NPASS Compound

Structure

NPC469858 OpenBabel07101718292D 71 75 0 0 1 0 0 0 0 0999 V2000 -5.4051 -6.0791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1427 -0.9045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5935 -6.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0935 -5.2440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3506 -2.7409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8127 -4.4515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5967 -3.8399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5732 -3.4805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9937 -5.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1133 -5.9858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8714 -0.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8384 0.9889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5502 -2.3782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4654 -6.4211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1495 -1.0206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6994 -5.7783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3337 -1.4970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6279 -1.1963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5073 -0.5122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8016 -0.2115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9547 -2.3295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9662 -0.1677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5616 -0.8817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3617 -0.4807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0935 -5.2440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7534 -1.9388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8730 -4.7935 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7031 -3.3911 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6335 -3.1385 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1673 -4.4927 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1736 -5.6438 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3940 -1.8391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7413 0.1306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0018 -0.4321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8909 -2.8750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8909 -1.7840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7602 -2.0549 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -4.6589 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7602 -2.6041 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5935 -4.3780 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1070 -4.1507 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4013 -3.8499 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0892 -4.5955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5261 -0.1575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3870 -3.6293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2203 -2.8239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5261 -4.5014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3870 -1.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0892 -0.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0340 -0.6089 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5483 0.0319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9149 1.1154 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.9552 -1.4310 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5483 -4.6909 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6335 -1.5205 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 1.5935 -0.2810 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5924 -6.2865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7534 -2.7202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3760 -5.5535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2225 -4.1788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9864 -3.4667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9222 -5.4196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2225 -0.4801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8639 -3.1056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0340 -4.0500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2806 -3.1659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0018 -4.2268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5157 -1.0032 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.1755 -0.5754 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1.0892 -0.6089 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 13 65 1 0 0 0 0 14 16 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 17 32 2 0 0 0 0 18 20 2 0 0 0 0 18 32 1 0 0 0 0 19 33 2 0 0 0 0 20 33 1 0 0 0 0 21 35 1 0 0 0 0 21 36 1 0 0 0 0 22 34 2 0 0 0 0 22 69 1 0 0 0 0 23 50 1 0 0 0 0 23 71 1 0 0 0 0 24 51 1 0 0 0 0 24 70 1 0 0 0 0 26 5 1 6 0 0 0 27 6 1 1 0 0 0 27 41 1 0 0 0 0 28 7 1 1 0 0 0 28 35 1 0 0 0 0 28 42 1 0 0 0 0 29 8 1 1 0 0 0 29 39 1 0 0 0 0 29 45 1 0 0 0 0 30 9 1 1 0 0 0 30 41 1 0 0 0 0 31 10 1 6 0 0 0 31 58 1 0 0 0 0 32 46 1 0 0 0 0 33 52 1 0 0 0 0 34 44 1 0 0 0 0 34 53 1 0 0 0 0 35 65 1 1 0 0 0 36 53 2 0 0 0 0 36 69 1 0 0 0 0 37 26 1 1 0 0 0 37 39 1 0 0 0 0 37 55 1 0 0 0 0 38 31 1 1 0 0 0 38 47 1 0 0 0 0 38 54 1 0 0 0 0 39 59 1 1 0 0 0 40 25 1 1 0 0 0 40 43 1 0 0 0 0 40 66 1 0 0 0 0 41 67 1 6 0 0 0 42 30 1 6 0 0 0 42 68 1 0 0 0 0 43 54 2 3 0 0 0 43 60 1 0 0 0 0 44 56 2 0 0 0 0 44 70 1 0 0 0 0 45 61 2 0 0 0 0 45 66 1 0 0 0 0 46 62 2 0 0 0 0 46 67 1 0 0 0 0 47 63 2 0 0 0 0 47 68 1 0 0 0 0 48 50 1 0 0 0 0 48 55 2 3 0 0 0 48 64 1 0 0 0 0 49 51 1 0 0 0 0 49 57 2 0 0 0 0 49 71 1 0 0 0 0 50 11 1 6 0 0 0 50 57 1 0 0 0 0 51 12 1 6 0 0 0 51 56 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1107.37
Volume:	1042.719
LogP:	7.763
LogD:	5.836
LogS:	-4.085
# Rotatable Bonds:	13
TPSA:	224.4
# H-Bond Aceptor:	16
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.12
Synthetic Accessibility Score:	6.476
Fsp3:	0.686
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:	-5.253
MDCK Permeability:	1.3984134966449346e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.379
Human Intestinal Absorption (HIA):	0.911
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	100.6076889038086%
Volume Distribution (VD):	1.627
Pgp-substrate:	4.943703651428223%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.298
CYP2C19-inhibitor:	0.666
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.911
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.119
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.984
CYP3A4-substrate:	0.926

ADMET: Excretion

Clearance (CL):	5.171
Half-life (T1/2):	0.014

ADMET: Toxicity

hERG Blockers:	0.335
Human Hepatotoxicity (H-HT):	0.95
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.625
Skin Sensitization:	0.021
Carcinogencity:	0.043
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.519

Download Data

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

Natural Product: NPC469858

Natural Product ID:	NPC469858
*Common Name:**	IRINHXGRZWMAAI-VSMSWBIESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IRINHXGRZWMAAI-VSMSWBIESA-N
Standard InCHI:	InChI=1S/C51H74BrN5O11S3/c1-14-16-27(6)41(67-46(62)32-17-19-33(52)20-18-32)30(9)42-28(7)35(65-13)21-36-53-34(22-69-36)44-56-51(12,24-70-44)49-57-50(11,23-71-49)48(64)55-37(26(5)15-2)39(59)29(8)45(61)66-40(25(3)4)43(60)54-38(31(10)58)47(63)68-42/h17-20,22,25-31,35,37-42,58-59H,14-16,21,23-24H2,1-13H3,(H,54,60)(H,55,64)/t26-,27+,28-,29+,30-,31+,35-,37-,38-,39-,40-,41-,42-,50+,51+/m0/s1
SMILES:	CCC[C@H]([C@@H]([C@@H]([C@H]1OC(=O)[C@@H](N=C(O)[C@@H](OC(=O)[C@H](C)[C@H](O)[C@@H](N=C([C@@]2(N=C([C@@]3(N=C(c4nc(C[C@@H]([C@@H]1C)OC)sc4)SC3)C)SC2)C)O)[C@H](CC)C)C(C)C)[C@H](O)C)C)OC(=O)c1ccc(cc1)Br)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215861
PubChem CID:	49864268
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
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12350160]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762794]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	Sunday Island, Papua New Guinea	n.a.	PMID[18163584]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[20687534]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	Panamanian	n.a.	PMID[24164245]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24588245]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[28055219]
NPO33200	symploca sp.	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29808677]

☑ 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
EC50	1
IC50	2

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	EC50	=	9300.0	nM	PMID[502351]
NPT2	Others	Unspecified	IC50	=	87.3	nM	PMID[502351]
NPT2	Others	Unspecified	IC50	=	3400.0	nM	PMID[502351]

☑ 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 NPC469858 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	292
0.1-0.2	1755
0.2-0.3	7958
0.3-0.4	14619
0.4-0.5	15952
0.5-0.6	2031
0.6-0.7	84
0.7-0.8	5
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
0.7206	Intermediate Similarity	NPC522
0.7206	Intermediate Similarity	NPC56058
0.716	Intermediate Similarity	NPC314254
0.716	Intermediate Similarity	NPC313966
0.7033	Intermediate Similarity	NPC24990
0.7	Intermediate Similarity	NPC165538
0.6971	Remote Similarity	NPC475196
0.693	Remote Similarity	NPC229160
0.693	Remote Similarity	NPC263485
0.693	Remote Similarity	NPC25316
0.6916	Remote Similarity	NPC161242
0.6913	Remote Similarity	NPC475350
0.6913	Remote Similarity	NPC14877
0.6913	Remote Similarity	NPC145178
0.6909	Remote Similarity	NPC122427
0.6909	Remote Similarity	NPC329961
0.6884	Remote Similarity	NPC475330
0.6852	Remote Similarity	NPC174652
0.6837	Remote Similarity	NPC476080
0.6837	Remote Similarity	NPC475534
0.6824	Remote Similarity	NPC251036
0.6714	Remote Similarity	NPC470146
0.6714	Remote Similarity	NPC97078
0.6714	Remote Similarity	NPC101980
0.6711	Remote Similarity	NPC239660
0.6711	Remote Similarity	NPC106235
0.6605	Remote Similarity	NPC476103
0.6514	Remote Similarity	NPC473704
0.6468	Remote Similarity	NPC134480
0.6462	Remote Similarity	NPC127775
0.6442	Remote Similarity	NPC119481
0.6429	Remote Similarity	NPC96016
0.6411	Remote Similarity	NPC474079
0.6411	Remote Similarity	NPC21449
0.6411	Remote Similarity	NPC157194
0.6411	Remote Similarity	NPC474080
0.6411	Remote Similarity	NPC474102
0.6411	Remote Similarity	NPC475683
0.6394	Remote Similarity	NPC473398
0.6364	Remote Similarity	NPC82436
0.6364	Remote Similarity	NPC474064
0.6364	Remote Similarity	NPC474103
0.6364	Remote Similarity	NPC474068
0.6351	Remote Similarity	NPC163147
0.6351	Remote Similarity	NPC474090
0.6351	Remote Similarity	NPC45576
0.6351	Remote Similarity	NPC252616
0.6351	Remote Similarity	NPC109498
0.6351	Remote Similarity	NPC32583
0.6351	Remote Similarity	NPC61667
0.6323	Remote Similarity	NPC470900
0.6321	Remote Similarity	NPC224609
0.6321	Remote Similarity	NPC268063
0.6311	Remote Similarity	NPC469801
0.6308	Remote Similarity	NPC474538
0.6303	Remote Similarity	NPC475737
0.6303	Remote Similarity	NPC185665
0.6303	Remote Similarity	NPC474094
0.6303	Remote Similarity	NPC474067
0.6298	Remote Similarity	NPC319751
0.6279	Remote Similarity	NPC231110
0.6274	Remote Similarity	NPC154873
0.6274	Remote Similarity	NPC206724
0.6274	Remote Similarity	NPC474515
0.625	Remote Similarity	NPC312887
0.6233	Remote Similarity	NPC132662
0.6233	Remote Similarity	NPC52587
0.6225	Remote Similarity	NPC473506
0.622	Remote Similarity	NPC474069
0.6215	Remote Similarity	NPC212214
0.6215	Remote Similarity	NPC202591
0.6207	Remote Similarity	NPC476516
0.62	Remote Similarity	NPC470901
0.6186	Remote Similarity	NPC21126
0.6185	Remote Similarity	NPC475498
0.6185	Remote Similarity	NPC475137
0.6175	Remote Similarity	NPC471190
0.6175	Remote Similarity	NPC471977
0.6175	Remote Similarity	NPC475644
0.6175	Remote Similarity	NPC470486
0.6164	Remote Similarity	NPC475554
0.6146	Remote Similarity	NPC216507
0.6145	Remote Similarity	NPC76565
0.6143	Remote Similarity	NPC317362
0.6143	Remote Similarity	NPC318930
0.6137	Remote Similarity	NPC184933
0.6137	Remote Similarity	NPC59827
0.6135	Remote Similarity	NPC475600
0.6135	Remote Similarity	NPC476110
0.6135	Remote Similarity	NPC475631
0.6135	Remote Similarity	NPC87152
0.6134	Remote Similarity	NPC75498
0.6126	Remote Similarity	NPC115282
0.6123	Remote Similarity	NPC161143
0.6109	Remote Similarity	NPC257511
0.6102	Remote Similarity	NPC30456
0.6101	Remote Similarity	NPC210424
0.6099	Remote Similarity	NPC315061
0.6085	Remote Similarity	NPC315411
0.6083	Remote Similarity	NPC472287
0.6083	Remote Similarity	NPC472286
0.6081	Remote Similarity	NPC164006
0.6066	Remote Similarity	NPC476467
0.6063	Remote Similarity	NPC475596
0.6063	Remote Similarity	NPC475303
0.6059	Remote Similarity	NPC477527
0.6056	Remote Similarity	NPC473850
0.6055	Remote Similarity	NPC475426
0.6055	Remote Similarity	NPC327769
0.6055	Remote Similarity	NPC35208
0.6055	Remote Similarity	NPC216720
0.6055	Remote Similarity	NPC170751
0.6054	Remote Similarity	NPC476517
0.6047	Remote Similarity	NPC475362
0.6037	Remote Similarity	NPC75609
0.6037	Remote Similarity	NPC140284
0.6032	Remote Similarity	NPC312645
0.6032	Remote Similarity	NPC79386
0.6019	Remote Similarity	NPC190329
0.6017	Remote Similarity	NPC4910
0.6016	Remote Similarity	NPC57797
0.6016	Remote Similarity	NPC250807
0.6016	Remote Similarity	NPC237702
0.6014	Remote Similarity	NPC321939
0.6008	Remote Similarity	NPC328186
0.6008	Remote Similarity	NPC477787
0.6008	Remote Similarity	NPC122968
0.6008	Remote Similarity	NPC146824
0.6008	Remote Similarity	NPC228377
0.6	Remote Similarity	NPC181081
0.6	Remote Similarity	NPC292416
0.6	Remote Similarity	NPC473689
0.5993	Remote Similarity	NPC197881
0.5992	Remote Similarity	NPC477902
0.5992	Remote Similarity	NPC74969
0.5992	Remote Similarity	NPC233727
0.5992	Remote Similarity	NPC102008
0.5984	Remote Similarity	NPC314834
0.5977	Remote Similarity	NPC319880
0.5977	Remote Similarity	NPC244839
0.5977	Remote Similarity	NPC320324
0.5962	Remote Similarity	NPC253482
0.5945	Remote Similarity	NPC211920
0.5945	Remote Similarity	NPC124029
0.5944	Remote Similarity	NPC314270
0.5944	Remote Similarity	NPC62367
0.5938	Remote Similarity	NPC316841
0.5938	Remote Similarity	NPC14288
0.5938	Remote Similarity	NPC477906
0.5936	Remote Similarity	NPC315252
0.593	Remote Similarity	NPC475406
0.5929	Remote Similarity	NPC477462
0.5929	Remote Similarity	NPC326407
0.5929	Remote Similarity	NPC317725
0.5927	Remote Similarity	NPC477907
0.5927	Remote Similarity	NPC477909
0.5927	Remote Similarity	NPC42678
0.5926	Remote Similarity	NPC315545
0.5926	Remote Similarity	NPC314297
0.592	Remote Similarity	NPC301368
0.592	Remote Similarity	NPC84815
0.592	Remote Similarity	NPC216428
0.5914	Remote Similarity	NPC321592
0.5914	Remote Similarity	NPC54803
0.5911	Remote Similarity	NPC89508
0.5907	Remote Similarity	NPC38959
0.5907	Remote Similarity	NPC327904
0.5906	Remote Similarity	NPC148860
0.5904	Remote Similarity	NPC471014
0.5904	Remote Similarity	NPC471016
0.5904	Remote Similarity	NPC475408
0.5902	Remote Similarity	NPC478030
0.5898	Remote Similarity	NPC322135
0.5898	Remote Similarity	NPC223409
0.5894	Remote Similarity	NPC475648
0.5889	Remote Similarity	NPC471980
0.5885	Remote Similarity	NPC246303
0.5885	Remote Similarity	NPC477587
0.5885	Remote Similarity	NPC313796
0.5885	Remote Similarity	NPC314855
0.5885	Remote Similarity	NPC313345
0.5885	Remote Similarity	NPC477589
0.5885	Remote Similarity	NPC315638
0.588	Remote Similarity	NPC294579
0.588	Remote Similarity	NPC329731
0.588	Remote Similarity	NPC144779
0.588	Remote Similarity	NPC162104
0.5878	Remote Similarity	NPC472752
0.5875	Remote Similarity	NPC150698
0.5875	Remote Similarity	NPC96801
0.5873	Remote Similarity	NPC477912
0.5872	Remote Similarity	NPC477526
0.587	Remote Similarity	NPC280473
0.587	Remote Similarity	NPC323551
0.587	Remote Similarity	NPC472553
0.5869	Remote Similarity	NPC245055
0.5868	Remote Similarity	NPC317572
0.5863	Remote Similarity	NPC470306
0.586	Remote Similarity	NPC283783
0.5859	Remote Similarity	NPC100547

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 NPC469858 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	560
0.2-0.3	1053
0.3-0.4	2767
0.4-0.5	3892
0.5-0.6	677
0.6-0.7	17
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
0.6711	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7496	Phase 2
0.646	Remote Similarity	NPD6348	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD3328	Phase 2
0.6374	Remote Similarity	NPD5050	Approved
0.6368	Remote Similarity	NPD6915	Approved
0.6344	Remote Similarity	NPD6349	Phase 1
0.6339	Remote Similarity	NPD7977	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6907	Phase 2
0.6268	Remote Similarity	NPD8253	Phase 3
0.6255	Remote Similarity	NPD7806	Phase 2
0.6245	Remote Similarity	NPD3074	Discontinued
0.6192	Remote Similarity	NPD8071	Approved
0.6186	Remote Similarity	NPD6910	Phase 3
0.6182	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD6891	Phase 2
0.6157	Remote Similarity	NPD6632	Clinical (unspecified phase)
0.6151	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6659	Phase 2
0.6123	Remote Similarity	NPD6627	Discontinued
0.6111	Remote Similarity	NPD6911	Discontinued
0.6078	Remote Similarity	NPD5076	Approved
0.6078	Remote Similarity	NPD5077	Approved
0.6077	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD8462	Phase 1
0.6062	Remote Similarity	NPD2957	Phase 2
0.6032	Remote Similarity	NPD1976	Approved
0.603	Remote Similarity	NPD8255	Phase 2
0.6025	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD53	Approved
0.5992	Remote Similarity	NPD7778	Approved
0.5992	Remote Similarity	NPD7777	Approved
0.597	Remote Similarity	NPD8468	Phase 2
0.5967	Remote Similarity	NPD8399	Phase 1
0.5967	Remote Similarity	NPD8423	Phase 2
0.5929	Remote Similarity	NPD8107	Approved
0.5918	Remote Similarity	NPD5857	Phase 3
0.5914	Remote Similarity	NPD8108	Approved
0.5909	Remote Similarity	NPD5817	Discontinued
0.5907	Remote Similarity	NPD6347	Phase 2
0.5902	Remote Similarity	NPD8260	Approved
0.5892	Remote Similarity	NPD6863	Phase 2
0.589	Remote Similarity	NPD6751	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD6205	Discontinued
0.5887	Remote Similarity	NPD6276	Discontinued
0.5882	Remote Similarity	NPD5003	Discontinued
0.5878	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD4949	Discontinued
0.5872	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.5863	Remote Similarity	NPD8160	Phase 2
0.5861	Remote Similarity	NPD5461	Discontinued
0.5856	Remote Similarity	NPD3494	Approved
0.5856	Remote Similarity	NPD3493	Approved
0.5856	Remote Similarity	NPD3492	Approved
0.584	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.584	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.584	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.584	Remote Similarity	NPD8326	Phase 3
0.584	Remote Similarity	NPD8325	Phase 3
0.5833	Remote Similarity	NPD7565	Approved
0.5823	Remote Similarity	NPD4679	Discontinued
0.582	Remote Similarity	NPD7826	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5634	Approved
0.5817	Remote Similarity	NPD7878	Phase 2
0.5816	Remote Similarity	NPD7490	Discontinued
0.5808	Remote Similarity	NPD6641	Approved
0.5808	Remote Similarity	NPD6642	Approved
0.5806	Remote Similarity	NPD5452	Phase 2
0.5806	Remote Similarity	NPD8096	Phase 3
0.5806	Remote Similarity	NPD8097	Phase 3
0.5797	Remote Similarity	NPD6023	Discontinued
0.5792	Remote Similarity	NPD7946	Pre-registration
0.5789	Remote Similarity	NPD4741	Phase 3
0.5789	Remote Similarity	NPD4742	Phase 3
0.5784	Remote Similarity	NPD7769	Phase 3
0.5784	Remote Similarity	NPD6475	Phase 2
0.5778	Remote Similarity	NPD7133	Discontinued
0.5771	Remote Similarity	NPD1996	Discontinued
0.5768	Remote Similarity	NPD7214	Phase 3
0.5763	Remote Similarity	NPD2564	Approved
0.5763	Remote Similarity	NPD2565	Phase 2
0.5761	Remote Similarity	NPD8284	Discontinued
0.5755	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5866	Approved
0.5736	Remote Similarity	NPD7770	Phase 3
0.5726	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD7215	Phase 2
0.5725	Remote Similarity	NPD5891	Approved
0.5714	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD4508	Discontinued
0.5708	Remote Similarity	NPD1745	Approved
0.5703	Remote Similarity	NPD4417	Approved
0.5697	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD1004	Phase 2
0.5688	Remote Similarity	NPD1005	Phase 2
0.5688	Remote Similarity	NPD8102	Discontinued
0.5687	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.5685	Remote Similarity	NPD4506	Discontinued
0.5685	Remote Similarity	NPD4520	Approved
0.568	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.5671	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD6770	Approved
0.5669	Remote Similarity	NPD6974	Phase 3
0.5667	Remote Similarity	NPD8101	Phase 3
0.5662	Remote Similarity	NPD6390	Discontinued
0.566	Remote Similarity	NPD2893	Phase 3
0.5659	Remote Similarity	NPD7711	Discontinued
0.5657	Remote Similarity	NPD4331	Approved
0.5652	Remote Similarity	NPD5524	Approved
0.5652	Remote Similarity	NPD5523	Approved
0.5651	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.565	Remote Similarity	NPD8098	Approved
0.5645	Remote Similarity	NPD2509	Approved
0.5645	Remote Similarity	NPD2510	Approved
0.5642	Remote Similarity	NPD6173	Approved
0.564	Remote Similarity	NPD3878	Approved
0.5638	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.5637	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD7688	Phase 1
0.563	Remote Similarity	NPD5632	Approved
0.5629	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD7001	Phase 3
0.5618	Remote Similarity	NPD8061	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD7605	Discovery
0.5618	Remote Similarity	NPD3879	Approved
0.5617	Remote Similarity	NPD2306	Approved
0.561	Remote Similarity	NPD6324	Phase 1
0.5605	Remote Similarity	NPD3350	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