NPASS Compound

Structure

NPC58674 OpenBabel07101719512D 26 26 0 0 1 0 0 0 0 0999 V2000 7.7942 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 26 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 11 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 14 21 2 0 0 0 0 15 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 24 1 0 0 0 0 22 16 1 6 0 0 0 22 26 1 0 0 0 0 23 24 2 3 0 0 0 23 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	359.28
Volume:	413.203
LogP:	5.142
LogD:	4.327
LogS:	-4.358
# Rotatable Bonds:	16
TPSA:	38.33
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	2.701
Fsp3:	0.609
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.606
MDCK Permeability:	2.5474015274085104e-05
Pgp-inhibitor:	0.64
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.872
30% Bioavailability (F30%):	0.887

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.296
Plasma Protein Binding (PPB):	97.83846282958984%
Volume Distribution (VD):	0.889
Pgp-substrate:	0.835760235786438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.282
CYP1A2-substrate:	0.684
CYP2C19-inhibitor:	0.645
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.551
CYP2C9-substrate:	0.198
CYP2D6-inhibitor:	0.745
CYP2D6-substrate:	0.299
CYP3A4-inhibitor:	0.897
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	4.556
Half-life (T1/2):	0.676

ADMET: Toxicity

hERG Blockers:	0.575
Human Hepatotoxicity (H-HT):	0.511
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.957
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.103
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC58674

Natural Product ID:	NPC58674
*Common Name:**	Hermitamide A
IUPAC Name:	(E,7S)-7-methoxy-N-(2-phenylethyl)tetradec-4-enamide
Synonyms:
Standard InCHIKey:	VPNLGLXHRKAYHD-UBQCRTFRSA-N
Standard InCHI:	InChI=1S/C23H37NO2/c1-3-4-5-6-11-16-22(26-2)17-12-8-13-18-23(25)24-20-19-21-14-9-7-10-15-21/h7-10,12,14-15,22H,3-6,11,13,16-20H2,1-2H3,(H,24,25)/b12-8+/t22-/m0/s1
SMILES:	CCCCCCC[C@@H](C/C=C/CCC(=NCCc1ccccc1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498041
PubChem CID:	10473646
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000331] Fatty amides [CHEMONTID:0001096] N-acyl amines

*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	9
LD50	2
Others	4

Activity Type	# Activity
Cell Line	7
Individual Protein	3
NON-MOLECULAR	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3715	Individual Protein	Sodium channel protein type II alpha subunit	Homo sapiens	Inhibition	=	94.4	%	PMID[489952]
NPT3715	Individual Protein	Sodium channel protein type II alpha subunit	Homo sapiens	Inhibition	=	74.4	%	PMID[489952]
NPT3715	Individual Protein	Sodium channel protein type II alpha subunit	Homo sapiens	Inhibition	=	15.5	%	PMID[489952]
NPT379	Cell Line	HOP-62	Homo sapiens	IC50	>	100000.0	nM	PMID[489953]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	>	100000.0	nM	PMID[489953]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[489953]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[489953]
NPT136	Cell Line	SK-N-SH	Homo sapiens	IC50	>	100000.0	nM	PMID[489953]
NPT744	Cell Line	IMR-32	Homo sapiens	IC50	>	100000.0	nM	PMID[489953]
NPT399	Cell Line	SF-295	Homo sapiens	IC50	>	100000.0	nM	PMID[489953]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	5.0	uM	PMID[489951]
NPT1042	Organism	Carassius auratus	Carassius auratus	LD50	=	19.0	uM	PMID[489951]
NPT27	Others	Unspecified		IC50	=	2200.0	nM	PMID[489951]
NPT2	Others	Unspecified		Activity	=	15.89	%	PMID[489952]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[489953]

☑ 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 NPC58674 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	81
0.1-0.2	619
0.2-0.3	3905
0.3-0.4	16944
0.4-0.5	15694
0.5-0.6	4363
0.6-0.7	869
0.7-0.8	183
0.8-0.85	18
0.85-0.9	17
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8901	High Similarity	NPC471307
0.8901	High Similarity	NPC121872
0.8901	High Similarity	NPC141139
0.8901	High Similarity	NPC74936
0.8901	High Similarity	NPC209764
0.8901	High Similarity	NPC159178
0.8901	High Similarity	NPC78041
0.8791	High Similarity	NPC470877
0.8776	High Similarity	NPC224610
0.8776	High Similarity	NPC113326
0.8776	High Similarity	NPC88267
0.8776	High Similarity	NPC194390
0.8632	High Similarity	NPC25565
0.8617	High Similarity	NPC471309
0.8602	High Similarity	NPC245259
0.8542	High Similarity	NPC473501
0.8542	High Similarity	NPC475439
0.8495	Intermediate Similarity	NPC172128
0.837	Intermediate Similarity	NPC471638
0.8333	Intermediate Similarity	NPC161972
0.8333	Intermediate Similarity	NPC303045
0.83	Intermediate Similarity	NPC471317
0.828	Intermediate Similarity	NPC12429
0.8211	Intermediate Similarity	NPC226438
0.8163	Intermediate Similarity	NPC311242
0.8119	Intermediate Similarity	NPC202613
0.8105	Intermediate Similarity	NPC316108
0.8	Intermediate Similarity	NPC258056
0.7961	Intermediate Similarity	NPC211551
0.7941	Intermediate Similarity	NPC471310
0.7925	Intermediate Similarity	NPC474149
0.7921	Intermediate Similarity	NPC469457
0.7917	Intermediate Similarity	NPC258627
0.7909	Intermediate Similarity	NPC169328
0.7895	Intermediate Similarity	NPC325441
0.7885	Intermediate Similarity	NPC231705
0.7838	Intermediate Similarity	NPC237420
0.7838	Intermediate Similarity	NPC310467
0.781	Intermediate Similarity	NPC142297
0.7802	Intermediate Similarity	NPC192623
0.78	Intermediate Similarity	NPC33168
0.7789	Intermediate Similarity	NPC473031
0.7766	Intermediate Similarity	NPC3210
0.7755	Intermediate Similarity	NPC265521
0.7745	Intermediate Similarity	NPC214200
0.7745	Intermediate Similarity	NPC228400
0.7706	Intermediate Similarity	NPC474544
0.7706	Intermediate Similarity	NPC1986
0.7699	Intermediate Similarity	NPC45777
0.7699	Intermediate Similarity	NPC477061
0.7699	Intermediate Similarity	NPC190663
0.7684	Intermediate Similarity	NPC203076
0.7647	Intermediate Similarity	NPC12730
0.7634	Intermediate Similarity	NPC14326
0.7604	Intermediate Similarity	NPC198747
0.76	Intermediate Similarity	NPC20142
0.76	Intermediate Similarity	NPC215351
0.7596	Intermediate Similarity	NPC178902
0.7568	Intermediate Similarity	NPC317254
0.7568	Intermediate Similarity	NPC188010
0.7565	Intermediate Similarity	NPC160493
0.7549	Intermediate Similarity	NPC164514
0.7549	Intermediate Similarity	NPC303611
0.7549	Intermediate Similarity	NPC226096
0.7549	Intermediate Similarity	NPC290515
0.7549	Intermediate Similarity	NPC108606
0.7547	Intermediate Similarity	NPC327481
0.7544	Intermediate Similarity	NPC53596
0.7544	Intermediate Similarity	NPC471308
0.7544	Intermediate Similarity	NPC17388
0.7544	Intermediate Similarity	NPC478015
0.7544	Intermediate Similarity	NPC289330
0.7544	Intermediate Similarity	NPC160120
0.7544	Intermediate Similarity	NPC478014
0.7544	Intermediate Similarity	NPC478016
0.7522	Intermediate Similarity	NPC314992
0.75	Intermediate Similarity	NPC327226
0.75	Intermediate Similarity	NPC2265
0.7477	Intermediate Similarity	NPC471318
0.7455	Intermediate Similarity	NPC474584
0.7455	Intermediate Similarity	NPC273814
0.7447	Intermediate Similarity	NPC73637
0.7447	Intermediate Similarity	NPC121478
0.7419	Intermediate Similarity	NPC164449
0.7419	Intermediate Similarity	NPC309279
0.7419	Intermediate Similarity	NPC184030
0.7414	Intermediate Similarity	NPC252878
0.7407	Intermediate Similarity	NPC24101
0.7407	Intermediate Similarity	NPC96224
0.7391	Intermediate Similarity	NPC80150
0.7387	Intermediate Similarity	NPC35850
0.7387	Intermediate Similarity	NPC276949
0.7373	Intermediate Similarity	NPC47667
0.7358	Intermediate Similarity	NPC150254
0.7358	Intermediate Similarity	NPC226778
0.7358	Intermediate Similarity	NPC304761
0.7358	Intermediate Similarity	NPC147000
0.735	Intermediate Similarity	NPC46427
0.7339	Intermediate Similarity	NPC292758
0.7339	Intermediate Similarity	NPC65855
0.7333	Intermediate Similarity	NPC108218
0.7321	Intermediate Similarity	NPC33742
0.7321	Intermediate Similarity	NPC118202
0.7312	Intermediate Similarity	NPC469894
0.7304	Intermediate Similarity	NPC43275
0.7304	Intermediate Similarity	NPC283760
0.7303	Intermediate Similarity	NPC208302
0.7292	Intermediate Similarity	NPC304538
0.7281	Intermediate Similarity	NPC254088
0.7273	Intermediate Similarity	NPC319579
0.7273	Intermediate Similarity	NPC323007
0.7264	Intermediate Similarity	NPC164859
0.7263	Intermediate Similarity	NPC283012
0.7263	Intermediate Similarity	NPC87299
0.7263	Intermediate Similarity	NPC99394
0.7263	Intermediate Similarity	NPC475199
0.7263	Intermediate Similarity	NPC103326
0.7263	Intermediate Similarity	NPC329319
0.7257	Intermediate Similarity	NPC235421
0.7257	Intermediate Similarity	NPC197470
0.7253	Intermediate Similarity	NPC189371
0.7248	Intermediate Similarity	NPC153690
0.7241	Intermediate Similarity	NPC476990
0.7241	Intermediate Similarity	NPC476183
0.7227	Intermediate Similarity	NPC95733
0.7227	Intermediate Similarity	NPC62101
0.7227	Intermediate Similarity	NPC472414
0.7222	Intermediate Similarity	NPC191215
0.7222	Intermediate Similarity	NPC274089
0.7216	Intermediate Similarity	NPC99482
0.7204	Intermediate Similarity	NPC224544
0.7203	Intermediate Similarity	NPC472415
0.7203	Intermediate Similarity	NPC35996
0.7203	Intermediate Similarity	NPC471314
0.7203	Intermediate Similarity	NPC471315
0.7193	Intermediate Similarity	NPC82963
0.7193	Intermediate Similarity	NPC470544
0.7188	Intermediate Similarity	NPC477770
0.7184	Intermediate Similarity	NPC3371
0.7179	Intermediate Similarity	NPC202521
0.7179	Intermediate Similarity	NPC476281
0.7179	Intermediate Similarity	NPC476184
0.717	Intermediate Similarity	NPC318154
0.7167	Intermediate Similarity	NPC29477
0.7167	Intermediate Similarity	NPC278097
0.7158	Intermediate Similarity	NPC117180
0.7143	Intermediate Similarity	NPC211218
0.713	Intermediate Similarity	NPC470545
0.713	Intermediate Similarity	NPC311737
0.713	Intermediate Similarity	NPC38458
0.7119	Intermediate Similarity	NPC474862
0.7107	Intermediate Similarity	NPC319766
0.7094	Intermediate Similarity	NPC263835
0.7091	Intermediate Similarity	NPC114741
0.7091	Intermediate Similarity	NPC182549
0.7083	Intermediate Similarity	NPC4974
0.7075	Intermediate Similarity	NPC316797
0.7071	Intermediate Similarity	NPC211237
0.7069	Intermediate Similarity	NPC470546
0.7059	Intermediate Similarity	NPC476278
0.7059	Intermediate Similarity	NPC6975
0.7054	Intermediate Similarity	NPC166837
0.7054	Intermediate Similarity	NPC329011
0.7049	Intermediate Similarity	NPC295478
0.7049	Intermediate Similarity	NPC71271
0.7041	Intermediate Similarity	NPC475710
0.7033	Intermediate Similarity	NPC244738
0.7018	Intermediate Similarity	NPC142599
0.7016	Intermediate Similarity	NPC246079
0.7009	Intermediate Similarity	NPC268572
0.7	Intermediate Similarity	NPC476260
0.7	Intermediate Similarity	NPC476241
0.6947	Remote Similarity	NPC170484
0.6944	Remote Similarity	NPC178681
0.6942	Remote Similarity	NPC474479
0.6942	Remote Similarity	NPC476125
0.6942	Remote Similarity	NPC325013
0.6942	Remote Similarity	NPC476179
0.6931	Remote Similarity	NPC1793
0.6929	Remote Similarity	NPC6570
0.6916	Remote Similarity	NPC155847
0.6916	Remote Similarity	NPC289381
0.6911	Remote Similarity	NPC116057
0.6911	Remote Similarity	NPC472413
0.6911	Remote Similarity	NPC101372
0.6911	Remote Similarity	NPC296712
0.6907	Remote Similarity	NPC323103
0.6907	Remote Similarity	NPC103387
0.6905	Remote Similarity	NPC90693
0.6905	Remote Similarity	NPC64897
0.6905	Remote Similarity	NPC248283
0.6893	Remote Similarity	NPC323164
0.6891	Remote Similarity	NPC71684
0.6887	Remote Similarity	NPC107619
0.688	Remote Similarity	NPC246913
0.688	Remote Similarity	NPC42423
0.6875	Remote Similarity	NPC121800
0.6875	Remote Similarity	NPC290566
0.6875	Remote Similarity	NPC145638
0.6857	Remote Similarity	NPC471320

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 NPC58674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	81
0.1-0.2	424
0.2-0.3	936
0.3-0.4	2588
0.4-0.5	3016
0.5-0.6	1576
0.6-0.7	468
0.7-0.8	57
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD6690	Approved
0.8526	High Similarity	NPD4814	Discontinued
0.8155	Intermediate Similarity	NPD6406	Approved
0.8125	Intermediate Similarity	NPD1812	Approved
0.8125	Intermediate Similarity	NPD1814	Approved
0.81	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1080	Approved
0.7789	Intermediate Similarity	NPD9538	Approved
0.7778	Intermediate Similarity	NPD1081	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1101	Approved
0.767	Intermediate Similarity	NPD855	Approved
0.767	Intermediate Similarity	NPD854	Approved
0.767	Intermediate Similarity	NPD4719	Phase 2
0.7653	Intermediate Similarity	NPD530	Approved
0.7642	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD7522	Discontinued
0.7576	Intermediate Similarity	NPD752	Approved
0.7568	Intermediate Similarity	NPD7508	Discontinued
0.7549	Intermediate Similarity	NPD9611	Approved
0.7549	Intermediate Similarity	NPD9612	Approved
0.7549	Intermediate Similarity	NPD9609	Approved
0.7544	Intermediate Similarity	NPD7342	Discontinued
0.7522	Intermediate Similarity	NPD2218	Phase 2
0.7522	Intermediate Similarity	NPD2217	Approved
0.75	Intermediate Similarity	NPD4119	Approved
0.75	Intermediate Similarity	NPD1066	Discontinued
0.75	Intermediate Similarity	NPD3719	Approved
0.75	Intermediate Similarity	NPD3718	Approved
0.7453	Intermediate Similarity	NPD5717	Approved
0.7431	Intermediate Similarity	NPD3643	Approved
0.7431	Intermediate Similarity	NPD3644	Approved
0.7431	Intermediate Similarity	NPD3642	Approved
0.7423	Intermediate Similarity	NPD187	Approved
0.7358	Intermediate Similarity	NPD310	Approved
0.7358	Intermediate Similarity	NPD311	Approved
0.7358	Intermediate Similarity	NPD314	Approved
0.7358	Intermediate Similarity	NPD10	Approved
0.7358	Intermediate Similarity	NPD315	Approved
0.7358	Intermediate Similarity	NPD309	Approved
0.7358	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4818	Approved
0.7333	Intermediate Similarity	NPD4817	Approved
0.7327	Intermediate Similarity	NPD719	Approved
0.7327	Intermediate Similarity	NPD720	Approved
0.7327	Intermediate Similarity	NPD1409	Phase 3
0.7315	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1067	Discontinued
0.7304	Intermediate Similarity	NPD5981	Approved
0.729	Intermediate Similarity	NPD999	Phase 2
0.7257	Intermediate Similarity	NPD1348	Approved
0.7222	Intermediate Similarity	NPD5706	Approved
0.7222	Intermediate Similarity	NPD5705	Approved
0.7222	Intermediate Similarity	NPD5704	Approved
0.7212	Intermediate Similarity	NPD4117	Approved
0.7203	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2895	Discontinued
0.7184	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD9713	Approved
0.717	Intermediate Similarity	NPD5716	Approved
0.7143	Intermediate Similarity	NPD4165	Phase 2
0.7143	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3066	Phase 2
0.713	Intermediate Similarity	NPD6360	Discontinued
0.713	Intermediate Similarity	NPD1018	Approved
0.713	Intermediate Similarity	NPD1040	Phase 2
0.7117	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2583	Phase 2
0.7115	Intermediate Similarity	NPD1875	Phase 1
0.7103	Intermediate Similarity	NPD1542	Approved
0.7094	Intermediate Similarity	NPD5723	Approved
0.7087	Intermediate Similarity	NPD7344	Phase 1
0.7087	Intermediate Similarity	NPD7343	Discovery
0.7075	Intermediate Similarity	NPD2550	Approved
0.7075	Intermediate Similarity	NPD2552	Approved
0.7075	Intermediate Similarity	NPD2553	Approved
0.7075	Intermediate Similarity	NPD2549	Approved
0.7075	Intermediate Similarity	NPD2558	Approved
0.7075	Intermediate Similarity	NPD2555	Approved
0.7073	Intermediate Similarity	NPD4738	Phase 2
0.7064	Intermediate Similarity	NPD810	Approved
0.7064	Intermediate Similarity	NPD3526	Approved
0.7064	Intermediate Similarity	NPD812	Approved
0.7064	Intermediate Similarity	NPD3524	Approved
0.7064	Intermediate Similarity	NPD811	Approved
0.7043	Intermediate Similarity	NPD3123	Discovery
0.7033	Intermediate Similarity	NPD9728	Phase 1
0.7009	Intermediate Similarity	NPD1737	Approved
0.7009	Intermediate Similarity	NPD4189	Approved
0.7009	Intermediate Similarity	NPD4188	Approved
0.7009	Intermediate Similarity	NPD1736	Approved
0.7009	Intermediate Similarity	NPD1735	Approved
0.7009	Intermediate Similarity	NPD1540	Approved
0.7	Intermediate Similarity	NPD531	Approved
0.6981	Remote Similarity	NPD9712	Approved
0.6964	Remote Similarity	NPD4254	Approved
0.6964	Remote Similarity	NPD4253	Approved
0.696	Remote Similarity	NPD8118	Discontinued
0.696	Remote Similarity	NPD7477	Discontinued
0.6952	Remote Similarity	NPD1076	Approved
0.6944	Remote Similarity	NPD4229	Approved
0.6944	Remote Similarity	NPD1415	Approved
0.6944	Remote Similarity	NPD3680	Approved
0.6944	Remote Similarity	NPD4658	Approved
0.6944	Remote Similarity	NPD3681	Approved
0.6944	Remote Similarity	NPD3682	Approved
0.6944	Remote Similarity	NPD3683	Approved
0.6944	Remote Similarity	NPD4656	Approved
0.6944	Remote Similarity	NPD4231	Approved
0.6923	Remote Similarity	NPD2617	Discontinued
0.6903	Remote Similarity	NPD3651	Discontinued
0.6897	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD9711	Approved
0.6887	Remote Similarity	NPD4813	Approved
0.6887	Remote Similarity	NPD9710	Approved
0.6887	Remote Similarity	NPD4263	Approved
0.6887	Remote Similarity	NPD1724	Approved
0.6881	Remote Similarity	NPD3048	Approved
0.6881	Remote Similarity	NPD3046	Approved
0.6881	Remote Similarity	NPD3047	Approved
0.6875	Remote Similarity	NPD5372	Approved
0.6875	Remote Similarity	NPD5371	Approved
0.6875	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2212	Approved
0.6864	Remote Similarity	NPD2210	Approved
0.6864	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD821	Approved
0.6838	Remote Similarity	NPD16	Approved
0.6838	Remote Similarity	NPD856	Approved
0.6833	Remote Similarity	NPD4480	Approved
0.6829	Remote Similarity	NPD7451	Discontinued
0.6827	Remote Similarity	NPD1394	Approved
0.6825	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7725	Approved
0.6804	Remote Similarity	NPD472	Approved
0.68	Remote Similarity	NPD3136	Phase 2
0.6797	Remote Similarity	NPD8173	Phase 2
0.6797	Remote Similarity	NPD8172	Phase 2
0.6792	Remote Similarity	NPD9566	Approved
0.6786	Remote Similarity	NPD2678	Approved
0.6786	Remote Similarity	NPD2679	Approved
0.6783	Remote Similarity	NPD2652	Approved
0.6783	Remote Similarity	NPD2229	Approved
0.6783	Remote Similarity	NPD3150	Approved
0.6783	Remote Similarity	NPD3149	Approved
0.6783	Remote Similarity	NPD2658	Approved
0.6783	Remote Similarity	NPD2228	Approved
0.6783	Remote Similarity	NPD3148	Approved
0.6783	Remote Similarity	NPD3147	Approved
0.6783	Remote Similarity	NPD2650	Approved
0.6783	Remote Similarity	NPD2234	Approved
0.6783	Remote Similarity	NPD2659	Approved
0.678	Remote Similarity	NPD6093	Discontinued
0.678	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4479	Discontinued
0.6777	Remote Similarity	NPD2584	Suspended
0.6774	Remote Similarity	NPD1712	Approved
0.6772	Remote Similarity	NPD8265	Approved
0.6762	Remote Similarity	NPD3772	Phase 3
0.6759	Remote Similarity	NPD2657	Approved
0.6757	Remote Similarity	NPD2559	Approved
0.6757	Remote Similarity	NPD2551	Approved
0.6757	Remote Similarity	NPD1445	Approved
0.6757	Remote Similarity	NPD1444	Approved
0.6757	Remote Similarity	NPD467	Phase 1
0.6754	Remote Similarity	NPD4572	Approved
0.6754	Remote Similarity	NPD4571	Approved
0.6754	Remote Similarity	NPD4573	Approved
0.6746	Remote Similarity	NPD7908	Discontinued
0.6744	Remote Similarity	NPD6852	Discontinued
0.6737	Remote Similarity	NPD4144	Approved
0.6737	Remote Similarity	NPD9294	Approved
0.6737	Remote Similarity	NPD4147	Approved
0.6729	Remote Similarity	NPD253	Approved
0.6727	Remote Similarity	NPD9610	Approved
0.6727	Remote Similarity	NPD3407	Phase 3
0.6727	Remote Similarity	NPD9608	Approved
0.6726	Remote Similarity	NPD550	Approved
0.6726	Remote Similarity	NPD551	Approved
0.6724	Remote Similarity	NPD9614	Approved
0.6724	Remote Similarity	NPD9618	Approved
0.6723	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1669	Approved
0.6697	Remote Similarity	NPD9722	Approved
0.6697	Remote Similarity	NPD9721	Approved
0.6696	Remote Similarity	NPD1764	Approved
0.6696	Remote Similarity	NPD1762	Approved
0.6696	Remote Similarity	NPD2607	Approved
0.6696	Remote Similarity	NPD1401	Approved
0.6696	Remote Similarity	NPD181	Approved
0.6695	Remote Similarity	NPD9613	Approved
0.6695	Remote Similarity	NPD317	Approved
0.6695	Remote Similarity	NPD828	Approved
0.6695	Remote Similarity	NPD318	Approved
0.6695	Remote Similarity	NPD9616	Approved
0.6695	Remote Similarity	NPD1758	Phase 1
0.6695	Remote Similarity	NPD9615	Approved
0.6694	Remote Similarity	NPD4216	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