NPASS Compound

Structure

NPC131273 OpenBabel07101718312D 52 60 0 0 1 0 0 0 0 0999 V2000 4.2809 1.9235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3008 0.5312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5743 0.8839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5057 -3.1116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3341 -2.5824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2253 -0.1604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3528 0.2925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3444 -0.2388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3673 -2.1647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1020 -0.8340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6860 -3.2131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8274 -2.7344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6419 -0.2643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7833 0.2144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4693 -2.9987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7953 -1.9393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6302 -2.1669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0238 -1.5904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1928 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0530 0.0253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5299 -2.7089 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3613 -1.3292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9654 -1.8771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0351 -2.1948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1822 -1.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5659 -0.8039 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8127 -1.7514 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2373 -0.5064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5166 -0.0903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5656 -0.7269 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9966 0.3786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9507 -0.8941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5488 -0.8186 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9815 -0.1341 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9269 0.6963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4455 -1.4082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0360 0.0106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4616 -2.1295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3969 -0.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6566 -1.2472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9541 -1.2727 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5152 -1.7260 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9394 -0.2898 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0113 -0.6044 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0275 -1.6772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1426 0.8357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2167 1.6357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5402 0.8545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5147 -0.8480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3257 0.6142 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 9.8449 -1.3909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 4 38 1 0 0 0 0 5 38 1 0 0 0 0 6 39 1 0 0 0 0 7 39 1 0 0 0 0 8 40 1 0 0 0 0 9 41 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 27 1 0 0 0 0 13 14 1 0 0 0 0 13 40 1 0 0 0 0 14 43 1 0 0 0 0 15 21 1 0 0 0 0 15 24 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 25 2 0 0 0 0 17 38 1 0 0 0 0 18 26 1 0 0 0 0 18 41 1 0 0 0 0 20 3 1 1 0 0 0 20 33 1 0 0 0 0 20 37 1 0 0 0 0 21 42 1 6 0 0 0 22 25 1 0 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 23 32 2 0 0 0 0 24 36 2 0 0 0 0 26 33 1 1 0 0 0 26 51 1 0 0 0 0 27 40 1 1 0 0 0 27 41 1 0 0 0 0 28 29 2 0 0 0 0 28 34 1 0 0 0 0 29 32 1 0 0 0 0 29 35 1 0 0 0 0 30 25 1 6 0 0 0 30 34 1 0 0 0 0 30 39 1 0 0 0 0 31 19 1 1 0 0 0 31 35 1 0 0 0 0 31 44 1 0 0 0 0 32 44 1 0 0 0 0 33 45 1 6 0 0 0 34 46 1 1 0 0 0 35 47 2 0 0 0 0 36 42 1 0 0 0 0 36 44 1 0 0 0 0 37 48 2 0 0 0 0 37 49 1 0 0 0 0 38 52 1 0 0 0 0 39 52 1 0 0 0 0 40 42 1 6 0 0 0 41 43 1 1 0 0 0 42 10 1 6 0 0 0 43 50 1 6 0 0 0 43 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	713.39
Volume:	735.503
LogP:	7.175
LogD:	4.338
LogS:	-3.255
# Rotatable Bonds:	4
TPSA:	141.09
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	9
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.193
Synthetic Accessibility Score:	6.2
Fsp3:	0.651
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:	-5.421
MDCK Permeability:	2.1103276594658382e-05
Pgp-inhibitor:	0.891
Pgp-substrate:	0.964
Human Intestinal Absorption (HIA):	0.092
20% Bioavailability (F20%):	0.582
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.636
Plasma Protein Binding (PPB):	94.59578704833984%
Volume Distribution (VD):	1.69
Pgp-substrate:	5.9925642013549805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.975
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.798
CYP2C9-inhibitor:	0.249
CYP2C9-substrate:	0.14
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.3
CYP3A4-substrate:	0.559

ADMET: Excretion

Clearance (CL):	7.35
Half-life (T1/2):	0.136

ADMET: Toxicity

hERG Blockers:	0.234
Human Hepatotoxicity (H-HT):	0.427
Drug-inuced Liver Injury (DILI):	0.089
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.498
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.09
Carcinogencity:	0.93
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC131273

Natural Product ID:	NPC131273
*Common Name:**	Nodulisporic Acid A12
IUPAC Name:	n.a.
Synonyms:	Nodulisporic Acid A12
Standard InCHIKey:	UVWBKHSYPWQMOP-KRNOYFLTSA-N
Standard InCHI:	InChI=1S/C43H55NO8/c1-19(2)31-35(47)29-28-22(25-17-38(4,5)52-39(6,7)30(25)34(28)46)16-23-24-15-21-11-12-27-40(8,42(21,10)36(24)44(31)32(23)29)13-14-43(50)41(27,9)18-26(51-43)33(45)20(3)37(48)49/h16-17,20-21,26-27,30-31,33-34,45-46,50H,1,11-15,18H2,2-10H3,(H,48,49)/t20-,21-,26-,27+,30+,31-,33+,34+,40-,41-,42+,43-/m0/s1
SMILES:	C=C(C)[C@H]1C(=O)c2c3c(cc4c5C[C@@H]6CC[C@@H]7[C@](C)(CC[C@]8([C@@]7(C)C[C@@H]([C@@H]([C@H](C)C(=O)O)O)O8)O)[C@@]6(C)c5n1c24)C1=CC(C)(C)OC(C)(C)[C@H]1[C@@H]3O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446320
PubChem CID:	44584351
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO32628	nodulisporium	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387649]

☑ 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	1
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	70.0	nM	PMID[478637]
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	=	14.0	uM	PMID[478637]

☑ 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 NPC131273 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	406
0.1-0.2	1674
0.2-0.3	3815
0.3-0.4	13734
0.4-0.5	17093
0.5-0.6	4596
0.6-0.7	1187
0.7-0.8	173
0.8-0.85	6
0.85-0.9	6
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473441
0.9596	High Similarity	NPC311451
0.9459	High Similarity	NPC473565
0.9372	High Similarity	NPC278540
0.933	High Similarity	NPC471583
0.933	High Similarity	NPC471782
0.8969	High Similarity	NPC183426
0.8795	High Similarity	NPC245756
0.8705	High Similarity	NPC469312
0.8705	High Similarity	NPC41318
0.864	High Similarity	NPC473806
0.864	High Similarity	NPC471634
0.819	Intermediate Similarity	NPC475424
0.819	Intermediate Similarity	NPC79107
0.8166	Intermediate Similarity	NPC242446
0.8166	Intermediate Similarity	NPC475476
0.8125	Intermediate Similarity	NPC470843
0.8125	Intermediate Similarity	NPC94541
0.7913	Intermediate Similarity	NPC160527
0.7913	Intermediate Similarity	NPC473650
0.775	Intermediate Similarity	NPC282033
0.7682	Intermediate Similarity	NPC97388
0.7639	Intermediate Similarity	NPC473547
0.7595	Intermediate Similarity	NPC61813
0.7565	Intermediate Similarity	NPC187456
0.7479	Intermediate Similarity	NPC250129
0.7436	Intermediate Similarity	NPC475165
0.7395	Intermediate Similarity	NPC96131
0.7393	Intermediate Similarity	NPC284102
0.739	Intermediate Similarity	NPC253482
0.7377	Intermediate Similarity	NPC470486
0.7377	Intermediate Similarity	NPC475644
0.7377	Intermediate Similarity	NPC471190
0.7377	Intermediate Similarity	NPC471977
0.7336	Intermediate Similarity	NPC477787
0.7336	Intermediate Similarity	NPC328186
0.7336	Intermediate Similarity	NPC475631
0.7336	Intermediate Similarity	NPC122968
0.7336	Intermediate Similarity	NPC87152
0.7336	Intermediate Similarity	NPC476110
0.7336	Intermediate Similarity	NPC228377
0.7336	Intermediate Similarity	NPC475600
0.7328	Intermediate Similarity	NPC237702
0.7317	Intermediate Similarity	NPC292416
0.7317	Intermediate Similarity	NPC473689
0.7311	Intermediate Similarity	NPC471284
0.7302	Intermediate Similarity	NPC475648
0.7295	Intermediate Similarity	NPC473506
0.7287	Intermediate Similarity	NPC244839
0.7287	Intermediate Similarity	NPC319880
0.7287	Intermediate Similarity	NPC320324
0.7287	Intermediate Similarity	NPC30456
0.7265	Intermediate Similarity	NPC211920
0.7254	Intermediate Similarity	NPC473850
0.7254	Intermediate Similarity	NPC477902
0.7254	Intermediate Similarity	NPC475137
0.7254	Intermediate Similarity	NPC475498
0.7247	Intermediate Similarity	NPC475596
0.7247	Intermediate Similarity	NPC316841
0.7247	Intermediate Similarity	NPC96801
0.7247	Intermediate Similarity	NPC475303
0.7247	Intermediate Similarity	NPC150698
0.7236	Intermediate Similarity	NPC475362
0.7229	Intermediate Similarity	NPC475406
0.7229	Intermediate Similarity	NPC263937
0.7229	Intermediate Similarity	NPC475426
0.7229	Intermediate Similarity	NPC170751
0.7229	Intermediate Similarity	NPC35208
0.7229	Intermediate Similarity	NPC94428
0.7227	Intermediate Similarity	NPC235900
0.7213	Intermediate Similarity	NPC76565
0.7213	Intermediate Similarity	NPC57797
0.7213	Intermediate Similarity	NPC250807
0.72	Intermediate Similarity	NPC327904
0.72	Intermediate Similarity	NPC38959
0.7195	Intermediate Similarity	NPC124029
0.7195	Intermediate Similarity	NPC146824
0.719	Intermediate Similarity	NPC84815
0.719	Intermediate Similarity	NPC301368
0.7189	Intermediate Similarity	NPC238278
0.7184	Intermediate Similarity	NPC233727
0.7172	Intermediate Similarity	NPC477788
0.7172	Intermediate Similarity	NPC106593
0.716	Intermediate Similarity	NPC327769
0.7149	Intermediate Similarity	NPC294579
0.7149	Intermediate Similarity	NPC475316
0.7149	Intermediate Similarity	NPC144779
0.7149	Intermediate Similarity	NPC473486
0.7149	Intermediate Similarity	NPC213143
0.7148	Intermediate Similarity	NPC107836
0.7143	Intermediate Similarity	NPC471980
0.7131	Intermediate Similarity	NPC470280
0.7124	Intermediate Similarity	NPC475151
0.7119	Intermediate Similarity	NPC216428
0.7108	Intermediate Similarity	NPC473781
0.7108	Intermediate Similarity	NPC470631
0.7108	Intermediate Similarity	NPC35390
0.7107	Intermediate Similarity	NPC6981
0.7102	Intermediate Similarity	NPC127026
0.7102	Intermediate Similarity	NPC127720
0.709	Intermediate Similarity	NPC140311
0.7078	Intermediate Similarity	NPC62367
0.7073	Intermediate Similarity	NPC473667
0.707	Intermediate Similarity	NPC476090
0.7061	Intermediate Similarity	NPC477903
0.7056	Intermediate Similarity	NPC14116
0.7056	Intermediate Similarity	NPC285411
0.7056	Intermediate Similarity	NPC475601
0.7046	Intermediate Similarity	NPC18661
0.7045	Intermediate Similarity	NPC328154
0.704	Intermediate Similarity	NPC477906
0.7039	Intermediate Similarity	NPC473747
0.7037	Intermediate Similarity	NPC471016
0.7037	Intermediate Similarity	NPC475408
0.7037	Intermediate Similarity	NPC471014
0.7028	Intermediate Similarity	NPC311196
0.7028	Intermediate Similarity	NPC134384
0.7025	Intermediate Similarity	NPC4421
0.7012	Intermediate Similarity	NPC469748
0.7012	Intermediate Similarity	NPC476467
0.6996	Remote Similarity	NPC477907
0.6996	Remote Similarity	NPC42678
0.6996	Remote Similarity	NPC470306
0.6996	Remote Similarity	NPC477909
0.6992	Remote Similarity	NPC123019
0.6992	Remote Similarity	NPC477912
0.6976	Remote Similarity	NPC235885
0.6967	Remote Similarity	NPC162812
0.6955	Remote Similarity	NPC264674
0.6953	Remote Similarity	NPC37473
0.6948	Remote Similarity	NPC148860
0.6939	Remote Similarity	NPC158020
0.6939	Remote Similarity	NPC212768
0.6939	Remote Similarity	NPC473115
0.6939	Remote Similarity	NPC6576
0.6939	Remote Similarity	NPC75600
0.6939	Remote Similarity	NPC473089
0.6923	Remote Similarity	NPC237901
0.6923	Remote Similarity	NPC195788
0.692	Remote Similarity	NPC478045
0.692	Remote Similarity	NPC470873
0.6917	Remote Similarity	NPC70155
0.6911	Remote Similarity	NPC223590
0.6908	Remote Similarity	NPC477899
0.6908	Remote Similarity	NPC477900
0.6907	Remote Similarity	NPC475489
0.6898	Remote Similarity	NPC249428
0.6895	Remote Similarity	NPC235364
0.6894	Remote Similarity	NPC102008
0.6891	Remote Similarity	NPC1203
0.6891	Remote Similarity	NPC471978
0.689	Remote Similarity	NPC475619
0.6883	Remote Similarity	NPC477901
0.688	Remote Similarity	NPC473833
0.6877	Remote Similarity	NPC471979
0.6872	Remote Similarity	NPC472553
0.6872	Remote Similarity	NPC280473
0.6872	Remote Similarity	NPC323551
0.686	Remote Similarity	NPC234999
0.6857	Remote Similarity	NPC30570
0.6857	Remote Similarity	NPC204491
0.6857	Remote Similarity	NPC62844
0.6857	Remote Similarity	NPC193361
0.6846	Remote Similarity	NPC472842
0.6844	Remote Similarity	NPC51008
0.6844	Remote Similarity	NPC41724
0.6842	Remote Similarity	NPC472555
0.684	Remote Similarity	NPC26881
0.684	Remote Similarity	NPC141428
0.683	Remote Similarity	NPC13603
0.6829	Remote Similarity	NPC473837
0.6823	Remote Similarity	NPC260909
0.6818	Remote Similarity	NPC329982
0.6815	Remote Similarity	NPC470874
0.6809	Remote Similarity	NPC231342
0.6803	Remote Similarity	NPC475778
0.6803	Remote Similarity	NPC292517
0.6803	Remote Similarity	NPC111732
0.6802	Remote Similarity	NPC187494
0.6792	Remote Similarity	NPC475301
0.6792	Remote Similarity	NPC85879
0.6792	Remote Similarity	NPC53255
0.6792	Remote Similarity	NPC326930
0.679	Remote Similarity	NPC314834
0.6789	Remote Similarity	NPC477910
0.6787	Remote Similarity	NPC2395
0.6786	Remote Similarity	NPC249342
0.6786	Remote Similarity	NPC57690
0.6778	Remote Similarity	NPC475223
0.6777	Remote Similarity	NPC63041
0.6766	Remote Similarity	NPC181502
0.6766	Remote Similarity	NPC85066
0.6761	Remote Similarity	NPC206343
0.6761	Remote Similarity	NPC477908
0.676	Remote Similarity	NPC477911
0.6754	Remote Similarity	NPC472846
0.675	Remote Similarity	NPC475448
0.675	Remote Similarity	NPC246983
0.6749	Remote Similarity	NPC472550
0.6749	Remote Similarity	NPC469743

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 NPC131273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	574
0.2-0.3	777
0.3-0.4	2384
0.4-0.5	3371
0.5-0.6	1477
0.6-0.7	312
0.7-0.8	5
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
0.7388	Intermediate Similarity	NPD7688	Phase 1
0.7314	Intermediate Similarity	NPD6995	Phase 1
0.7027	Intermediate Similarity	NPD7769	Phase 3
0.7008	Intermediate Similarity	NPD7878	Phase 2
0.7004	Intermediate Similarity	NPD7921	Approved
0.6992	Remote Similarity	NPD7770	Phase 3
0.6929	Remote Similarity	NPD6456	Discontinued
0.6923	Remote Similarity	NPD8467	Approved
0.6923	Remote Similarity	NPD8429	Approved
0.6923	Remote Similarity	NPD8465	Approved
0.6923	Remote Similarity	NPD8428	Approved
0.6923	Remote Similarity	NPD8427	Approved
0.6923	Remote Similarity	NPD8466	Approved
0.6911	Remote Similarity	NPD8468	Phase 2
0.6911	Remote Similarity	NPD6455	Phase 3
0.6894	Remote Similarity	NPD7777	Approved
0.6894	Remote Similarity	NPD7778	Approved
0.6894	Remote Similarity	NPD53	Approved
0.6883	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD8363	Approved
0.6827	Remote Similarity	NPD8364	Approved
0.6823	Remote Similarity	NPD8425	Approved
0.6823	Remote Similarity	NPD8459	Approved
0.6823	Remote Similarity	NPD8460	Approved
0.6823	Remote Similarity	NPD8426	Approved
0.6797	Remote Similarity	NPD5891	Approved
0.6792	Remote Similarity	NPD6987	Phase 1
0.6777	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD3925	Approved
0.6724	Remote Similarity	NPD4948	Discontinued
0.6692	Remote Similarity	NPD7417	Discontinued
0.6691	Remote Similarity	NPD7181	Phase 3
0.6654	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD8016	Phase 3
0.6653	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD8160	Phase 2
0.663	Remote Similarity	NPD7708	Approved
0.6627	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8325	Phase 3
0.6627	Remote Similarity	NPD8326	Phase 3
0.6627	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD2920	Discontinued
0.6588	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6978	Phase 2
0.6588	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8489	Phase 1
0.6557	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7803	Approved
0.6528	Remote Similarity	NPD5488	Discontinued
0.6525	Remote Similarity	NPD2564	Approved
0.6525	Remote Similarity	NPD2565	Phase 2
0.6525	Remote Similarity	NPD4373	Phase 2
0.6522	Remote Similarity	NPD5506	Approved
0.6522	Remote Similarity	NPD5507	Approved
0.652	Remote Similarity	NPD6733	Discontinued
0.651	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7772	Phase 3
0.6492	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4600	Approved
0.6488	Remote Similarity	NPD4601	Approved
0.648	Remote Similarity	NPD7707	Approved
0.6478	Remote Similarity	NPD7941	Phase 3
0.6471	Remote Similarity	NPD7956	Approved
0.6471	Remote Similarity	NPD7955	Approved
0.6466	Remote Similarity	NPD5899	Approved
0.6466	Remote Similarity	NPD5898	Approved
0.6466	Remote Similarity	NPD5897	Approved
0.6454	Remote Similarity	NPD3393	Approved
0.6454	Remote Similarity	NPD3394	Approved
0.6454	Remote Similarity	NPD3389	Approved
0.6449	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD6962	Phase 2
0.644	Remote Similarity	NPD3795	Approved
0.644	Remote Similarity	NPD3794	Approved
0.6437	Remote Similarity	NPD2510	Approved
0.6437	Remote Similarity	NPD2509	Approved
0.6434	Remote Similarity	NPD7767	Approved
0.6434	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5003	Discontinued
0.642	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6716	Phase 1
0.6414	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD5834	Phase 3
0.6411	Remote Similarity	NPD5835	Phase 3
0.6409	Remote Similarity	NPD4952	Phase 3
0.6402	Remote Similarity	NPD8146	Phase 2
0.64	Remote Similarity	NPD8096	Phase 3
0.64	Remote Similarity	NPD8097	Phase 3
0.6387	Remote Similarity	NPD6281	Approved
0.6386	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD3947	Discontinued
0.6382	Remote Similarity	NPD5901	Discontinued
0.6377	Remote Similarity	NPD7576	Discontinued
0.6357	Remote Similarity	NPD7398	Approved
0.6357	Remote Similarity	NPD7397	Approved
0.6349	Remote Similarity	NPD4897	Phase 2
0.6345	Remote Similarity	NPD7234	Approved
0.6345	Remote Similarity	NPD7233	Approved
0.6339	Remote Similarity	NPD7395	Discontinued
0.6336	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8357	Approved
0.6332	Remote Similarity	NPD3259	Approved
0.6332	Remote Similarity	NPD7994	Phase 2
0.632	Remote Similarity	NPD8358	Approved
0.6316	Remote Similarity	NPD6790	Phase 1
0.6314	Remote Similarity	NPD7776	Approved
0.6312	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD6641	Approved
0.6309	Remote Similarity	NPD6642	Approved
0.6308	Remote Similarity	NPD7924	Phase 2
0.6308	Remote Similarity	NPD7925	Phase 2
0.6305	Remote Similarity	NPD8399	Phase 1
0.6305	Remote Similarity	NPD8423	Phase 2
0.6296	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD7470	Discontinued
0.6292	Remote Similarity	NPD2336	Approved
0.629	Remote Similarity	NPD7010	Phase 3
0.629	Remote Similarity	NPD7001	Phase 3
0.6286	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD7824	Approved
0.6281	Remote Similarity	NPD4602	Approved
0.6274	Remote Similarity	NPD7951	Approved
0.6274	Remote Similarity	NPD7790	Approved
0.6274	Remote Similarity	NPD7791	Approved
0.6274	Remote Similarity	NPD7789	Approved
0.6274	Remote Similarity	NPD7952	Approved
0.6274	Remote Similarity	NPD7953	Approved
0.6274	Remote Similarity	NPD7950	Approved
0.626	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6142	Phase 3
0.625	Remote Similarity	NPD8361	Approved
0.625	Remote Similarity	NPD8360	Approved
0.625	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3763	Approved
0.625	Remote Similarity	NPD6770	Approved
0.6245	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.624	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5164	Discontinued
0.6231	Remote Similarity	NPD6517	Phase 3
0.623	Remote Similarity	NPD8485	Approved
0.6226	Remote Similarity	NPD7853	Phase 2
0.6225	Remote Similarity	NPD7957	Phase 1
0.6225	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6217	Remote Similarity	NPD4561	Discontinued
0.6213	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6208	Remote Similarity	NPD4334	Discontinued
0.6207	Remote Similarity	NPD7730	Approved
0.6207	Remote Similarity	NPD7731	Approved
0.6206	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD8463	Approved
0.6203	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5429	Discontinued
0.6196	Remote Similarity	NPD5050	Approved
0.6192	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6189	Remote Similarity	NPD2307	Discontinued
0.6185	Remote Similarity	NPD8098	Approved
0.6183	Remote Similarity	NPD7781	Approved
0.6183	Remote Similarity	NPD8435	Approved
0.6183	Remote Similarity	NPD7780	Approved
0.6182	Remote Similarity	NPD8492	Approved
0.6179	Remote Similarity	NPD6999	Discontinued
0.6179	Remote Similarity	NPD6248	Phase 2
0.6179	Remote Similarity	NPD6249	Phase 2
0.6179	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7797	Approved
0.6174	Remote Similarity	NPD3746	Discontinued
0.6174	Remote Similarity	NPD7796	Approved
0.6171	Remote Similarity	NPD5821	Approved
0.6166	Remote Similarity	NPD5475	Discontinued
0.6165	Remote Similarity	NPD3006	Discontinued
0.6164	Remote Similarity	NPD1573	Approved
0.6164	Remote Similarity	NPD1575	Approved
0.6163	Remote Similarity	NPD6206	Phase 1
0.616	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6151	Remote Similarity	NPD4506	Discontinued
0.6148	Remote Similarity	NPD7944	Discontinued
0.6148	Remote Similarity	NPD4946	Phase 2
0.6145	Remote Similarity	NPD6176	Phase 1
0.6142	Remote Similarity	NPD7454	Approved
0.6142	Remote Similarity	NPD7455	Approved
0.6142	Remote Similarity	NPD5866	Approved
0.6142	Remote Similarity	NPD7069	Discontinued
0.6138	Remote Similarity	NPD6261	Phase 3

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