NPASS Compound

Structure

NPC473879 OpenBabel07101719522D 42 44 0 0 1 0 0 0 0 0999 V2000 7.1801 -0.1377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4672 1.0213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8855 0.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1290 2.5075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5254 2.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8199 1.5565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8418 1.3486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4891 0.8133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1945 1.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4598 3.2507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0388 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1727 2.0917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7688 4.2017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0388 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4817 3.0428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 34 1 0 0 0 0 9 34 1 0 0 0 0 12 13 1 0 0 0 0 12 14 2 0 0 0 0 13 23 2 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 22 2 0 0 0 0 17 19 1 0 0 0 0 17 30 1 0 0 0 0 18 20 1 0 0 0 0 18 32 1 0 0 0 0 19 36 1 0 0 0 0 20 35 1 0 0 0 0 21 29 1 0 0 0 0 21 31 1 0 0 0 0 23 28 1 0 0 0 0 24 33 2 0 0 0 0 25 37 2 0 0 0 0 25 40 1 0 0 0 0 26 38 2 0 0 0 0 26 41 1 0 0 0 0 27 39 2 0 0 0 0 27 42 1 0 0 0 0 28 16 1 1 0 0 0 28 40 1 0 0 0 0 29 33 1 0 0 0 0 29 41 1 1 0 0 0 30 34 1 0 0 0 0 30 35 1 6 0 0 0 31 35 1 1 0 0 0 31 36 1 0 0 0 0 32 34 1 0 0 0 0 32 42 1 6 0 0 0 33 36 1 0 0 0 0 35 10 1 6 0 0 0 36 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.39
Volume:	639.829
LogP:	6.876
LogD:	4.62
LogS:	-6.176
# Rotatable Bonds:	11
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.124
Synthetic Accessibility Score:	5.12
Fsp3:	0.694
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:	-4.724
MDCK Permeability:	4.780600647791289e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.18
Plasma Protein Binding (PPB):	99.21561431884766%
Volume Distribution (VD):	2.466
Pgp-substrate:	5.557539463043213%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.18
CYP2C19-substrate:	0.756
CYP2C9-inhibitor:	0.697
CYP2C9-substrate:	0.174
CYP2D6-inhibitor:	0.584
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.768
CYP3A4-substrate:	0.641

ADMET: Excretion

Clearance (CL):	3.502
Half-life (T1/2):	0.006

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.857
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.389
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.666
Carcinogencity:	0.159
Eye Corrosion:	0.89
Eye Irritation:	0.056
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC473879

Natural Product ID:	NPC473879
*Common Name:**	Acetic Acid (2S,3As,5Ar,7S,9Ar,9Bs)-2-Acetoxy-3-[(2E,4E)-(S)-6-Acetoxy-1,5,9-Trimethyl-Deca-2,4,8-Trien-(Z)-Ylidene]-3A,6,6,9A-Tetramethyl-Dodecahydro-Cyclopenta[A]Naphthalen-7-Yl Ester
IUPAC Name:	[(2S,3Z,3aS,5aR,7S,9aR,9bS)-2-acetyloxy-3-[(3E,5E,7S)-7-acetyloxy-6,10-dimethylundeca-3,5,9-trien-2-ylidene]-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-cyclopenta[a]naphthalen-7-yl] acetate
Synonyms:
Standard InCHIKey:	KIUCPARZJQMLDT-MFQPFHAFSA-N
Standard InCHI:	InChI=1S/C36H54O6/c1-22(2)15-16-28(40-25(5)37)23(3)13-12-14-24(4)33-29(41-26(6)38)21-31-35(10)20-18-32(42-27(7)39)34(8,9)30(35)17-19-36(31,33)11/h12-15,28-32H,16-21H2,1-11H3/b14-12+,23-13+,33-24+/t28-,29-,30-,31-,32-,35-,36-/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@@H]2[C@](/C/1=C(/C=C/C=C(/[C@@H](OC(=O)C)CC=C(C)C)C)C)(C)CC[C@@H]1[C@]2(C)CC[C@@H](C1(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454131
PubChem CID:	10722013
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691710]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	Kubat, Malaysia	1991	PMID[18327911]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778241]
NPO10924	Stelletta globostellata	Species	Ancorinidae	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
GI50	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	GI50	=	1600.0	nM	PMID[484340]
NPT27	Others	Unspecified		GI50	=	1300.0	nM	PMID[484340]

☑ 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 NPC473879 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	195
0.1-0.2	1098
0.2-0.3	4229
0.3-0.4	12842
0.4-0.5	10489
0.5-0.6	7506
0.6-0.7	5064
0.7-0.8	1195
0.8-0.85	69
0.85-0.9	9
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8901	High Similarity	NPC110937
0.8764	High Similarity	NPC177641
0.8621	High Similarity	NPC286153
0.8526	High Similarity	NPC155332
0.8526	High Similarity	NPC32577
0.8526	High Similarity	NPC114540
0.8506	High Similarity	NPC474013
0.8471	Intermediate Similarity	NPC25554
0.8421	Intermediate Similarity	NPC168319
0.8421	Intermediate Similarity	NPC194028
0.8391	Intermediate Similarity	NPC96055
0.8372	Intermediate Similarity	NPC471218
0.8353	Intermediate Similarity	NPC269791
0.8353	Intermediate Similarity	NPC469802
0.8333	Intermediate Similarity	NPC177141
0.8316	Intermediate Similarity	NPC266955
0.8315	Intermediate Similarity	NPC166857
0.8298	Intermediate Similarity	NPC2049
0.828	Intermediate Similarity	NPC474909
0.8276	Intermediate Similarity	NPC139206
0.8261	Intermediate Similarity	NPC205034
0.8261	Intermediate Similarity	NPC162615
0.8261	Intermediate Similarity	NPC152778
0.8247	Intermediate Similarity	NPC329345
0.8247	Intermediate Similarity	NPC473283
0.8247	Intermediate Similarity	NPC475526
0.8242	Intermediate Similarity	NPC302280
0.8242	Intermediate Similarity	NPC474842
0.8242	Intermediate Similarity	NPC310479
0.8242	Intermediate Similarity	NPC78973
0.8242	Intermediate Similarity	NPC475965
0.8235	Intermediate Similarity	NPC153987
0.8235	Intermediate Similarity	NPC44083
0.8229	Intermediate Similarity	NPC115899
0.8222	Intermediate Similarity	NPC472220
0.8222	Intermediate Similarity	NPC93411
0.8222	Intermediate Similarity	NPC97884
0.8211	Intermediate Similarity	NPC108368
0.8211	Intermediate Similarity	NPC57079
0.8202	Intermediate Similarity	NPC474970
0.8191	Intermediate Similarity	NPC16967
0.8172	Intermediate Similarity	NPC473431
0.8172	Intermediate Similarity	NPC473280
0.8172	Intermediate Similarity	NPC473435
0.8172	Intermediate Similarity	NPC471078
0.8163	Intermediate Similarity	NPC165969
0.8152	Intermediate Similarity	NPC234335
0.814	Intermediate Similarity	NPC233332
0.8132	Intermediate Similarity	NPC473647
0.8125	Intermediate Similarity	NPC473510
0.8105	Intermediate Similarity	NPC141401
0.81	Intermediate Similarity	NPC475418
0.81	Intermediate Similarity	NPC473482
0.81	Intermediate Similarity	NPC318363
0.809	Intermediate Similarity	NPC35933
0.8085	Intermediate Similarity	NPC471362
0.8085	Intermediate Similarity	NPC471372
0.8085	Intermediate Similarity	NPC472189
0.8068	Intermediate Similarity	NPC132386
0.8065	Intermediate Similarity	NPC473678
0.8065	Intermediate Similarity	NPC38232
0.8061	Intermediate Similarity	NPC171014
0.8046	Intermediate Similarity	NPC170303
0.8043	Intermediate Similarity	NPC273199
0.8043	Intermediate Similarity	NPC280149
0.8043	Intermediate Similarity	NPC221111
0.8043	Intermediate Similarity	NPC182136
0.8022	Intermediate Similarity	NPC470612
0.8022	Intermediate Similarity	NPC470613
0.8022	Intermediate Similarity	NPC477128
0.8022	Intermediate Similarity	NPC106332
0.802	Intermediate Similarity	NPC475065
0.802	Intermediate Similarity	NPC75389
0.8	Intermediate Similarity	NPC79298
0.8	Intermediate Similarity	NPC88009
0.8	Intermediate Similarity	NPC54248
0.8	Intermediate Similarity	NPC43063
0.8	Intermediate Similarity	NPC171598
0.8	Intermediate Similarity	NPC307164
0.8	Intermediate Similarity	NPC276103
0.8	Intermediate Similarity	NPC473153
0.8	Intermediate Similarity	NPC131813
0.8	Intermediate Similarity	NPC264127
0.7979	Intermediate Similarity	NPC120351
0.7979	Intermediate Similarity	NPC477129
0.7979	Intermediate Similarity	NPC477130
0.7979	Intermediate Similarity	NPC191521
0.7979	Intermediate Similarity	NPC166143
0.7979	Intermediate Similarity	NPC474922
0.7979	Intermediate Similarity	NPC471994
0.7979	Intermediate Similarity	NPC38830
0.7979	Intermediate Similarity	NPC470255
0.7978	Intermediate Similarity	NPC139566
0.7959	Intermediate Similarity	NPC476471
0.7959	Intermediate Similarity	NPC320447
0.7959	Intermediate Similarity	NPC475344
0.7957	Intermediate Similarity	NPC329842
0.7955	Intermediate Similarity	NPC286786
0.7955	Intermediate Similarity	NPC256112
0.7941	Intermediate Similarity	NPC16270
0.7938	Intermediate Similarity	NPC473204
0.7938	Intermediate Similarity	NPC251680
0.7938	Intermediate Similarity	NPC230546
0.7938	Intermediate Similarity	NPC472187
0.7938	Intermediate Similarity	NPC473545
0.7935	Intermediate Similarity	NPC246028
0.7935	Intermediate Similarity	NPC16265
0.7931	Intermediate Similarity	NPC304194
0.7931	Intermediate Similarity	NPC268827
0.7921	Intermediate Similarity	NPC275060
0.7917	Intermediate Similarity	NPC210337
0.7917	Intermediate Similarity	NPC472188
0.7912	Intermediate Similarity	NPC478104
0.7912	Intermediate Similarity	NPC131329
0.7907	Intermediate Similarity	NPC184737
0.79	Intermediate Similarity	NPC295843
0.79	Intermediate Similarity	NPC266570
0.7895	Intermediate Similarity	NPC281134
0.7895	Intermediate Similarity	NPC276110
0.7895	Intermediate Similarity	NPC33473
0.7889	Intermediate Similarity	NPC157257
0.7879	Intermediate Similarity	NPC72151
0.7879	Intermediate Similarity	NPC474124
0.7879	Intermediate Similarity	NPC297617
0.7879	Intermediate Similarity	NPC85742
0.7872	Intermediate Similarity	NPC53555
0.7872	Intermediate Similarity	NPC7349
0.7865	Intermediate Similarity	NPC23748
0.7865	Intermediate Similarity	NPC49208
0.7865	Intermediate Similarity	NPC476927
0.7865	Intermediate Similarity	NPC474789
0.7865	Intermediate Similarity	NPC52108
0.7857	Intermediate Similarity	NPC247701
0.7857	Intermediate Similarity	NPC222875
0.7857	Intermediate Similarity	NPC475617
0.7857	Intermediate Similarity	NPC298233
0.7857	Intermediate Similarity	NPC25177
0.7857	Intermediate Similarity	NPC295110
0.7857	Intermediate Similarity	NPC268829
0.7849	Intermediate Similarity	NPC161638
0.7849	Intermediate Similarity	NPC471896
0.7841	Intermediate Similarity	NPC195334
0.7841	Intermediate Similarity	NPC108476
0.7841	Intermediate Similarity	NPC290495
0.7841	Intermediate Similarity	NPC142163
0.7835	Intermediate Similarity	NPC471366
0.7835	Intermediate Similarity	NPC278673
0.7835	Intermediate Similarity	NPC474440
0.7835	Intermediate Similarity	NPC252295
0.7835	Intermediate Similarity	NPC472186
0.7835	Intermediate Similarity	NPC476800
0.7835	Intermediate Similarity	NPC318917
0.7835	Intermediate Similarity	NPC92275
0.7826	Intermediate Similarity	NPC471952
0.7822	Intermediate Similarity	NPC329048
0.7822	Intermediate Similarity	NPC330011
0.7822	Intermediate Similarity	NPC473284
0.7816	Intermediate Similarity	NPC242767
0.7816	Intermediate Similarity	NPC305835
0.7816	Intermediate Similarity	NPC47808
0.7812	Intermediate Similarity	NPC94905
0.7812	Intermediate Similarity	NPC8954
0.7812	Intermediate Similarity	NPC304899
0.7812	Intermediate Similarity	NPC253115
0.7812	Intermediate Similarity	NPC122324
0.7812	Intermediate Similarity	NPC475178
0.7812	Intermediate Similarity	NPC151725
0.7812	Intermediate Similarity	NPC190713
0.7812	Intermediate Similarity	NPC301534
0.7812	Intermediate Similarity	NPC106425
0.7812	Intermediate Similarity	NPC250757
0.7802	Intermediate Similarity	NPC102996
0.7802	Intermediate Similarity	NPC329692
0.78	Intermediate Similarity	NPC272632
0.78	Intermediate Similarity	NPC473543
0.7791	Intermediate Similarity	NPC189206
0.7789	Intermediate Similarity	NPC140277
0.7789	Intermediate Similarity	NPC88507
0.7789	Intermediate Similarity	NPC105490
0.7789	Intermediate Similarity	NPC201725
0.7788	Intermediate Similarity	NPC44537
0.7778	Intermediate Similarity	NPC470077
0.7778	Intermediate Similarity	NPC306951
0.7778	Intermediate Similarity	NPC11956
0.7767	Intermediate Similarity	NPC238850
0.7767	Intermediate Similarity	NPC103491
0.7766	Intermediate Similarity	NPC49420
0.7766	Intermediate Similarity	NPC72845
0.7766	Intermediate Similarity	NPC472811
0.7766	Intermediate Similarity	NPC26888
0.7766	Intermediate Similarity	NPC477574
0.7755	Intermediate Similarity	NPC470906
0.7755	Intermediate Similarity	NPC476303
0.7753	Intermediate Similarity	NPC470049
0.7745	Intermediate Similarity	NPC137462
0.7745	Intermediate Similarity	NPC304276
0.7742	Intermediate Similarity	NPC475049
0.7742	Intermediate Similarity	NPC20946
0.7742	Intermediate Similarity	NPC293044
0.7742	Intermediate Similarity	NPC82876

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 NPC473879 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1170
0.2-0.3	3824
0.3-0.4	2668
0.4-0.5	829
0.5-0.6	241
0.6-0.7	223
0.7-0.8	33
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8132	Intermediate Similarity	NPD6051	Approved
0.8021	Intermediate Similarity	NPD7638	Approved
0.7938	Intermediate Similarity	NPD7640	Approved
0.7938	Intermediate Similarity	NPD7639	Approved
0.7419	Intermediate Similarity	NPD7334	Approved
0.7419	Intermediate Similarity	NPD7521	Approved
0.7419	Intermediate Similarity	NPD6684	Approved
0.7419	Intermediate Similarity	NPD5330	Approved
0.7419	Intermediate Similarity	NPD6409	Approved
0.7419	Intermediate Similarity	NPD7146	Approved
0.7396	Intermediate Similarity	NPD7637	Suspended
0.7363	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6399	Phase 3
0.73	Intermediate Similarity	NPD4225	Approved
0.7263	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6903	Approved
0.7255	Intermediate Similarity	NPD7632	Discontinued
0.7159	Intermediate Similarity	NPD8039	Approved
0.7143	Intermediate Similarity	NPD7525	Registered
0.7128	Intermediate Similarity	NPD1694	Approved
0.7097	Intermediate Similarity	NPD6695	Phase 3
0.7083	Intermediate Similarity	NPD5737	Approved
0.7083	Intermediate Similarity	NPD6672	Approved
0.7079	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7900	Approved
0.7071	Intermediate Similarity	NPD7748	Approved
0.7045	Intermediate Similarity	NPD6924	Approved
0.7045	Intermediate Similarity	NPD6926	Approved
0.7041	Intermediate Similarity	NPD8034	Phase 2
0.7041	Intermediate Similarity	NPD8035	Phase 2
0.7041	Intermediate Similarity	NPD5693	Phase 1
0.7027	Intermediate Similarity	NPD7115	Discovery
0.7021	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7150	Approved
0.7011	Intermediate Similarity	NPD7151	Approved
0.7011	Intermediate Similarity	NPD7152	Approved
0.7	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7750	Discontinued
0.6966	Remote Similarity	NPD7339	Approved
0.6966	Remote Similarity	NPD8264	Approved
0.6966	Remote Similarity	NPD6942	Approved
0.693	Remote Similarity	NPD8033	Approved
0.693	Remote Similarity	NPD7503	Approved
0.6916	Remote Similarity	NPD6899	Approved
0.6916	Remote Similarity	NPD6881	Approved
0.6897	Remote Similarity	NPD7143	Approved
0.6897	Remote Similarity	NPD7144	Approved
0.6893	Remote Similarity	NPD6648	Approved
0.6889	Remote Similarity	NPD6933	Approved
0.6887	Remote Similarity	NPD6402	Approved
0.6887	Remote Similarity	NPD6008	Approved
0.6887	Remote Similarity	NPD5739	Approved
0.6887	Remote Similarity	NPD7128	Approved
0.6887	Remote Similarity	NPD6675	Approved
0.6881	Remote Similarity	NPD8130	Phase 1
0.6875	Remote Similarity	NPD6098	Approved
0.6869	Remote Similarity	NPD5694	Approved
0.6869	Remote Similarity	NPD6050	Approved
0.6863	Remote Similarity	NPD7902	Approved
0.6848	Remote Similarity	NPD6929	Approved
0.6842	Remote Similarity	NPD4786	Approved
0.6842	Remote Similarity	NPD3668	Phase 3
0.6842	Remote Similarity	NPD8294	Approved
0.6842	Remote Similarity	NPD8377	Approved
0.6837	Remote Similarity	NPD6673	Approved
0.6837	Remote Similarity	NPD6080	Approved
0.6837	Remote Similarity	NPD6904	Approved
0.6822	Remote Similarity	NPD5697	Approved
0.6818	Remote Similarity	NPD8297	Approved
0.6814	Remote Similarity	NPD7327	Approved
0.6814	Remote Similarity	NPD7328	Approved
0.6809	Remote Similarity	NPD3667	Approved
0.6804	Remote Similarity	NPD7524	Approved
0.6789	Remote Similarity	NPD7102	Approved
0.6789	Remote Similarity	NPD7290	Approved
0.6789	Remote Similarity	NPD6883	Approved
0.6783	Remote Similarity	NPD8380	Approved
0.6783	Remote Similarity	NPD8296	Approved
0.6783	Remote Similarity	NPD8379	Approved
0.6783	Remote Similarity	NPD8378	Approved
0.6783	Remote Similarity	NPD8335	Approved
0.6782	Remote Similarity	NPD6923	Approved
0.6782	Remote Similarity	NPD6922	Approved
0.6774	Remote Similarity	NPD6931	Approved
0.6774	Remote Similarity	NPD6930	Phase 2
0.6774	Remote Similarity	NPD7514	Phase 3
0.6771	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5692	Phase 3
0.6768	Remote Similarity	NPD5207	Approved
0.6759	Remote Similarity	NPD7320	Approved
0.6759	Remote Similarity	NPD6011	Approved
0.6754	Remote Similarity	NPD7516	Approved
0.6739	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7145	Approved
0.6727	Remote Similarity	NPD6869	Approved
0.6727	Remote Similarity	NPD6649	Approved
0.6727	Remote Similarity	NPD6847	Approved
0.6727	Remote Similarity	NPD6617	Approved
0.6727	Remote Similarity	NPD6650	Approved
0.6702	Remote Similarity	NPD6902	Approved
0.6701	Remote Similarity	NPD3618	Phase 1
0.67	Remote Similarity	NPD6079	Approved
0.67	Remote Similarity	NPD7515	Phase 2
0.67	Remote Similarity	NPD6411	Approved
0.6699	Remote Similarity	NPD6083	Phase 2
0.6699	Remote Similarity	NPD6084	Phase 2
0.6697	Remote Similarity	NPD6013	Approved
0.6697	Remote Similarity	NPD6014	Approved
0.6697	Remote Similarity	NPD6373	Approved
0.6697	Remote Similarity	NPD6372	Approved
0.6697	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD5701	Approved
0.6634	Remote Similarity	NPD5779	Approved
0.6634	Remote Similarity	NPD5778	Approved
0.6633	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3573	Approved
0.6632	Remote Similarity	NPD5209	Approved
0.663	Remote Similarity	NPD6925	Approved
0.663	Remote Similarity	NPD5776	Phase 2
0.663	Remote Similarity	NPD6932	Approved
0.66	Remote Similarity	NPD5785	Approved
0.6598	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7509	Discontinued
0.6596	Remote Similarity	NPD7332	Phase 2
0.6577	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6001	Approved
0.6566	Remote Similarity	NPD5208	Approved
0.6562	Remote Similarity	NPD5362	Discontinued
0.6535	Remote Similarity	NPD7087	Discontinued
0.6535	Remote Similarity	NPD5284	Approved
0.6535	Remote Similarity	NPD5281	Approved
0.6509	Remote Similarity	NPD5344	Discontinued
0.6505	Remote Similarity	NPD5695	Phase 3
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6101	Approved
0.6495	Remote Similarity	NPD3665	Phase 1
0.6495	Remote Similarity	NPD3666	Approved
0.6495	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD3133	Approved
0.6489	Remote Similarity	NPD4195	Approved
0.6476	Remote Similarity	NPD5696	Approved
0.6471	Remote Similarity	NPD4202	Approved
0.6449	Remote Similarity	NPD5211	Phase 2
0.6444	Remote Similarity	NPD4243	Approved
0.6442	Remote Similarity	NPD5222	Approved
0.6442	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5221	Approved
0.6442	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7838	Discovery
0.6429	Remote Similarity	NPD6893	Approved
0.6421	Remote Similarity	NPD4819	Approved
0.6421	Remote Similarity	NPD4821	Approved
0.6421	Remote Similarity	NPD4822	Approved
0.6421	Remote Similarity	NPD4820	Approved
0.6417	Remote Similarity	NPD7507	Approved
0.6415	Remote Similarity	NPD5285	Approved
0.6415	Remote Similarity	NPD5286	Approved
0.6415	Remote Similarity	NPD4696	Approved
0.6392	Remote Similarity	NPD7154	Phase 3
0.6392	Remote Similarity	NPD5331	Approved
0.6392	Remote Similarity	NPD5332	Approved
0.6383	Remote Similarity	NPD4268	Approved
0.6383	Remote Similarity	NPD4271	Approved
0.6383	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5173	Approved
0.6381	Remote Similarity	NPD4755	Approved
0.6379	Remote Similarity	NPD6335	Approved
0.6364	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4159	Approved
0.6355	Remote Similarity	NPD5223	Approved
0.6354	Remote Similarity	NPD4790	Discontinued
0.6348	Remote Similarity	NPD6868	Approved
0.6346	Remote Similarity	NPD5654	Approved
0.633	Remote Similarity	NPD5141	Approved
0.6325	Remote Similarity	NPD7101	Approved
0.6325	Remote Similarity	NPD7100	Approved
0.6322	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6683	Phase 2
0.6316	Remote Similarity	NPD4632	Approved
0.6316	Remote Similarity	NPD6858	Approved
0.6316	Remote Similarity	NPD7094	Approved
0.6306	Remote Similarity	NPD6686	Approved
0.6296	Remote Similarity	NPD5226	Approved
0.6296	Remote Similarity	NPD5224	Approved
0.6296	Remote Similarity	NPD4633	Approved
0.6296	Remote Similarity	NPD5225	Approved
0.6293	Remote Similarity	NPD6317	Approved
0.6289	Remote Similarity	NPD4270	Approved
0.6289	Remote Similarity	NPD4269	Approved
0.6286	Remote Similarity	NPD4697	Phase 3
0.6264	Remote Similarity	NPD5777	Approved
0.6262	Remote Similarity	NPD4700	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