NPASS Compound

Structure

NPC128066 OpenBabel07101719142D 29 32 0 0 1 0 0 0 0 0999 V2000 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -0.8660 -3.5000 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 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 3.4641 -7.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -6.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 7 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 7 14 2 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 9 15 2 0 0 0 0 11 20 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 26 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 4 1 1 0 0 0 16 22 1 0 0 0 0 17 10 1 6 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 11 1 1 0 0 0 18 19 1 0 0 0 0 19 12 1 6 0 0 0 19 23 1 0 0 0 0 20 24 1 1 0 0 0 20 28 1 0 0 0 0 21 25 1 6 0 0 0 22 27 1 6 0 0 0 23 25 1 6 0 0 0 23 29 1 0 0 0 0 24 5 1 6 0 0 0 24 28 1 0 0 0 0 25 6 1 6 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.28
Volume:	433.982
LogP:	3.48
LogD:	3.727
LogS:	-4.373
# Rotatable Bonds:	6
TPSA:	65.52
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	5.721
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.624
MDCK Permeability:	2.5217659640475176e-05
Pgp-inhibitor:	0.215
Pgp-substrate:	0.946
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.254
Plasma Protein Binding (PPB):	90.67622375488281%
Volume Distribution (VD):	1.758
Pgp-substrate:	7.671858310699463%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.441
CYP3A4-inhibitor:	0.757
CYP3A4-substrate:	0.471

ADMET: Excretion

Clearance (CL):	7.262
Half-life (T1/2):	0.376

ADMET: Toxicity

hERG Blockers:	0.186
Human Hepatotoxicity (H-HT):	0.837
Drug-inuced Liver Injury (DILI):	0.727
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.622
Skin Sensitization:	0.373
Carcinogencity:	0.026
Eye Corrosion:	0.021
Eye Irritation:	0.058
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC128066

Natural Product ID:	NPC128066
*Common Name:**	Fusarielin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LRMWKBJDHOHUEZ-HCZQMODJSA-N
Standard InCHI:	InChI=1S/C25H38O4/c1-7-14(2)21-17(10-8-9-15(3)22(27)16(4)13-26)18-11-20-24(5,28-20)12-19(18)23-25(21,6)29-23/h7-10,16-23,26-27H,11-13H2,1-6H3/b10-8+,14-7+,15-9+/t16-,17-,18-,19+,20-,21-,22+,23-,24+,25+/m0/s1
SMILES:	OC[C@@H]([C@@H](/C(=C/C=C/[C@H]1[C@@H]2C[C@@H]3O[C@@]3(C[C@H]2[C@H]2[C@]([C@H]1/C(=C/C)/C)(C)O2)C)/C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228444
PubChem CID:	10453753
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21090694]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24175613]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.5	ug.mL-1	PMID[542351]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	62.5	ug.mL-1	PMID[542351]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	31.5	ug.mL-1	PMID[542352]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	62.5	ug.mL-1	PMID[542352]

☑ 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 NPC128066 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	215
0.1-0.2	1480
0.2-0.3	4647
0.3-0.4	10595
0.4-0.5	14529
0.5-0.6	7820
0.6-0.7	3143
0.7-0.8	265
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9419	High Similarity	NPC191323
0.8421	Intermediate Similarity	NPC269713
0.8172	Intermediate Similarity	NPC119379
0.8161	Intermediate Similarity	NPC476646
0.8105	Intermediate Similarity	NPC210717
0.8105	Intermediate Similarity	NPC103165
0.8046	Intermediate Similarity	NPC96362
0.8043	Intermediate Similarity	NPC115607
0.8043	Intermediate Similarity	NPC49783
0.8043	Intermediate Similarity	NPC16265
0.8021	Intermediate Similarity	NPC261807
0.7957	Intermediate Similarity	NPC295668
0.7955	Intermediate Similarity	NPC249423
0.7917	Intermediate Similarity	NPC72204
0.7912	Intermediate Similarity	NPC255143
0.7912	Intermediate Similarity	NPC6391
0.7912	Intermediate Similarity	NPC261266
0.7889	Intermediate Similarity	NPC83702
0.7889	Intermediate Similarity	NPC102048
0.7882	Intermediate Similarity	NPC32832
0.7872	Intermediate Similarity	NPC41554
0.7872	Intermediate Similarity	NPC97404
0.7865	Intermediate Similarity	NPC259858
0.7865	Intermediate Similarity	NPC155521
0.7857	Intermediate Similarity	NPC265485
0.7857	Intermediate Similarity	NPC220939
0.7849	Intermediate Similarity	NPC97103
0.7835	Intermediate Similarity	NPC476040
0.7835	Intermediate Similarity	NPC474994
0.7835	Intermediate Similarity	NPC476021
0.7816	Intermediate Similarity	NPC68119
0.7816	Intermediate Similarity	NPC476314
0.7816	Intermediate Similarity	NPC13823
0.7802	Intermediate Similarity	NPC298595
0.7791	Intermediate Similarity	NPC63958
0.7791	Intermediate Similarity	NPC265588
0.7789	Intermediate Similarity	NPC310013
0.7778	Intermediate Similarity	NPC476896
0.7778	Intermediate Similarity	NPC477978
0.7766	Intermediate Similarity	NPC11216
0.7766	Intermediate Similarity	NPC329596
0.7766	Intermediate Similarity	NPC291484
0.7766	Intermediate Similarity	NPC80561
0.7766	Intermediate Similarity	NPC204188
0.7766	Intermediate Similarity	NPC3345
0.7765	Intermediate Similarity	NPC476366
0.7765	Intermediate Similarity	NPC306727
0.7765	Intermediate Similarity	NPC201048
0.7738	Intermediate Similarity	NPC23954
0.7732	Intermediate Similarity	NPC90583
0.7732	Intermediate Similarity	NPC288970
0.7732	Intermediate Similarity	NPC57664
0.7717	Intermediate Similarity	NPC299068
0.7717	Intermediate Similarity	NPC281316
0.7711	Intermediate Similarity	NPC329989
0.7711	Intermediate Similarity	NPC304690
0.7711	Intermediate Similarity	NPC74722
0.7711	Intermediate Similarity	NPC239373
0.7708	Intermediate Similarity	NPC144202
0.7701	Intermediate Similarity	NPC91594
0.7701	Intermediate Similarity	NPC471798
0.7701	Intermediate Similarity	NPC470711
0.7701	Intermediate Similarity	NPC470758
0.77	Intermediate Similarity	NPC109195
0.77	Intermediate Similarity	NPC470571
0.77	Intermediate Similarity	NPC475038
0.7692	Intermediate Similarity	NPC205845
0.7692	Intermediate Similarity	NPC474047
0.7692	Intermediate Similarity	NPC474493
0.7684	Intermediate Similarity	NPC114389
0.766	Intermediate Similarity	NPC470361
0.7653	Intermediate Similarity	NPC476893
0.7647	Intermediate Similarity	NPC68443
0.7634	Intermediate Similarity	NPC189777
0.7634	Intermediate Similarity	NPC476948
0.7634	Intermediate Similarity	NPC149224
0.7629	Intermediate Similarity	NPC8774
0.7629	Intermediate Similarity	NPC276110
0.7614	Intermediate Similarity	NPC52755
0.7609	Intermediate Similarity	NPC164424
0.7609	Intermediate Similarity	NPC470360
0.7609	Intermediate Similarity	NPC290731
0.7604	Intermediate Similarity	NPC27531
0.7604	Intermediate Similarity	NPC137461
0.759	Intermediate Similarity	NPC305698
0.7586	Intermediate Similarity	NPC253190
0.7586	Intermediate Similarity	NPC106432
0.7586	Intermediate Similarity	NPC470749
0.7582	Intermediate Similarity	NPC82538
0.7582	Intermediate Similarity	NPC237795
0.7582	Intermediate Similarity	NPC475789
0.7579	Intermediate Similarity	NPC48732
0.7579	Intermediate Similarity	NPC220216
0.7576	Intermediate Similarity	NPC476895
0.7576	Intermediate Similarity	NPC278673
0.7556	Intermediate Similarity	NPC471270
0.7556	Intermediate Similarity	NPC320525
0.7553	Intermediate Similarity	NPC67872
0.7553	Intermediate Similarity	NPC133588
0.7553	Intermediate Similarity	NPC474668
0.7551	Intermediate Similarity	NPC54248
0.7551	Intermediate Similarity	NPC12103
0.7551	Intermediate Similarity	NPC227583
0.7551	Intermediate Similarity	NPC98457
0.7551	Intermediate Similarity	NPC276103
0.7529	Intermediate Similarity	NPC167706
0.7527	Intermediate Similarity	NPC293287
0.7527	Intermediate Similarity	NPC152808
0.7527	Intermediate Similarity	NPC139724
0.7527	Intermediate Similarity	NPC476217
0.7526	Intermediate Similarity	NPC105490
0.7526	Intermediate Similarity	NPC65402
0.7526	Intermediate Similarity	NPC127718
0.7525	Intermediate Similarity	NPC471889
0.75	Intermediate Similarity	NPC124374
0.75	Intermediate Similarity	NPC476703
0.75	Intermediate Similarity	NPC306951
0.75	Intermediate Similarity	NPC477427
0.75	Intermediate Similarity	NPC231310
0.75	Intermediate Similarity	NPC477425
0.75	Intermediate Similarity	NPC275671
0.75	Intermediate Similarity	NPC38855
0.75	Intermediate Similarity	NPC210268
0.75	Intermediate Similarity	NPC474826
0.75	Intermediate Similarity	NPC238485
0.75	Intermediate Similarity	NPC234511
0.75	Intermediate Similarity	NPC477426
0.75	Intermediate Similarity	NPC86238
0.75	Intermediate Similarity	NPC302360
0.7475	Intermediate Similarity	NPC473244
0.7475	Intermediate Similarity	NPC240372
0.7475	Intermediate Similarity	NPC99726
0.7474	Intermediate Similarity	NPC261320
0.7474	Intermediate Similarity	NPC246028
0.7474	Intermediate Similarity	NPC161560
0.7474	Intermediate Similarity	NPC477917
0.7474	Intermediate Similarity	NPC187785
0.7474	Intermediate Similarity	NPC101886
0.7474	Intermediate Similarity	NPC259875
0.7473	Intermediate Similarity	NPC49964
0.7473	Intermediate Similarity	NPC50964
0.7473	Intermediate Similarity	NPC101462
0.7473	Intermediate Similarity	NPC296701
0.7473	Intermediate Similarity	NPC477390
0.7473	Intermediate Similarity	NPC477385
0.7473	Intermediate Similarity	NPC218616
0.7471	Intermediate Similarity	NPC291503
0.747	Intermediate Similarity	NPC259299
0.7451	Intermediate Similarity	NPC471450
0.7451	Intermediate Similarity	NPC134270
0.7451	Intermediate Similarity	NPC45897
0.7451	Intermediate Similarity	NPC476848
0.7449	Intermediate Similarity	NPC476894
0.7449	Intermediate Similarity	NPC135224
0.7449	Intermediate Similarity	NPC477969
0.7449	Intermediate Similarity	NPC476720
0.7447	Intermediate Similarity	NPC233744
0.7447	Intermediate Similarity	NPC166857
0.7444	Intermediate Similarity	NPC471266
0.7444	Intermediate Similarity	NPC95124
0.7444	Intermediate Similarity	NPC236707
0.7444	Intermediate Similarity	NPC287749
0.7444	Intermediate Similarity	NPC324772
0.7423	Intermediate Similarity	NPC99653
0.7423	Intermediate Similarity	NPC7349
0.7419	Intermediate Similarity	NPC474349
0.7419	Intermediate Similarity	NPC274448
0.7419	Intermediate Similarity	NPC474189
0.7419	Intermediate Similarity	NPC266511
0.7416	Intermediate Similarity	NPC148977
0.7416	Intermediate Similarity	NPC83351
0.7416	Intermediate Similarity	NPC167891
0.7416	Intermediate Similarity	NPC11908
0.7416	Intermediate Similarity	NPC477089
0.74	Intermediate Similarity	NPC312325
0.7396	Intermediate Similarity	NPC470817
0.7396	Intermediate Similarity	NPC192437
0.7396	Intermediate Similarity	NPC92885
0.7396	Intermediate Similarity	NPC78973
0.7396	Intermediate Similarity	NPC245410
0.7396	Intermediate Similarity	NPC77796
0.7396	Intermediate Similarity	NPC270511
0.7396	Intermediate Similarity	NPC470390
0.7396	Intermediate Similarity	NPC14380
0.7396	Intermediate Similarity	NPC476226
0.7391	Intermediate Similarity	NPC82623
0.7391	Intermediate Similarity	NPC185605
0.7391	Intermediate Similarity	NPC470384
0.7391	Intermediate Similarity	NPC52108
0.7391	Intermediate Similarity	NPC474789
0.7391	Intermediate Similarity	NPC476927
0.7391	Intermediate Similarity	NPC57370
0.7391	Intermediate Similarity	NPC320548
0.7386	Intermediate Similarity	NPC170148
0.7381	Intermediate Similarity	NPC266578
0.7379	Intermediate Similarity	NPC201880
0.7379	Intermediate Similarity	NPC264867
0.7379	Intermediate Similarity	NPC473207
0.7379	Intermediate Similarity	NPC81567
0.7379	Intermediate Similarity	NPC470321

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 NPC128066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1569
0.2-0.3	3878
0.3-0.4	2303
0.4-0.5	875
0.5-0.6	264
0.6-0.7	55
0.7-0.8	9
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
0.7889	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6648	Approved
0.7778	Intermediate Similarity	NPD5344	Discontinued
0.7778	Intermediate Similarity	NPD6695	Phase 3
0.7447	Intermediate Similarity	NPD7524	Approved
0.7447	Intermediate Similarity	NPD7750	Discontinued
0.7444	Intermediate Similarity	NPD6931	Approved
0.7444	Intermediate Similarity	NPD7514	Phase 3
0.7444	Intermediate Similarity	NPD7332	Phase 2
0.7444	Intermediate Similarity	NPD6930	Phase 2
0.7363	Intermediate Similarity	NPD6902	Approved
0.7333	Intermediate Similarity	NPD6929	Approved
0.7273	Intermediate Similarity	NPD8264	Approved
0.7253	Intermediate Similarity	NPD7525	Registered
0.7222	Intermediate Similarity	NPD7145	Approved
0.7216	Intermediate Similarity	NPD3168	Discontinued
0.7143	Intermediate Similarity	NPD7087	Discontinued
0.7143	Intermediate Similarity	NPD7645	Phase 2
0.7111	Intermediate Similarity	NPD6932	Approved
0.7111	Intermediate Similarity	NPD6925	Approved
0.7111	Intermediate Similarity	NPD5776	Phase 2
0.7071	Intermediate Similarity	NPD5778	Approved
0.7071	Intermediate Similarity	NPD5779	Approved
0.7053	Intermediate Similarity	NPD6893	Approved
0.7033	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7639	Approved
0.699	Remote Similarity	NPD7640	Approved
0.6989	Remote Similarity	NPD6898	Phase 1
0.697	Remote Similarity	NPD7637	Suspended
0.6966	Remote Similarity	NPD6926	Approved
0.6966	Remote Similarity	NPD6924	Approved
0.6907	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7638	Approved
0.6882	Remote Similarity	NPD7509	Discontinued
0.6869	Remote Similarity	NPD7838	Discovery
0.6813	Remote Similarity	NPD6933	Approved
0.6789	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6683	Phase 2
0.6742	Remote Similarity	NPD7151	Approved
0.6742	Remote Similarity	NPD7150	Approved
0.6742	Remote Similarity	NPD7152	Approved
0.6703	Remote Similarity	NPD7339	Approved
0.6703	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD368	Approved
0.6667	Remote Similarity	NPD5357	Phase 1
0.663	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7144	Approved
0.6629	Remote Similarity	NPD7143	Approved
0.6577	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4225	Approved
0.6542	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7136	Phase 2
0.6522	Remote Similarity	NPD7115	Discovery
0.6517	Remote Similarity	NPD6923	Approved
0.6517	Remote Similarity	NPD6922	Approved
0.6484	Remote Similarity	NPD4732	Discontinued
0.6471	Remote Similarity	NPD7983	Approved
0.6441	Remote Similarity	NPD7503	Approved
0.6436	Remote Similarity	NPD6101	Approved
0.6436	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7632	Discontinued
0.6389	Remote Similarity	NPD5211	Phase 2
0.6373	Remote Similarity	NPD6698	Approved
0.6373	Remote Similarity	NPD46	Approved
0.6325	Remote Similarity	NPD7327	Approved
0.6325	Remote Similarity	NPD7328	Approved
0.6311	Remote Similarity	NPD6411	Approved
0.6306	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8033	Approved
0.6296	Remote Similarity	NPD4159	Approved
0.6273	Remote Similarity	NPD5141	Approved
0.6271	Remote Similarity	NPD7516	Approved
0.6263	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD6899	Approved
0.6238	Remote Similarity	NPD4250	Approved
0.6238	Remote Similarity	NPD4251	Approved
0.6237	Remote Similarity	NPD4785	Approved
0.6237	Remote Similarity	NPD4784	Approved
0.6224	Remote Similarity	NPD3667	Approved
0.6218	Remote Similarity	NPD7741	Discontinued
0.6218	Remote Similarity	NPD8377	Approved
0.6218	Remote Similarity	NPD8294	Approved
0.6216	Remote Similarity	NPD6008	Approved
0.6216	Remote Similarity	NPD6675	Approved
0.6216	Remote Similarity	NPD7128	Approved
0.6216	Remote Similarity	NPD5739	Approved
0.6216	Remote Similarity	NPD6402	Approved
0.6216	Remote Similarity	NPD6640	Phase 3
0.6204	Remote Similarity	NPD5286	Approved
0.6204	Remote Similarity	NPD4696	Approved
0.6204	Remote Similarity	NPD5285	Approved
0.619	Remote Similarity	NPD7748	Approved
0.6186	Remote Similarity	NPD4822	Approved
0.6186	Remote Similarity	NPD4819	Approved
0.6186	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4821	Approved
0.6186	Remote Similarity	NPD4820	Approved
0.6168	Remote Similarity	NPD4755	Approved
0.6168	Remote Similarity	NPD7902	Approved
0.6167	Remote Similarity	NPD8513	Phase 3
0.6167	Remote Similarity	NPD8296	Approved
0.6167	Remote Similarity	NPD8335	Approved
0.6167	Remote Similarity	NPD8380	Approved
0.6167	Remote Similarity	NPD8379	Approved
0.6167	Remote Similarity	NPD8516	Approved
0.6167	Remote Similarity	NPD8515	Approved
0.6167	Remote Similarity	NPD8378	Approved
0.6167	Remote Similarity	NPD8517	Approved
0.6161	Remote Similarity	NPD5697	Approved
0.6154	Remote Similarity	NPD6079	Approved
0.6154	Remote Similarity	NPD7515	Phase 2
0.614	Remote Similarity	NPD6883	Approved
0.614	Remote Similarity	NPD7290	Approved
0.614	Remote Similarity	NPD7102	Approved
0.6139	Remote Similarity	NPD4249	Approved
0.6139	Remote Similarity	NPD3618	Phase 1
0.6117	Remote Similarity	NPD5328	Approved
0.6106	Remote Similarity	NPD6686	Approved
0.6106	Remote Similarity	NPD7320	Approved
0.6106	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4202	Approved
0.6091	Remote Similarity	NPD5226	Approved
0.6091	Remote Similarity	NPD5225	Approved
0.6091	Remote Similarity	NPD4633	Approved
0.6091	Remote Similarity	NPD5224	Approved
0.6087	Remote Similarity	NPD8130	Phase 1
0.6087	Remote Similarity	NPD6617	Approved
0.6087	Remote Similarity	NPD6649	Approved
0.6087	Remote Similarity	NPD6847	Approved
0.6087	Remote Similarity	NPD6869	Approved
0.6087	Remote Similarity	NPD6650	Approved
0.6083	Remote Similarity	NPD6054	Approved
0.6075	Remote Similarity	NPD7839	Suspended
0.6055	Remote Similarity	NPD4700	Approved
0.6053	Remote Similarity	NPD6372	Approved
0.6053	Remote Similarity	NPD6013	Approved
0.6053	Remote Similarity	NPD6014	Approved
0.6053	Remote Similarity	NPD6373	Approved
0.6053	Remote Similarity	NPD6012	Approved
0.604	Remote Similarity	NPD1696	Phase 3
0.6036	Remote Similarity	NPD5175	Approved
0.6036	Remote Similarity	NPD5174	Approved
0.6034	Remote Similarity	NPD6053	Discontinued
0.6034	Remote Similarity	NPD6882	Approved
0.6034	Remote Similarity	NPD8297	Approved
0.6022	Remote Similarity	NPD4243	Approved
0.602	Remote Similarity	NPD4748	Discontinued
0.6018	Remote Similarity	NPD5701	Approved
0.6018	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD7154	Phase 3
0.5984	Remote Similarity	NPD6370	Approved
0.5983	Remote Similarity	NPD4632	Approved
0.5979	Remote Similarity	NPD4268	Approved
0.5979	Remote Similarity	NPD4271	Approved
0.5968	Remote Similarity	NPD7507	Approved
0.5965	Remote Similarity	NPD6011	Approved
0.5962	Remote Similarity	NPD6051	Approved
0.5955	Remote Similarity	NPD371	Approved
0.5952	Remote Similarity	NPD342	Phase 1
0.595	Remote Similarity	NPD6319	Approved
0.595	Remote Similarity	NPD6059	Approved
0.5935	Remote Similarity	NPD7604	Phase 2
0.5926	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5222	Approved
0.5926	Remote Similarity	NPD5221	Approved
0.592	Remote Similarity	NPD8074	Phase 3
0.5913	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6015	Approved
0.5902	Remote Similarity	NPD6016	Approved
0.5888	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7900	Approved
0.5888	Remote Similarity	NPD5282	Discontinued
0.5887	Remote Similarity	NPD7492	Approved
0.5872	Remote Similarity	NPD6083	Phase 2
0.5872	Remote Similarity	NPD6084	Phase 2
0.5872	Remote Similarity	NPD5173	Approved
0.5859	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD5988	Approved
0.5854	Remote Similarity	NPD5125	Phase 3
0.5854	Remote Similarity	NPD5126	Approved
0.5849	Remote Similarity	NPD8035	Phase 2
0.5849	Remote Similarity	NPD8034	Phase 2
0.5842	Remote Similarity	NPD5362	Discontinued
0.584	Remote Similarity	NPD6616	Approved
0.5833	Remote Similarity	NPD6009	Approved
0.5827	Remote Similarity	NPD7319	Approved
0.5826	Remote Similarity	NPD4730	Approved
0.5826	Remote Similarity	NPD4729	Approved
0.5825	Remote Similarity	NPD4519	Discontinued
0.5825	Remote Similarity	NPD4623	Approved
0.5812	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.581	Remote Similarity	NPD4753	Phase 2
0.5806	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7078	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