NPASS Compound

Structure

NPC329961 OpenBabel07101719522D 44 46 0 0 1 0 0 0 0 0999 V2000 2.9566 2.2971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2458 2.5681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1206 2.1241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3453 0.8993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1600 -1.2442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8910 -2.0720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0666 -2.0720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5550 1.1582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1526 1.9387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5826 -1.1799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6916 -1.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6349 -0.1813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8529 -1.0893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7963 0.3633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0666 0.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8968 -3.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0230 1.9387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3794 1.1582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1723 -1.0878 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.1756 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9052 -0.0906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1756 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8666 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3277 0.4511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7788 -2.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3479 -0.5302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8479 -2.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3968 0.7788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7788 0.7788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1723 -0.5302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3277 -2.0691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3479 -1.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8968 -1.7601 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8479 0.4511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3248 -3.2878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3355 -0.3738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8508 1.6698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3248 1.6698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1600 -0.3738 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 2.8479 -3.0691 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 8 36 1 0 0 0 0 9 37 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 22 2 0 0 0 0 14 22 1 0 0 0 0 15 22 1 0 0 0 0 16 23 2 0 0 0 0 16 44 1 0 0 0 0 19 20 1 0 0 0 0 19 32 1 0 0 0 0 20 33 1 0 0 0 0 21 7 1 1 0 0 0 21 29 1 0 0 0 0 21 34 1 0 0 0 0 23 27 1 0 0 0 0 23 35 1 0 0 0 0 24 15 1 1 0 0 0 24 28 1 0 0 0 0 24 36 1 0 0 0 0 25 17 1 1 0 0 0 25 30 1 0 0 0 0 25 37 1 0 0 0 0 26 18 1 1 0 0 0 26 31 1 0 0 0 0 26 43 1 0 0 0 0 27 33 2 3 0 0 0 27 38 1 0 0 0 0 28 34 2 3 0 0 0 28 39 1 0 0 0 0 29 35 2 0 0 0 0 29 44 1 0 0 0 0 30 36 1 0 0 0 0 30 40 2 0 0 0 0 31 37 1 0 0 0 0 31 41 2 0 0 0 0 32 42 2 0 0 0 0 32 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	627.31
Volume:	636.228
LogP:	3.726
LogD:	2.786
LogS:	-4.087
# Rotatable Bonds:	4
TPSA:	138.01
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	5.761
Fsp3:	0.562
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:	-5.104
MDCK Permeability:	1.7184616808663122e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.609
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.522

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	87.34590148925781%
Volume Distribution (VD):	0.557
Pgp-substrate:	8.435790061950684%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.338
CYP2C19-substrate:	0.669
CYP2C9-inhibitor:	0.398
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.894

ADMET: Excretion

Clearance (CL):	6.695
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.976
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.625
Skin Sensitization:	0.018
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.443

Download Data

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

Natural Product: NPC329961

Natural Product ID:	NPC329961
*Common Name:**	Guineamide B
IUPAC Name:	(8S,11S,14S,17S)-14-benzyl-4,5,10,13,17-pentamethyl-8,11-di(propan-2-yl)-7-oxa-19-thia-3,10,13,16,21-pentazabicyclo[16.2.1]henicosa-1(20),18(21)-diene-2,6,9,12,15-pentone
Synonyms:
Standard InCHIKey:	HCDWKPJRUMSHJR-LYUNOVLRSA-N
Standard InCHI:	InChI=1S/C32H45N5O6S/c1-17(2)25-30(40)36(8)24(15-22-13-11-10-12-14-22)28(39)34-21(7)29-35-23(16-44-29)27(38)33-20(6)19(5)32(42)43-26(18(3)4)31(41)37(25)9/h10-14,16-21,24-26H,15H2,1-9H3,(H,33,38)(H,34,39)/t19?,20?,21-,24-,25-,26-/m0/s1
SMILES:	O=C1O[C@@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N(C)[C@@H](Cc2ccccc2)C(=N[C@H](c2nc(C(=NC(C1C)C)O)cs2)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510424
PubChem CID:	10461639
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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15000.0	nM	PMID[473870]

☑ 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 NPC329961 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	204
0.1-0.2	1641
0.2-0.3	12074
0.3-0.4	20228
0.4-0.5	6059
0.5-0.6	2065
0.6-0.7	391
0.7-0.8	26
0.8-0.85	2
0.85-0.9	1
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC122427
0.9766	High Similarity	NPC165538
0.9081	High Similarity	NPC145178
0.9081	High Similarity	NPC14877
0.9081	High Similarity	NPC475350
0.8936	High Similarity	NPC251036
0.8242	Intermediate Similarity	NPC96016
0.8182	Intermediate Similarity	NPC24990
0.8111	Intermediate Similarity	NPC161242
0.8022	Intermediate Similarity	NPC25316
0.8022	Intermediate Similarity	NPC263485
0.8022	Intermediate Similarity	NPC229160
0.8011	Intermediate Similarity	NPC475534
0.8011	Intermediate Similarity	NPC476080
0.7967	Intermediate Similarity	NPC475330
0.7935	Intermediate Similarity	NPC161143
0.7933	Intermediate Similarity	NPC476103
0.7923	Intermediate Similarity	NPC174652
0.7801	Intermediate Similarity	NPC106235
0.7801	Intermediate Similarity	NPC239660
0.7594	Intermediate Similarity	NPC475196
0.7471	Intermediate Similarity	NPC105717
0.7313	Intermediate Similarity	NPC75498
0.7303	Intermediate Similarity	NPC286551
0.7251	Intermediate Similarity	NPC471264
0.7251	Intermediate Similarity	NPC471265
0.7234	Intermediate Similarity	NPC317362
0.7234	Intermediate Similarity	NPC326407
0.7234	Intermediate Similarity	NPC318930
0.7234	Intermediate Similarity	NPC317725
0.7225	Intermediate Similarity	NPC269398
0.7225	Intermediate Similarity	NPC263493
0.72	Intermediate Similarity	NPC209509
0.7119	Intermediate Similarity	NPC319751
0.711	Intermediate Similarity	NPC98424
0.711	Intermediate Similarity	NPC178662
0.711	Intermediate Similarity	NPC476133
0.711	Intermediate Similarity	NPC92784
0.711	Intermediate Similarity	NPC470884
0.7006	Intermediate Similarity	NPC322878
0.7	Intermediate Similarity	NPC119481
0.6966	Remote Similarity	NPC475390
0.6944	Remote Similarity	NPC473398
0.6944	Remote Similarity	NPC283783
0.6942	Remote Similarity	NPC257511
0.691	Remote Similarity	NPC5620
0.6909	Remote Similarity	NPC469858
0.6906	Remote Similarity	NPC7817
0.6906	Remote Similarity	NPC475168
0.6893	Remote Similarity	NPC139326
0.6878	Remote Similarity	NPC475920
0.6857	Remote Similarity	NPC68865
0.6822	Remote Similarity	NPC79386
0.6816	Remote Similarity	NPC316008
0.6816	Remote Similarity	NPC313867
0.6802	Remote Similarity	NPC300315
0.6798	Remote Similarity	NPC161069
0.6793	Remote Similarity	NPC470902
0.6778	Remote Similarity	NPC314358
0.676	Remote Similarity	NPC314388
0.676	Remote Similarity	NPC315283
0.6758	Remote Similarity	NPC129666
0.674	Remote Similarity	NPC225648
0.674	Remote Similarity	NPC329761
0.6704	Remote Similarity	NPC468984
0.6703	Remote Similarity	NPC240848
0.6684	Remote Similarity	NPC297145
0.6684	Remote Similarity	NPC197743
0.6683	Remote Similarity	NPC49051
0.6667	Remote Similarity	NPC470146
0.6667	Remote Similarity	NPC469801
0.6667	Remote Similarity	NPC97078
0.6667	Remote Similarity	NPC101980
0.6667	Remote Similarity	NPC127741
0.6648	Remote Similarity	NPC145113
0.6648	Remote Similarity	NPC138775
0.6648	Remote Similarity	NPC168113
0.6629	Remote Similarity	NPC89489
0.6619	Remote Similarity	NPC314930
0.6619	Remote Similarity	NPC214827
0.6617	Remote Similarity	NPC4910
0.6617	Remote Similarity	NPC329731
0.6615	Remote Similarity	NPC477462
0.6612	Remote Similarity	NPC471821
0.6612	Remote Similarity	NPC471820
0.6611	Remote Similarity	NPC176226
0.6611	Remote Similarity	NPC197682
0.6606	Remote Similarity	NPC313804
0.6606	Remote Similarity	NPC315804
0.6595	Remote Similarity	NPC162104
0.6593	Remote Similarity	NPC262077
0.6592	Remote Similarity	NPC307357
0.6592	Remote Similarity	NPC46098
0.6592	Remote Similarity	NPC268841
0.6575	Remote Similarity	NPC476978
0.6571	Remote Similarity	NPC143325
0.6556	Remote Similarity	NPC469427
0.6556	Remote Similarity	NPC469426
0.6545	Remote Similarity	NPC471051
0.6545	Remote Similarity	NPC471053
0.6545	Remote Similarity	NPC471052
0.6526	Remote Similarity	NPC475024
0.6505	Remote Similarity	NPC59827
0.6505	Remote Similarity	NPC184933
0.6503	Remote Similarity	NPC190329
0.65	Remote Similarity	NPC476259
0.65	Remote Similarity	NPC239762
0.65	Remote Similarity	NPC163392
0.6486	Remote Similarity	NPC2501
0.6486	Remote Similarity	NPC13470
0.6484	Remote Similarity	NPC52748
0.6482	Remote Similarity	NPC249662
0.6474	Remote Similarity	NPC315252
0.6471	Remote Similarity	NPC122590
0.6461	Remote Similarity	NPC248283
0.6459	Remote Similarity	NPC313421
0.6453	Remote Similarity	NPC46427
0.6448	Remote Similarity	NPC315266
0.6447	Remote Similarity	NPC469938
0.6445	Remote Similarity	NPC182507
0.6441	Remote Similarity	NPC246079
0.6441	Remote Similarity	NPC478141
0.6439	Remote Similarity	NPC477526
0.6417	Remote Similarity	NPC475683
0.6417	Remote Similarity	NPC474079
0.6417	Remote Similarity	NPC21449
0.6417	Remote Similarity	NPC157194
0.6417	Remote Similarity	NPC474080
0.6417	Remote Similarity	NPC474102
0.6411	Remote Similarity	NPC477527
0.6404	Remote Similarity	NPC287401
0.6404	Remote Similarity	NPC323752
0.6404	Remote Similarity	NPC323198
0.6402	Remote Similarity	NPC268063
0.6402	Remote Similarity	NPC316403
0.6402	Remote Similarity	NPC224609
0.64	Remote Similarity	NPC319766
0.6397	Remote Similarity	NPC313966
0.6397	Remote Similarity	NPC314254
0.6395	Remote Similarity	NPC252878
0.6378	Remote Similarity	NPC474069
0.6378	Remote Similarity	NPC135121
0.6378	Remote Similarity	NPC164006
0.6373	Remote Similarity	NPC238242
0.6364	Remote Similarity	NPC474103
0.6364	Remote Similarity	NPC82436
0.6364	Remote Similarity	NPC474064
0.6364	Remote Similarity	NPC474068
0.6359	Remote Similarity	NPC477217
0.6359	Remote Similarity	NPC201244
0.6359	Remote Similarity	NPC471680
0.6358	Remote Similarity	NPC6975
0.6354	Remote Similarity	NPC231110
0.6349	Remote Similarity	NPC109498
0.6349	Remote Similarity	NPC32583
0.6349	Remote Similarity	NPC252616
0.6349	Remote Similarity	NPC154873
0.6349	Remote Similarity	NPC474090
0.6349	Remote Similarity	NPC61667
0.6349	Remote Similarity	NPC163147
0.6349	Remote Similarity	NPC45576
0.6343	Remote Similarity	NPC478158
0.6337	Remote Similarity	NPC202521
0.6329	Remote Similarity	NPC478030
0.6327	Remote Similarity	NPC186351
0.6324	Remote Similarity	NPC81026
0.6321	Remote Similarity	NPC312887
0.6313	Remote Similarity	NPC248670
0.631	Remote Similarity	NPC254798
0.6305	Remote Similarity	NPC470003
0.6302	Remote Similarity	NPC474538
0.6302	Remote Similarity	NPC127775
0.63	Remote Similarity	NPC132662
0.6296	Remote Similarity	NPC474094
0.6296	Remote Similarity	NPC473341
0.6296	Remote Similarity	NPC474067
0.6296	Remote Similarity	NPC185665
0.6296	Remote Similarity	NPC475737
0.6294	Remote Similarity	NPC475204
0.6294	Remote Similarity	NPC475123
0.6292	Remote Similarity	NPC130309
0.6283	Remote Similarity	NPC319232
0.6283	Remote Similarity	NPC24370
0.6281	Remote Similarity	NPC26108
0.6281	Remote Similarity	NPC158277
0.6281	Remote Similarity	NPC279871
0.6281	Remote Similarity	NPC471165
0.628	Remote Similarity	NPC129909
0.628	Remote Similarity	NPC243716
0.628	Remote Similarity	NPC117244
0.628	Remote Similarity	NPC473763
0.6279	Remote Similarity	NPC476990
0.6276	Remote Similarity	NPC473502
0.6271	Remote Similarity	NPC473322
0.627	Remote Similarity	NPC266741
0.6267	Remote Similarity	NPC64216
0.6264	Remote Similarity	NPC103268
0.6263	Remote Similarity	NPC206724
0.6263	Remote Similarity	NPC474515
0.6261	Remote Similarity	NPC49195

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 NPC329961 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	441
0.2-0.3	858
0.3-0.4	1837
0.4-0.5	4240
0.5-0.6	1449
0.6-0.7	183
0.7-0.8	6
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
0.7801	Intermediate Similarity	NPD8339	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD6348	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6632	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7977	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6349	Phase 1
0.7127	Intermediate Similarity	NPD5189	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5634	Approved
0.7039	Intermediate Similarity	NPD8071	Approved
0.6976	Remote Similarity	NPD6888	Discontinued
0.6943	Remote Similarity	NPD2957	Phase 2
0.6842	Remote Similarity	NPD8260	Approved
0.6798	Remote Similarity	NPD2022	Approved
0.6793	Remote Similarity	NPD4648	Approved
0.6793	Remote Similarity	NPD4647	Approved
0.6793	Remote Similarity	NPD4646	Approved
0.6791	Remote Similarity	NPD4557	Approved
0.678	Remote Similarity	NPD3480	Approved
0.6763	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2051	Approved
0.6763	Remote Similarity	NPD2043	Approved
0.6763	Remote Similarity	NPD2045	Approved
0.6763	Remote Similarity	NPD2044	Approved
0.6763	Remote Similarity	NPD2047	Approved
0.6763	Remote Similarity	NPD21	Approved
0.6763	Remote Similarity	NPD2046	Approved
0.6763	Remote Similarity	NPD2048	Approved
0.6763	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4125	Approved
0.6704	Remote Similarity	NPD2087	Approved
0.6704	Remote Similarity	NPD2088	Approved
0.6699	Remote Similarity	NPD8272	Phase 2
0.6685	Remote Similarity	NPD5230	Approved
0.6685	Remote Similarity	NPD5638	Approved
0.6685	Remote Similarity	NPD5229	Approved
0.6683	Remote Similarity	NPD4949	Discontinued
0.6667	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7711	Discontinued
0.6631	Remote Similarity	NPD2891	Approved
0.6616	Remote Similarity	NPD2852	Approved
0.6584	Remote Similarity	NPD2015	Discontinued
0.6576	Remote Similarity	NPD3987	Approved
0.6576	Remote Similarity	NPD3988	Approved
0.6576	Remote Similarity	NPD5613	Approved
0.6576	Remote Similarity	NPD5614	Approved
0.6554	Remote Similarity	NPD5323	Approved
0.6553	Remote Similarity	NPD6347	Phase 2
0.6543	Remote Similarity	NPD2020	Approved
0.6543	Remote Similarity	NPD6915	Approved
0.654	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD6751	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1979	Approved
0.6502	Remote Similarity	NPD3335	Approved
0.6489	Remote Similarity	NPD2019	Approved
0.6489	Remote Similarity	NPD2018	Approved
0.6486	Remote Similarity	NPD2014	Approved
0.6486	Remote Similarity	NPD2016	Approved
0.6486	Remote Similarity	NPD2013	Approved
0.6485	Remote Similarity	NPD3334	Approved
0.6484	Remote Similarity	NPD2437	Approved
0.6484	Remote Similarity	NPD2436	Approved
0.648	Remote Similarity	NPD8172	Phase 2
0.648	Remote Similarity	NPD8173	Phase 2
0.6462	Remote Similarity	NPD4652	Approved
0.6442	Remote Similarity	NPD7490	Discontinued
0.6441	Remote Similarity	NPD5299	Approved
0.6441	Remote Similarity	NPD8356	Approved
0.6432	Remote Similarity	NPD4928	Approved
0.6432	Remote Similarity	NPD4929	Approved
0.6432	Remote Similarity	NPD4930	Approved
0.6429	Remote Similarity	NPD647	Approved
0.6425	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2098	Approved
0.6413	Remote Similarity	NPD1978	Approved
0.6408	Remote Similarity	NPD3288	Approved
0.6406	Remote Similarity	NPD2097	Approved
0.6404	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7496	Phase 2
0.6386	Remote Similarity	NPD7483	Phase 2
0.6386	Remote Similarity	NPD7482	Phase 2
0.6385	Remote Similarity	NPD4906	Approved
0.6385	Remote Similarity	NPD4905	Approved
0.6385	Remote Similarity	NPD4903	Approved
0.6378	Remote Similarity	NPD2055	Phase 3
0.6378	Remote Similarity	NPD2054	Approved
0.6364	Remote Similarity	NPD1004	Phase 2
0.6364	Remote Similarity	NPD1005	Phase 2
0.6359	Remote Similarity	NPD5265	Approved
0.6359	Remote Similarity	NPD5264	Approved
0.6359	Remote Similarity	NPD4508	Discontinued
0.6359	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6092	Discontinued
0.6355	Remote Similarity	NPD4904	Approved
0.6341	Remote Similarity	NPD2855	Approved
0.6341	Remote Similarity	NPD2854	Approved
0.6341	Remote Similarity	NPD2856	Approved
0.6339	Remote Similarity	NPD6173	Approved
0.6338	Remote Similarity	NPD8072	Approved
0.6337	Remote Similarity	NPD5461	Discontinued
0.633	Remote Similarity	NPD5452	Phase 2
0.633	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6303	Approved
0.6327	Remote Similarity	NPD6304	Approved
0.6327	Remote Similarity	NPD8430	Approved
0.6327	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD8169	Discontinued
0.6305	Remote Similarity	NPD2417	Approved
0.6305	Remote Similarity	NPD2416	Approved
0.6304	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6907	Phase 2
0.6291	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3487	Phase 1
0.6286	Remote Similarity	NPD5367	Discontinued
0.6284	Remote Similarity	NPD3223	Clinical (unspecified phase)
0.628	Remote Similarity	NPD5076	Approved
0.628	Remote Similarity	NPD5077	Approved
0.628	Remote Similarity	NPD6659	Phase 2
0.628	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD4567	Approved
0.6269	Remote Similarity	NPD4566	Approved
0.6264	Remote Similarity	NPD2584	Suspended
0.6263	Remote Similarity	NPD5633	Discontinued
0.6262	Remote Similarity	NPD4334	Discontinued
0.6261	Remote Similarity	NPD3759	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4415	Approved
0.6245	Remote Similarity	NPD7806	Phase 2
0.6245	Remote Similarity	NPD3328	Phase 2
0.6243	Remote Similarity	NPD3576	Approved
0.6243	Remote Similarity	NPD3575	Approved
0.6238	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6857	Phase 3
0.6226	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD1582	Approved
0.6223	Remote Similarity	NPD1581	Approved
0.6221	Remote Similarity	NPD3351	Approved
0.6221	Remote Similarity	NPD4960	Approved
0.6221	Remote Similarity	NPD4959	Approved
0.622	Remote Similarity	NPD8284	Discontinued
0.6216	Remote Similarity	NPD1976	Approved
0.6215	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD8073	Approved
0.6211	Remote Similarity	NPD8075	Discontinued
0.621	Remote Similarity	NPD3878	Approved
0.6204	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7944	Discontinued
0.619	Remote Similarity	NPD4432	Discontinued
0.6188	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD8416	Discontinued
0.6186	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD5851	Approved
0.6184	Remote Similarity	NPD5852	Approved
0.6182	Remote Similarity	NPD3879	Approved
0.6175	Remote Similarity	NPD3350	Approved
0.6168	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD6910	Phase 3
0.6166	Remote Similarity	NPD2513	Approved
0.6166	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD5444	Phase 1
0.6164	Remote Similarity	NPD2853	Approved
0.6164	Remote Similarity	NPD4741	Phase 3
0.6164	Remote Similarity	NPD4742	Phase 3
0.6162	Remote Similarity	NPD2890	Approved
0.6162	Remote Similarity	NPD2889	Approved
0.6162	Remote Similarity	NPD2888	Approved
0.6162	Remote Similarity	NPD2017	Approved
0.6158	Remote Similarity	NPD7613	Discontinued
0.615	Remote Similarity	NPD6248	Phase 2
0.615	Remote Similarity	NPD6249	Phase 2
0.615	Remote Similarity	NPD8124	Phase 3
0.615	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD8271	Discontinued
0.6143	Remote Similarity	NPD2717	Phase 2
0.6139	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD6891	Phase 2
0.6135	Remote Similarity	NPD3919	Approved
0.6134	Remote Similarity	NPD2515	Approved
0.6134	Remote Similarity	NPD3007	Approved
0.6132	Remote Similarity	NPD8255	Phase 2
0.6132	Remote Similarity	NPD6206	Phase 1
0.6131	Remote Similarity	NPD2517	Approved
0.6128	Remote Similarity	NPD2893	Phase 3
0.6124	Remote Similarity	NPD5994	Discontinued
0.6122	Remote Similarity	NPD3493	Approved
0.6122	Remote Similarity	NPD3492	Approved
0.6122	Remote Similarity	NPD3494	Approved
0.6117	Remote Similarity	NPD8323	Discontinued
0.6114	Remote Similarity	NPD4602	Approved
0.6113	Remote Similarity	NPD4884	Discovery
0.6111	Remote Similarity	NPD5487	Phase 1
0.6109	Remote Similarity	NPD6205	Discontinued
0.6108	Remote Similarity	NPD5485	Approved
0.6108	Remote Similarity	NPD5484	Approved
0.6108	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD6261	Phase 3

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