NPASS Compound

Structure

NPC470186 OpenBabel07101719132D 49 52 0 0 1 0 0 0 0 0999 V2000 3.8893 -3.7931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0396 -5.2648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3118 -2.6246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0396 -1.3403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0752 1.3145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7339 -4.9078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3403 0.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3952 2.7311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0156 -1.5923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5158 -0.0774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8020 -3.1151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8689 -3.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1899 -3.7931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1899 -2.8119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9811 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0396 -4.2836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3787 -2.3214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0396 -2.3214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8689 0.7378 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7582 -4.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1899 0.1314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1815 1.9373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3403 -2.3214 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9358 -3.1151 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3403 -4.2836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3787 -1.3403 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3591 -1.3403 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4906 -2.8119 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3403 -1.3403 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8020 -0.5465 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9358 -0.5465 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8020 1.0410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3591 -2.3214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4906 -0.8497 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8689 -0.2433 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8893 -2.8119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1815 -5.5989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0396 0.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1572 2.0399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3403 -5.2648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1052 1.9741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8689 -1.2244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3118 -1.0371 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 -0.3591 -3.9089 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1899 -0.8497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2176 1.0410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4906 -3.7931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3787 0.2473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 2 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 10 43 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 15 44 1 0 0 0 0 17 26 1 0 0 0 0 18 36 2 0 0 0 0 19 32 1 0 0 0 0 19 35 1 6 0 0 0 20 37 2 0 0 0 0 20 45 1 0 0 0 0 21 38 2 0 0 0 0 21 46 1 0 0 0 0 22 39 2 0 0 0 0 22 47 1 0 0 0 0 23 14 1 6 0 0 0 23 28 1 0 0 0 0 23 29 1 0 0 0 0 24 33 1 1 0 0 0 24 45 1 0 0 0 0 25 40 2 0 0 0 0 25 48 1 0 0 0 0 26 30 1 0 0 0 0 26 43 1 1 0 0 0 27 31 1 0 0 0 0 27 33 1 1 0 0 0 27 34 1 0 0 0 0 28 33 1 1 0 0 0 28 48 1 0 0 0 0 29 34 1 6 0 0 0 29 46 1 0 0 0 0 30 35 1 6 0 0 0 30 49 1 0 0 0 0 31 35 1 1 0 0 0 31 47 1 0 0 0 0 32 41 2 0 0 0 0 32 49 1 0 0 0 0 33 9 1 1 0 0 0 34 15 1 1 0 0 0 34 44 1 0 0 0 0 35 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	692.3
Volume:	681.662
LogP:	2.191
LogD:	1.149
LogS:	-4.695
# Rotatable Bonds:	13
TPSA:	190.56
# H-Bond Aceptor:	14
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	6.649
Fsp3:	0.714
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.234
MDCK Permeability:	0.00011707451631082222
Pgp-inhibitor:	1.0
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.672
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	44.5930061340332%
Volume Distribution (VD):	1.135
Pgp-substrate:	36.383819580078125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.245
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.511
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	2.819
Half-life (T1/2):	0.545

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.985
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.484
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.444
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.9

Download Data

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

Natural Product: NPC470186

Natural Product ID:	NPC470186
*Common Name:**	Gemmacolide M
IUPAC Name:	n.a.
Synonyms:	Gemmacolide M
Standard InCHIKey:	NZKRQIBWUBZFOS-GTSHZXQHSA-N
Standard InCHI:	InChI=1S/C35H48O14/c1-16(2)13-25(40)48-28-23(14-18(4)36)29(46-21(7)38)34(15-44-34)27-31(47-22(8)39)35(42)19(5)32(41)49-30(35)26(43-10)17(3)11-12-24(33(27,28)9)45-20(6)37/h11-12,16,19,23-24,26-31,42H,3,13-15H2,1-2,4-10H3/b12-11+/t19-,23+,24-,26+,27+,28+,29+,30-,31-,33+,34-,35-/m0/s1
SMILES:	CC1C(=O)OC2C1(C(C3C(C(C=CC(=C)C2OC)OC(=O)C)(C(C(C(C34CO4)OC(=O)C)CC(=O)C)OC(=O)CC(C)C)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1812332
PubChem CID:	56673114
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[21721519]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21721519]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[22647719]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477504]
NPO15994	Dichotella gemmacea	Species	Ellisellidae	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	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	27400.0	nM	PMID[549775]
NPT827	Organism	Mycosphaerella graminicola	Mycosphaerella graminicola	IZ	=	15.0	mm	PMID[549775]

☑ 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 NPC470186 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	240
0.1-0.2	1283
0.2-0.3	4017
0.3-0.4	6737
0.4-0.5	13652
0.5-0.6	9005
0.6-0.7	6061
0.7-0.8	1497
0.8-0.85	165
0.85-0.9	34
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9633	High Similarity	NPC73314
0.9083	High Similarity	NPC470185
0.9083	High Similarity	NPC94377
0.9043	High Similarity	NPC475003
0.8974	High Similarity	NPC303006
0.8889	High Similarity	NPC310035
0.8889	High Similarity	NPC282003
0.8889	High Similarity	NPC188222
0.8783	High Similarity	NPC296822
0.8761	High Similarity	NPC473877
0.875	High Similarity	NPC281624
0.8707	High Similarity	NPC284707
0.8696	High Similarity	NPC474333
0.8667	High Similarity	NPC471939
0.8661	High Similarity	NPC42662
0.8621	High Similarity	NPC98249
0.8621	High Similarity	NPC53396
0.8595	High Similarity	NPC471940
0.8571	High Similarity	NPC473595
0.8571	High Similarity	NPC473939
0.8534	High Similarity	NPC477509
0.8525	High Similarity	NPC236999
0.8512	High Similarity	NPC181999
0.8512	High Similarity	NPC473635
0.8509	High Similarity	NPC194619
0.85	High Similarity	NPC473802
0.8482	Intermediate Similarity	NPC475587
0.8482	Intermediate Similarity	NPC475510
0.8462	Intermediate Similarity	NPC476712
0.8462	Intermediate Similarity	NPC476713
0.8462	Intermediate Similarity	NPC469684
0.8455	Intermediate Similarity	NPC183571
0.843	Intermediate Similarity	NPC473919
0.843	Intermediate Similarity	NPC473709
0.8421	Intermediate Similarity	NPC473594
0.8421	Intermediate Similarity	NPC474586
0.8421	Intermediate Similarity	NPC473975
0.8421	Intermediate Similarity	NPC473843
0.8403	Intermediate Similarity	NPC475885
0.8403	Intermediate Similarity	NPC472759
0.8403	Intermediate Similarity	NPC329080
0.839	Intermediate Similarity	NPC146280
0.839	Intermediate Similarity	NPC124676
0.8378	Intermediate Similarity	NPC69171
0.8378	Intermediate Similarity	NPC474165
0.8376	Intermediate Similarity	NPC476711
0.8376	Intermediate Similarity	NPC476710
0.8364	Intermediate Similarity	NPC98225
0.8362	Intermediate Similarity	NPC471204
0.8362	Intermediate Similarity	NPC477126
0.8333	Intermediate Similarity	NPC100017
0.8333	Intermediate Similarity	NPC475500
0.8333	Intermediate Similarity	NPC471136
0.8333	Intermediate Similarity	NPC182266
0.8333	Intermediate Similarity	NPC223356
0.8333	Intermediate Similarity	NPC475154
0.8333	Intermediate Similarity	NPC473548
0.8333	Intermediate Similarity	NPC471137
0.8333	Intermediate Similarity	NPC475922
0.8319	Intermediate Similarity	NPC472667
0.8319	Intermediate Similarity	NPC156745
0.8319	Intermediate Similarity	NPC236918
0.8305	Intermediate Similarity	NPC478204
0.8305	Intermediate Similarity	NPC58662
0.8279	Intermediate Similarity	NPC145238
0.8264	Intermediate Similarity	NPC162009
0.8264	Intermediate Similarity	NPC170538
0.8264	Intermediate Similarity	NPC257017
0.8261	Intermediate Similarity	NPC161816
0.8261	Intermediate Similarity	NPC115257
0.825	Intermediate Similarity	NPC143755
0.8246	Intermediate Similarity	NPC327286
0.8246	Intermediate Similarity	NPC169888
0.8246	Intermediate Similarity	NPC55972
0.824	Intermediate Similarity	NPC473838
0.824	Intermediate Similarity	NPC475389
0.8235	Intermediate Similarity	NPC478206
0.8235	Intermediate Similarity	NPC478205
0.8235	Intermediate Similarity	NPC108581
0.823	Intermediate Similarity	NPC9303
0.823	Intermediate Similarity	NPC16313
0.822	Intermediate Similarity	NPC179626
0.822	Intermediate Similarity	NPC270478
0.8211	Intermediate Similarity	NPC293112
0.8203	Intermediate Similarity	NPC68282
0.8197	Intermediate Similarity	NPC472399
0.8197	Intermediate Similarity	NPC11895
0.819	Intermediate Similarity	NPC474846
0.819	Intermediate Similarity	NPC469655
0.819	Intermediate Similarity	NPC469656
0.8182	Intermediate Similarity	NPC310511
0.8175	Intermediate Similarity	NPC473485
0.8175	Intermediate Similarity	NPC475139
0.8175	Intermediate Similarity	NPC180902
0.8175	Intermediate Similarity	NPC474508
0.8174	Intermediate Similarity	NPC469370
0.8174	Intermediate Similarity	NPC15218
0.8158	Intermediate Similarity	NPC72813
0.8158	Intermediate Similarity	NPC194620
0.8158	Intermediate Similarity	NPC324327
0.8158	Intermediate Similarity	NPC474421
0.8158	Intermediate Similarity	NPC326994
0.8151	Intermediate Similarity	NPC10721
0.8151	Intermediate Similarity	NPC470775
0.8151	Intermediate Similarity	NPC176513
0.8151	Intermediate Similarity	NPC473590
0.8136	Intermediate Similarity	NPC226608
0.8136	Intermediate Similarity	NPC88867
0.8136	Intermediate Similarity	NPC117712
0.813	Intermediate Similarity	NPC81736
0.813	Intermediate Similarity	NPC172154
0.8125	Intermediate Similarity	NPC474709
0.812	Intermediate Similarity	NPC269530
0.8115	Intermediate Similarity	NPC19464
0.8103	Intermediate Similarity	NPC472215
0.8103	Intermediate Similarity	NPC253906
0.8103	Intermediate Similarity	NPC472214
0.8099	Intermediate Similarity	NPC251226
0.8095	Intermediate Similarity	NPC477189
0.8095	Intermediate Similarity	NPC251564
0.8095	Intermediate Similarity	NPC475606
0.8095	Intermediate Similarity	NPC475314
0.8087	Intermediate Similarity	NPC318363
0.8087	Intermediate Similarity	NPC233379
0.8087	Intermediate Similarity	NPC473482
0.8087	Intermediate Similarity	NPC14862
0.8087	Intermediate Similarity	NPC474664
0.8087	Intermediate Similarity	NPC475418
0.808	Intermediate Similarity	NPC476078
0.808	Intermediate Similarity	NPC476091
0.807	Intermediate Similarity	NPC470979
0.807	Intermediate Similarity	NPC470975
0.807	Intermediate Similarity	NPC475802
0.807	Intermediate Similarity	NPC103088
0.8067	Intermediate Similarity	NPC154363
0.8067	Intermediate Similarity	NPC470466
0.8067	Intermediate Similarity	NPC471127
0.8067	Intermediate Similarity	NPC234858
0.8053	Intermediate Similarity	NPC474166
0.8053	Intermediate Similarity	NPC19239
0.8053	Intermediate Similarity	NPC475321
0.8053	Intermediate Similarity	NPC4620
0.8051	Intermediate Similarity	NPC469496
0.8051	Intermediate Similarity	NPC469454
0.8051	Intermediate Similarity	NPC469463
0.8051	Intermediate Similarity	NPC89018
0.8051	Intermediate Similarity	NPC478212
0.8049	Intermediate Similarity	NPC67251
0.8049	Intermediate Similarity	NPC91693
0.8049	Intermediate Similarity	NPC105926
0.8049	Intermediate Similarity	NPC18945
0.8049	Intermediate Similarity	NPC469789
0.8049	Intermediate Similarity	NPC265557
0.8034	Intermediate Similarity	NPC304180
0.8034	Intermediate Similarity	NPC179798
0.8033	Intermediate Similarity	NPC477046
0.8033	Intermediate Similarity	NPC4021
0.8033	Intermediate Similarity	NPC470779
0.8033	Intermediate Similarity	NPC159456
0.8033	Intermediate Similarity	NPC472401
0.8033	Intermediate Similarity	NPC52839
0.8033	Intermediate Similarity	NPC102822
0.8017	Intermediate Similarity	NPC473839
0.8017	Intermediate Similarity	NPC211093
0.8017	Intermediate Similarity	NPC475065
0.8017	Intermediate Similarity	NPC473636
0.8017	Intermediate Similarity	NPC77689
0.8016	Intermediate Similarity	NPC231529
0.8016	Intermediate Similarity	NPC162495
0.8	Intermediate Similarity	NPC122033
0.8	Intermediate Similarity	NPC470854
0.8	Intermediate Similarity	NPC180744
0.8	Intermediate Similarity	NPC474654
0.8	Intermediate Similarity	NPC474518
0.8	Intermediate Similarity	NPC474716
0.8	Intermediate Similarity	NPC13713
0.8	Intermediate Similarity	NPC97908
0.8	Intermediate Similarity	NPC112780
0.8	Intermediate Similarity	NPC470780
0.8	Intermediate Similarity	NPC287343
0.7984	Intermediate Similarity	NPC8369
0.7984	Intermediate Similarity	NPC476729
0.7984	Intermediate Similarity	NPC24651
0.7983	Intermediate Similarity	NPC472400
0.7982	Intermediate Similarity	NPC220964
0.7982	Intermediate Similarity	NPC475676
0.7982	Intermediate Similarity	NPC283850
0.7967	Intermediate Similarity	NPC312833
0.7967	Intermediate Similarity	NPC470265
0.7967	Intermediate Similarity	NPC23786
0.7966	Intermediate Similarity	NPC317687
0.7966	Intermediate Similarity	NPC472002
0.7966	Intermediate Similarity	NPC476801
0.7965	Intermediate Similarity	NPC478156
0.7951	Intermediate Similarity	NPC185876
0.7951	Intermediate Similarity	NPC157252
0.7951	Intermediate Similarity	NPC4548
0.7951	Intermediate Similarity	NPC268530
0.7951	Intermediate Similarity	NPC471126
0.7951	Intermediate Similarity	NPC154491

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 NPC470186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1545
0.2-0.3	3591
0.3-0.4	2442
0.4-0.5	840
0.5-0.6	367
0.6-0.7	148
0.7-0.8	10
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
0.7931	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8513	Phase 3
0.76	Intermediate Similarity	NPD8515	Approved
0.76	Intermediate Similarity	NPD8516	Approved
0.76	Intermediate Similarity	NPD8517	Approved
0.7563	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7115	Discovery
0.7478	Intermediate Similarity	NPD6648	Approved
0.7477	Intermediate Similarity	NPD7983	Approved
0.7414	Intermediate Similarity	NPD5344	Discontinued
0.7395	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD6921	Approved
0.7308	Intermediate Similarity	NPD8074	Phase 3
0.7241	Intermediate Similarity	NPD4225	Approved
0.7197	Intermediate Similarity	NPD7319	Approved
0.7109	Intermediate Similarity	NPD6319	Approved
0.7107	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5778	Approved
0.7105	Intermediate Similarity	NPD5779	Approved
0.708	Intermediate Similarity	NPD6698	Approved
0.708	Intermediate Similarity	NPD46	Approved
0.708	Intermediate Similarity	NPD7838	Discovery
0.7073	Intermediate Similarity	NPD6371	Approved
0.7025	Intermediate Similarity	NPD6008	Approved
0.697	Remote Similarity	NPD7507	Approved
0.696	Remote Similarity	NPD8297	Approved
0.6947	Remote Similarity	NPD8328	Phase 3
0.6937	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6686	Approved
0.6894	Remote Similarity	NPD7492	Approved
0.6875	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6411	Approved
0.6866	Remote Similarity	NPD7736	Approved
0.6855	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6054	Approved
0.6842	Remote Similarity	NPD6616	Approved
0.6838	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7638	Approved
0.6791	Remote Similarity	NPD7078	Approved
0.6791	Remote Similarity	NPD8293	Discontinued
0.6772	Remote Similarity	NPD4632	Approved
0.6769	Remote Similarity	NPD7516	Approved
0.675	Remote Similarity	NPD7640	Approved
0.675	Remote Similarity	NPD7639	Approved
0.6746	Remote Similarity	NPD6649	Approved
0.6746	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6650	Approved
0.6742	Remote Similarity	NPD6370	Approved
0.6724	Remote Similarity	NPD7637	Suspended
0.672	Remote Similarity	NPD6373	Approved
0.672	Remote Similarity	NPD6372	Approved
0.6718	Remote Similarity	NPD6059	Approved
0.6715	Remote Similarity	NPD7260	Phase 2
0.6696	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6101	Approved
0.6694	Remote Similarity	NPD1700	Approved
0.6692	Remote Similarity	NPD7327	Approved
0.6692	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6641	Remote Similarity	NPD8133	Approved
0.664	Remote Similarity	NPD6899	Approved
0.664	Remote Similarity	NPD6881	Approved
0.6639	Remote Similarity	NPD7839	Suspended
0.6617	Remote Similarity	NPD5988	Approved
0.6614	Remote Similarity	NPD8130	Phase 1
0.6613	Remote Similarity	NPD6675	Approved
0.6613	Remote Similarity	NPD7128	Approved
0.6613	Remote Similarity	NPD6402	Approved
0.6613	Remote Similarity	NPD5739	Approved
0.661	Remote Similarity	NPD5282	Discontinued
0.6583	Remote Similarity	NPD7902	Approved
0.6567	Remote Similarity	NPD7604	Phase 2
0.6562	Remote Similarity	NPD6882	Approved
0.656	Remote Similarity	NPD5697	Approved
0.6541	Remote Similarity	NPD8379	Approved
0.6541	Remote Similarity	NPD8380	Approved
0.6541	Remote Similarity	NPD8378	Approved
0.6541	Remote Similarity	NPD7503	Approved
0.6541	Remote Similarity	NPD8033	Approved
0.6541	Remote Similarity	NPD8296	Approved
0.6541	Remote Similarity	NPD8335	Approved
0.6535	Remote Similarity	NPD6883	Approved
0.6535	Remote Similarity	NPD7102	Approved
0.6535	Remote Similarity	NPD4634	Approved
0.6535	Remote Similarity	NPD7290	Approved
0.6529	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD7320	Approved
0.6491	Remote Similarity	NPD1694	Approved
0.6489	Remote Similarity	NPD6009	Approved
0.6484	Remote Similarity	NPD6617	Approved
0.6484	Remote Similarity	NPD6847	Approved
0.6484	Remote Similarity	NPD6869	Approved
0.6479	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8273	Phase 1
0.6471	Remote Similarity	NPD7748	Approved
0.6471	Remote Similarity	NPD8451	Approved
0.6466	Remote Similarity	NPD8377	Approved
0.6466	Remote Similarity	NPD8294	Approved
0.6457	Remote Similarity	NPD6013	Approved
0.6457	Remote Similarity	NPD6014	Approved
0.6457	Remote Similarity	NPD6012	Approved
0.6444	Remote Similarity	NPD7829	Approved
0.6444	Remote Similarity	NPD7830	Approved
0.6434	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD6845	Suspended
0.6423	Remote Similarity	NPD8448	Approved
0.6418	Remote Similarity	NPD5983	Phase 2
0.6418	Remote Similarity	NPD8444	Approved
0.6379	Remote Similarity	NPD7524	Approved
0.6378	Remote Similarity	NPD6011	Approved
0.6356	Remote Similarity	NPD5785	Approved
0.635	Remote Similarity	NPD6336	Discontinued
0.6333	Remote Similarity	NPD7900	Approved
0.6333	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD7642	Approved
0.6303	Remote Similarity	NPD8034	Phase 2
0.6303	Remote Similarity	NPD8035	Phase 2
0.6299	Remote Similarity	NPD6412	Phase 2
0.6293	Remote Similarity	NPD5786	Approved
0.6286	Remote Similarity	NPD8391	Approved
0.6286	Remote Similarity	NPD8390	Approved
0.6286	Remote Similarity	NPD8392	Approved
0.6277	Remote Similarity	NPD8340	Approved
0.6277	Remote Similarity	NPD8341	Approved
0.6277	Remote Similarity	NPD8342	Approved
0.6277	Remote Similarity	NPD8299	Approved
0.6271	Remote Similarity	NPD1695	Approved
0.6259	Remote Similarity	NPD6033	Approved
0.625	Remote Similarity	NPD8407	Phase 2
0.624	Remote Similarity	NPD7632	Discontinued
0.624	Remote Similarity	NPD5211	Phase 2
0.6231	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD3168	Discontinued
0.621	Remote Similarity	NPD5286	Approved
0.621	Remote Similarity	NPD5285	Approved
0.621	Remote Similarity	NPD4696	Approved
0.6182	Remote Similarity	NPD8039	Approved
0.6179	Remote Similarity	NPD4755	Approved
0.6176	Remote Similarity	NPD8434	Phase 2
0.6168	Remote Similarity	NPD8368	Discontinued
0.6167	Remote Similarity	NPD5284	Approved
0.6167	Remote Similarity	NPD6079	Approved
0.6167	Remote Similarity	NPD5281	Approved
0.6167	Remote Similarity	NPD7515	Phase 2
0.6148	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7100	Approved
0.6148	Remote Similarity	NPD7101	Approved
0.6142	Remote Similarity	NPD5141	Approved
0.614	Remote Similarity	NPD5369	Approved
0.6134	Remote Similarity	NPD5328	Approved
0.6121	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5224	Approved
0.6111	Remote Similarity	NPD8415	Approved
0.6111	Remote Similarity	NPD5225	Approved
0.6111	Remote Similarity	NPD5226	Approved
0.6111	Remote Similarity	NPD4633	Approved
0.6102	Remote Similarity	NPD3573	Approved
0.6087	Remote Similarity	NPD4270	Approved
0.6087	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6435	Approved
0.6087	Remote Similarity	NPD4269	Approved
0.6087	Remote Similarity	NPD5209	Approved
0.608	Remote Similarity	NPD4700	Approved
0.6074	Remote Similarity	NPD6335	Approved
0.6069	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD5174	Approved
0.6063	Remote Similarity	NPD5175	Approved
0.6058	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6083	Phase 2
0.6048	Remote Similarity	NPD6084	Phase 2
0.6045	Remote Similarity	NPD6274	Approved
0.6034	Remote Similarity	NPD6695	Phase 3
0.6032	Remote Similarity	NPD5223	Approved
0.6024	Remote Similarity	NPD7799	Discontinued
0.6017	Remote Similarity	NPD3618	Phase 1
0.6016	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD4729	Approved
0.6	Remote Similarity	NPD4730	Approved
0.6	Remote Similarity	NPD6317	Approved
0.5984	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4786	Approved
0.5969	Remote Similarity	NPD4768	Approved
0.5969	Remote Similarity	NPD4767	Approved
0.5968	Remote Similarity	NPD5221	Approved
0.5968	Remote Similarity	NPD5222	Approved
0.5968	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD4697	Phase 3
0.5966	Remote Similarity	NPD7750	Discontinued
0.5966	Remote Similarity	NPD4251	Approved
0.5966	Remote Similarity	NPD4250	Approved
0.5956	Remote Similarity	NPD6313	Approved
0.5956	Remote Similarity	NPD7641	Discontinued
0.5956	Remote Similarity	NPD6314	Approved
0.595	Remote Similarity	NPD5207	Approved
0.5948	Remote Similarity	NPD3667	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