NPASS Compound

Structure

NPC160493 OpenBabel07101719512D 44 45 0 0 1 0 0 0 0 0999 V2000 -3.6582 2.4048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1515 3.0494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5291 -5.7437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0809 -6.0669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2156 1.6370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2402 -3.7465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1593 -1.1178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3284 0.7703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2275 -4.5474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0348 -4.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8427 2.9451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8871 -2.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8871 -1.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0399 -2.6731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0399 -0.7166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1927 -2.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9068 1.5327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8285 -4.2686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7310 -4.7093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7180 -0.6836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3455 -0.7166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9670 2.5091 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0663 -4.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1577 -5.1182 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0311 1.0966 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3176 -3.4214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2584 -1.4991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9196 -0.1184 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4120 -4.0070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9604 -3.2563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1927 -1.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4983 -1.2057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1341 -5.1784 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4677 -2.4547 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9708 0.1202 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7933 -3.1062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8619 -0.4628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8235 -2.1284 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.9382 -3.2262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2543 -6.1493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7490 -3.3154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4752 0.2993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4455 -2.4246 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 11 1 0 0 0 0 3 23 1 0 0 0 0 7 27 1 0 0 0 0 9 29 1 0 0 0 0 10 30 1 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 15 31 2 0 0 0 0 16 31 1 0 0 0 0 17 22 1 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 19 29 2 0 0 0 0 20 27 2 0 0 0 0 20 28 1 0 0 0 0 21 31 1 0 0 0 0 22 2 1 6 0 0 0 23 33 1 0 0 0 0 24 4 1 6 0 0 0 24 33 1 0 0 0 0 25 5 1 6 0 0 0 26 6 1 6 0 0 0 26 34 1 0 0 0 0 27 34 1 0 0 0 0 28 8 1 6 0 0 0 28 35 1 0 0 0 0 29 36 1 0 0 0 0 30 39 2 0 0 0 0 30 43 1 0 0 0 0 32 21 1 6 0 0 0 32 37 1 0 0 0 0 32 38 1 0 0 0 0 33 40 1 1 0 0 0 34 43 1 6 0 0 0 35 25 1 1 0 0 0 35 44 1 0 0 0 0 36 38 2 3 0 0 0 36 41 1 0 0 0 0 37 42 2 0 0 0 0 37 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	609.4
Volume:	671.405
LogP:	5.85
LogD:	5.628
LogS:	-5.593
# Rotatable Bonds:	8
TPSA:	102.26
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.257
Synthetic Accessibility Score:	5.508
Fsp3:	0.622
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.841
MDCK Permeability:	2.978346310555935e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.142
Human Intestinal Absorption (HIA):	0.879
20% Bioavailability (F20%):	0.394
30% Bioavailability (F30%):	0.655

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	98.971923828125%
Volume Distribution (VD):	1.568
Pgp-substrate:	2.339787483215332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.241
CYP2C19-substrate:	0.575
CYP2C9-inhibitor:	0.843
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.793

ADMET: Excretion

Clearance (CL):	7.049
Half-life (T1/2):	0.038

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.992
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.797
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.172
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC160493

Natural Product ID:	NPC160493
*Common Name:**	Metacridamide A
IUPAC Name:	[(3S,6E,8S,9R,10E,12S,13S,14E,16S,17R)-3-benzyl-9-hydroxy-6,8,10,12,14,16-hexamethyl-17-[(2S,4S)-4-methylhexan-2-yl]-2,5-dioxo-1-oxa-4-azacycloheptadeca-6,10,14-trien-13-yl] acetate
Synonyms:	Metacridamide A
Standard InCHIKey:	WIRRTALUVUQONX-HVCDBQLESA-N
Standard InCHI:	InChI=1S/C37H55NO6/c1-11-22(2)17-25(5)35-28(8)20-27(7)34(43-30(10)39)26(6)18-23(3)33(40)24(4)19-29(9)36(41)38-32(37(42)44-35)21-31-15-13-12-14-16-31/h12-16,18-20,22,24-26,28,32-35,40H,11,17,21H2,1-10H3,(H,38,41)/b23-18+,27-20+,29-19+/t22-,24-,25-,26-,28-,32-,33-,34-,35+/m0/s1
SMILES:	CC[C@@H](C[C@@H]([C@H]1OC(=O)[C@H](Cc2ccccc2)N=C(O)/C(=C/[C@@H]([C@H](/C(=C/[C@@H]([C@@H](/C(=C/[C@@H]1C)/C)OC(=O)C)C)/C)O)C)/C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011789
PubChem CID:	57332100
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO20240	Discodermia calyx	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276742]
NPO17498	Metarhizium acridum	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22292922]
NPO20240	Discodermia calyx	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28290701]
NPO20240	Discodermia calyx	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17498	Metarhizium acridum	Species	Clavicipitaceae	Eukaryota	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	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	11000.0	nM	PMID[497542]
NPT492	Cell Line	Caco-2	Homo sapiens	IC50	=	6200.0	nM	PMID[497542]
NPT492	Cell Line	Caco-2	Homo sapiens	IC50	=	6200.0	nM	PMID[497543]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	11000.0	nM	PMID[497543]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10800.0	nM	PMID[497542]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10800.0	nM	PMID[497543]

☑ 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 NPC160493 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	97
0.1-0.2	509
0.2-0.3	2140
0.3-0.4	7093
0.4-0.5	20276
0.5-0.6	10719
0.6-0.7	1546
0.7-0.8	282
0.8-0.85	24
0.85-0.9	8
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9825	High Similarity	NPC190663
0.8992	High Similarity	NPC80150
0.8983	High Similarity	NPC310467
0.8898	High Similarity	NPC169328
0.8512	High Similarity	NPC237420
0.8475	Intermediate Similarity	NPC273814
0.8374	Intermediate Similarity	NPC478014
0.8374	Intermediate Similarity	NPC478016
0.8374	Intermediate Similarity	NPC478015
0.8333	Intermediate Similarity	NPC4974
0.8281	Intermediate Similarity	NPC296712
0.8226	Intermediate Similarity	NPC477061
0.8226	Intermediate Similarity	NPC476183
0.8226	Intermediate Similarity	NPC45777
0.8203	Intermediate Similarity	NPC199738
0.8203	Intermediate Similarity	NPC210950
0.8189	Intermediate Similarity	NPC47667
0.816	Intermediate Similarity	NPC476281
0.816	Intermediate Similarity	NPC476184
0.811	Intermediate Similarity	NPC476260
0.811	Intermediate Similarity	NPC476241
0.8047	Intermediate Similarity	NPC476179
0.8047	Intermediate Similarity	NPC476125
0.8043	Intermediate Similarity	NPC135121
0.8031	Intermediate Similarity	NPC476278
0.8017	Intermediate Similarity	NPC474584
0.8015	Intermediate Similarity	NPC91953
0.7955	Intermediate Similarity	NPC246079
0.7941	Intermediate Similarity	NPC197921
0.792	Intermediate Similarity	NPC314992
0.7913	Intermediate Similarity	NPC12730
0.7899	Intermediate Similarity	NPC477217
0.7899	Intermediate Similarity	NPC201244
0.7891	Intermediate Similarity	NPC35996
0.7852	Intermediate Similarity	NPC6570
0.7851	Intermediate Similarity	NPC323007
0.7823	Intermediate Similarity	NPC197470
0.7812	Intermediate Similarity	NPC474862
0.7761	Intermediate Similarity	NPC470392
0.776	Intermediate Similarity	NPC2265
0.7754	Intermediate Similarity	NPC469360
0.7704	Intermediate Similarity	NPC64897
0.7704	Intermediate Similarity	NPC90693
0.7698	Intermediate Similarity	NPC476978
0.7692	Intermediate Similarity	NPC470274
0.7687	Intermediate Similarity	NPC246913
0.7686	Intermediate Similarity	NPC182549
0.7686	Intermediate Similarity	NPC114741
0.7681	Intermediate Similarity	NPC263493
0.7681	Intermediate Similarity	NPC239770
0.7681	Intermediate Similarity	NPC269398
0.7667	Intermediate Similarity	NPC327481
0.7652	Intermediate Similarity	NPC476353
0.7647	Intermediate Similarity	NPC224610
0.7647	Intermediate Similarity	NPC113326
0.7647	Intermediate Similarity	NPC194390
0.7647	Intermediate Similarity	NPC88267
0.7626	Intermediate Similarity	NPC139326
0.7626	Intermediate Similarity	NPC161069
0.7609	Intermediate Similarity	NPC471201
0.7609	Intermediate Similarity	NPC322526
0.7594	Intermediate Similarity	NPC472413
0.7578	Intermediate Similarity	NPC319950
0.7565	Intermediate Similarity	NPC58674
0.7563	Intermediate Similarity	NPC164859
0.7561	Intermediate Similarity	NPC319579
0.7556	Intermediate Similarity	NPC45191
0.7552	Intermediate Similarity	NPC132771
0.754	Intermediate Similarity	NPC188010
0.7538	Intermediate Similarity	NPC142577
0.7537	Intermediate Similarity	NPC478147
0.7536	Intermediate Similarity	NPC473055
0.7536	Intermediate Similarity	NPC473052
0.7521	Intermediate Similarity	NPC191215
0.7521	Intermediate Similarity	NPC274089
0.7521	Intermediate Similarity	NPC477251
0.7518	Intermediate Similarity	NPC5620
0.75	Intermediate Similarity	NPC329011
0.75	Intermediate Similarity	NPC328070
0.75	Intermediate Similarity	NPC472414
0.75	Intermediate Similarity	NPC244866
0.7482	Intermediate Similarity	NPC239762
0.7482	Intermediate Similarity	NPC307357
0.7482	Intermediate Similarity	NPC163392
0.7482	Intermediate Similarity	NPC46098
0.7482	Intermediate Similarity	NPC268841
0.7481	Intermediate Similarity	NPC472415
0.7481	Intermediate Similarity	NPC183722
0.7465	Intermediate Similarity	NPC314358
0.7464	Intermediate Similarity	NPC127741
0.7464	Intermediate Similarity	NPC471265
0.7464	Intermediate Similarity	NPC471264
0.7463	Intermediate Similarity	NPC116057
0.7438	Intermediate Similarity	NPC211551
0.7436	Intermediate Similarity	NPC475439
0.7436	Intermediate Similarity	NPC473501
0.7432	Intermediate Similarity	NPC56635
0.7417	Intermediate Similarity	NPC471317
0.7413	Intermediate Similarity	NPC138775
0.7413	Intermediate Similarity	NPC329761
0.7413	Intermediate Similarity	NPC225648
0.741	Intermediate Similarity	NPC178662
0.741	Intermediate Similarity	NPC470884
0.741	Intermediate Similarity	NPC92784
0.741	Intermediate Similarity	NPC476133
0.741	Intermediate Similarity	NPC98424
0.7405	Intermediate Similarity	NPC169485
0.7405	Intermediate Similarity	NPC213126
0.7405	Intermediate Similarity	NPC317474
0.7405	Intermediate Similarity	NPC84281
0.7405	Intermediate Similarity	NPC291027
0.7394	Intermediate Similarity	NPC313867
0.7394	Intermediate Similarity	NPC209509
0.7394	Intermediate Similarity	NPC473922
0.7394	Intermediate Similarity	NPC316008
0.7381	Intermediate Similarity	NPC1986
0.7381	Intermediate Similarity	NPC474544
0.7379	Intermediate Similarity	NPC475168
0.7379	Intermediate Similarity	NPC7817
0.7376	Intermediate Similarity	NPC111586
0.7376	Intermediate Similarity	NPC108852
0.7376	Intermediate Similarity	NPC261709
0.735	Intermediate Similarity	NPC25565
0.7343	Intermediate Similarity	NPC262216
0.7343	Intermediate Similarity	NPC81026
0.7338	Intermediate Similarity	NPC68865
0.7338	Intermediate Similarity	NPC208725
0.7333	Intermediate Similarity	NPC165726
0.7333	Intermediate Similarity	NPC71271
0.7333	Intermediate Similarity	NPC213969
0.7324	Intermediate Similarity	NPC314388
0.7324	Intermediate Similarity	NPC315283
0.7315	Intermediate Similarity	NPC212699
0.7315	Intermediate Similarity	NPC207675
0.7313	Intermediate Similarity	NPC65310
0.731	Intermediate Similarity	NPC2501
0.731	Intermediate Similarity	NPC129666
0.7299	Intermediate Similarity	NPC326966
0.7292	Intermediate Similarity	NPC145113
0.7288	Intermediate Similarity	NPC10781
0.7288	Intermediate Similarity	NPC293628
0.7288	Intermediate Similarity	NPC122493
0.7279	Intermediate Similarity	NPC473341
0.7279	Intermediate Similarity	NPC69496
0.7279	Intermediate Similarity	NPC325651
0.7273	Intermediate Similarity	NPC27581
0.7273	Intermediate Similarity	NPC266741
0.7259	Intermediate Similarity	NPC152850
0.7259	Intermediate Similarity	NPC71933
0.7259	Intermediate Similarity	NPC89923
0.7259	Intermediate Similarity	NPC105114
0.7259	Intermediate Similarity	NPC239990
0.7254	Intermediate Similarity	NPC197682
0.7246	Intermediate Similarity	NPC233910
0.7246	Intermediate Similarity	NPC245836
0.7241	Intermediate Similarity	NPC105717
0.7239	Intermediate Similarity	NPC474847
0.723	Intermediate Similarity	NPC470902
0.723	Intermediate Similarity	NPC39431
0.7227	Intermediate Similarity	NPC322598
0.7211	Intermediate Similarity	NPC162104
0.7208	Intermediate Similarity	NPC473502
0.7203	Intermediate Similarity	NPC3371
0.7203	Intermediate Similarity	NPC52748
0.7192	Intermediate Similarity	NPC94602
0.719	Intermediate Similarity	NPC318154
0.7185	Intermediate Similarity	NPC136453
0.7185	Intermediate Similarity	NPC477937
0.7183	Intermediate Similarity	NPC469426
0.7183	Intermediate Similarity	NPC168113
0.7183	Intermediate Similarity	NPC469427
0.7174	Intermediate Similarity	NPC42423
0.7172	Intermediate Similarity	NPC237240
0.7172	Intermediate Similarity	NPC31171
0.7162	Intermediate Similarity	NPC122590
0.7162	Intermediate Similarity	NPC472761
0.7154	Intermediate Similarity	NPC67043
0.7143	Intermediate Similarity	NPC324569
0.7143	Intermediate Similarity	NPC113325
0.7143	Intermediate Similarity	NPC279045
0.7133	Intermediate Similarity	NPC57976
0.7133	Intermediate Similarity	NPC176226
0.7132	Intermediate Similarity	NPC319766
0.7124	Intermediate Similarity	NPC471053
0.7124	Intermediate Similarity	NPC471052
0.7124	Intermediate Similarity	NPC471051
0.7123	Intermediate Similarity	NPC471820
0.7123	Intermediate Similarity	NPC471821
0.7122	Intermediate Similarity	NPC313663
0.7115	Intermediate Similarity	NPC196091
0.7113	Intermediate Similarity	NPC476259
0.7111	Intermediate Similarity	NPC101719
0.7109	Intermediate Similarity	NPC35850
0.7109	Intermediate Similarity	NPC276949
0.7107	Intermediate Similarity	NPC214200
0.7107	Intermediate Similarity	NPC228400
0.7107	Intermediate Similarity	NPC469457
0.7105	Intermediate Similarity	NPC476194
0.7103	Intermediate Similarity	NPC262077
0.7101	Intermediate Similarity	NPC157311

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 NPC160493 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	91
0.1-0.2	336
0.2-0.3	804
0.3-0.4	1943
0.4-0.5	3204
0.5-0.6	2093
0.6-0.7	598
0.7-0.8	81
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
0.8031	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD4738	Phase 2
0.8	Intermediate Similarity	NPD3643	Approved
0.8	Intermediate Similarity	NPD3642	Approved
0.8	Intermediate Similarity	NPD3644	Approved
0.792	Intermediate Similarity	NPD2217	Approved
0.792	Intermediate Similarity	NPD2218	Phase 2
0.7857	Intermediate Similarity	NPD5981	Approved
0.7823	Intermediate Similarity	NPD1348	Approved
0.7612	Intermediate Similarity	NPD3136	Phase 2
0.7481	Intermediate Similarity	NPD2584	Suspended
0.748	Intermediate Similarity	NPD3123	Discovery
0.7448	Intermediate Similarity	NPD6390	Discontinued
0.7442	Intermediate Similarity	NPD4209	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6852	Discontinued
0.7405	Intermediate Similarity	NPD4806	Approved
0.7405	Intermediate Similarity	NPD2610	Approved
0.7405	Intermediate Similarity	NPD2608	Approved
0.7405	Intermediate Similarity	NPD4218	Approved
0.7405	Intermediate Similarity	NPD3132	Approved
0.7405	Intermediate Similarity	NPD2612	Approved
0.7405	Intermediate Similarity	NPD2611	Approved
0.7405	Intermediate Similarity	NPD4480	Approved
0.7405	Intermediate Similarity	NPD4215	Approved
0.7405	Intermediate Similarity	NPD4807	Approved
0.7405	Intermediate Similarity	NPD4217	Approved
0.7405	Intermediate Similarity	NPD3131	Approved
0.7405	Intermediate Similarity	NPD4216	Approved
0.7405	Intermediate Similarity	NPD2609	Approved
0.7381	Intermediate Similarity	NPD2650	Approved
0.7381	Intermediate Similarity	NPD2652	Approved
0.7372	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD4479	Discontinued
0.7348	Intermediate Similarity	NPD6624	Discontinued
0.7338	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD8172	Phase 2
0.7338	Intermediate Similarity	NPD8173	Phase 2
0.7324	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD2625	Approved
0.7313	Intermediate Similarity	NPD2159	Approved
0.7313	Intermediate Similarity	NPD2627	Approved
0.7313	Intermediate Similarity	NPD2626	Approved
0.7313	Intermediate Similarity	NPD2160	Approved
0.7313	Intermediate Similarity	NPD2628	Approved
0.7295	Intermediate Similarity	NPD1040	Phase 2
0.7292	Intermediate Similarity	NPD8323	Discontinued
0.7288	Intermediate Similarity	NPD9566	Approved
0.7287	Intermediate Similarity	NPD1758	Phase 1
0.7279	Intermediate Similarity	NPD2613	Approved
0.7279	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6647	Phase 2
0.7254	Intermediate Similarity	NPD7978	Discontinued
0.7246	Intermediate Similarity	NPD2571	Approved
0.7246	Intermediate Similarity	NPD4746	Phase 3
0.7246	Intermediate Similarity	NPD3089	Approved
0.7246	Intermediate Similarity	NPD2573	Approved
0.7246	Intermediate Similarity	NPD3616	Approved
0.7246	Intermediate Similarity	NPD3090	Approved
0.7246	Intermediate Similarity	NPD2570	Approved
0.7246	Intermediate Similarity	NPD2574	Discontinued
0.7246	Intermediate Similarity	NPD3614	Approved
0.7246	Intermediate Similarity	NPD4745	Approved
0.7246	Intermediate Similarity	NPD3087	Approved
0.7246	Intermediate Similarity	NPD3615	Approved
0.7246	Intermediate Similarity	NPD2566	Approved
0.7246	Intermediate Similarity	NPD2572	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3088	Approved
0.7239	Intermediate Similarity	NPD6325	Discontinued
0.7234	Intermediate Similarity	NPD6865	Phase 2
0.7234	Intermediate Similarity	NPD6864	Phase 2
0.7231	Intermediate Similarity	NPD1759	Phase 1
0.7209	Intermediate Similarity	NPD4576	Approved
0.7209	Intermediate Similarity	NPD4574	Approved
0.7206	Intermediate Similarity	NPD3661	Approved
0.7206	Intermediate Similarity	NPD3663	Approved
0.7206	Intermediate Similarity	NPD3664	Approved
0.7206	Intermediate Similarity	NPD3662	Phase 3
0.7197	Intermediate Similarity	NPD4135	Approved
0.7197	Intermediate Similarity	NPD4106	Approved
0.7197	Intermediate Similarity	NPD4136	Approved
0.7194	Intermediate Similarity	NPD8265	Approved
0.7177	Intermediate Similarity	NPD6406	Approved
0.7176	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4621	Approved
0.7174	Intermediate Similarity	NPD4619	Approved
0.7172	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2607	Approved
0.7153	Intermediate Similarity	NPD5203	Approved
0.7153	Intermediate Similarity	NPD4620	Approved
0.7153	Intermediate Similarity	NPD5201	Approved
0.7153	Intermediate Similarity	NPD4617	Approved
0.7143	Intermediate Similarity	NPD4685	Phase 3
0.7143	Intermediate Similarity	NPD4686	Approved
0.7143	Intermediate Similarity	NPD4684	Phase 3
0.7143	Intermediate Similarity	NPD5618	Discontinued
0.7143	Intermediate Similarity	NPD3603	Phase 3
0.7122	Intermediate Similarity	NPD7714	Approved
0.7122	Intermediate Similarity	NPD7715	Approved
0.7121	Intermediate Similarity	NPD5306	Approved
0.7121	Intermediate Similarity	NPD5305	Approved
0.7119	Intermediate Similarity	NPD4814	Discontinued
0.7111	Intermediate Similarity	NPD2198	Approved
0.7111	Intermediate Similarity	NPD2199	Approved
0.7107	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7972	Discontinued
0.7101	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6681	Discovery
0.708	Intermediate Similarity	NPD7828	Discontinued
0.708	Intermediate Similarity	NPD5204	Approved
0.7077	Intermediate Similarity	NPD5292	Approved
0.7077	Intermediate Similarity	NPD5291	Approved
0.7071	Intermediate Similarity	NPD5121	Approved
0.7071	Intermediate Similarity	NPD8416	Discontinued
0.7071	Intermediate Similarity	NPD5120	Approved
0.7071	Intermediate Similarity	NPD5119	Approved
0.7059	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD855	Approved
0.7049	Intermediate Similarity	NPD854	Approved
0.7047	Intermediate Similarity	NPD7131	Phase 3
0.7045	Intermediate Similarity	NPD4105	Approved
0.7045	Intermediate Similarity	NPD4102	Approved
0.7034	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9712	Approved
0.6992	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3400	Discontinued
0.6986	Remote Similarity	NPD2575	Approved
0.6985	Remote Similarity	NPD3125	Approved
0.698	Remote Similarity	NPD7613	Discontinued
0.6974	Remote Similarity	NPD6913	Approved
0.6974	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6093	Discontinued
0.697	Remote Similarity	NPD2617	Discontinued
0.696	Remote Similarity	NPD5705	Approved
0.696	Remote Similarity	NPD5704	Approved
0.696	Remote Similarity	NPD467	Phase 1
0.696	Remote Similarity	NPD5706	Approved
0.6949	Remote Similarity	NPD6690	Approved
0.6947	Remote Similarity	NPD9568	Approved
0.6942	Remote Similarity	NPD9612	Approved
0.6942	Remote Similarity	NPD9609	Approved
0.6942	Remote Similarity	NPD9710	Approved
0.6942	Remote Similarity	NPD253	Approved
0.6942	Remote Similarity	NPD9611	Approved
0.6942	Remote Similarity	NPD9711	Approved
0.694	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5909	Discontinued
0.6929	Remote Similarity	NPD4233	Approved
0.6929	Remote Similarity	NPD5239	Approved
0.6929	Remote Similarity	NPD5237	Approved
0.6929	Remote Similarity	NPD5240	Approved
0.6929	Remote Similarity	NPD4234	Approved
0.6929	Remote Similarity	NPD5235	Approved
0.6929	Remote Similarity	NPD5236	Approved
0.6923	Remote Similarity	NPD2629	Approved
0.6918	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5159	Phase 2
0.6912	Remote Similarity	NPD5157	Phase 1
0.6906	Remote Similarity	NPD4125	Approved
0.6901	Remote Similarity	NPD555	Phase 2
0.6901	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6065	Approved
0.6891	Remote Similarity	NPD1066	Discontinued
0.6889	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5048	Discontinued
0.6879	Remote Similarity	NPD6746	Phase 2
0.6875	Remote Similarity	NPD2201	Approved
0.687	Remote Similarity	NPD7508	Discontinued
0.687	Remote Similarity	NPD255	Approved
0.687	Remote Similarity	NPD256	Approved
0.6861	Remote Similarity	NPD3098	Discontinued
0.6861	Remote Similarity	NPD196	Phase 1
0.6861	Remote Similarity	NPD5667	Approved
0.6857	Remote Similarity	NPD6039	Approved
0.6849	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1373	Approved
0.6846	Remote Similarity	NPD1371	Approved
0.6846	Remote Similarity	NPD1370	Approved
0.6846	Remote Similarity	NPD1374	Approved
0.6838	Remote Similarity	NPD5346	Phase 2
0.6838	Remote Similarity	NPD5347	Phase 2
0.6835	Remote Similarity	NPD4177	Approved
0.6835	Remote Similarity	NPD4175	Approved
0.6835	Remote Similarity	NPD3626	Phase 3
0.6831	Remote Similarity	NPD6311	Approved
0.6831	Remote Similarity	NPD825	Approved
0.6831	Remote Similarity	NPD6310	Approved
0.6831	Remote Similarity	NPD826	Approved
0.6831	Remote Similarity	NPD3373	Approved
0.6831	Remote Similarity	NPD6309	Approved
0.6828	Remote Similarity	NPD4173	Approved
0.6828	Remote Similarity	NPD4172	Approved
0.6828	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6685	Approved
0.6825	Remote Similarity	NPD812	Approved
0.6825	Remote Similarity	NPD811	Approved
0.6825	Remote Similarity	NPD810	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