NPASS Compound

Structure

NPC77430 OpenBabel07101719132D 42 44 0 0 0 0 0 0 0 0999 V2000 -6.2701 -8.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3797 7.4705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2701 -7.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1887 6.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4041 -6.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0842 5.8882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4041 -5.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8932 5.3004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7887 4.3059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5977 3.7181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4931 2.7236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3022 2.1358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1976 1.1412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0067 0.5535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9021 -0.4411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9886 -0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 -0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 -1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7807 -1.8259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0180 0.6467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4498 -2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -3.9781 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 2.7861 -1.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 40 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 24 27 1 0 0 0 0 24 28 2 0 0 0 0 25 30 2 0 0 0 0 25 32 1 0 0 0 0 26 31 2 0 0 0 0 26 34 1 0 0 0 0 27 29 1 0 0 0 0 27 32 2 0 0 0 0 28 30 1 0 0 0 0 28 40 1 0 0 0 0 29 33 2 0 0 0 0 29 35 1 0 0 0 0 30 36 1 0 0 0 0 31 33 1 0 0 0 0 31 37 1 0 0 0 0 32 41 1 0 0 0 0 33 42 1 0 0 0 0 34 38 2 0 0 0 0 34 42 1 0 0 0 0 35 39 2 0 0 0 0 35 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.37
Volume:	631.323
LogP:	10.892
LogD:	6.204
LogS:	-3.382
# Rotatable Bonds:	21
TPSA:	116.43
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.092
Synthetic Accessibility Score:	3.365
Fsp3:	0.6
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.256
MDCK Permeability:	1.830408291425556e-05
Pgp-inhibitor:	0.808
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.932
30% Bioavailability (F30%):	0.073

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	104.55651092529297%
Volume Distribution (VD):	5.121
Pgp-substrate:	1.5217655897140503%

ADMET: Metabolism

CYP1A2-inhibitor:	0.151
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.575
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.121
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.218
CYP2D6-substrate:	0.67
CYP3A4-inhibitor:	0.104
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	4.379
Half-life (T1/2):	0.078

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.153
Rat Oral Acute Toxicity:	0.379
Maximum Recommended Daily Dose:	0.597
Skin Sensitization:	0.924
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.513
Respiratory Toxicity:	0.488

Download Data

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

Natural Product: NPC77430

Natural Product ID:	NPC77430
*Common Name:**	10-Hydroxy-4-O-Methyl-2,11-Diundecylgomphilactone
IUPAC Name:	(3E)-6-hydroxy-3-(3-hydroxy-5-oxo-4-undecylfuran-2-ylidene)-5-methoxy-7-undecyl-1-benzofuran-2-one
Synonyms:
Standard InCHIKey:	VLDCOHDFSSUUGT-XPXRSFDGSA-N
Standard InCHI:	InChI=1S/C35H52O7/c1-4-6-8-10-12-14-16-18-20-22-25-30(36)28(40-3)24-27-29(35(39)41-32(25)27)33-31(37)26(34(38)42-33)23-21-19-17-15-13-11-9-7-5-2/h24,36-37H,4-23H2,1-3H3/p-1/b33-29+
SMILES:	CCCCCCCCCCCc1c(c(cc2/C(=C3/C(=C(CCCCCCCCCCC)C(=O)O3)O)/C(=O)Oc12)OC)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453891
PubChem CID:	54716641
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165134]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22316191]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778454]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[450346]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[450346]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[450346]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[450346]

☑ 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 NPC77430 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	363
0.1-0.2	1612
0.2-0.3	4462
0.3-0.4	9834
0.4-0.5	8403
0.5-0.6	3835
0.6-0.7	5922
0.7-0.8	7295
0.8-0.85	916
0.85-0.9	51
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC221085
0.8854	High Similarity	NPC83763
0.8854	High Similarity	NPC168616
0.8654	High Similarity	NPC289968
0.8642	High Similarity	NPC472452
0.8634	High Similarity	NPC234004
0.8608	High Similarity	NPC472456
0.8571	High Similarity	NPC8300
0.8571	High Similarity	NPC81679
0.8571	High Similarity	NPC139839
0.8562	High Similarity	NPC287275
0.8553	High Similarity	NPC262286
0.8553	High Similarity	NPC36852
0.8553	High Similarity	NPC78225
0.8544	High Similarity	NPC79998
0.8535	High Similarity	NPC199773
0.8528	High Similarity	NPC471823
0.8519	High Similarity	NPC474350
0.8516	High Similarity	NPC107636
0.8509	High Similarity	NPC278052
0.8509	High Similarity	NPC40491
0.85	High Similarity	NPC238381
0.8497	Intermediate Similarity	NPC213900
0.8494	Intermediate Similarity	NPC233956
0.8491	Intermediate Similarity	NPC317383
0.8491	Intermediate Similarity	NPC191146
0.8491	Intermediate Similarity	NPC150227
0.8491	Intermediate Similarity	NPC54928
0.8491	Intermediate Similarity	NPC68093
0.8491	Intermediate Similarity	NPC138243
0.8485	Intermediate Similarity	NPC180768
0.8485	Intermediate Similarity	NPC281835
0.8485	Intermediate Similarity	NPC109827
0.8485	Intermediate Similarity	NPC124470
0.8485	Intermediate Similarity	NPC17219
0.8481	Intermediate Similarity	NPC476631
0.8466	Intermediate Similarity	NPC85057
0.8466	Intermediate Similarity	NPC326520
0.8466	Intermediate Similarity	NPC130920
0.8457	Intermediate Similarity	NPC144843
0.8452	Intermediate Similarity	NPC61871
0.8452	Intermediate Similarity	NPC30647
0.8452	Intermediate Similarity	NPC55557
0.8452	Intermediate Similarity	NPC251188
0.8447	Intermediate Similarity	NPC476980
0.8447	Intermediate Similarity	NPC14353
0.8447	Intermediate Similarity	NPC228785
0.8447	Intermediate Similarity	NPC320359
0.8447	Intermediate Similarity	NPC292415
0.8447	Intermediate Similarity	NPC200594
0.8447	Intermediate Similarity	NPC56085
0.8447	Intermediate Similarity	NPC246478
0.8438	Intermediate Similarity	NPC190020
0.8438	Intermediate Similarity	NPC77679
0.8438	Intermediate Similarity	NPC84935
0.8438	Intermediate Similarity	NPC223787
0.8434	Intermediate Similarity	NPC158226
0.8428	Intermediate Similarity	NPC18954
0.8428	Intermediate Similarity	NPC199926
0.8428	Intermediate Similarity	NPC113906
0.8424	Intermediate Similarity	NPC163130
0.8424	Intermediate Similarity	NPC165979
0.8421	Intermediate Similarity	NPC469564
0.8421	Intermediate Similarity	NPC472332
0.8421	Intermediate Similarity	NPC472335
0.8418	Intermediate Similarity	NPC471982
0.8418	Intermediate Similarity	NPC249570
0.8415	Intermediate Similarity	NPC170245
0.8408	Intermediate Similarity	NPC96501
0.8405	Intermediate Similarity	NPC7483
0.8405	Intermediate Similarity	NPC156082
0.8405	Intermediate Similarity	NPC236132
0.84	Intermediate Similarity	NPC105493
0.84	Intermediate Similarity	NPC110899
0.84	Intermediate Similarity	NPC25305
0.84	Intermediate Similarity	NPC95679
0.84	Intermediate Similarity	NPC112068
0.84	Intermediate Similarity	NPC125417
0.8395	Intermediate Similarity	NPC258331
0.8395	Intermediate Similarity	NPC61010
0.8395	Intermediate Similarity	NPC103201
0.8395	Intermediate Similarity	NPC474351
0.8395	Intermediate Similarity	NPC473106
0.8395	Intermediate Similarity	NPC349525
0.8395	Intermediate Similarity	NPC475883
0.8395	Intermediate Similarity	NPC266314
0.8389	Intermediate Similarity	NPC252095
0.8387	Intermediate Similarity	NPC165389
0.8385	Intermediate Similarity	NPC267627
0.8385	Intermediate Similarity	NPC40702
0.8385	Intermediate Similarity	NPC100123
0.8385	Intermediate Similarity	NPC250214
0.8385	Intermediate Similarity	NPC87317
0.8385	Intermediate Similarity	NPC195832
0.8385	Intermediate Similarity	NPC95936
0.8385	Intermediate Similarity	NPC196879
0.8385	Intermediate Similarity	NPC45846
0.8385	Intermediate Similarity	NPC37502
0.8383	Intermediate Similarity	NPC261471
0.8383	Intermediate Similarity	NPC37606
0.8378	Intermediate Similarity	NPC474810
0.8377	Intermediate Similarity	NPC113397
0.8375	Intermediate Similarity	NPC472626
0.8375	Intermediate Similarity	NPC209614
0.8375	Intermediate Similarity	NPC470328
0.8373	Intermediate Similarity	NPC78830
0.8373	Intermediate Similarity	NPC218533
0.8367	Intermediate Similarity	NPC147317
0.8366	Intermediate Similarity	NPC256555
0.8366	Intermediate Similarity	NPC34245
0.8366	Intermediate Similarity	NPC110067
0.8366	Intermediate Similarity	NPC7439
0.8366	Intermediate Similarity	NPC91492
0.8365	Intermediate Similarity	NPC276409
0.8365	Intermediate Similarity	NPC475895
0.8365	Intermediate Similarity	NPC250822
0.8365	Intermediate Similarity	NPC69394
0.8365	Intermediate Similarity	NPC298802
0.8365	Intermediate Similarity	NPC183878
0.8365	Intermediate Similarity	NPC75279
0.8365	Intermediate Similarity	NPC22519
0.8365	Intermediate Similarity	NPC231018
0.8365	Intermediate Similarity	NPC160951
0.8365	Intermediate Similarity	NPC255350
0.8365	Intermediate Similarity	NPC145379
0.8365	Intermediate Similarity	NPC274327
0.8365	Intermediate Similarity	NPC176775
0.8365	Intermediate Similarity	NPC47781
0.8364	Intermediate Similarity	NPC247973
0.8354	Intermediate Similarity	NPC171010
0.8354	Intermediate Similarity	NPC300053
0.8354	Intermediate Similarity	NPC8070
0.8354	Intermediate Similarity	NPC142614
0.8354	Intermediate Similarity	NPC75695
0.8354	Intermediate Similarity	NPC39306
0.8354	Intermediate Similarity	NPC112981
0.8354	Intermediate Similarity	NPC267153
0.8344	Intermediate Similarity	NPC83922
0.8344	Intermediate Similarity	NPC312056
0.8344	Intermediate Similarity	NPC472448
0.8344	Intermediate Similarity	NPC84515
0.8344	Intermediate Similarity	NPC207516
0.8344	Intermediate Similarity	NPC261470
0.8333	Intermediate Similarity	NPC53889
0.8333	Intermediate Similarity	NPC472624
0.8333	Intermediate Similarity	NPC475886
0.8333	Intermediate Similarity	NPC47623
0.8333	Intermediate Similarity	NPC126682
0.8333	Intermediate Similarity	NPC139350
0.8333	Intermediate Similarity	NPC82271
0.8333	Intermediate Similarity	NPC289244
0.8333	Intermediate Similarity	NPC474287
0.8333	Intermediate Similarity	NPC204290
0.8323	Intermediate Similarity	NPC247713
0.8323	Intermediate Similarity	NPC162869
0.8323	Intermediate Similarity	NPC472911
0.8323	Intermediate Similarity	NPC475669
0.8323	Intermediate Similarity	NPC245758
0.8323	Intermediate Similarity	NPC469584
0.8323	Intermediate Similarity	NPC262282
0.8323	Intermediate Similarity	NPC217677
0.8323	Intermediate Similarity	NPC222814
0.8323	Intermediate Similarity	NPC472914
0.8323	Intermediate Similarity	NPC156057
0.8323	Intermediate Similarity	NPC475267
0.8323	Intermediate Similarity	NPC157133
0.8323	Intermediate Similarity	NPC472913
0.8323	Intermediate Similarity	NPC96167
0.8323	Intermediate Similarity	NPC241904
0.8323	Intermediate Similarity	NPC300727
0.8323	Intermediate Similarity	NPC474208
0.8323	Intermediate Similarity	NPC236796
0.8323	Intermediate Similarity	NPC472910
0.8323	Intermediate Similarity	NPC474836
0.8323	Intermediate Similarity	NPC476981
0.8323	Intermediate Similarity	NPC48208
0.8323	Intermediate Similarity	NPC472917
0.8323	Intermediate Similarity	NPC165977
0.8313	Intermediate Similarity	NPC130589
0.8313	Intermediate Similarity	NPC256612
0.8313	Intermediate Similarity	NPC183597
0.8313	Intermediate Similarity	NPC45849
0.8313	Intermediate Similarity	NPC200761
0.8313	Intermediate Similarity	NPC82592
0.8313	Intermediate Similarity	NPC134287
0.8313	Intermediate Similarity	NPC99613
0.8313	Intermediate Similarity	NPC50715
0.8313	Intermediate Similarity	NPC20830
0.8313	Intermediate Similarity	NPC476642
0.8313	Intermediate Similarity	NPC16082
0.8313	Intermediate Similarity	NPC477503
0.8313	Intermediate Similarity	NPC167815
0.8313	Intermediate Similarity	NPC211309
0.8313	Intermediate Similarity	NPC128863
0.8313	Intermediate Similarity	NPC4455
0.8313	Intermediate Similarity	NPC163780
0.8313	Intermediate Similarity	NPC208197
0.8313	Intermediate Similarity	NPC152951
0.8313	Intermediate Similarity	NPC280339
0.8313	Intermediate Similarity	NPC117992

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 NPC77430 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	985
0.2-0.3	2155
0.3-0.4	2576
0.4-0.5	1674
0.5-0.6	913
0.6-0.7	402
0.7-0.8	113
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8365	Intermediate Similarity	NPD2801	Approved
0.8261	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD3882	Suspended
0.8137	Intermediate Similarity	NPD1465	Phase 2
0.8137	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5844	Phase 1
0.8075	Intermediate Similarity	NPD1934	Approved
0.8013	Intermediate Similarity	NPD230	Phase 1
0.7975	Intermediate Similarity	NPD2532	Approved
0.7975	Intermediate Similarity	NPD2534	Approved
0.7975	Intermediate Similarity	NPD2533	Approved
0.7939	Intermediate Similarity	NPD6234	Discontinued
0.7929	Intermediate Similarity	NPD3818	Discontinued
0.7911	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6232	Discontinued
0.7892	Intermediate Similarity	NPD5494	Approved
0.787	Intermediate Similarity	NPD7473	Discontinued
0.7866	Intermediate Similarity	NPD3817	Phase 2
0.7803	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1511	Approved
0.7791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7075	Discontinued
0.7738	Intermediate Similarity	NPD7199	Phase 2
0.7733	Intermediate Similarity	NPD7074	Phase 3
0.7725	Intermediate Similarity	NPD919	Approved
0.7719	Intermediate Similarity	NPD7228	Approved
0.7716	Intermediate Similarity	NPD1653	Approved
0.7711	Intermediate Similarity	NPD4966	Approved
0.7711	Intermediate Similarity	NPD4967	Phase 2
0.7711	Intermediate Similarity	NPD4965	Approved
0.7706	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6166	Phase 2
0.7702	Intermediate Similarity	NPD1512	Approved
0.7697	Intermediate Similarity	NPD7819	Suspended
0.7697	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7054	Approved
0.7662	Intermediate Similarity	NPD447	Suspended
0.7658	Intermediate Similarity	NPD2800	Approved
0.7647	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD37	Approved
0.7633	Intermediate Similarity	NPD1247	Approved
0.763	Intermediate Similarity	NPD7472	Approved
0.761	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2935	Discontinued
0.7546	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD920	Approved
0.753	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6799	Approved
0.7451	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7251	Discontinued
0.7438	Intermediate Similarity	NPD1243	Approved
0.741	Intermediate Similarity	NPD4380	Phase 2
0.7403	Intermediate Similarity	NPD3027	Phase 3
0.74	Intermediate Similarity	NPD9269	Phase 2
0.7396	Intermediate Similarity	NPD7768	Phase 2
0.7386	Intermediate Similarity	NPD6797	Phase 2
0.7384	Intermediate Similarity	NPD7229	Phase 3
0.7372	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1613	Approved
0.7371	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7411	Suspended
0.7355	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6190	Approved
0.7345	Intermediate Similarity	NPD6559	Discontinued
0.7337	Intermediate Similarity	NPD5402	Approved
0.7337	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7329	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6599	Discontinued
0.7284	Intermediate Similarity	NPD3750	Approved
0.7284	Intermediate Similarity	NPD4628	Phase 3
0.7283	Intermediate Similarity	NPD5710	Approved
0.7283	Intermediate Similarity	NPD5711	Approved
0.7273	Intermediate Similarity	NPD9494	Approved
0.7251	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3749	Approved
0.725	Intermediate Similarity	NPD6100	Approved
0.725	Intermediate Similarity	NPD6099	Approved
0.7247	Intermediate Similarity	NPD7240	Approved
0.7241	Intermediate Similarity	NPD3926	Phase 2
0.7235	Intermediate Similarity	NPD5353	Approved
0.7225	Intermediate Similarity	NPD8127	Discontinued
0.7225	Intermediate Similarity	NPD6959	Discontinued
0.7222	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6005	Phase 3
0.7205	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6002	Phase 3
0.7205	Intermediate Similarity	NPD6004	Phase 3
0.7205	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7286	Phase 2
0.717	Intermediate Similarity	NPD6651	Approved
0.716	Intermediate Similarity	NPD1549	Phase 2
0.716	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1240	Approved
0.7152	Intermediate Similarity	NPD943	Approved
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7133	Intermediate Similarity	NPD9268	Approved
0.7107	Intermediate Similarity	NPD6355	Discontinued
0.7107	Intermediate Similarity	NPD5124	Phase 1
0.7107	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1510	Phase 2
0.7078	Intermediate Similarity	NPD6696	Suspended
0.7063	Intermediate Similarity	NPD1607	Approved
0.7059	Intermediate Similarity	NPD1608	Approved
0.7049	Intermediate Similarity	NPD8434	Phase 2
0.7045	Intermediate Similarity	NPD5242	Approved
0.7044	Intermediate Similarity	NPD4060	Phase 1
0.7041	Intermediate Similarity	NPD3226	Approved
0.7039	Intermediate Similarity	NPD3496	Discontinued
0.7037	Intermediate Similarity	NPD1551	Phase 2
0.7037	Intermediate Similarity	NPD2796	Approved
0.7032	Intermediate Similarity	NPD2797	Approved
0.7025	Intermediate Similarity	NPD7985	Registered
0.7025	Intermediate Similarity	NPD3268	Approved
0.7025	Intermediate Similarity	NPD1296	Phase 2
0.7013	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1652	Phase 2
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5953	Discontinued
0.6981	Remote Similarity	NPD6233	Phase 2
0.6977	Remote Similarity	NPD8455	Phase 2
0.6975	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3748	Approved
0.6975	Remote Similarity	NPD2799	Discontinued
0.697	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4110	Phase 3
0.6964	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6386	Approved
0.6959	Remote Similarity	NPD6385	Approved
0.6951	Remote Similarity	NPD2424	Discontinued
0.6948	Remote Similarity	NPD9717	Approved
0.6947	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4357	Discontinued
0.6923	Remote Similarity	NPD7549	Discontinued
0.6923	Remote Similarity	NPD5403	Approved
0.6918	Remote Similarity	NPD6798	Discontinued
0.6918	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3146	Approved
0.6891	Remote Similarity	NPD7680	Approved
0.6871	Remote Similarity	NPD7033	Discontinued
0.6867	Remote Similarity	NPD8166	Discontinued
0.6863	Remote Similarity	NPD1778	Approved
0.6863	Remote Similarity	NPD17	Approved
0.6863	Remote Similarity	NPD4626	Approved
0.6859	Remote Similarity	NPD3225	Approved
0.6857	Remote Similarity	NPD6971	Discontinued
0.6852	Remote Similarity	NPD6653	Approved
0.6842	Remote Similarity	NPD9545	Approved
0.6839	Remote Similarity	NPD1481	Phase 2
0.6833	Remote Similarity	NPD3751	Discontinued
0.6824	Remote Similarity	NPD228	Approved
0.6823	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7783	Phase 2
0.6818	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2403	Approved
0.6815	Remote Similarity	NPD1203	Approved
0.6813	Remote Similarity	NPD2313	Discontinued
0.6813	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD411	Approved
0.6805	Remote Similarity	NPD5401	Approved
0.6798	Remote Similarity	NPD3787	Discontinued
0.6795	Remote Similarity	NPD4749	Approved
0.6793	Remote Similarity	NPD8313	Approved
0.6793	Remote Similarity	NPD8312	Approved
0.6792	Remote Similarity	NPD4908	Phase 1
0.6792	Remote Similarity	NPD6832	Phase 2
0.679	Remote Similarity	NPD1933	Approved
0.6788	Remote Similarity	NPD2346	Discontinued
0.6788	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7266	Discontinued
0.6788	Remote Similarity	NPD2344	Approved
0.6774	Remote Similarity	NPD1535	Discovery
0.6774	Remote Similarity	NPD3705	Approved
0.6768	Remote Similarity	NPD4308	Phase 3
0.6766	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6671	Approved
0.6754	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7095	Approved
0.675	Remote Similarity	NPD4625	Phase 3
0.6744	Remote Similarity	NPD7458	Discontinued
0.6739	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3018	Phase 2
0.673	Remote Similarity	NPD2861	Phase 2

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