NPASS Compound

Structure

NPC473786 OpenBabel07101718192D 56 64 0 0 1 0 0 0 0 0999 V2000 6.2981 1.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5004 0.2115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6620 0.6955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8833 0.2115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4172 -4.8265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0818 2.5260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6295 -0.3953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9289 0.2727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3701 -0.1492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7536 -1.2171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1019 -2.0041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2442 -2.5496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3682 -3.1767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0979 -2.2940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5524 -0.4363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1493 -3.2568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4259 0.5950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8236 -0.7566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8236 1.1796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4012 -1.3361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6978 -0.4730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4724 -1.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2066 -1.7246 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3682 -2.2087 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6915 -2.2087 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8736 -2.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9448 -3.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0813 -0.0526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8531 -1.7246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8531 -0.7566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3682 -0.2725 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5298 -0.7566 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1370 0.6915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8094 1.0153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0147 -0.2725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8236 -1.7246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0147 -2.2087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6915 -0.2725 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2282 -1.5404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2282 -0.9408 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3682 -4.1448 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2066 -0.7566 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5298 -1.7246 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.8236 2.1476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -3.6130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3372 1.2369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6295 -2.0859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9601 0.7710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7166 -4.1584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8817 1.9807 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5524 -2.0449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5431 -2.3724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1866 -3.1556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0147 0.6955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0979 -0.1872 0.0000 S 0 0 3 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 43 1 0 0 0 0 5 50 1 0 0 0 0 6 51 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 42 1 0 0 0 0 9 17 2 0 0 0 0 9 21 1 0 0 0 0 10 21 1 0 0 0 0 11 20 2 0 0 0 0 11 26 1 0 0 0 0 12 22 2 0 0 0 0 12 27 1 0 0 0 0 13 24 1 0 0 0 0 13 41 3 0 0 0 0 14 25 1 0 0 0 0 14 52 1 0 0 0 0 15 56 1 0 0 0 0 16 53 1 0 0 0 0 16 54 1 0 0 0 0 17 34 1 0 0 0 0 18 35 2 0 0 0 0 18 36 1 0 0 0 0 19 45 2 0 0 0 0 19 55 1 0 0 0 0 20 22 1 0 0 0 0 21 28 2 0 0 0 0 22 40 1 0 0 0 0 23 10 1 1 0 0 0 23 24 1 0 0 0 0 23 43 1 0 0 0 0 24 44 1 6 0 0 0 25 29 1 0 0 0 0 25 44 1 1 0 0 0 26 27 2 0 0 0 0 26 46 1 0 0 0 0 27 50 1 0 0 0 0 28 33 1 0 0 0 0 29 30 2 0 0 0 0 29 37 1 0 0 0 0 30 35 1 0 0 0 0 30 38 1 0 0 0 0 31 28 1 6 0 0 0 31 32 1 0 0 0 0 31 43 1 0 0 0 0 32 38 1 0 0 0 0 32 44 1 1 0 0 0 33 34 2 0 0 0 0 33 47 1 0 0 0 0 34 51 1 0 0 0 0 35 55 1 0 0 0 0 36 37 2 0 0 0 0 36 53 1 0 0 0 0 37 54 1 0 0 0 0 38 56 1 1 0 0 0 39 40 1 0 0 0 0 39 48 2 0 0 0 0 39 52 1 0 0 0 0 40 15 1 6 0 0 0 40 42 1 0 0 0 0 49 56 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	786.26
Volume:	748.302
LogP:	1.28
LogD:	1.007
LogS:	-1.955
# Rotatable Bonds:	4
TPSA:	195.34
# H-Bond Aceptor:	15
# H-Bond Donor:	3
# Rings:	10
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.199
Synthetic Accessibility Score:	7.657
Fsp3:	0.475
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.687
MDCK Permeability:	1.466949652240146e-05
Pgp-inhibitor:	0.127
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.496
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	88.65506744384766%
Volume Distribution (VD):	1.42
Pgp-substrate:	4.014167785644531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.144
CYP2C9-inhibitor:	0.425
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.685
CYP3A4-substrate:	0.956

ADMET: Excretion

Clearance (CL):	3.682
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.828
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.62
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.25
Carcinogencity:	0.171
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC473786

Natural Product ID:	NPC473786
*Common Name:**	Ecteinascidin 786
IUPAC Name:	n.a.
Synonyms:	Ecteinascidin 786
Standard InCHIKey:	RRCYSJADSSZEAZ-GEFZJANUSA-N
Standard InCHI:	InChI=1S/C40H42N4O11S/c1-17-9-21-10-23-24(13-41)44-25-14-52-39(48)40(22-12-27(50-5)26(46)11-20(22)7-8-42-40)15-56(49)38(32(44)31(43(23)4)28(21)33(47)34(17)51-6)30-29(25)37-36(53-16-54-37)18(2)35(30)55-19(3)45/h9,11-12,23-25,31-32,38,42,46-47H,7-8,10,14-16H2,1-6H3/t23-,24-,25-,31-,32+,38+,40+,56?/m0/s1
SMILES:	CC1=CC2=C(C3C4C5C6=C(C(=C7C(=C6C(N4C(C(C2)N3C)C#N)COC(=O)C8(CS5=O)C9=CC(=C(C=C9CCN8)O)OC)OCO7)C)OC(=O)C)C(=C1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451892
PubChem CID:	44575987
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004007] Benzazocines

*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
NPO15773	Ecteinascidia thurstoni	Species	Perophoridae	Eukaryota	n.a.	Thai	n.a.	PMID[12088444]
NPO15773	Ecteinascidia thurstoni	Species	Perophoridae	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	2
MIC	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.15	nM	PMID[488223]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.6	nM	PMID[488223]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	2000.0	nM	PMID[488223]

☑ 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 NPC473786 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	382
0.1-0.2	2040
0.2-0.3	8332
0.3-0.4	10833
0.4-0.5	8010
0.5-0.6	11164
0.6-0.7	1893
0.7-0.8	40
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9824	High Similarity	NPC133864
0.9561	High Similarity	NPC131258
0.7652	Intermediate Similarity	NPC473660
0.7449	Intermediate Similarity	NPC211215
0.7368	Intermediate Similarity	NPC315914
0.7336	Intermediate Similarity	NPC44040
0.7304	Intermediate Similarity	NPC24260
0.7303	Intermediate Similarity	NPC473746
0.7273	Intermediate Similarity	NPC256124
0.7265	Intermediate Similarity	NPC475654
0.7261	Intermediate Similarity	NPC191132
0.7261	Intermediate Similarity	NPC60295
0.7243	Intermediate Similarity	NPC475180
0.7238	Intermediate Similarity	NPC46990
0.7231	Intermediate Similarity	NPC319774
0.7217	Intermediate Similarity	NPC82457
0.7217	Intermediate Similarity	NPC175890
0.7217	Intermediate Similarity	NPC274661
0.7217	Intermediate Similarity	NPC11296
0.7217	Intermediate Similarity	NPC48490
0.7217	Intermediate Similarity	NPC281581
0.7213	Intermediate Similarity	NPC82056
0.7154	Intermediate Similarity	NPC314743
0.7131	Intermediate Similarity	NPC38964
0.713	Intermediate Similarity	NPC116465
0.713	Intermediate Similarity	NPC212237
0.71	Intermediate Similarity	NPC476576
0.71	Intermediate Similarity	NPC22115
0.71	Intermediate Similarity	NPC275680
0.71	Intermediate Similarity	NPC186546
0.7069	Intermediate Similarity	NPC206900
0.7056	Intermediate Similarity	NPC65312
0.7056	Intermediate Similarity	NPC57036
0.7056	Intermediate Similarity	NPC139783
0.7047	Intermediate Similarity	NPC185031
0.7047	Intermediate Similarity	NPC316292
0.7043	Intermediate Similarity	NPC254441
0.7043	Intermediate Similarity	NPC167116
0.7043	Intermediate Similarity	NPC274716
0.7013	Intermediate Similarity	NPC302245
0.7013	Intermediate Similarity	NPC95426
0.7013	Intermediate Similarity	NPC16357
0.7	Intermediate Similarity	NPC182052
0.7	Intermediate Similarity	NPC328155
0.7	Intermediate Similarity	NPC252156
0.7	Intermediate Similarity	NPC299990
0.7	Intermediate Similarity	NPC239824
0.7	Intermediate Similarity	NPC285931
0.7	Intermediate Similarity	NPC90998
0.7	Intermediate Similarity	NPC271013
0.7	Intermediate Similarity	NPC217748
0.7	Intermediate Similarity	NPC251735
0.7	Intermediate Similarity	NPC311973
0.7	Intermediate Similarity	NPC104196
0.7	Intermediate Similarity	NPC290582
0.7	Intermediate Similarity	NPC8836
0.7	Intermediate Similarity	NPC290005
0.7	Intermediate Similarity	NPC185639
0.7	Intermediate Similarity	NPC181796
0.7	Intermediate Similarity	NPC73492
0.7	Intermediate Similarity	NPC49075
0.7	Intermediate Similarity	NPC229373
0.7	Intermediate Similarity	NPC42663
0.7	Intermediate Similarity	NPC30779
0.7	Intermediate Similarity	NPC222661
0.7	Intermediate Similarity	NPC258657
0.7	Intermediate Similarity	NPC15414
0.7	Intermediate Similarity	NPC279228
0.7	Intermediate Similarity	NPC54654
0.7	Intermediate Similarity	NPC223690
0.7	Intermediate Similarity	NPC7715
0.698	Remote Similarity	NPC315253
0.6979	Remote Similarity	NPC478091
0.6979	Remote Similarity	NPC30182
0.6979	Remote Similarity	NPC478092
0.6979	Remote Similarity	NPC473589
0.6966	Remote Similarity	NPC473716
0.6966	Remote Similarity	NPC475597
0.6957	Remote Similarity	NPC286119
0.6957	Remote Similarity	NPC239584
0.6936	Remote Similarity	NPC478093
0.6936	Remote Similarity	NPC117717
0.6923	Remote Similarity	NPC82763
0.6913	Remote Similarity	NPC243454
0.6913	Remote Similarity	NPC475479
0.6897	Remote Similarity	NPC135772
0.6894	Remote Similarity	NPC475754
0.6885	Remote Similarity	NPC153365
0.6883	Remote Similarity	NPC155442
0.6883	Remote Similarity	NPC476574
0.6883	Remote Similarity	NPC477561
0.6883	Remote Similarity	NPC230276
0.6883	Remote Similarity	NPC312918
0.6883	Remote Similarity	NPC257269
0.6846	Remote Similarity	NPC328700
0.6846	Remote Similarity	NPC2173
0.6846	Remote Similarity	NPC119818
0.6846	Remote Similarity	NPC202771
0.6844	Remote Similarity	NPC257728
0.684	Remote Similarity	NPC258695
0.684	Remote Similarity	NPC470879
0.684	Remote Similarity	NPC119068
0.684	Remote Similarity	NPC40496
0.6838	Remote Similarity	NPC47077
0.6838	Remote Similarity	NPC14507
0.6835	Remote Similarity	NPC471563
0.6833	Remote Similarity	NPC242728
0.6831	Remote Similarity	NPC314946
0.6826	Remote Similarity	NPC293093
0.6813	Remote Similarity	NPC170101
0.681	Remote Similarity	NPC474506
0.681	Remote Similarity	NPC32413
0.6803	Remote Similarity	NPC257266
0.6803	Remote Similarity	NPC11708
0.6778	Remote Similarity	NPC234318
0.6767	Remote Similarity	NPC474507
0.6766	Remote Similarity	NPC230098
0.6766	Remote Similarity	NPC214116
0.6765	Remote Similarity	NPC469816
0.6765	Remote Similarity	NPC469815
0.675	Remote Similarity	NPC50548
0.6739	Remote Similarity	NPC152680
0.6739	Remote Similarity	NPC190783
0.6739	Remote Similarity	NPC41376
0.6739	Remote Similarity	NPC251580
0.6739	Remote Similarity	NPC129518
0.6739	Remote Similarity	NPC232386
0.6739	Remote Similarity	NPC2314
0.6739	Remote Similarity	NPC12424
0.6725	Remote Similarity	NPC109925
0.6724	Remote Similarity	NPC23219
0.6724	Remote Similarity	NPC114364
0.6724	Remote Similarity	NPC320223
0.6722	Remote Similarity	NPC267414
0.6721	Remote Similarity	NPC477666
0.671	Remote Similarity	NPC199465
0.671	Remote Similarity	NPC128560
0.671	Remote Similarity	NPC229166
0.6709	Remote Similarity	NPC116284
0.6708	Remote Similarity	NPC204580
0.6708	Remote Similarity	NPC144314
0.6696	Remote Similarity	NPC317439
0.6696	Remote Similarity	NPC76682
0.6696	Remote Similarity	NPC108434
0.6696	Remote Similarity	NPC317145
0.6696	Remote Similarity	NPC227060
0.6696	Remote Similarity	NPC10908
0.6696	Remote Similarity	NPC115284
0.6696	Remote Similarity	NPC276890
0.6696	Remote Similarity	NPC24465
0.6696	Remote Similarity	NPC63646
0.6696	Remote Similarity	NPC475215
0.6696	Remote Similarity	NPC198498
0.6695	Remote Similarity	NPC32154
0.6694	Remote Similarity	NPC80472
0.6693	Remote Similarity	NPC328856
0.6693	Remote Similarity	NPC180210
0.6693	Remote Similarity	NPC314914
0.6693	Remote Similarity	NPC478047
0.6693	Remote Similarity	NPC478046
0.6693	Remote Similarity	NPC321226
0.6681	Remote Similarity	NPC476577
0.6681	Remote Similarity	NPC112575
0.6681	Remote Similarity	NPC156576
0.6681	Remote Similarity	NPC302275
0.6681	Remote Similarity	NPC173416
0.6681	Remote Similarity	NPC148709
0.668	Remote Similarity	NPC83019
0.668	Remote Similarity	NPC73020
0.668	Remote Similarity	NPC215098
0.668	Remote Similarity	NPC70290
0.668	Remote Similarity	NPC14622
0.668	Remote Similarity	NPC46744
0.668	Remote Similarity	NPC254581
0.668	Remote Similarity	NPC124302
0.6667	Remote Similarity	NPC316164
0.6667	Remote Similarity	NPC254045
0.6667	Remote Similarity	NPC151470
0.6667	Remote Similarity	NPC125924
0.6667	Remote Similarity	NPC264850
0.6667	Remote Similarity	NPC470646
0.6667	Remote Similarity	NPC149962
0.6667	Remote Similarity	NPC29531
0.6667	Remote Similarity	NPC316368
0.6667	Remote Similarity	NPC201055
0.6667	Remote Similarity	NPC64576
0.6667	Remote Similarity	NPC13916
0.6667	Remote Similarity	NPC284236
0.6653	Remote Similarity	NPC478048
0.6653	Remote Similarity	NPC123859
0.6652	Remote Similarity	NPC329816
0.6641	Remote Similarity	NPC3921
0.6638	Remote Similarity	NPC476575
0.6638	Remote Similarity	NPC248642
0.6638	Remote Similarity	NPC477558
0.6627	Remote Similarity	NPC478008
0.6626	Remote Similarity	NPC314100
0.6626	Remote Similarity	NPC246303
0.6626	Remote Similarity	NPC226652
0.6626	Remote Similarity	NPC72788

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 NPC473786 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	709
0.2-0.3	1446
0.3-0.4	2704
0.4-0.5	2641
0.5-0.6	1216
0.6-0.7	230
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9561	High Similarity	NPD8152	Approved
0.9561	High Similarity	NPD8153	Approved
0.7292	Intermediate Similarity	NPD7827	Phase 1
0.7222	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7783	Phase 2
0.7056	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8053	Approved
0.7	Intermediate Similarity	NPD8054	Approved
0.6944	Remote Similarity	NPD7224	Discontinued
0.6944	Remote Similarity	NPD7223	Discontinued
0.6926	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6853	Approved
0.6853	Remote Similarity	NPD6851	Approved
0.6846	Remote Similarity	NPD5006	Approved
0.6846	Remote Similarity	NPD5005	Approved
0.6844	Remote Similarity	NPD7585	Approved
0.684	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7583	Approved
0.6739	Remote Similarity	NPD8156	Discontinued
0.6718	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6723	Discontinued
0.6718	Remote Similarity	NPD6625	Approved
0.6707	Remote Similarity	NPD7701	Phase 2
0.6696	Remote Similarity	NPD8251	Approved
0.6696	Remote Similarity	NPD8252	Approved
0.6696	Remote Similarity	NPD8099	Discontinued
0.6695	Remote Similarity	NPD7906	Approved
0.6681	Remote Similarity	NPD6297	Approved
0.668	Remote Similarity	NPD4420	Approved
0.6667	Remote Similarity	NPD3452	Approved
0.6667	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD2494	Approved
0.6667	Remote Similarity	NPD3450	Approved
0.6599	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD8059	Phase 3
0.6585	Remote Similarity	NPD4582	Approved
0.6585	Remote Similarity	NPD4583	Approved
0.6585	Remote Similarity	NPD4040	Phase 1
0.6579	Remote Similarity	NPD5677	Discontinued
0.6562	Remote Similarity	NPD6997	Phase 2
0.6559	Remote Similarity	NPD7999	Approved
0.655	Remote Similarity	NPD6107	Approved
0.6548	Remote Similarity	NPD7930	Approved
0.6545	Remote Similarity	NPD7696	Phase 3
0.6545	Remote Similarity	NPD4002	Approved
0.6545	Remote Similarity	NPD7680	Approved
0.6545	Remote Similarity	NPD7698	Approved
0.6545	Remote Similarity	NPD7697	Approved
0.6545	Remote Similarity	NPD4004	Approved
0.6532	Remote Similarity	NPD7584	Approved
0.6518	Remote Similarity	NPD7871	Phase 2
0.6518	Remote Similarity	NPD7870	Phase 2
0.6511	Remote Similarity	NPD7039	Approved
0.6511	Remote Similarity	NPD7038	Approved
0.6502	Remote Similarity	NPD2974	Approved
0.6502	Remote Similarity	NPD2973	Approved
0.6502	Remote Similarity	NPD2975	Approved
0.649	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8151	Discontinued
0.6459	Remote Similarity	NPD7907	Approved
0.6452	Remote Similarity	NPD8320	Phase 1
0.6452	Remote Similarity	NPD8319	Approved
0.6436	Remote Similarity	NPD8461	Discontinued
0.6432	Remote Similarity	NPD2488	Approved
0.6432	Remote Similarity	NPD2490	Approved
0.6429	Remote Similarity	NPD7801	Approved
0.6423	Remote Similarity	NPD6780	Approved
0.6423	Remote Similarity	NPD6777	Approved
0.6423	Remote Similarity	NPD6778	Approved
0.6423	Remote Similarity	NPD6776	Approved
0.6423	Remote Similarity	NPD6781	Approved
0.6423	Remote Similarity	NPD4580	Approved
0.6423	Remote Similarity	NPD6779	Approved
0.6423	Remote Similarity	NPD6782	Approved
0.641	Remote Similarity	NPD7228	Approved
0.6409	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7047	Phase 3
0.6391	Remote Similarity	NPD7048	Phase 3
0.639	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7281	Phase 3
0.6387	Remote Similarity	NPD7280	Phase 3
0.6379	Remote Similarity	NPD7229	Phase 3
0.6375	Remote Similarity	NPD4663	Approved
0.6371	Remote Similarity	NPD6823	Phase 2
0.636	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7549	Discontinued
0.6341	Remote Similarity	NPD7699	Phase 2
0.6341	Remote Similarity	NPD7700	Phase 2
0.634	Remote Similarity	NPD6620	Discovery
0.6336	Remote Similarity	NPD8469	Approved
0.6333	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD4578	Approved
0.6318	Remote Similarity	NPD4577	Approved
0.6316	Remote Similarity	NPD7298	Approved
0.6314	Remote Similarity	NPD5844	Phase 1
0.6304	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD5564	Approved
0.6301	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD5242	Approved
0.6281	Remote Similarity	NPD6841	Approved
0.6281	Remote Similarity	NPD6843	Phase 3
0.6281	Remote Similarity	NPD6842	Approved
0.628	Remote Similarity	NPD7435	Discontinued
0.6278	Remote Similarity	NPD7922	Phase 1
0.626	Remote Similarity	NPD7874	Approved
0.626	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8285	Discontinued
0.625	Remote Similarity	NPD7313	Approved
0.625	Remote Similarity	NPD7310	Approved
0.625	Remote Similarity	NPD6234	Discontinued
0.625	Remote Similarity	NPD7311	Approved
0.625	Remote Similarity	NPD7312	Approved
0.6245	Remote Similarity	NPD8492	Approved
0.624	Remote Similarity	NPD5980	Discovery
0.6236	Remote Similarity	NPD8491	Approved
0.6235	Remote Similarity	NPD5676	Approved
0.6225	Remote Similarity	NPD5457	Discontinued
0.6224	Remote Similarity	NPD7309	Approved
0.6223	Remote Similarity	NPD4666	Phase 3
0.622	Remote Similarity	NPD6535	Approved
0.622	Remote Similarity	NPD6534	Approved
0.6218	Remote Similarity	NPD8367	Approved
0.6217	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6217	Remote Similarity	NPD2977	Approved
0.6217	Remote Similarity	NPD2978	Approved
0.6214	Remote Similarity	NPD7708	Approved
0.6208	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6208	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8366	Approved
0.6204	Remote Similarity	NPD7296	Approved
0.6197	Remote Similarity	NPD7802	Discontinued
0.6197	Remote Similarity	NPD7199	Phase 2
0.6192	Remote Similarity	NPD4665	Approved
0.6192	Remote Similarity	NPD4111	Phase 1
0.6189	Remote Similarity	NPD7861	Discontinued
0.6186	Remote Similarity	NPD4481	Phase 3
0.6185	Remote Similarity	NPD8095	Phase 1
0.6185	Remote Similarity	NPD7810	Phase 3
0.6185	Remote Similarity	NPD7811	Phase 3
0.6184	Remote Similarity	NPD7803	Approved
0.6183	Remote Similarity	NPD2968	Approved
0.6183	Remote Similarity	NPD2971	Approved
0.618	Remote Similarity	NPD5709	Phase 3
0.6179	Remote Similarity	NPD6212	Phase 3
0.6179	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6213	Phase 3
0.6176	Remote Similarity	NPD42	Phase 2
0.6176	Remote Similarity	NPD6042	Phase 2
0.617	Remote Similarity	NPD5711	Approved
0.617	Remote Similarity	NPD5710	Approved
0.6169	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD6788	Approved
0.6151	Remote Similarity	NPD7074	Phase 3
0.6148	Remote Similarity	NPD4435	Approved
0.6144	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD8149	Discontinued
0.6135	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7955	Approved
0.6121	Remote Similarity	NPD7956	Approved
0.6118	Remote Similarity	NPD2489	Approved
0.6118	Remote Similarity	NPD27	Approved
0.6111	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD5313	Approved
0.6109	Remote Similarity	NPD5312	Approved
0.6107	Remote Similarity	NPD4434	Approved
0.6104	Remote Similarity	NPD5356	Approved
0.6104	Remote Similarity	NPD37	Approved
0.6104	Remote Similarity	NPD5355	Approved
0.6102	Remote Similarity	NPD8161	Suspended
0.6102	Remote Similarity	NPD3051	Approved
0.61	Remote Similarity	NPD7240	Approved
0.6098	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD4967	Phase 2
0.6094	Remote Similarity	NPD4965	Approved
0.6094	Remote Similarity	NPD4966	Approved
0.6087	Remote Similarity	NPD7497	Discontinued
0.6076	Remote Similarity	NPD2970	Approved
0.6076	Remote Similarity	NPD2969	Approved
0.6069	Remote Similarity	NPD2899	Discontinued
0.6067	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD8404	Phase 2
0.6053	Remote Similarity	NPD6090	Discontinued
0.605	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7054	Approved
0.6034	Remote Similarity	NPD3383	Approved
0.6034	Remote Similarity	NPD6071	Discontinued
0.6034	Remote Similarity	NPD3382	Approved
0.6034	Remote Similarity	NPD4166	Phase 2
0.6034	Remote Similarity	NPD3384	Approved
0.6029	Remote Similarity	NPD4846	Phase 2
0.6026	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD6556	Clinical (unspecified phase)

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