508	Discontinued
0.6978	Remote Similarity	NPD3125	Approved
0.6968	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5725	Approved
0.6966	Remote Similarity	NPD6073	Approved
0.696	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6088	Approved
0.695	Remote Similarity	NPD3040	Approved
0.6944	Remote Similarity	NPD6623	Phase 3
0.6944	Remote Similarity	NPD4153	Approved
0.6944	Remote Similarity	NPD5323	Approved
0.694	Remote Similarity	NPD5291	Approved
0.694	Remote Similarity	NPD5292	Approved
0.6933	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD8124	Phase 3
0.6914	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD854	Approved
0.6905	Remote Similarity	NPD855	Approved
0.6901	Remote Similarity	NPD5263	Approved
0.6901	Remote Similarity	NPD4676	Approved
0.6901	Remote Similarity	NPD2613	Approved
0.6897	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2609	Approved
0.6884	Remote Similarity	NPD3132	Approved
0.6884	Remote Similarity	NPD2610	Approved
0.6884	Remote Similarity	NPD4215	Approved
0.6884	Remote Similarity	NPD2608	Approved
0.6884	Remote Similarity	NPD3131	Approved
0.6884	Remote Similarity	NPD2612	Approved
0.6884	Remote Similarity	NPD4217	Approved
0.6884	Remote Similarity	NPD4218	Approved
0.6884	Remote Similarity	NPD2611	Approved
0.6884	Remote Similarity	NPD4216	Approved
0.6883	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4557	Approved
0.6875	Remote Similarity	NPD999	Phase 2
0.6875	Remote Similarity	NPD5747	Discontinued
0.6875	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8118	Discontinued
0.6871	Remote Similarity	NPD3480	Approved
0.6871	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.687	Remote Similarity	NPD3644	Approved
0.687	Remote Similarity	NPD3642	Approved
0.687	Remote Similarity	NPD3643	Approved
0.6866	Remote Similarity	NPD1348	Approved
0.6853	Remote Similarity	NPD4738	Phase 2
0.6842	Remote Similarity	NPD5613	Approved
0.6842	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3987	Approved
0.6842	Remote Similarity	NPD3988	Approved
0.6842	Remote Similarity	NPD5614	Approved
0.6835	Remote Similarity	NPD7814	Approved
0.6832	Remote Similarity	NPD7484	Phase 3
0.6832	Remote Similarity	NPD7485	Phase 3
0.6829	Remote Similarity	NPD4814	Discontinued
0.6821	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD8303	Discontinued
0.6806	Remote Similarity	NPD5299	Approved
0.6806	Remote Similarity	NPD1330	Phase 2
0.6806	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5581	Approved
0.6803	Remote Similarity	NPD6295	Approved
0.6803	Remote Similarity	NPD6294	Approved
0.6803	Remote Similarity	NPD6690	Approved
0.6795	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8351	Phase 2
0.6783	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4648	Approved
0.6774	Remote Similarity	NPD4647	Approved
0.6774	Remote Similarity	NPD4646	Approved
0.6769	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3090	Approved
0.6759	Remote Similarity	NPD2571	Approved
0.6759	Remote Similarity	NPD2573	Approved
0.6759	Remote Similarity	NPD3089	Approved
0.6759	Remote Similarity	NPD3615	Approved
0.6759	Remote Similarity	NPD2574	Discontinued
0.6759	Remote Similarity	NPD2570	Approved
0.6759	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4746	Phase 3
0.6759	Remote Similarity	NPD2566	Approved
0.6759	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3087	Approved
0.6759	Remote Similarity	NPD3614	Approved
0.6759	Remote Similarity	NPD3088	Approved
0.6759	Remote Similarity	NPD4745	Approved
0.6759	Remote Similarity	NPD3616	Approved
0.6755	Remote Similarity	NPD1967	Approved
0.6755	Remote Similarity	NPD1968	Approved
0.6753	Remote Similarity	NPD5229	Approved
0.6753	Remote Similarity	NPD5230	Approved
0.6738	Remote Similarity	NPD6325	Discontinued
0.6738	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4794	Discontinued
0.6736	Remote Similarity	NPD3136	Phase 2
0.6733	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD998	Approved
0.6714	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5296	Approved
0.671	Remote Similarity	NPD7131	Phase 3
0.6707	Remote Similarity	NPD7965	Phase 2
0.6707	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7813	Approved
0.6691	Remote Similarity	NPD7815	Approved
0.669	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7599	Phase 2
0.6667	Remote Similarity	NPD1814	Approved
0.6667	Remote Similarity	NPD4684	Phase 3
0.6667	Remote Similarity	NPD4685	Phase 3
0.6667	Remote Similarity	NPD4686	Approved
0.6667	Remote Similarity	NPD1812	Approved
0.6645	Remote Similarity	NPD7303	Discontinued
0.6645	Remote Similarity	NPD3821	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3822	Approved
0.6645	Remote Similarity	NPD3820	Approved
0.6643	Remote Similarity	NPD4151	Approved
0.6642	Remote Similarity	NPD480	Approved
0.6641	Remote Similarity	NPD6406	Approved
0.6625	Remote Similarity	NPD7600	Phase 2
0.6623	Remote Similarity	NPD2014	Approved
0.6623	Remote Similarity	NPD2013	Approved
0.6623	Remote Similarity	NPD2016	Approved
0.662	Remote Similarity	NPD2031	Discontinued
0.6619	Remote Similarity	NPD5723	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