NPASS Compound

Structure

NPC311451 OpenBabel07101719172D 51 59 0 0 1 0 0 0 0 0999 V2000 4.2796 1.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2998 0.5310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5229 -2.5203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5028 -3.1107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3310 -2.5816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2223 -0.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3500 0.2924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3431 -0.2387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3669 -2.1640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1010 -0.8337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6852 -3.2122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8269 -2.7336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6411 -0.2642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7827 0.2144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5483 -0.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4680 -2.9978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7933 -1.9387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0238 -1.5900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6277 -2.1662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1915 0.9441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0269 -1.6767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5289 -2.7081 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5657 -0.8036 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3591 -1.3288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9637 -1.8765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0336 -2.1942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1798 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8122 -1.7509 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2351 -0.5062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5146 -0.0902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5630 -0.7267 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9952 0.3785 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9490 -0.8939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9792 -0.1341 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9252 0.6961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4442 -1.4078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0096 -1.6914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4588 -2.1289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3941 -0.6894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6558 -1.2469 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9538 -1.2723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5142 -1.7255 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9391 -0.2897 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0099 -0.6042 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.1402 0.8354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2148 1.6352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4882 -2.5497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5136 -0.8477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 0.6140 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 9.8420 -1.3905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 20 1 0 0 0 0 3 21 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 22 1 0 0 0 0 12 28 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 2 0 0 0 0 16 22 1 0 0 0 0 16 26 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 23 1 0 0 0 0 18 41 1 0 0 0 0 19 27 2 0 0 0 0 19 38 1 0 0 0 0 21 37 1 0 0 0 0 22 42 1 6 0 0 0 23 15 1 1 0 0 0 23 50 1 0 0 0 0 24 27 1 0 0 0 0 24 29 1 0 0 0 0 25 26 1 0 0 0 0 25 33 2 0 0 0 0 26 36 2 0 0 0 0 28 40 1 1 0 0 0 28 41 1 0 0 0 0 29 30 2 0 0 0 0 29 34 1 0 0 0 0 30 33 1 0 0 0 0 30 35 1 0 0 0 0 31 27 1 6 0 0 0 31 34 1 0 0 0 0 31 39 1 0 0 0 0 32 20 1 1 0 0 0 32 35 1 0 0 0 0 32 44 1 0 0 0 0 33 44 1 0 0 0 0 34 45 1 1 0 0 0 35 46 2 0 0 0 0 36 42 1 0 0 0 0 36 44 1 0 0 0 0 37 47 2 0 0 0 0 37 48 1 0 0 0 0 38 51 1 0 0 0 0 39 51 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 49 1 6 0 0 0 43 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	695.38
Volume:	724.076
LogP:	7.786
LogD:	4.796
LogS:	-3.098
# Rotatable Bonds:	3
TPSA:	120.86
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	9
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.218
Synthetic Accessibility Score:	6.143
Fsp3:	0.605
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:	-5.372
MDCK Permeability:	2.4262091756099835e-05
Pgp-inhibitor:	0.937
Pgp-substrate:	0.773
Human Intestinal Absorption (HIA):	0.12
20% Bioavailability (F20%):	0.725
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.669
Plasma Protein Binding (PPB):	95.39165496826172%
Volume Distribution (VD):	1.553
Pgp-substrate:	3.7125377655029297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.696
CYP2C9-inhibitor:	0.635
CYP2C9-substrate:	0.208
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.466
CYP3A4-substrate:	0.849

ADMET: Excretion

Clearance (CL):	6.359
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.312
Human Hepatotoxicity (H-HT):	0.786
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.222
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.104
Carcinogencity:	0.919
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC311451

Natural Product ID:	NPC311451
*Common Name:**	Nodulisporic Acid A1
IUPAC Name:	n.a.
Synonyms:	Nodulisporic Acid A1
Standard InCHIKey:	ISIUAWYGRFWXQR-DKNYIOSXSA-N
Standard InCHI:	InChI=1S/C43H53NO7/c1-20(2)32-35(46)30-29-24(27-19-38(4,5)51-39(6,7)31(27)34(29)45)17-25-26-16-22-11-12-28-40(8,42(22,10)36(26)44(32)33(25)30)13-14-43(49)41(28,9)18-23(50-43)15-21(3)37(47)48/h15,17,19,22-23,28,31-32,34,45,49H,1,11-14,16,18H2,2-10H3,(H,47,48)/b21-15+/t22-,23+,28+,31+,32-,34+,40-,41-,42+,43-/m0/s1
SMILES:	C/C(=C[C@@H]1C[C@@]2([C@](O1)(O)CC[C@]1([C@H]2CC[C@@H]2[C@]1(C)c1n3[C@@H](C(=C)C)C(=O)c4c3c(c1C2)cc1c4[C@@H](O)[C@H]2C1=CC(OC2(C)C)(C)C)C)C)/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL98206
PubChem CID:	10723360
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
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12270179]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542359]
NPO32628	nodulisporium	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387649]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17363259]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25978520]

☑ 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	5

Activity Type	# Activity
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		LD90	=	5.0	p.p.m.	PMID[533039]
NPT2	Others	Unspecified		IC50	=	10.5	nM	PMID[533040]
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	=	7.3	uM	PMID[533040]
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	=	5.0	ug ml-1	PMID[533041]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	LD90	=	200.0	ng/ml	PMID[533041]
NPT6371	Organism	Lucilia sericata	Lucilia sericata	LD90	=	300.0	ng/ml	PMID[533041]

☑ 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 NPC311451 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	401
0.1-0.2	1650
0.2-0.3	3945
0.3-0.4	15531
0.4-0.5	15769
0.5-0.6	3896
0.6-0.7	1377
0.7-0.8	110
0.8-0.85	5
0.85-0.9	4
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC278540
0.9722	High Similarity	NPC471782
0.9722	High Similarity	NPC471583
0.9596	High Similarity	NPC473441
0.9596	High Similarity	NPC131273
0.9349	High Similarity	NPC183426
0.9167	High Similarity	NPC245756
0.9144	High Similarity	NPC473565
0.9074	High Similarity	NPC41318
0.9074	High Similarity	NPC469312
0.8507	High Similarity	NPC242446
0.8507	High Similarity	NPC475476
0.8333	Intermediate Similarity	NPC471634
0.8333	Intermediate Similarity	NPC473806
0.8243	Intermediate Similarity	NPC473650
0.8243	Intermediate Similarity	NPC160527
0.8	Intermediate Similarity	NPC97388
0.7956	Intermediate Similarity	NPC473547
0.7908	Intermediate Similarity	NPC94541
0.7908	Intermediate Similarity	NPC470843
0.7888	Intermediate Similarity	NPC79107
0.7888	Intermediate Similarity	NPC475424
0.7883	Intermediate Similarity	NPC187456
0.7788	Intermediate Similarity	NPC250129
0.7743	Intermediate Similarity	NPC475165
0.7699	Intermediate Similarity	NPC284102
0.7531	Intermediate Similarity	NPC282033
0.7424	Intermediate Similarity	NPC470280
0.7422	Intermediate Similarity	NPC475151
0.7333	Intermediate Similarity	NPC473747
0.73	Intermediate Similarity	NPC61813
0.7231	Intermediate Similarity	NPC475644
0.7231	Intermediate Similarity	NPC470486
0.7231	Intermediate Similarity	NPC471977
0.7231	Intermediate Similarity	NPC471190
0.719	Intermediate Similarity	NPC87152
0.719	Intermediate Similarity	NPC122968
0.719	Intermediate Similarity	NPC476110
0.719	Intermediate Similarity	NPC477787
0.719	Intermediate Similarity	NPC328186
0.719	Intermediate Similarity	NPC475631
0.719	Intermediate Similarity	NPC228377
0.719	Intermediate Similarity	NPC475600
0.7184	Intermediate Similarity	NPC237702
0.7172	Intermediate Similarity	NPC473689
0.7172	Intermediate Similarity	NPC292416
0.7149	Intermediate Similarity	NPC473506
0.7143	Intermediate Similarity	NPC30456
0.7143	Intermediate Similarity	NPC244839
0.7143	Intermediate Similarity	NPC319880
0.7143	Intermediate Similarity	NPC320324
0.7119	Intermediate Similarity	NPC14116
0.7119	Intermediate Similarity	NPC285411
0.7108	Intermediate Similarity	NPC253482
0.7107	Intermediate Similarity	NPC475137
0.7107	Intermediate Similarity	NPC475498
0.7107	Intermediate Similarity	NPC235885
0.7107	Intermediate Similarity	NPC473850
0.7102	Intermediate Similarity	NPC316841
0.7102	Intermediate Similarity	NPC475303
0.7102	Intermediate Similarity	NPC475596
0.7101	Intermediate Similarity	NPC96131
0.7095	Intermediate Similarity	NPC477788
0.709	Intermediate Similarity	NPC475362
0.709	Intermediate Similarity	NPC311196
0.709	Intermediate Similarity	NPC134384
0.7085	Intermediate Similarity	NPC94428
0.7085	Intermediate Similarity	NPC263937
0.7085	Intermediate Similarity	NPC475406
0.7085	Intermediate Similarity	NPC170751
0.7066	Intermediate Similarity	NPC250807
0.7066	Intermediate Similarity	NPC57797
0.7066	Intermediate Similarity	NPC76565
0.7056	Intermediate Similarity	NPC38959
0.7056	Intermediate Similarity	NPC327904
0.7049	Intermediate Similarity	NPC146824
0.7045	Intermediate Similarity	NPC70155
0.7042	Intermediate Similarity	NPC301368
0.7042	Intermediate Similarity	NPC84815
0.7025	Intermediate Similarity	NPC106593
0.7024	Intermediate Similarity	NPC475648
0.7017	Intermediate Similarity	NPC471284
0.7016	Intermediate Similarity	NPC327769
0.7008	Intermediate Similarity	NPC107836
0.7004	Intermediate Similarity	NPC475316
0.7004	Intermediate Similarity	NPC473486
0.7	Intermediate Similarity	NPC144779
0.7	Intermediate Similarity	NPC294579
0.6996	Remote Similarity	NPC471980
0.698	Remote Similarity	NPC211920
0.6971	Remote Similarity	NPC216428
0.697	Remote Similarity	NPC470279
0.6967	Remote Similarity	NPC477902
0.6964	Remote Similarity	NPC150698
0.6964	Remote Similarity	NPC96801
0.6964	Remote Similarity	NPC35390
0.6964	Remote Similarity	NPC470631
0.6964	Remote Similarity	NPC473781
0.6958	Remote Similarity	NPC6981
0.6955	Remote Similarity	NPC127026
0.6955	Remote Similarity	NPC127720
0.695	Remote Similarity	NPC478083
0.6948	Remote Similarity	NPC475426
0.6948	Remote Similarity	NPC35208
0.6947	Remote Similarity	NPC206967
0.6946	Remote Similarity	NPC4421
0.6942	Remote Similarity	NPC140311
0.6938	Remote Similarity	NPC329982
0.6935	Remote Similarity	NPC213143
0.6933	Remote Similarity	NPC235900
0.6929	Remote Similarity	NPC476090
0.6929	Remote Similarity	NPC62367
0.6926	Remote Similarity	NPC473667
0.692	Remote Similarity	NPC234999
0.6917	Remote Similarity	NPC477909
0.6917	Remote Similarity	NPC42678
0.6917	Remote Similarity	NPC477907
0.6914	Remote Similarity	NPC2395
0.6911	Remote Similarity	NPC124029
0.6908	Remote Similarity	NPC238278
0.6898	Remote Similarity	NPC233727
0.6898	Remote Similarity	NPC328154
0.6888	Remote Similarity	NPC471016
0.6888	Remote Similarity	NPC475408
0.6888	Remote Similarity	NPC471014
0.6862	Remote Similarity	NPC475778
0.6862	Remote Similarity	NPC476467
0.686	Remote Similarity	NPC212768
0.686	Remote Similarity	NPC75600
0.686	Remote Similarity	NPC473115
0.686	Remote Similarity	NPC473089
0.686	Remote Similarity	NPC6576
0.686	Remote Similarity	NPC158020
0.6846	Remote Similarity	NPC203614
0.6846	Remote Similarity	NPC204491
0.6846	Remote Similarity	NPC470306
0.6844	Remote Similarity	NPC477912
0.6844	Remote Similarity	NPC477903
0.6838	Remote Similarity	NPC123019
0.6836	Remote Similarity	NPC469734
0.6826	Remote Similarity	NPC181502
0.6826	Remote Similarity	NPC85066
0.6824	Remote Similarity	NPC475489
0.6811	Remote Similarity	NPC37473
0.681	Remote Similarity	NPC102008
0.6807	Remote Similarity	NPC469743
0.6802	Remote Similarity	NPC472762
0.6802	Remote Similarity	NPC148860
0.6793	Remote Similarity	NPC315545
0.6793	Remote Similarity	NPC314297
0.6792	Remote Similarity	NPC280473
0.6792	Remote Similarity	NPC323551
0.678	Remote Similarity	NPC314648
0.6778	Remote Similarity	NPC314834
0.6774	Remote Similarity	NPC475601
0.6774	Remote Similarity	NPC470873
0.6774	Remote Similarity	NPC57690
0.6773	Remote Similarity	NPC126492
0.6763	Remote Similarity	NPC317752
0.6763	Remote Similarity	NPC51008
0.6763	Remote Similarity	NPC41724
0.6762	Remote Similarity	NPC223590
0.676	Remote Similarity	NPC477906
0.6755	Remote Similarity	NPC1203
0.6751	Remote Similarity	NPC314855
0.6751	Remote Similarity	NPC18661
0.6751	Remote Similarity	NPC313345
0.6751	Remote Similarity	NPC315638
0.6751	Remote Similarity	NPC313796
0.6749	Remote Similarity	NPC473837
0.6749	Remote Similarity	NPC249428
0.6746	Remote Similarity	NPC475619
0.6736	Remote Similarity	NPC264674
0.6735	Remote Similarity	NPC477901
0.6733	Remote Similarity	NPC469748
0.6728	Remote Similarity	NPC195788
0.6728	Remote Similarity	NPC237901
0.6722	Remote Similarity	NPC472553
0.6722	Remote Similarity	NPC318299
0.6721	Remote Similarity	NPC147446
0.6718	Remote Similarity	NPC478080
0.6718	Remote Similarity	NPC478045
0.6709	Remote Similarity	NPC32200
0.6709	Remote Similarity	NPC289086
0.6695	Remote Similarity	NPC63041
0.6695	Remote Similarity	NPC137589
0.6695	Remote Similarity	NPC475223
0.6694	Remote Similarity	NPC472555
0.6694	Remote Similarity	NPC477899
0.6694	Remote Similarity	NPC477900
0.6694	Remote Similarity	NPC141428
0.6693	Remote Similarity	NPC474701
0.6692	Remote Similarity	NPC13603
0.6682	Remote Similarity	NPC84347
0.6681	Remote Similarity	NPC34271
0.668	Remote Similarity	NPC246658
0.668	Remote Similarity	NPC206343
0.668	Remote Similarity	NPC477908
0.668	Remote Similarity	NPC235364
0.668	Remote Similarity	NPC162812

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 NPC311451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	587
0.2-0.3	726
0.3-0.4	2253
0.4-0.5	3364
0.5-0.6	1608
0.6-0.7	364
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
0.7605	Intermediate Similarity	NPD7688	Phase 1
0.7532	Intermediate Similarity	NPD6995	Phase 1
0.7131	Intermediate Similarity	NPD7921	Approved
0.7069	Intermediate Similarity	NPD6987	Phase 1
0.7056	Intermediate Similarity	NPD5891	Approved
0.7052	Intermediate Similarity	NPD7770	Phase 3
0.7009	Intermediate Similarity	NPD4948	Discontinued
0.6929	Remote Similarity	NPD7878	Phase 2
0.6901	Remote Similarity	NPD6455	Phase 3
0.6888	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7769	Phase 3
0.688	Remote Similarity	NPD8364	Approved
0.688	Remote Similarity	NPD8363	Approved
0.6872	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD8160	Phase 2
0.6842	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8016	Phase 3
0.6838	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7417	Discontinued
0.681	Remote Similarity	NPD7777	Approved
0.681	Remote Similarity	NPD7778	Approved
0.681	Remote Similarity	NPD53	Approved
0.6787	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8468	Phase 2
0.6761	Remote Similarity	NPD3925	Approved
0.6738	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6456	Discontinued
0.6728	Remote Similarity	NPD8428	Approved
0.6728	Remote Similarity	NPD8427	Approved
0.6728	Remote Similarity	NPD8429	Approved
0.6728	Remote Similarity	NPD8465	Approved
0.6728	Remote Similarity	NPD8466	Approved
0.6728	Remote Similarity	NPD8467	Approved
0.6708	Remote Similarity	NPD3393	Approved
0.6708	Remote Similarity	NPD6733	Discontinued
0.6708	Remote Similarity	NPD3394	Approved
0.6708	Remote Similarity	NPD3389	Approved
0.6695	Remote Similarity	NPD2510	Approved
0.6695	Remote Similarity	NPD2509	Approved
0.6681	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7767	Approved
0.668	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7707	Approved
0.6667	Remote Similarity	NPD2920	Discontinued
0.6641	Remote Similarity	NPD5488	Discontinued
0.664	Remote Similarity	NPD6978	Phase 2
0.664	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3947	Discontinued
0.6639	Remote Similarity	NPD5901	Discontinued
0.663	Remote Similarity	NPD8425	Approved
0.663	Remote Similarity	NPD8460	Approved
0.663	Remote Similarity	NPD8459	Approved
0.663	Remote Similarity	NPD8426	Approved
0.6612	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7395	Discontinued
0.658	Remote Similarity	NPD2565	Phase 2
0.658	Remote Similarity	NPD6281	Approved
0.658	Remote Similarity	NPD2564	Approved
0.6575	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7994	Phase 2
0.6574	Remote Similarity	NPD3259	Approved
0.6569	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7010	Phase 3
0.6542	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7776	Approved
0.654	Remote Similarity	NPD4600	Approved
0.654	Remote Similarity	NPD4601	Approved
0.6537	Remote Similarity	NPD7234	Approved
0.6537	Remote Similarity	NPD7233	Approved
0.6529	Remote Similarity	NPD7941	Phase 3
0.6525	Remote Similarity	NPD6716	Phase 1
0.6516	Remote Similarity	NPD8097	Phase 3
0.6516	Remote Similarity	NPD8096	Phase 3
0.651	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4373	Phase 2
0.65	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD7181	Phase 3
0.6496	Remote Similarity	NPD6962	Phase 2
0.649	Remote Similarity	NPD3795	Approved
0.649	Remote Similarity	NPD3794	Approved
0.6489	Remote Similarity	NPD8358	Approved
0.6488	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6142	Phase 3
0.6483	Remote Similarity	NPD5003	Discontinued
0.6475	Remote Similarity	NPD7470	Discontinued
0.6473	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7001	Phase 3
0.6463	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD7853	Phase 2
0.6457	Remote Similarity	NPD4952	Phase 3
0.6457	Remote Similarity	NPD7824	Approved
0.6453	Remote Similarity	NPD8146	Phase 2
0.6445	Remote Similarity	NPD7791	Approved
0.6445	Remote Similarity	NPD7790	Approved
0.6445	Remote Similarity	NPD7952	Approved
0.6445	Remote Similarity	NPD7950	Approved
0.6445	Remote Similarity	NPD7953	Approved
0.6445	Remote Similarity	NPD7789	Approved
0.6445	Remote Similarity	NPD7951	Approved
0.6434	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD7708	Approved
0.6429	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1573	Approved
0.6429	Remote Similarity	NPD1575	Approved
0.6426	Remote Similarity	NPD6770	Approved
0.6423	Remote Similarity	NPD7576	Discontinued
0.6423	Remote Similarity	NPD6790	Phase 1
0.641	Remote Similarity	NPD7925	Phase 2
0.641	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2336	Approved
0.641	Remote Similarity	NPD7924	Phase 2
0.6408	Remote Similarity	NPD5475	Discontinued
0.6405	Remote Similarity	NPD7957	Phase 1
0.6405	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7398	Approved
0.6402	Remote Similarity	NPD7397	Approved
0.6398	Remote Similarity	NPD5821	Approved
0.639	Remote Similarity	NPD6176	Phase 1
0.6382	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7455	Approved
0.6382	Remote Similarity	NPD7454	Approved
0.6379	Remote Similarity	NPD5429	Discontinued
0.6378	Remote Similarity	NPD7730	Approved
0.6378	Remote Similarity	NPD7731	Approved
0.6376	Remote Similarity	NPD8489	Phase 1
0.6376	Remote Similarity	NPD5897	Approved
0.6376	Remote Similarity	NPD5899	Approved
0.6376	Remote Similarity	NPD5898	Approved
0.6375	Remote Similarity	NPD5506	Approved
0.6375	Remote Similarity	NPD5507	Approved
0.6374	Remote Similarity	NPD4946	Phase 2
0.6367	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD8463	Approved
0.636	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.636	Remote Similarity	NPD6999	Discontinued
0.6357	Remote Similarity	NPD7772	Phase 3
0.6356	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD7780	Approved
0.6353	Remote Similarity	NPD7781	Approved
0.6345	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6342	Remote Similarity	NPD3746	Discontinued
0.6337	Remote Similarity	NPD7803	Approved
0.6331	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7944	Discontinued
0.6323	Remote Similarity	NPD1631	Approved
0.6322	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7962	Phase 2
0.6316	Remote Similarity	NPD7069	Discontinued
0.6304	Remote Similarity	NPD6452	Discontinued
0.6303	Remote Similarity	NPD2307	Discontinued
0.6299	Remote Similarity	NPD7271	Approved
0.6299	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD56	Approved
0.6296	Remote Similarity	NPD8098	Approved
0.6296	Remote Similarity	NPD8283	Approved
0.6296	Remote Similarity	NPD8282	Approved
0.6295	Remote Similarity	NPD3763	Approved
0.6286	Remote Similarity	NPD6376	Discontinued
0.6286	Remote Similarity	NPD7665	Phase 2
0.6286	Remote Similarity	NPD2916	Discontinued
0.6286	Remote Similarity	NPD8423	Phase 2
0.6286	Remote Similarity	NPD7666	Phase 3
0.6286	Remote Similarity	NPD8399	Phase 1
0.6285	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7474	Suspended
0.628	Remote Similarity	NPD5164	Discontinued
0.628	Remote Similarity	NPD8325	Phase 3
0.628	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.628	Remote Similarity	NPD8326	Phase 3
0.6279	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD8289	Discontinued
0.6273	Remote Similarity	NPD7955	Approved
0.6273	Remote Similarity	NPD7956	Approved
0.6272	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.627	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD3006	Discontinued
0.6266	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4602	Approved
0.626	Remote Similarity	NPD4561	Discontinued
0.626	Remote Similarity	NPD5835	Phase 3
0.626	Remote Similarity	NPD5834	Phase 3
0.6255	Remote Similarity	NPD4334	Discontinued
0.625	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5866	Approved
0.625	Remote Similarity	NPD7946	Pre-registration
0.6245	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5809	Phase 3
0.6236	Remote Similarity	NPD8091	Phase 3
0.6236	Remote Similarity	NPD5050	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