NPASS Compound

Structure

CID161069 OpenBabel06191715532D 54 57 0 0 1 0 0 0 0 0999 V2000 -5.1661 4.1651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2430 -0.8706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4874 0.6224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1514 1.5918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1116 1.6981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2692 -5.3093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7821 -2.8515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9548 3.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0328 2.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7285 -2.8615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3319 -7.9185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8215 1.9913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9501 -2.2894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6223 -3.8218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4952 -7.4354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1685 -7.4354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0883 -6.3790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0654 -2.6775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7375 -4.2099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4952 -6.4693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1685 -6.4693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9751 -5.9958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8995 1.7029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4498 -5.6540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1896 -4.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3319 -4.0541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7949 -1.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4342 -0.3422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9591 -3.6377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3319 -5.9863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8847 -5.0339 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4112 -3.8417 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4952 -3.5710 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6882 0.7602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3118 -0.2379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5722 -0.7785 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8474 -2.9797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8450 -4.9277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1190 -4.3168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8606 -1.7005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7939 0.5505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7236 0.8134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9801 -2.0227 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 -3.7187 -4.5154 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8339 -2.6662 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9420 -4.8227 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0576 0.3763 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7695 -3.2681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1079 -5.8573 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5155 -5.0453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8175 -1.5678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3816 1.4242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5833 0.3966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 28 1 0 0 0 0 3 28 1 0 0 0 0 4 42 1 0 0 0 0 5 42 1 0 0 0 0 6 45 1 0 0 0 0 7 46 1 0 0 0 0 8 9 1 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 23 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 18 29 2 0 0 0 0 19 29 1 0 0 0 0 20 30 2 0 0 0 0 21 30 1 0 0 0 0 24 47 1 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 27 35 1 0 0 0 0 27 43 1 0 0 0 0 31 22 1 1 0 0 0 31 38 1 0 0 0 0 31 47 1 0 0 0 0 32 25 1 1 0 0 0 32 37 1 0 0 0 0 32 45 1 0 0 0 0 33 26 1 1 0 0 0 33 39 1 0 0 0 0 33 46 1 0 0 0 0 34 23 1 1 0 0 0 34 42 1 0 0 0 0 34 54 1 0 0 0 0 35 48 2 0 0 0 0 35 54 1 0 0 0 0 36 28 1 1 0 0 0 36 40 1 0 0 0 0 36 44 1 0 0 0 0 37 43 2 3 0 0 0 37 49 1 0 0 0 0 38 45 1 0 0 0 0 38 50 2 0 0 0 0 39 47 1 0 0 0 0 39 51 2 0 0 0 0 40 46 1 0 0 0 0 40 52 2 0 0 0 0 41 42 1 0 0 0 0 41 44 2 3 0 0 0 41 53 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	743.43
Volume:	783.003
LogP:	4.572
LogD:	3.735
LogS:	-4.587
# Rotatable Bonds:	9
TPSA:	145.43
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.227
Synthetic Accessibility Score:	5.14
Fsp3:	0.524
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.847
MDCK Permeability:	8.510956831742078e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.344

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	91.8537368774414%
Volume Distribution (VD):	0.309
Pgp-substrate:	4.333846092224121%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.281
CYP2C19-substrate:	0.768
CYP2C9-inhibitor:	0.847
CYP2C9-substrate:	0.329
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.976
CYP3A4-substrate:	0.908

ADMET: Excretion

Clearance (CL):	6.636
Half-life (T1/2):	0.423

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.92
Drug-inuced Liver Injury (DILI):	0.541
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.896
Maximum Recommended Daily Dose:	0.508
Skin Sensitization:	0.041
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC161069

Natural Product ID:	NPC161069
*Common Name:**	Cocosamide A
IUPAC Name:	(3S,6S,10S,16S,19S)-3,16-dibenzyl-4,9,9,17-tetramethyl-10-pent-4-enyl-6-propan-2-yl-11-oxa-1,4,7,14,17-pentazabicyclo[17.3.0]docosane-2,5,8,12,15,18-hexone
Synonyms:	Cocosamide A
Standard InCHIKey:	DYRQQWGTDVBUND-NRYNYGQJSA-N
Standard InCHI:	InChI=1S/C42H57N5O7/c1-8-9-12-23-34-42(4,5)41(53)44-36(28(2)3)40(52)46(7)33(26-30-20-15-11-16-21-30)39(51)47-24-17-22-31(47)38(50)45(6)32(25-29-18-13-10-14-19-29)37(49)43-27-35(48)54-34/h8,10-11,13-16,18-21,28,31-34,36H,1,9,12,17,22-27H2,2-7H3,(H,43,49)(H,44,53)/t31-,32-,33-,34-,36-/m0/s1
SMILES:	C=CCCC[C@@H]1OC(=O)CN=C(O)[C@H](Cc2ccccc2)N(C)C(=O)[C@H]2N(C(=O)[C@@H](N(C(=O)[C@@H](N=C(C1(C)C)O)C(C)C)C)Cc1ccccc1)CCC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773901
PubChem CID:	52952542
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
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10514329]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10654420]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10691708]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	palauan	n.a.	PMID[10691729]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10843570]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10924172]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10978206]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076571]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076573]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076574]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11277744]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11389621]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11430000]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473443]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11922791]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762816]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[12828459]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14575437]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1517734]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[16643028]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125217]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17441769]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18444683]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Singapore	n.a.	PMID[19093843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19489598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	eastern Caribbean	n.a.	PMID[19739598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19839606]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20030365]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	panamanian	n.a.	PMID[20158242]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Floridian	n.a.	PMID[20166701]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20936843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21138309]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2128518]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21341718]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21539315]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21806011]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21999614]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22035372]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29792428]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3924698]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[7623050]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[8699186]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9584405]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599278]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599279]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9784156]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	30000.0	nM	PMID[475014]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	24000.0	nM	PMID[475014]

☑ 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 NPC161069 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	133
0.1-0.2	665
0.2-0.3	2188
0.3-0.4	12601
0.4-0.5	21842
0.5-0.6	4233
0.6-0.7	654
0.7-0.8	273
0.8-0.85	61
0.85-0.9	41
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9704	High Similarity	NPC138775
0.927	High Similarity	NPC5620
0.9191	High Similarity	NPC269398
0.9191	High Similarity	NPC263493
0.913	High Similarity	NPC209509
0.9007	High Similarity	NPC129666
0.8951	High Similarity	NPC122590
0.8929	High Similarity	NPC262077
0.8921	High Similarity	NPC476978
0.8865	High Similarity	NPC145113
0.8865	High Similarity	NPC225648
0.8865	High Similarity	NPC329761
0.8768	High Similarity	NPC476133
0.8768	High Similarity	NPC470884
0.8768	High Similarity	NPC178662
0.8768	High Similarity	NPC92784
0.8768	High Similarity	NPC98424
0.8741	High Similarity	NPC2501
0.8731	High Similarity	NPC473322
0.8705	High Similarity	NPC163392
0.8705	High Similarity	NPC239762
0.8696	High Similarity	NPC127741
0.8696	High Similarity	NPC471265
0.8696	High Similarity	NPC471264
0.8582	High Similarity	NPC139326
0.8521	High Similarity	NPC52748
0.8456	Intermediate Similarity	NPC197743
0.8456	Intermediate Similarity	NPC297145
0.8451	Intermediate Similarity	NPC197682
0.8429	Intermediate Similarity	NPC68865
0.8414	Intermediate Similarity	NPC471821
0.8414	Intermediate Similarity	NPC240848
0.8414	Intermediate Similarity	NPC471820
0.8414	Intermediate Similarity	NPC105717
0.8397	Intermediate Similarity	NPC310467
0.8397	Intermediate Similarity	NPC470546
0.838	Intermediate Similarity	NPC168113
0.8367	Intermediate Similarity	NPC162104
0.8358	Intermediate Similarity	NPC46427
0.8358	Intermediate Similarity	NPC6975
0.8345	Intermediate Similarity	NPC135121
0.8333	Intermediate Similarity	NPC316008
0.8333	Intermediate Similarity	NPC130309
0.8333	Intermediate Similarity	NPC313867
0.8333	Intermediate Similarity	NPC255447
0.8322	Intermediate Similarity	NPC176226
0.8321	Intermediate Similarity	NPC470545
0.8321	Intermediate Similarity	NPC169328
0.831	Intermediate Similarity	NPC46098
0.831	Intermediate Similarity	NPC307357
0.831	Intermediate Similarity	NPC268841
0.8284	Intermediate Similarity	NPC252878
0.8276	Intermediate Similarity	NPC314358
0.8271	Intermediate Similarity	NPC200964
0.8264	Intermediate Similarity	NPC315283
0.8264	Intermediate Similarity	NPC314388
0.8244	Intermediate Similarity	NPC470544
0.8209	Intermediate Similarity	NPC202521
0.8207	Intermediate Similarity	NPC477217
0.8207	Intermediate Similarity	NPC201244
0.8188	Intermediate Similarity	NPC286551
0.8182	Intermediate Similarity	NPC476259
0.8165	Intermediate Similarity	NPC26108
0.8156	Intermediate Similarity	NPC248283
0.8143	Intermediate Similarity	NPC246079
0.8134	Intermediate Similarity	NPC476990
0.8129	Intermediate Similarity	NPC200589
0.8125	Intermediate Similarity	NPC469427
0.8125	Intermediate Similarity	NPC469426
0.8117	Intermediate Similarity	NPC471051
0.8117	Intermediate Similarity	NPC471053
0.8117	Intermediate Similarity	NPC471052
0.8116	Intermediate Similarity	NPC152850
0.8116	Intermediate Similarity	NPC71933
0.8116	Intermediate Similarity	NPC319766
0.8116	Intermediate Similarity	NPC89923
0.8116	Intermediate Similarity	NPC239990
0.8116	Intermediate Similarity	NPC105114
0.8112	Intermediate Similarity	NPC132636
0.8102	Intermediate Similarity	NPC101719
0.8101	Intermediate Similarity	NPC137627
0.8082	Intermediate Similarity	NPC315266
0.8067	Intermediate Similarity	NPC473341
0.8054	Intermediate Similarity	NPC7817
0.8054	Intermediate Similarity	NPC475168
0.805	Intermediate Similarity	NPC477462
0.805	Intermediate Similarity	NPC318930
0.805	Intermediate Similarity	NPC317362
0.8043	Intermediate Similarity	NPC136453
0.8029	Intermediate Similarity	NPC222466
0.8	Intermediate Similarity	NPC477061
0.8	Intermediate Similarity	NPC45777
0.7987	Intermediate Similarity	NPC471527
0.7958	Intermediate Similarity	NPC287401
0.7943	Intermediate Similarity	NPC157311
0.7941	Intermediate Similarity	NPC71684
0.7937	Intermediate Similarity	NPC326407
0.7937	Intermediate Similarity	NPC317725
0.7929	Intermediate Similarity	NPC111428
0.7895	Intermediate Similarity	NPC470902
0.7887	Intermediate Similarity	NPC8761
0.7887	Intermediate Similarity	NPC44805
0.7867	Intermediate Similarity	NPC283783
0.7852	Intermediate Similarity	NPC237420
0.7842	Intermediate Similarity	NPC47667
0.7834	Intermediate Similarity	NPC63931
0.7834	Intermediate Similarity	NPC472923
0.7826	Intermediate Similarity	NPC175726
0.7826	Intermediate Similarity	NPC474082
0.7806	Intermediate Similarity	NPC1390
0.7806	Intermediate Similarity	NPC62104
0.7764	Intermediate Similarity	NPC306804
0.7763	Intermediate Similarity	NPC233702
0.775	Intermediate Similarity	NPC475204
0.775	Intermediate Similarity	NPC475123
0.7737	Intermediate Similarity	NPC478015
0.7737	Intermediate Similarity	NPC478016
0.7737	Intermediate Similarity	NPC190663
0.7737	Intermediate Similarity	NPC478014
0.7736	Intermediate Similarity	NPC294516
0.7736	Intermediate Similarity	NPC107938
0.7733	Intermediate Similarity	NPC16188
0.7727	Intermediate Similarity	NPC469903
0.7718	Intermediate Similarity	NPC322878
0.7716	Intermediate Similarity	NPC159767
0.7716	Intermediate Similarity	NPC279871
0.7716	Intermediate Similarity	NPC476227
0.7716	Intermediate Similarity	NPC155506
0.7704	Intermediate Similarity	NPC239357
0.7704	Intermediate Similarity	NPC315276
0.7704	Intermediate Similarity	NPC285926
0.7704	Intermediate Similarity	NPC14672
0.7687	Intermediate Similarity	NPC33742
0.7643	Intermediate Similarity	NPC469902
0.764	Intermediate Similarity	NPC40234
0.7626	Intermediate Similarity	NPC160493
0.7622	Intermediate Similarity	NPC300315
0.7612	Intermediate Similarity	NPC35850
0.7612	Intermediate Similarity	NPC276949
0.761	Intermediate Similarity	NPC217804
0.761	Intermediate Similarity	NPC22883
0.761	Intermediate Similarity	NPC5719
0.761	Intermediate Similarity	NPC210377
0.7609	Intermediate Similarity	NPC80150
0.7607	Intermediate Similarity	NPC471165
0.7593	Intermediate Similarity	NPC230611
0.7576	Intermediate Similarity	NPC269750
0.7576	Intermediate Similarity	NPC194671
0.7576	Intermediate Similarity	NPC475421
0.7562	Intermediate Similarity	NPC15068
0.7551	Intermediate Similarity	NPC43755
0.755	Intermediate Similarity	NPC81026
0.7546	Intermediate Similarity	NPC273755
0.7535	Intermediate Similarity	NPC477937
0.7532	Intermediate Similarity	NPC469901
0.7518	Intermediate Similarity	NPC22746
0.7516	Intermediate Similarity	NPC63040
0.7516	Intermediate Similarity	NPC324850
0.75	Intermediate Similarity	NPC473354
0.75	Intermediate Similarity	NPC473402
0.7485	Intermediate Similarity	NPC89831
0.7484	Intermediate Similarity	NPC262166
0.7484	Intermediate Similarity	NPC202198
0.7483	Intermediate Similarity	NPC266741
0.7471	Intermediate Similarity	NPC4910
0.7455	Intermediate Similarity	NPC50016
0.7453	Intermediate Similarity	NPC254700
0.7447	Intermediate Similarity	NPC35996
0.744	Intermediate Similarity	NPC470903
0.744	Intermediate Similarity	NPC470112
0.744	Intermediate Similarity	NPC167763
0.7439	Intermediate Similarity	NPC248670
0.7436	Intermediate Similarity	NPC39431
0.7431	Intermediate Similarity	NPC469666
0.7423	Intermediate Similarity	NPC46009
0.7407	Intermediate Similarity	NPC302597
0.7407	Intermediate Similarity	NPC273814
0.7407	Intermediate Similarity	NPC474584
0.7407	Intermediate Similarity	NPC473502
0.74	Intermediate Similarity	NPC476989
0.7397	Intermediate Similarity	NPC246913
0.7396	Intermediate Similarity	NPC471050
0.7396	Intermediate Similarity	NPC471049
0.7396	Intermediate Similarity	NPC471048
0.7396	Intermediate Similarity	NPC294951
0.7383	Intermediate Similarity	NPC89489
0.7379	Intermediate Similarity	NPC69496
0.7376	Intermediate Similarity	NPC84281
0.7376	Intermediate Similarity	NPC169485
0.7376	Intermediate Similarity	NPC213126
0.7376	Intermediate Similarity	NPC291027
0.7376	Intermediate Similarity	NPC317474
0.7368	Intermediate Similarity	NPC329731
0.7365	Intermediate Similarity	NPC45037
0.7362	Intermediate Similarity	NPC469904
0.7358	Intermediate Similarity	NPC319320
0.7358	Intermediate Similarity	NPC287757
0.7355	Intermediate Similarity	NPC473491
0.7353	Intermediate Similarity	NPC299806
0.7351	Intermediate Similarity	NPC77905

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 NPC161069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	98
0.1-0.2	300
0.2-0.3	647
0.3-0.4	1705
0.4-0.5	3841
0.5-0.6	2006
0.6-0.7	411
0.7-0.8	134
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD8172	Phase 2
0.8696	High Similarity	NPD8173	Phase 2
0.8358	Intermediate Similarity	NPD2584	Suspended
0.8357	Intermediate Similarity	NPD8643	Discontinued
0.8345	Intermediate Similarity	NPD8323	Discontinued
0.8169	Intermediate Similarity	NPD6073	Approved
0.8156	Intermediate Similarity	NPD8416	Discontinued
0.8112	Intermediate Similarity	NPD6852	Discontinued
0.8099	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD4175	Approved
0.8058	Intermediate Similarity	NPD4177	Approved
0.7986	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5725	Approved
0.7914	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD6623	Phase 3
0.7838	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7599	Phase 2
0.7754	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4125	Approved
0.7746	Intermediate Similarity	NPD5263	Approved
0.773	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5747	Discontinued
0.7707	Intermediate Similarity	NPD7600	Phase 2
0.7698	Intermediate Similarity	NPD3071	Approved
0.7698	Intermediate Similarity	NPD3072	Approved
0.7698	Intermediate Similarity	NPD3073	Approved
0.7692	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD8315	Phase 1
0.7655	Intermediate Similarity	NPD4153	Approved
0.7635	Intermediate Similarity	NPD7512	Approved
0.7635	Intermediate Similarity	NPD7511	Approved
0.7632	Intermediate Similarity	NPD6088	Approved
0.7626	Intermediate Similarity	NPD4762	Approved
0.7626	Intermediate Similarity	NPD4761	Approved
0.7619	Intermediate Similarity	NPD6294	Approved
0.7619	Intermediate Similarity	NPD6295	Approved
0.7591	Intermediate Similarity	NPD6343	Approved
0.7591	Intermediate Similarity	NPD6345	Approved
0.7552	Intermediate Similarity	NPD5759	Approved
0.7551	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD8265	Approved
0.7532	Intermediate Similarity	NPD7613	Discontinued
0.7518	Intermediate Similarity	NPD4677	Discontinued
0.7518	Intermediate Similarity	NPD5990	Approved
0.7518	Intermediate Similarity	NPD5991	Approved
0.75	Intermediate Similarity	NPD4676	Approved
0.75	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7720	Phase 2
0.7465	Intermediate Similarity	NPD6792	Phase 3
0.7438	Intermediate Similarity	NPD8351	Phase 2
0.7432	Intermediate Similarity	NPD7510	Approved
0.7417	Intermediate Similarity	NPD2437	Approved
0.7417	Intermediate Similarity	NPD2436	Approved
0.7415	Intermediate Similarity	NPD5296	Approved
0.741	Intermediate Similarity	NPD5981	Approved
0.7388	Intermediate Similarity	NPD3642	Approved
0.7388	Intermediate Similarity	NPD3643	Approved
0.7388	Intermediate Similarity	NPD3644	Approved
0.7386	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2613	Approved
0.7376	Intermediate Similarity	NPD3131	Approved
0.7376	Intermediate Similarity	NPD2611	Approved
0.7376	Intermediate Similarity	NPD2609	Approved
0.7376	Intermediate Similarity	NPD4217	Approved
0.7376	Intermediate Similarity	NPD2608	Approved
0.7376	Intermediate Similarity	NPD4218	Approved
0.7376	Intermediate Similarity	NPD2610	Approved
0.7376	Intermediate Similarity	NPD4216	Approved
0.7376	Intermediate Similarity	NPD2612	Approved
0.7376	Intermediate Similarity	NPD3132	Approved
0.7376	Intermediate Similarity	NPD4215	Approved
0.7375	Intermediate Similarity	NPD7080	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5264	Approved
0.7368	Intermediate Similarity	NPD5265	Approved
0.7361	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4152	Approved
0.7351	Intermediate Similarity	NPD8076	Discontinued
0.7347	Intermediate Similarity	NPD2566	Approved
0.7347	Intermediate Similarity	NPD2570	Approved
0.7347	Intermediate Similarity	NPD2574	Discontinued
0.7347	Intermediate Similarity	NPD3616	Approved
0.7347	Intermediate Similarity	NPD3088	Approved
0.7347	Intermediate Similarity	NPD4745	Approved
0.7347	Intermediate Similarity	NPD3089	Approved
0.7347	Intermediate Similarity	NPD2572	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3087	Approved
0.7347	Intermediate Similarity	NPD4746	Phase 3
0.7347	Intermediate Similarity	NPD2573	Approved
0.7347	Intermediate Similarity	NPD3090	Approved
0.7347	Intermediate Similarity	NPD3615	Approved
0.7347	Intermediate Similarity	NPD3614	Approved
0.7347	Intermediate Similarity	NPD2571	Approved
0.7342	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD8417	Discontinued
0.7329	Intermediate Similarity	NPD4738	Phase 2
0.7312	Intermediate Similarity	NPD4557	Approved
0.731	Intermediate Similarity	NPD3040	Approved
0.731	Intermediate Similarity	NPD3626	Phase 3
0.7303	Intermediate Similarity	NPD6681	Discovery
0.7297	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5581	Approved
0.7267	Intermediate Similarity	NPD6901	Phase 3
0.7248	Intermediate Similarity	NPD4684	Phase 3
0.7248	Intermediate Similarity	NPD4686	Approved
0.7248	Intermediate Similarity	NPD4685	Phase 3
0.7237	Intermediate Similarity	NPD2022	Approved
0.723	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8126	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8124	Phase 3
0.7226	Intermediate Similarity	NPD3598	Phase 3
0.7219	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3480	Approved
0.7218	Intermediate Similarity	NPD7130	Phase 3
0.7215	Intermediate Similarity	NPD4647	Approved
0.7215	Intermediate Similarity	NPD4648	Approved
0.7215	Intermediate Similarity	NPD4646	Approved
0.7211	Intermediate Similarity	NPD2051	Approved
0.7211	Intermediate Similarity	NPD21	Approved
0.7211	Intermediate Similarity	NPD2047	Approved
0.7211	Intermediate Similarity	NPD2043	Approved
0.7211	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2046	Approved
0.7211	Intermediate Similarity	NPD4794	Discontinued
0.7211	Intermediate Similarity	NPD2045	Approved
0.7211	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2044	Approved
0.7211	Intermediate Similarity	NPD2048	Approved
0.7208	Intermediate Similarity	NPD5298	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5229	Approved
0.7197	Intermediate Similarity	NPD5230	Approved
0.7194	Intermediate Similarity	NPD4574	Approved
0.7194	Intermediate Similarity	NPD4576	Approved
0.719	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7105	Phase 1
0.7188	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5323	Approved
0.7179	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1330	Phase 2
0.7162	Intermediate Similarity	NPD4619	Approved
0.7162	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4621	Approved
0.7161	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7131	Phase 3
0.7143	Intermediate Similarity	NPD7522	Discontinued
0.7143	Intermediate Similarity	NPD6065	Approved
0.7134	Intermediate Similarity	NPD8303	Discontinued
0.7133	Intermediate Similarity	NPD3908	Approved
0.7124	Intermediate Similarity	NPD2088	Approved
0.7124	Intermediate Similarity	NPD2087	Approved
0.7122	Intermediate Similarity	NPD1348	Approved
0.7115	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD8118	Discontinued
0.7092	Intermediate Similarity	NPD2218	Phase 2
0.7092	Intermediate Similarity	NPD2217	Approved
0.7083	Intermediate Similarity	NPD7814	Approved
0.7083	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5204	Approved
0.707	Intermediate Similarity	NPD5613	Approved
0.707	Intermediate Similarity	NPD5614	Approved
0.7048	Intermediate Similarity	NPD7484	Phase 3
0.7048	Intermediate Similarity	NPD7485	Phase 3
0.7047	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5299	Approved
0.7039	Intermediate Similarity	NPD4126	Approved
0.7025	Intermediate Similarity	NPD5941	Approved
0.7025	Intermediate Similarity	NPD4432	Discontinued
0.7025	Intermediate Similarity	NPD5942	Approved
0.7024	Intermediate Similarity	NPD7965	Phase 2
0.7024	Intermediate Similarity	NPD7964	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4151	Approved
0.7007	Intermediate Similarity	NPD3588	Discontinued
0.6993	Remote Similarity	NPD7342	Discontinued
0.6986	Remote Similarity	NPD5367	Discontinued
0.6986	Remote Similarity	NPD3125	Approved
0.6986	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2031	Discontinued
0.6986	Remote Similarity	NPD5578	Approved
0.6981	Remote Similarity	NPD5638	Approved
0.6978	Remote Similarity	NPD2650	Approved
0.6978	Remote Similarity	NPD2652	Approved
0.6963	Remote Similarity	NPD5704	Approved
0.6963	Remote Similarity	NPD5706	Approved
0.6963	Remote Similarity	NPD5705	Approved
0.6962	Remote Similarity	NPD3988	Approved
0.6962	Remote Similarity	NPD3987	Approved
0.6959	Remote Similarity	NPD7828	Discontinued
0.6944	Remote Similarity	NPD7815	Approved
0.6944	Remote Similarity	NPD7813	Approved
0.6941	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8352	Phase 1
0.6933	Remote Similarity	NPD7011	Discontinued
0.6929	Remote Similarity	NPD747	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