NPASS Compound

Structure

CID233932 OpenBabel06191716032D 38 37 0 0 1 0 0 0 0 0999 V2000 -18.1865 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.1865 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.3205 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.4545 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5885 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.9904 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 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 -4.3301 -4.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -4.5000 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 5 1 0 0 0 0 2 31 1 0 0 0 0 3 37 1 0 0 0 0 4 38 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 14 25 1 0 0 0 0 15 27 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 17 23 1 0 0 0 0 17 26 1 0 0 0 0 18 24 1 0 0 0 0 18 28 1 0 0 0 0 19 22 2 0 0 0 0 19 29 1 0 0 0 0 20 24 1 0 0 0 0 20 30 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 0 0 0 0 23 32 2 0 0 0 0 24 33 1 1 0 0 0 25 13 1 1 0 0 0 25 37 1 0 0 0 0 26 30 2 3 0 0 0 26 34 1 0 0 0 0 27 31 1 0 0 0 0 27 35 2 0 0 0 0 28 36 2 0 0 0 0 28 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.31
Volume:	575.761
LogP:	2.451
LogD:	2.351
LogS:	-3.767
# Rotatable Bonds:	25
TPSA:	122.24
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.068
Synthetic Accessibility Score:	4.211
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
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:	-5.103
MDCK Permeability:	5.144501483300701e-05
Pgp-inhibitor:	0.512
Pgp-substrate:	0.949
Human Intestinal Absorption (HIA):	0.674
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.885
Plasma Protein Binding (PPB):	39.515296936035156%
Volume Distribution (VD):	0.326
Pgp-substrate:	58.779380798339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.172
CYP2C19-substrate:	0.602
CYP2C9-inhibitor:	0.37
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.833
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	5.856
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.055
Drug-inuced Liver Injury (DILI):	0.168
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.968
Carcinogencity:	0.542
Eye Corrosion:	0.064
Eye Irritation:	0.025
Respiratory Toxicity:	0.316

Download Data

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

Natural Product: NPC233932

Natural Product ID:	NPC233932
*Common Name:**	Malyngamide 3
IUPAC Name:	methyl (3R)-4-[[(Z)-6-chloro-5-[[[(E,7S)-7-methoxytetradec-4-enoyl]-methylamino]methyl]-3-oxohex-5-enoyl]amino]-3-hydroxybutanoate
Synonyms:	Malyngamide 3
Standard InCHIKey:	FGRVZQUFZGRBFK-RBZBVOEWSA-N
Standard InCHI:	InChI=1S/C28H47ClN2O7/c1-5-6-7-8-10-13-25(37-3)14-11-9-12-15-27(35)31(2)21-22(19-29)16-23(32)17-26(34)30-20-24(33)18-28(36)38-4/h9,11,19,24-25,33H,5-8,10,12-18,20-21H2,1-4H3,(H,30,34)/b11-9+,22-19-/t24-,25+/m1/s1
SMILES:	CCCCCCC[C@@H](C/C=C/CCC(=O)N(C/C(=CCl)/CC(=O)CC(=NC[C@@H](CC(=O)OC)O)O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773900
PubChem CID:	52952438
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:0000347] Amino acids and derivatives [CHEMONTID:0001880] Gamma amino acids and derivatives

*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	=	29000.0	nM	PMID[513160]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	48000.0	nM	PMID[513160]

☑ 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 NPC233932 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	71
0.1-0.2	584
0.2-0.3	16197
0.3-0.4	18674
0.4-0.5	6163
0.5-0.6	920
0.6-0.7	83
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.75	Intermediate Similarity	NPC81195
0.7255	Intermediate Similarity	NPC53240
0.7143	Intermediate Similarity	NPC474312
0.7018	Intermediate Similarity	NPC476875
0.6847	Remote Similarity	NPC476877
0.6726	Remote Similarity	NPC476876
0.6696	Remote Similarity	NPC21324
0.6638	Remote Similarity	NPC46764
0.66	Remote Similarity	NPC477523
0.6585	Remote Similarity	NPC273185
0.6535	Remote Similarity	NPC477524
0.6509	Remote Similarity	NPC159369
0.6509	Remote Similarity	NPC39290
0.6491	Remote Similarity	NPC205176
0.6475	Remote Similarity	NPC323532
0.6455	Remote Similarity	NPC175614
0.6436	Remote Similarity	NPC209232
0.6417	Remote Similarity	NPC472536
0.6417	Remote Similarity	NPC103391
0.64	Remote Similarity	NPC474833
0.64	Remote Similarity	NPC469492
0.6372	Remote Similarity	NPC188785
0.6356	Remote Similarity	NPC251122
0.6354	Remote Similarity	NPC97614
0.6348	Remote Similarity	NPC74035
0.6337	Remote Similarity	NPC469517
0.6325	Remote Similarity	NPC171734
0.6304	Remote Similarity	NPC477106
0.6303	Remote Similarity	NPC12270
0.6293	Remote Similarity	NPC271269
0.6271	Remote Similarity	NPC473578
0.627	Remote Similarity	NPC280498
0.6239	Remote Similarity	NPC251330
0.622	Remote Similarity	NPC36254
0.6204	Remote Similarity	NPC469426
0.6204	Remote Similarity	NPC469427
0.6195	Remote Similarity	NPC234542
0.6195	Remote Similarity	NPC475758
0.6186	Remote Similarity	NPC475150
0.6186	Remote Similarity	NPC207820
0.6154	Remote Similarity	NPC475918
0.6154	Remote Similarity	NPC154601
0.6147	Remote Similarity	NPC47230
0.6147	Remote Similarity	NPC17143
0.6146	Remote Similarity	NPC474812
0.614	Remote Similarity	NPC13175
0.614	Remote Similarity	NPC473224
0.614	Remote Similarity	NPC475791
0.6134	Remote Similarity	NPC329305
0.6129	Remote Similarity	NPC316674
0.6116	Remote Similarity	NPC469865
0.6111	Remote Similarity	NPC315188
0.6106	Remote Similarity	NPC52820
0.61	Remote Similarity	NPC34672
0.61	Remote Similarity	NPC217095
0.61	Remote Similarity	NPC264417
0.6091	Remote Similarity	NPC314500
0.6071	Remote Similarity	NPC469739
0.6068	Remote Similarity	NPC14537
0.6066	Remote Similarity	NPC469597
0.6058	Remote Similarity	NPC277341
0.6058	Remote Similarity	NPC226982
0.6048	Remote Similarity	NPC201968
0.6034	Remote Similarity	NPC474244
0.6034	Remote Similarity	NPC128501
0.6034	Remote Similarity	NPC471097
0.6034	Remote Similarity	NPC475149
0.6033	Remote Similarity	NPC474431
0.6033	Remote Similarity	NPC474411
0.6018	Remote Similarity	NPC475503
0.6017	Remote Similarity	NPC473252
0.6016	Remote Similarity	NPC50694
0.6	Remote Similarity	NPC477487
0.5983	Remote Similarity	NPC474828
0.5983	Remote Similarity	NPC474827
0.5983	Remote Similarity	NPC199831
0.5983	Remote Similarity	NPC68001
0.598	Remote Similarity	NPC46268
0.5978	Remote Similarity	NPC325550
0.5978	Remote Similarity	NPC329003
0.5978	Remote Similarity	NPC326524
0.5969	Remote Similarity	NPC204639
0.5946	Remote Similarity	NPC315237
0.5943	Remote Similarity	NPC178758
0.5943	Remote Similarity	NPC196102
0.5926	Remote Similarity	NPC258824
0.5923	Remote Similarity	NPC309525
0.5922	Remote Similarity	NPC473984
0.5918	Remote Similarity	NPC291196
0.5918	Remote Similarity	NPC103712
0.5917	Remote Similarity	NPC474099
0.5905	Remote Similarity	NPC82799
0.5899	Remote Similarity	NPC476259
0.5888	Remote Similarity	NPC477199
0.5887	Remote Similarity	NPC145501
0.5882	Remote Similarity	NPC472615
0.5872	Remote Similarity	NPC324506
0.587	Remote Similarity	NPC321030
0.5865	Remote Similarity	NPC319766
0.5854	Remote Similarity	NPC7797
0.5854	Remote Similarity	NPC478024
0.5847	Remote Similarity	NPC6271
0.5842	Remote Similarity	NPC288086
0.5833	Remote Similarity	NPC477793
0.5833	Remote Similarity	NPC470651
0.5833	Remote Similarity	NPC329919
0.5833	Remote Similarity	NPC470655
0.5826	Remote Similarity	NPC265662
0.5826	Remote Similarity	NPC167380
0.5826	Remote Similarity	NPC475646
0.5825	Remote Similarity	NPC325936
0.5825	Remote Similarity	NPC316242
0.5816	Remote Similarity	NPC28348
0.5816	Remote Similarity	NPC473985
0.5816	Remote Similarity	NPC474298
0.5816	Remote Similarity	NPC474299
0.5816	Remote Similarity	NPC249713
0.5816	Remote Similarity	NPC176226
0.5816	Remote Similarity	NPC475808
0.5814	Remote Similarity	NPC478014
0.5814	Remote Similarity	NPC478016
0.5814	Remote Similarity	NPC478015
0.5812	Remote Similarity	NPC77703
0.5812	Remote Similarity	NPC316250
0.5798	Remote Similarity	NPC472616
0.5798	Remote Similarity	NPC64168
0.5786	Remote Similarity	NPC239762
0.5786	Remote Similarity	NPC163392
0.5785	Remote Similarity	NPC307903
0.5785	Remote Similarity	NPC476276
0.5785	Remote Similarity	NPC140251
0.5772	Remote Similarity	NPC475608
0.5772	Remote Similarity	NPC21713
0.5769	Remote Similarity	NPC16709
0.5769	Remote Similarity	NPC478017
0.5769	Remote Similarity	NPC315131
0.5769	Remote Similarity	NPC50520
0.5769	Remote Similarity	NPC315535
0.5763	Remote Similarity	NPC72401
0.5763	Remote Similarity	NPC325339
0.576	Remote Similarity	NPC471645
0.5758	Remote Similarity	NPC470436
0.5752	Remote Similarity	NPC38172
0.5745	Remote Similarity	NPC71866
0.5745	Remote Similarity	NPC247776
0.5745	Remote Similarity	NPC475278
0.5745	Remote Similarity	NPC309450
0.5745	Remote Similarity	NPC304299
0.5745	Remote Similarity	NPC475266
0.5743	Remote Similarity	NPC470435
0.5741	Remote Similarity	NPC475975
0.5739	Remote Similarity	NPC473597
0.5739	Remote Similarity	NPC121857
0.5738	Remote Similarity	NPC474725
0.5726	Remote Similarity	NPC316730
0.5726	Remote Similarity	NPC1111
0.5726	Remote Similarity	NPC261750
0.5714	Remote Similarity	NPC314050
0.5714	Remote Similarity	NPC173690
0.5714	Remote Similarity	NPC80439
0.5714	Remote Similarity	NPC474563
0.5714	Remote Similarity	NPC279833
0.5714	Remote Similarity	NPC471768
0.5714	Remote Similarity	NPC162104
0.5714	Remote Similarity	NPC315809
0.5704	Remote Similarity	NPC120335
0.5702	Remote Similarity	NPC475800
0.5701	Remote Similarity	NPC469838
0.5701	Remote Similarity	NPC469833
0.5701	Remote Similarity	NPC473810
0.57	Remote Similarity	NPC42526
0.5699	Remote Similarity	NPC325734
0.5693	Remote Similarity	NPC246079
0.569	Remote Similarity	NPC476344
0.5688	Remote Similarity	NPC319913
0.5686	Remote Similarity	NPC470994
0.5684	Remote Similarity	NPC201939
0.5684	Remote Similarity	NPC321838
0.5674	Remote Similarity	NPC307357
0.5674	Remote Similarity	NPC46098
0.5674	Remote Similarity	NPC268841
0.5669	Remote Similarity	NPC216335
0.5667	Remote Similarity	NPC470073
0.5667	Remote Similarity	NPC259476
0.5664	Remote Similarity	NPC319473
0.5656	Remote Similarity	NPC70235
0.5655	Remote Similarity	NPC145113
0.5652	Remote Similarity	NPC150041
0.5648	Remote Similarity	NPC228638
0.5645	Remote Similarity	NPC29501
0.5643	Remote Similarity	NPC68865
0.5643	Remote Similarity	NPC127741
0.5641	Remote Similarity	NPC132931
0.5641	Remote Similarity	NPC220234
0.5636	Remote Similarity	NPC322672
0.5635	Remote Similarity	NPC474984
0.5634	Remote Similarity	NPC168113
0.5625	Remote Similarity	NPC471109
0.562	Remote Similarity	NPC475637
0.562	Remote Similarity	NPC201128

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 NPC233932 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	68
0.1-0.2	294
0.2-0.3	3548
0.3-0.4	4184
0.4-0.5	980
0.5-0.6	73
0.6-0.7	3
0.7-0.8	0
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
0.6481	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4228	Discovery
0.6303	Remote Similarity	NPD1719	Phase 1
0.595	Remote Similarity	NPD6421	Discontinued
0.592	Remote Similarity	NPD6935	Phase 3
0.592	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD790	Approved
0.5802	Remote Similarity	NPD8273	Phase 1
0.5786	Remote Similarity	NPD8384	Approved
0.5769	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD3732	Approved
0.5755	Remote Similarity	NPD8172	Phase 2
0.5755	Remote Similarity	NPD8173	Phase 2
0.5748	Remote Similarity	NPD6918	Phase 1
0.5748	Remote Similarity	NPD7756	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6413	Approved
0.5714	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6420	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