NPASS Compound

Structure

CID216420 OpenBabel06191716002D 32 35 0 0 1 0 0 0 0 0999 V2000 -5.8145 3.0537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2759 3.8970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3023 5.5845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8924 4.7419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5346 3.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8408 4.7413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3535 3.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2222 2.4361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2220 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8452 2.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6899 2.9244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 1.4630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8441 -0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3018 3.8972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8149 4.7410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3793 3.8981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6879 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3790 2.9239 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5340 1.4620 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8450 1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6894 0.9747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6891 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8444 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5343 2.4366 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9752 0.0000 C 0 0 1 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 2.5541 -0.4993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5550 -0.5007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8441 -1.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0000 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 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 18 4 1 1 0 0 0 18 20 1 0 0 0 0 19 29 1 6 0 0 0 20 26 1 6 0 0 0 21 23 1 0 0 0 0 21 26 1 6 0 0 0 22 23 1 0 0 0 0 22 27 1 6 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 24 30 1 0 0 0 0 25 28 1 0 0 0 0 25 31 1 0 0 0 0 27 28 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.36
Volume:	491.143
LogP:	4.966
LogD:	5.024
LogS:	-4.418
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	4.884
Fsp3:	0.929
Lipinski Rule-of-5:	Accepted
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:	-4.728
MDCK Permeability:	3.390091660548933e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.702
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.863
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	96.18013000488281%
Volume Distribution (VD):	0.913
Pgp-substrate:	2.2524735927581787%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.333
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.875
CYP2C9-inhibitor:	0.114
CYP2C9-substrate:	0.24
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.464
CYP3A4-inhibitor:	0.313
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	6.35
Half-life (T1/2):	0.251

ADMET: Toxicity

hERG Blockers:	0.399
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.12
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.721
Carcinogencity:	0.021
Eye Corrosion:	0.011
Eye Irritation:	0.039
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC216420

Natural Product ID:	NPC216420
*Common Name:**	Ergost-24(28)-Ene-3-Beta,5-Alpha,6-Beta,7-Beta-Tetrol
IUPAC Name:	(3S,5R,6R,7R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5,6,7-tetrol
Synonyms:
Standard InCHIKey:	CSEIKYIGVBFUKD-MISHLHQHSA-N
Standard InCHI:	InChI=1S/C28H48O4/c1-16(2)17(3)7-8-18(4)20-9-10-21-23-22(12-13-26(20,21)5)27(6)14-11-19(29)15-28(27,32)25(31)24(23)30/h16,18-25,29-32H,3,7-15H2,1-2,4-6H3/t18-,19+,20-,21+,22+,23+,24-,25-,26-,27-,28+/m1/s1
SMILES:	CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@@H](C[C@@]1([C@@H]([C@@H]3O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520370
PubChem CID:	11037703
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*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
NPO9839	Polanisia dodecandra	Species	Cleomaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[1453183]
NPO32508	plexaura sp.	Species	Plexauridae	Eukaryota	n.a.	Bahamas	n.a.	PMID[16124770]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17689080]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	seed	n.a.	PMID[18449498]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24767839]
NPO9839	Polanisia dodecandra	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623025]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4070	Eupatorium sternbergianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9636	Micromonospora coerulea	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12496	Elsholtzia blanda	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9839	Polanisia dodecandra	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6821	Tricholoma muscarium	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11588	Astragalus sevangensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10954	Topsentia genitrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1260	Chlorosplenium aeruginosum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5679	Topsentia roquensis	Species	n.a.	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
EC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1794	Individual Protein	LXR-alpha	Homo sapiens	EC50	=	170.0	nM	PMID[538424]

☑ 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 NPC216420 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	202
0.1-0.2	2196
0.2-0.3	7371
0.3-0.4	15282
0.4-0.5	7064
0.5-0.6	4469
0.6-0.7	4360
0.7-0.8	1483
0.8-0.85	188
0.85-0.9	65
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC85095
1.0	High Similarity	NPC211135
0.9625	High Similarity	NPC121981
0.9375	High Similarity	NPC255882
0.9351	High Similarity	NPC31828
0.9268	High Similarity	NPC477600
0.925	High Similarity	NPC232023
0.9157	High Similarity	NPC473436
0.9114	High Similarity	NPC475679
0.9091	High Similarity	NPC91573
0.9059	High Similarity	NPC219516
0.9048	High Similarity	NPC109744
0.9012	High Similarity	NPC207013
0.9012	High Similarity	NPC470929
0.8987	High Similarity	NPC475727
0.8987	High Similarity	NPC116119
0.8987	High Similarity	NPC472742
0.8987	High Similarity	NPC80297
0.8961	High Similarity	NPC3403
0.8961	High Similarity	NPC243027
0.8961	High Similarity	NPC158208
0.8961	High Similarity	NPC196136
0.8941	High Similarity	NPC475751
0.8941	High Similarity	NPC473956
0.8916	High Similarity	NPC71520
0.8916	High Similarity	NPC201273
0.8916	High Similarity	NPC269058
0.8902	High Similarity	NPC86238
0.8875	High Similarity	NPC71535
0.8875	High Similarity	NPC78545
0.8861	High Similarity	NPC301707
0.8861	High Similarity	NPC102708
0.8861	High Similarity	NPC477819
0.8861	High Similarity	NPC477817
0.8831	High Similarity	NPC10476
0.8831	High Similarity	NPC192501
0.8831	High Similarity	NPC228994
0.8831	High Similarity	NPC472503
0.8831	High Similarity	NPC308440
0.881	High Similarity	NPC186145
0.881	High Similarity	NPC474657
0.8734	High Similarity	NPC105208
0.8734	High Similarity	NPC128951
0.8734	High Similarity	NPC302578
0.8734	High Similarity	NPC192046
0.8734	High Similarity	NPC202540
0.8734	High Similarity	NPC477227
0.8706	High Similarity	NPC475664
0.869	High Similarity	NPC6605
0.8675	High Similarity	NPC256567
0.8659	High Similarity	NPC477599
0.8659	High Similarity	NPC30166
0.8642	High Similarity	NPC236237
0.8642	High Similarity	NPC13554
0.8642	High Similarity	NPC322313
0.8642	High Similarity	NPC102253
0.8625	High Similarity	NPC18857
0.8625	High Similarity	NPC147993
0.8625	High Similarity	NPC67657
0.8621	High Similarity	NPC41554
0.8621	High Similarity	NPC97404
0.8621	High Similarity	NPC275671
0.8608	High Similarity	NPC163597
0.8608	High Similarity	NPC14112
0.8608	High Similarity	NPC278091
0.8608	High Similarity	NPC78067
0.8608	High Similarity	NPC86305
0.8608	High Similarity	NPC93662
0.8605	High Similarity	NPC470361
0.8605	High Similarity	NPC105495
0.8571	High Similarity	NPC111234
0.8556	High Similarity	NPC170978
0.8554	High Similarity	NPC110778
0.8554	High Similarity	NPC113978
0.8519	High Similarity	NPC24504
0.8519	High Similarity	NPC476316
0.8519	High Similarity	NPC80530
0.8519	High Similarity	NPC273410
0.8506	High Similarity	NPC3345
0.8506	High Similarity	NPC291484
0.8506	High Similarity	NPC10274
0.8506	High Similarity	NPC11216
0.8506	High Similarity	NPC204188
0.8506	High Similarity	NPC329596
0.8506	High Similarity	NPC80561
0.85	High Similarity	NPC185915
0.8488	Intermediate Similarity	NPC474668
0.8488	Intermediate Similarity	NPC133588
0.8481	Intermediate Similarity	NPC104387
0.8481	Intermediate Similarity	NPC240235
0.8481	Intermediate Similarity	NPC317242
0.8481	Intermediate Similarity	NPC178383
0.8481	Intermediate Similarity	NPC70982
0.8481	Intermediate Similarity	NPC230704
0.8481	Intermediate Similarity	NPC103822
0.8481	Intermediate Similarity	NPC212879
0.8481	Intermediate Similarity	NPC185536
0.8481	Intermediate Similarity	NPC231256
0.8471	Intermediate Similarity	NPC94462
0.8462	Intermediate Similarity	NPC95165
0.8444	Intermediate Similarity	NPC471903
0.8442	Intermediate Similarity	NPC45296
0.8434	Intermediate Similarity	NPC7988
0.8427	Intermediate Similarity	NPC277399
0.8415	Intermediate Similarity	NPC236112
0.8415	Intermediate Similarity	NPC47149
0.8409	Intermediate Similarity	NPC210268
0.8395	Intermediate Similarity	NPC244385
0.8395	Intermediate Similarity	NPC138621
0.8395	Intermediate Similarity	NPC472499
0.8395	Intermediate Similarity	NPC472342
0.8395	Intermediate Similarity	NPC475
0.8395	Intermediate Similarity	NPC6978
0.8395	Intermediate Similarity	NPC472502
0.8395	Intermediate Similarity	NPC285761
0.8395	Intermediate Similarity	NPC472501
0.8395	Intermediate Similarity	NPC472500
0.8395	Intermediate Similarity	NPC167037
0.8395	Intermediate Similarity	NPC42853
0.8375	Intermediate Similarity	NPC63958
0.8372	Intermediate Similarity	NPC470620
0.8354	Intermediate Similarity	NPC25511
0.8354	Intermediate Similarity	NPC196358
0.8354	Intermediate Similarity	NPC145552
0.8354	Intermediate Similarity	NPC62657
0.8354	Intermediate Similarity	NPC5046
0.8354	Intermediate Similarity	NPC192638
0.8354	Intermediate Similarity	NPC49168
0.8354	Intermediate Similarity	NPC254509
0.8354	Intermediate Similarity	NPC304499
0.8352	Intermediate Similarity	NPC476040
0.8352	Intermediate Similarity	NPC476021
0.8352	Intermediate Similarity	NPC477226
0.8352	Intermediate Similarity	NPC316604
0.8352	Intermediate Similarity	NPC474994
0.8333	Intermediate Similarity	NPC477818
0.8333	Intermediate Similarity	NPC193870
0.8333	Intermediate Similarity	NPC141941
0.8315	Intermediate Similarity	NPC291373
0.8313	Intermediate Similarity	NPC470383
0.8313	Intermediate Similarity	NPC474531
0.8313	Intermediate Similarity	NPC157655
0.8312	Intermediate Similarity	NPC470833
0.8312	Intermediate Similarity	NPC66407
0.8312	Intermediate Similarity	NPC107919
0.8295	Intermediate Similarity	NPC46758
0.8293	Intermediate Similarity	NPC49599
0.8293	Intermediate Similarity	NPC477282
0.8293	Intermediate Similarity	NPC49627
0.8293	Intermediate Similarity	NPC81074
0.8293	Intermediate Similarity	NPC287452
0.8276	Intermediate Similarity	NPC67872
0.8272	Intermediate Similarity	NPC331618
0.8272	Intermediate Similarity	NPC212241
0.8272	Intermediate Similarity	NPC248830
0.8272	Intermediate Similarity	NPC138502
0.8272	Intermediate Similarity	NPC257191
0.8272	Intermediate Similarity	NPC307336
0.8272	Intermediate Similarity	NPC119355
0.8272	Intermediate Similarity	NPC260301
0.8256	Intermediate Similarity	NPC145245
0.8256	Intermediate Similarity	NPC237344
0.8256	Intermediate Similarity	NPC6391
0.8256	Intermediate Similarity	NPC299068
0.8256	Intermediate Similarity	NPC24277
0.825	Intermediate Similarity	NPC200243
0.8242	Intermediate Similarity	NPC111834
0.8242	Intermediate Similarity	NPC169270
0.8242	Intermediate Similarity	NPC472989
0.8242	Intermediate Similarity	NPC288970
0.8242	Intermediate Similarity	NPC292718
0.8242	Intermediate Similarity	NPC306797
0.8235	Intermediate Similarity	NPC242016
0.8235	Intermediate Similarity	NPC475798
0.8235	Intermediate Similarity	NPC299963
0.8235	Intermediate Similarity	NPC124172
0.8235	Intermediate Similarity	NPC127606
0.8228	Intermediate Similarity	NPC153719
0.8228	Intermediate Similarity	NPC470610
0.8228	Intermediate Similarity	NPC195489
0.8222	Intermediate Similarity	NPC65402
0.8222	Intermediate Similarity	NPC127718
0.8214	Intermediate Similarity	NPC154043
0.8214	Intermediate Similarity	NPC202688
0.8214	Intermediate Similarity	NPC60018
0.8193	Intermediate Similarity	NPC22403
0.8193	Intermediate Similarity	NPC16449
0.8191	Intermediate Similarity	NPC52585
0.8191	Intermediate Similarity	NPC228049
0.8191	Intermediate Similarity	NPC68630
0.8182	Intermediate Similarity	NPC101886
0.8182	Intermediate Similarity	NPC187785
0.8182	Intermediate Similarity	NPC74258
0.8182	Intermediate Similarity	NPC259875
0.8182	Intermediate Similarity	NPC244790
0.8152	Intermediate Similarity	NPC476893
0.8152	Intermediate Similarity	NPC274793
0.8148	Intermediate Similarity	NPC38141
0.8148	Intermediate Similarity	NPC237460
0.814	Intermediate Similarity	NPC470360

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 NPC216420 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	2599
0.2-0.3	4165
0.3-0.4	1508
0.4-0.5	338
0.5-0.6	144
0.6-0.7	185
0.7-0.8	40
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD7525	Registered
0.8312	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7524	Approved
0.7614	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6942	Approved
0.759	Intermediate Similarity	NPD7339	Approved
0.7558	Intermediate Similarity	NPD6930	Phase 2
0.7558	Intermediate Similarity	NPD6931	Approved
0.7528	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6933	Approved
0.75	Intermediate Similarity	NPD6695	Phase 3
0.7442	Intermediate Similarity	NPD7645	Phase 2
0.7442	Intermediate Similarity	NPD6929	Approved
0.7412	Intermediate Similarity	NPD6932	Approved
0.7294	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6924	Approved
0.7262	Intermediate Similarity	NPD6926	Approved
0.7241	Intermediate Similarity	NPD6683	Phase 2
0.7234	Intermediate Similarity	NPD8035	Phase 2
0.7234	Intermediate Similarity	NPD8034	Phase 2
0.7209	Intermediate Similarity	NPD6925	Approved
0.7209	Intermediate Similarity	NPD5776	Phase 2
0.7174	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7750	Discontinued
0.7159	Intermediate Similarity	NPD7514	Phase 3
0.7143	Intermediate Similarity	NPD6893	Approved
0.7126	Intermediate Similarity	NPD7145	Approved
0.7126	Intermediate Similarity	NPD6697	Approved
0.7126	Intermediate Similarity	NPD6115	Approved
0.7126	Intermediate Similarity	NPD6118	Approved
0.7126	Intermediate Similarity	NPD6114	Approved
0.7111	Intermediate Similarity	NPD4788	Approved
0.7108	Intermediate Similarity	NPD4787	Phase 1
0.7064	Intermediate Similarity	NPD7516	Approved
0.7041	Intermediate Similarity	NPD4755	Approved
0.7033	Intermediate Similarity	NPD4786	Approved
0.7024	Intermediate Similarity	NPD4243	Approved
0.7021	Intermediate Similarity	NPD5328	Approved
0.7011	Intermediate Similarity	NPD6116	Phase 1
0.6979	Remote Similarity	NPD4202	Approved
0.6972	Remote Similarity	NPD7328	Approved
0.6972	Remote Similarity	NPD7327	Approved
0.697	Remote Similarity	NPD7638	Approved
0.6966	Remote Similarity	NPD4748	Discontinued
0.6966	Remote Similarity	NPD7509	Discontinued
0.6966	Remote Similarity	NPD7332	Phase 2
0.6952	Remote Similarity	NPD4634	Approved
0.69	Remote Similarity	NPD5286	Approved
0.69	Remote Similarity	NPD4700	Approved
0.69	Remote Similarity	NPD4696	Approved
0.69	Remote Similarity	NPD5285	Approved
0.69	Remote Similarity	NPD7640	Approved
0.69	Remote Similarity	NPD7639	Approved
0.6897	Remote Similarity	NPD6117	Approved
0.6889	Remote Similarity	NPD6902	Approved
0.6889	Remote Similarity	NPD6898	Phase 1
0.6882	Remote Similarity	NPD3618	Phase 1
0.6875	Remote Similarity	NPD6079	Approved
0.6875	Remote Similarity	NPD7087	Discontinued
0.686	Remote Similarity	NPD4784	Approved
0.686	Remote Similarity	NPD4785	Approved
0.6824	Remote Similarity	NPD7152	Approved
0.6824	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7151	Approved
0.6824	Remote Similarity	NPD7150	Approved
0.6824	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3667	Approved
0.679	Remote Similarity	NPD371	Approved
0.6786	Remote Similarity	NPD8380	Approved
0.6786	Remote Similarity	NPD8296	Approved
0.6786	Remote Similarity	NPD6923	Approved
0.6786	Remote Similarity	NPD8379	Approved
0.6786	Remote Similarity	NPD8335	Approved
0.6786	Remote Similarity	NPD6922	Approved
0.6786	Remote Similarity	NPD8378	Approved
0.6782	Remote Similarity	NPD3703	Phase 2
0.6778	Remote Similarity	NPD6928	Phase 2
0.6765	Remote Similarity	NPD5211	Phase 2
0.6765	Remote Similarity	NPD5225	Approved
0.6765	Remote Similarity	NPD5226	Approved
0.6765	Remote Similarity	NPD5224	Approved
0.6765	Remote Similarity	NPD4633	Approved
0.6759	Remote Similarity	NPD8133	Approved
0.6731	Remote Similarity	NPD6402	Approved
0.6731	Remote Similarity	NPD7128	Approved
0.6731	Remote Similarity	NPD5739	Approved
0.6731	Remote Similarity	NPD6675	Approved
0.6706	Remote Similarity	NPD7144	Approved
0.6706	Remote Similarity	NPD7143	Approved
0.6699	Remote Similarity	NPD5174	Approved
0.6699	Remote Similarity	NPD5175	Approved
0.6696	Remote Similarity	NPD8377	Approved
0.6696	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD8033	Approved
0.6635	Remote Similarity	NPD5141	Approved
0.6633	Remote Similarity	NPD6399	Phase 3
0.6633	Remote Similarity	NPD8171	Discontinued
0.6606	Remote Similarity	NPD4632	Approved
0.6604	Remote Similarity	NPD7320	Approved
0.6604	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6899	Approved
0.6604	Remote Similarity	NPD6881	Approved
0.66	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5222	Approved
0.66	Remote Similarity	NPD5221	Approved
0.66	Remote Similarity	NPD4697	Phase 3
0.6591	Remote Similarity	NPD4190	Phase 3
0.6591	Remote Similarity	NPD5275	Approved
0.6588	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4767	Approved
0.6571	Remote Similarity	NPD4768	Approved
0.6542	Remote Similarity	NPD6373	Approved
0.6542	Remote Similarity	NPD6372	Approved
0.6542	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4754	Approved
0.6535	Remote Similarity	NPD5173	Approved
0.6531	Remote Similarity	NPD7515	Phase 2
0.6514	Remote Similarity	NPD8297	Approved
0.6509	Remote Similarity	NPD6412	Phase 2
0.6509	Remote Similarity	NPD5701	Approved
0.6509	Remote Similarity	NPD5697	Approved
0.6489	Remote Similarity	NPD3133	Approved
0.6489	Remote Similarity	NPD3666	Approved
0.6489	Remote Similarity	NPD3665	Phase 1
0.6484	Remote Similarity	NPD4195	Approved
0.6481	Remote Similarity	NPD7290	Approved
0.6481	Remote Similarity	NPD7102	Approved
0.6481	Remote Similarity	NPD6883	Approved
0.6471	Remote Similarity	NPD5360	Phase 3
0.6471	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4729	Approved
0.6449	Remote Similarity	NPD4730	Approved
0.6449	Remote Similarity	NPD5128	Approved
0.6442	Remote Similarity	NPD7632	Discontinued
0.6422	Remote Similarity	NPD8130	Phase 1
0.6422	Remote Similarity	NPD6650	Approved
0.6422	Remote Similarity	NPD6869	Approved
0.6422	Remote Similarity	NPD6649	Approved
0.6422	Remote Similarity	NPD6617	Approved
0.6422	Remote Similarity	NPD6847	Approved
0.641	Remote Similarity	NPD7507	Approved
0.6404	Remote Similarity	NPD6054	Approved
0.6404	Remote Similarity	NPD6319	Approved
0.6404	Remote Similarity	NPD6059	Approved
0.6389	Remote Similarity	NPD6012	Approved
0.6389	Remote Similarity	NPD6013	Approved
0.6389	Remote Similarity	NPD6014	Approved
0.6387	Remote Similarity	NPD7319	Approved
0.6374	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6083	Phase 2
0.6373	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD7637	Suspended
0.6364	Remote Similarity	NPD6882	Approved
0.6348	Remote Similarity	NPD7503	Approved
0.6337	Remote Similarity	NPD4629	Approved
0.6337	Remote Similarity	NPD5210	Approved
0.633	Remote Similarity	NPD5251	Approved
0.633	Remote Similarity	NPD5250	Approved
0.633	Remote Similarity	NPD5249	Phase 3
0.633	Remote Similarity	NPD5247	Approved
0.633	Remote Similarity	NPD5248	Approved
0.6322	Remote Similarity	NPD4245	Approved
0.6322	Remote Similarity	NPD4789	Approved
0.6322	Remote Similarity	NPD4244	Approved
0.6316	Remote Similarity	NPD3668	Phase 3
0.6296	Remote Similarity	NPD6011	Approved
0.6293	Remote Similarity	NPD6370	Approved
0.6283	Remote Similarity	NPD6009	Approved
0.6283	Remote Similarity	NPD7115	Discovery
0.6277	Remote Similarity	NPD4221	Approved
0.6277	Remote Similarity	NPD4223	Phase 3
0.6273	Remote Similarity	NPD5217	Approved
0.6273	Remote Similarity	NPD5215	Approved
0.6273	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5216	Approved
0.6263	Remote Similarity	NPD7136	Phase 2
0.6263	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6700	Approved
0.625	Remote Similarity	NPD5329	Approved
0.6239	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7748	Approved
0.6214	Remote Similarity	NPD7902	Approved
0.6207	Remote Similarity	NPD3698	Phase 2
0.6207	Remote Similarity	NPD6016	Approved
0.6207	Remote Similarity	NPD6015	Approved
0.62	Remote Similarity	NPD6702	Approved
0.62	Remote Similarity	NPD6703	Approved
0.619	Remote Similarity	NPD5344	Discontinued
0.6186	Remote Similarity	NPD5279	Phase 3
0.6186	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7492	Approved
0.6182	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5169	Approved
0.6182	Remote Similarity	NPD5135	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