NPASS Compound

Structure

CID22014 OpenBabel06191715352D 40 42 0 0 1 0 0 0 0 0999 V2000 -7.0132 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7202 -5.0064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4112 -5.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0511 -4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0803 -6.7006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4773 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4405 -8.3948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3434 -3.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.4773 -1.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4186 -8.1869 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1314 -9.3459 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -2.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -3.3122 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.6113 -3.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7713 -7.6517 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -2.7770 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 3 1 0 0 0 0 1 13 1 0 0 0 0 2 4 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 11 2 0 0 0 0 5 18 1 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 9 1 0 0 0 0 7 19 2 0 0 0 0 8 10 2 0 0 0 0 8 19 1 0 0 0 0 9 20 2 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 33 1 0 0 0 0 14 34 1 0 0 0 0 15 35 1 0 0 0 0 16 36 1 0 0 0 0 17 18 2 0 0 0 0 17 21 1 0 0 0 0 20 37 1 0 0 0 0 21 22 2 0 0 0 0 21 24 1 0 0 0 0 22 40 1 0 0 0 0 23 33 2 3 0 0 0 23 38 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 6 0 0 0 25 19 1 1 0 0 0 25 40 1 0 0 0 0 26 34 2 3 0 0 0 26 39 1 0 0 0 0 27 29 2 0 0 0 0 27 30 1 0 0 0 0 27 35 1 0 0 0 0 28 31 2 0 0 0 0 28 32 1 0 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	550.3
Volume:	561.309
LogP:	0.742
LogD:	0.217
LogS:	-4.548
# Rotatable Bonds:	17
TPSA:	213.96
# H-Bond Aceptor:	12
# H-Bond Donor:	11
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.074
Synthetic Accessibility Score:	3.693
Fsp3:	0.357
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:	-5.786
MDCK Permeability:	8.550999154977035e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.539
Human Intestinal Absorption (HIA):	0.823
20% Bioavailability (F20%):	0.798
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.213
Plasma Protein Binding (PPB):	64.92701721191406%
Volume Distribution (VD):	1.434
Pgp-substrate:	47.529205322265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.547
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	5.585
Half-life (T1/2):	0.225

ADMET: Toxicity

hERG Blockers:	0.308
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.275
AMES Toxicity:	0.153
Rat Oral Acute Toxicity:	0.77
Maximum Recommended Daily Dose:	0.748
Skin Sensitization:	0.182
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.629

Download Data

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

Natural Product: NPC22014

Natural Product ID:	NPC22014
*Common Name:**	(2R,3R)-N-(4-Guanidinobutyl)-5-(3-(4-Guanidinobutylamino)-3-Oxoprop-1-Enyl)-2-(4-Hydroxyphenyl)-2,3-Dihydrobenzofuran-3-Carboxamide
IUPAC Name:	(2R,3R)-N-[4-(diaminomethylideneamino)butyl]-5-[(E)-3-[4-(diaminomethylideneamino)butylamino]-3-oxoprop-1-enyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-carboxamide
Synonyms:
Standard InCHIKey:	KVYNYRIOAYQBFK-ODMAYWLASA-N
Standard InCHI:	InChI=1S/C28H38N8O4/c29-27(30)35-15-3-1-13-33-23(38)12-6-18-5-11-22-21(17-18)24(25(40-22)19-7-9-20(37)10-8-19)26(39)34-14-2-4-16-36-28(31)32/h5-12,17,24-25,37H,1-4,13-16H2,(H,33,38)(H,34,39)(H4,29,30,35)(H4,31,32,36)/p+2/b12-6+/t24-,25+/m1/s1
SMILES:	C(CCNC(=[NH2+])[NH3+])CN=C(/C=C/c1ccc2c(c1)[C@H]([C@H](c1ccc(cc1)O)O2)C(=NCCCCNC(=N)N)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL566278
PubChem CID:	5281113
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18270436]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23793896]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[24967651]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22132	Hordeum vulgare	Species	Poaceae	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

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT219	Individual Protein	Alpha-1a adrenergic receptor	Rattus norvegicus	IC50	=	290000.0	nM	PMID[479808]
NPT219	Individual Protein	Alpha-1a adrenergic receptor	Rattus norvegicus	IC50	=	14300000.0	nM	PMID[479808]

☑ 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 NPC22014 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	258
0.1-0.2	1215
0.2-0.3	5322
0.3-0.4	12861
0.4-0.5	5780
0.5-0.6	12560
0.6-0.7	4499
0.7-0.8	201
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7811	Intermediate Similarity	NPC90984
0.7756	Intermediate Similarity	NPC214988
0.7733	Intermediate Similarity	NPC81641
0.7658	Intermediate Similarity	NPC168861
0.7654	Intermediate Similarity	NPC283207
0.7651	Intermediate Similarity	NPC150026
0.7613	Intermediate Similarity	NPC267237
0.761	Intermediate Similarity	NPC326241
0.7548	Intermediate Similarity	NPC129784
0.7548	Intermediate Similarity	NPC268917
0.7548	Intermediate Similarity	NPC271945
0.7548	Intermediate Similarity	NPC17343
0.7548	Intermediate Similarity	NPC181497
0.7548	Intermediate Similarity	NPC12875
0.7548	Intermediate Similarity	NPC280653
0.7548	Intermediate Similarity	NPC150011
0.7548	Intermediate Similarity	NPC206224
0.7548	Intermediate Similarity	NPC236014
0.7548	Intermediate Similarity	NPC228369
0.7548	Intermediate Similarity	NPC207892
0.7548	Intermediate Similarity	NPC476166
0.7548	Intermediate Similarity	NPC300875
0.7548	Intermediate Similarity	NPC196765
0.7548	Intermediate Similarity	NPC129106
0.7548	Intermediate Similarity	NPC164574
0.7548	Intermediate Similarity	NPC118114
0.7531	Intermediate Similarity	NPC313414
0.75	Intermediate Similarity	NPC13005
0.7484	Intermediate Similarity	NPC27187
0.7484	Intermediate Similarity	NPC470225
0.7442	Intermediate Similarity	NPC470936
0.7438	Intermediate Similarity	NPC212850
0.7438	Intermediate Similarity	NPC189724
0.7438	Intermediate Similarity	NPC83289
0.7436	Intermediate Similarity	NPC471953
0.7419	Intermediate Similarity	NPC93962
0.7405	Intermediate Similarity	NPC198154
0.7405	Intermediate Similarity	NPC225696
0.7405	Intermediate Similarity	NPC296915
0.7405	Intermediate Similarity	NPC115335
0.7405	Intermediate Similarity	NPC223008
0.7405	Intermediate Similarity	NPC97834
0.7405	Intermediate Similarity	NPC237227
0.7355	Intermediate Similarity	NPC53986
0.7355	Intermediate Similarity	NPC47283
0.7355	Intermediate Similarity	NPC39064
0.7355	Intermediate Similarity	NPC38664
0.7342	Intermediate Similarity	NPC26394
0.7342	Intermediate Similarity	NPC85435
0.7338	Intermediate Similarity	NPC471215
0.7338	Intermediate Similarity	NPC262573
0.7337	Intermediate Similarity	NPC87363
0.7321	Intermediate Similarity	NPC275027
0.732	Intermediate Similarity	NPC95733
0.732	Intermediate Similarity	NPC62101
0.7312	Intermediate Similarity	NPC10737
0.7312	Intermediate Similarity	NPC263367
0.7312	Intermediate Similarity	NPC54743
0.7312	Intermediate Similarity	NPC477939
0.7312	Intermediate Similarity	NPC29799
0.7312	Intermediate Similarity	NPC209985
0.7312	Intermediate Similarity	NPC156502
0.7312	Intermediate Similarity	NPC177160
0.7296	Intermediate Similarity	NPC117048
0.7296	Intermediate Similarity	NPC49603
0.7296	Intermediate Similarity	NPC124085
0.7296	Intermediate Similarity	NPC187616
0.7296	Intermediate Similarity	NPC193026
0.7278	Intermediate Similarity	NPC230219
0.7278	Intermediate Similarity	NPC51543
0.7273	Intermediate Similarity	NPC29477
0.7273	Intermediate Similarity	NPC245974
0.7267	Intermediate Similarity	NPC474687
0.7256	Intermediate Similarity	NPC247298
0.7255	Intermediate Similarity	NPC211218
0.725	Intermediate Similarity	NPC125579
0.7244	Intermediate Similarity	NPC274717
0.7226	Intermediate Similarity	NPC26879
0.7226	Intermediate Similarity	NPC230479
0.7226	Intermediate Similarity	NPC283049
0.7226	Intermediate Similarity	NPC50315
0.7222	Intermediate Similarity	NPC475836
0.7219	Intermediate Similarity	NPC263835
0.7216	Intermediate Similarity	NPC474881
0.7215	Intermediate Similarity	NPC68205
0.7215	Intermediate Similarity	NPC244888
0.7215	Intermediate Similarity	NPC293203
0.7215	Intermediate Similarity	NPC118683
0.7215	Intermediate Similarity	NPC162801
0.7215	Intermediate Similarity	NPC274732
0.7215	Intermediate Similarity	NPC211413
0.7215	Intermediate Similarity	NPC164804
0.7205	Intermediate Similarity	NPC3049
0.7205	Intermediate Similarity	NPC262585
0.7205	Intermediate Similarity	NPC20829
0.7205	Intermediate Similarity	NPC18189
0.7186	Intermediate Similarity	NPC471032
0.7186	Intermediate Similarity	NPC470935
0.7178	Intermediate Similarity	NPC195814
0.7161	Intermediate Similarity	NPC102540
0.7161	Intermediate Similarity	NPC188022
0.7161	Intermediate Similarity	NPC285040
0.7161	Intermediate Similarity	NPC103420
0.7161	Intermediate Similarity	NPC17809
0.716	Intermediate Similarity	NPC477938
0.716	Intermediate Similarity	NPC474560
0.7134	Intermediate Similarity	NPC5155
0.7134	Intermediate Similarity	NPC263261
0.7134	Intermediate Similarity	NPC471414
0.7134	Intermediate Similarity	NPC87725
0.7133	Intermediate Similarity	NPC476266
0.7126	Intermediate Similarity	NPC115144
0.7126	Intermediate Similarity	NPC277857
0.7126	Intermediate Similarity	NPC247251
0.7125	Intermediate Similarity	NPC77196
0.7115	Intermediate Similarity	NPC276212
0.7107	Intermediate Similarity	NPC247018
0.7107	Intermediate Similarity	NPC103799
0.7107	Intermediate Similarity	NPC97870
0.7107	Intermediate Similarity	NPC307123
0.7099	Intermediate Similarity	NPC471522
0.7099	Intermediate Similarity	NPC141717
0.7097	Intermediate Similarity	NPC134195
0.7097	Intermediate Similarity	NPC197351
0.7097	Intermediate Similarity	NPC256015
0.7097	Intermediate Similarity	NPC294156
0.7097	Intermediate Similarity	NPC106914
0.7097	Intermediate Similarity	NPC246648
0.7097	Intermediate Similarity	NPC86502
0.7091	Intermediate Similarity	NPC131971
0.7091	Intermediate Similarity	NPC253878
0.7089	Intermediate Similarity	NPC134360
0.7081	Intermediate Similarity	NPC473107
0.707	Intermediate Similarity	NPC98745
0.7063	Intermediate Similarity	NPC18842
0.7055	Intermediate Similarity	NPC470307
0.7055	Intermediate Similarity	NPC299583
0.7055	Intermediate Similarity	NPC470308
0.7052	Intermediate Similarity	NPC206736
0.7052	Intermediate Similarity	NPC195766
0.7039	Intermediate Similarity	NPC43275
0.7039	Intermediate Similarity	NPC256369
0.7037	Intermediate Similarity	NPC11727
0.7037	Intermediate Similarity	NPC79957
0.7037	Intermediate Similarity	NPC15109
0.7032	Intermediate Similarity	NPC76465
0.7032	Intermediate Similarity	NPC38761
0.7032	Intermediate Similarity	NPC328267
0.7029	Intermediate Similarity	NPC50380
0.7029	Intermediate Similarity	NPC179250
0.7025	Intermediate Similarity	NPC271808
0.7024	Intermediate Similarity	NPC14468
0.7024	Intermediate Similarity	NPC260397
0.7019	Intermediate Similarity	NPC92805
0.7013	Intermediate Similarity	NPC193364
0.7013	Intermediate Similarity	NPC54972
0.7006	Intermediate Similarity	NPC474444
0.7006	Intermediate Similarity	NPC45257
0.7006	Intermediate Similarity	NPC93323
0.7006	Intermediate Similarity	NPC280092
0.7006	Intermediate Similarity	NPC63879
0.7006	Intermediate Similarity	NPC264706
0.7006	Intermediate Similarity	NPC12641
0.7006	Intermediate Similarity	NPC93433
0.7006	Intermediate Similarity	NPC284881
0.6995	Remote Similarity	NPC315913
0.6994	Remote Similarity	NPC14600
0.6994	Remote Similarity	NPC41473
0.6994	Remote Similarity	NPC160607
0.6994	Remote Similarity	NPC312770
0.6994	Remote Similarity	NPC204848
0.6994	Remote Similarity	NPC126101
0.6989	Remote Similarity	NPC293871
0.6989	Remote Similarity	NPC124433
0.6988	Remote Similarity	NPC178466
0.6988	Remote Similarity	NPC63628
0.6982	Remote Similarity	NPC213074
0.6982	Remote Similarity	NPC114505
0.6982	Remote Similarity	NPC275284
0.6982	Remote Similarity	NPC31325
0.6982	Remote Similarity	NPC15956
0.6982	Remote Similarity	NPC193473
0.6982	Remote Similarity	NPC224674
0.698	Remote Similarity	NPC123175
0.698	Remote Similarity	NPC176730
0.6975	Remote Similarity	NPC184269
0.6975	Remote Similarity	NPC16485
0.697	Remote Similarity	NPC254759
0.697	Remote Similarity	NPC309124
0.697	Remote Similarity	NPC27495
0.697	Remote Similarity	NPC221134
0.697	Remote Similarity	NPC160283
0.697	Remote Similarity	NPC182509
0.697	Remote Similarity	NPC174787
0.697	Remote Similarity	NPC184797
0.697	Remote Similarity	NPC213607
0.6968	Remote Similarity	NPC476565
0.6968	Remote Similarity	NPC36016
0.6968	Remote Similarity	NPC100099
0.6964	Remote Similarity	NPC469557

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 NPC22014 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	540
0.2-0.3	943
0.3-0.4	2304
0.4-0.5	2744
0.5-0.6	1798
0.6-0.7	624
0.7-0.8	55
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
0.7697	Intermediate Similarity	NPD6072	Discontinued
0.7548	Intermediate Similarity	NPD6405	Approved
0.7548	Intermediate Similarity	NPD6407	Approved
0.7546	Intermediate Similarity	NPD7020	Approved
0.7546	Intermediate Similarity	NPD3985	Discontinued
0.7546	Intermediate Similarity	NPD7019	Approved
0.7532	Intermediate Similarity	NPD7425	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6087	Phase 1
0.7439	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2157	Approved
0.7405	Intermediate Similarity	NPD3052	Approved
0.7405	Intermediate Similarity	NPD3054	Approved
0.7371	Intermediate Similarity	NPD3489	Phase 3
0.7358	Intermediate Similarity	NPD3553	Approved
0.7358	Intermediate Similarity	NPD3554	Approved
0.7358	Intermediate Similarity	NPD3552	Approved
0.7358	Intermediate Similarity	NPD3555	Approved
0.7333	Intermediate Similarity	NPD6419	Discontinued
0.7329	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6666	Approved
0.7317	Intermediate Similarity	NPD6667	Approved
0.7312	Intermediate Similarity	NPD2661	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7526	Approved
0.7289	Intermediate Similarity	NPD52	Approved
0.7289	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3049	Approved
0.7267	Intermediate Similarity	NPD8070	Approved
0.7256	Intermediate Similarity	NPD2677	Approved
0.7229	Intermediate Similarity	NPD2874	Phase 2
0.7225	Intermediate Similarity	NPD5709	Phase 3
0.7219	Intermediate Similarity	NPD2556	Approved
0.7219	Intermediate Similarity	NPD2554	Approved
0.7209	Intermediate Similarity	NPD7773	Phase 2
0.7195	Intermediate Similarity	NPD6331	Phase 2
0.7191	Intermediate Similarity	NPD6042	Phase 2
0.7191	Intermediate Similarity	NPD42	Phase 2
0.719	Intermediate Similarity	NPD2235	Phase 2
0.719	Intermediate Similarity	NPD2231	Phase 2
0.7184	Intermediate Similarity	NPD4666	Phase 3
0.7179	Intermediate Similarity	NPD1712	Approved
0.7179	Intermediate Similarity	NPD2861	Phase 2
0.7178	Intermediate Similarity	NPD4149	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6556	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2505	Approved
0.7126	Intermediate Similarity	NPD7447	Phase 1
0.7126	Intermediate Similarity	NPD2504	Approved
0.7108	Intermediate Similarity	NPD3122	Phase 3
0.7107	Intermediate Similarity	NPD1423	Approved
0.7107	Intermediate Similarity	NPD7477	Discontinued
0.7101	Intermediate Similarity	NPD5267	Discontinued
0.7099	Intermediate Similarity	NPD6380	Phase 1
0.7093	Intermediate Similarity	NPD5773	Approved
0.7093	Intermediate Similarity	NPD5772	Approved
0.7093	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7466	Approved
0.7073	Intermediate Similarity	NPD1391	Approved
0.7073	Intermediate Similarity	NPD7037	Approved
0.7066	Intermediate Similarity	NPD7213	Phase 3
0.7066	Intermediate Similarity	NPD7212	Phase 2
0.7063	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2238	Phase 2
0.7063	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3567	Approved
0.7051	Intermediate Similarity	NPD3568	Approved
0.7039	Intermediate Similarity	NPD3909	Discontinued
0.7039	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5722	Discontinued
0.7032	Intermediate Similarity	NPD2428	Approved
0.7032	Intermediate Similarity	NPD2429	Approved
0.703	Intermediate Similarity	NPD5061	Approved
0.703	Intermediate Similarity	NPD2459	Approved
0.703	Intermediate Similarity	NPD3060	Approved
0.703	Intermediate Similarity	NPD2460	Phase 3
0.703	Intermediate Similarity	NPD5062	Approved
0.703	Intermediate Similarity	NPD2458	Approved
0.7025	Intermediate Similarity	NPD4908	Phase 1
0.7024	Intermediate Similarity	NPD3536	Discontinued
0.7024	Intermediate Similarity	NPD4123	Phase 3
0.7013	Intermediate Similarity	NPD1610	Phase 2
0.7	Intermediate Similarity	NPD3163	Approved
0.7	Intermediate Similarity	NPD839	Approved
0.7	Intermediate Similarity	NPD840	Approved
0.7	Intermediate Similarity	NPD3162	Approved
0.6994	Remote Similarity	NPD4108	Discontinued
0.6994	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1351	Approved
0.6982	Remote Similarity	NPD1349	Approved
0.6982	Remote Similarity	NPD2186	Approved
0.6982	Remote Similarity	NPD1350	Approved
0.6981	Remote Similarity	NPD3180	Approved
0.6981	Remote Similarity	NPD5163	Phase 2
0.6981	Remote Similarity	NPD3179	Approved
0.6975	Remote Similarity	NPD4097	Suspended
0.697	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6056	Approved
0.6959	Remote Similarity	NPD6057	Approved
0.6949	Remote Similarity	NPD7484	Phase 3
0.6949	Remote Similarity	NPD7485	Phase 3
0.6943	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5976	Discontinued
0.6937	Remote Similarity	NPD1039	Discontinued
0.6936	Remote Similarity	NPD7495	Discontinued
0.6936	Remote Similarity	NPD8019	Approved
0.6928	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6583	Phase 3
0.6923	Remote Similarity	NPD1669	Approved
0.6923	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6582	Phase 2
0.6923	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4129	Approved
0.6919	Remote Similarity	NPD4675	Approved
0.6919	Remote Similarity	NPD4678	Approved
0.6909	Remote Similarity	NPD1035	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6584	Phase 3
0.6899	Remote Similarity	NPD3690	Phase 2
0.6899	Remote Similarity	NPD3691	Phase 2
0.6899	Remote Similarity	NPD558	Phase 2
0.689	Remote Similarity	NPD2156	Approved
0.689	Remote Similarity	NPD2155	Approved
0.689	Remote Similarity	NPD2154	Approved
0.6889	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD2667	Approved
0.6883	Remote Similarity	NPD2668	Approved
0.6882	Remote Similarity	NPD6090	Discontinued
0.6875	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6179	Discontinued
0.6875	Remote Similarity	NPD4064	Discontinued
0.6868	Remote Similarity	NPD5557	Phase 1
0.6867	Remote Similarity	NPD7153	Discontinued
0.6859	Remote Similarity	NPD2232	Approved
0.6859	Remote Similarity	NPD2233	Approved
0.6859	Remote Similarity	NPD2230	Approved
0.6848	Remote Similarity	NPD4477	Approved
0.6848	Remote Similarity	NPD3156	Discontinued
0.6848	Remote Similarity	NPD2161	Phase 2
0.6848	Remote Similarity	NPD4476	Approved
0.6845	Remote Similarity	NPD3692	Discontinued
0.6842	Remote Similarity	NPD7523	Phase 3
0.6842	Remote Similarity	NPD2122	Discontinued
0.6835	Remote Similarity	NPD1131	Approved
0.6835	Remote Similarity	NPD1133	Approved
0.6835	Remote Similarity	NPD1134	Approved
0.6835	Remote Similarity	NPD1135	Approved
0.6835	Remote Similarity	NPD1129	Approved
0.6826	Remote Similarity	NPD4162	Approved
0.6824	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6502	Phase 2
0.6818	Remote Similarity	NPD3445	Approved
0.6818	Remote Similarity	NPD3443	Approved
0.6818	Remote Similarity	NPD3444	Approved
0.6818	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3685	Discontinued
0.6802	Remote Similarity	NPD3687	Approved
0.6802	Remote Similarity	NPD3686	Approved
0.68	Remote Similarity	NPD5929	Approved
0.68	Remote Similarity	NPD2977	Approved
0.68	Remote Similarity	NPD2978	Approved
0.6786	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3166	Approved
0.677	Remote Similarity	NPD3165	Approved
0.677	Remote Similarity	NPD3167	Approved
0.677	Remote Similarity	NPD3164	Approved
0.6769	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD8162	Phase 2
0.6768	Remote Similarity	NPD5314	Approved
0.6766	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1774	Approved
0.6755	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1548	Phase 1
0.6752	Remote Similarity	NPD2561	Approved
0.6752	Remote Similarity	NPD2562	Approved
0.675	Remote Similarity	NPD4993	Discontinued
0.675	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4227	Discontinued
0.6743	Remote Similarity	NPD5720	Discontinued
0.6738	Remote Similarity	NPD6967	Phase 2
0.673	Remote Similarity	NPD1794	Approved
0.673	Remote Similarity	NPD1819	Approved
0.673	Remote Similarity	NPD2082	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1820	Approved
0.673	Remote Similarity	NPD1817	Approved
0.673	Remote Similarity	NPD1818	Approved
0.6728	Remote Similarity	NPD1336	Approved
0.6727	Remote Similarity	NPD696	Discontinued
0.6727	Remote Similarity	NPD7119	Phase 2
0.6726	Remote Similarity	NPD2209	Approved
0.6726	Remote Similarity	NPD6364	Approved
0.6726	Remote Similarity	NPD44	Approved
0.6726	Remote Similarity	NPD2211	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