NPASS Compound

Structure

NPC469878 OpenBabel07101719142D 45 48 0 0 1 0 0 0 0 0999 V2000 12.8563 -5.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1621 -6.0143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2326 -2.7197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3915 -4.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3794 -1.7927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9706 -2.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5384 -3.0798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7463 -4.0580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9487 -4.4345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0352 -4.8412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8660 -4.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9053 -5.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4405 -3.6979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5873 -2.7708 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.6973 -4.3670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3660 -4.0981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.8442 -3.4400 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.3660 -4.0981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.8660 -3.2321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3660 -4.0981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.8660 -4.9641 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.8660 -3.2321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3660 -2.3660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.8660 -3.2321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.8660 -3.2321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3660 -4.8301 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 2.3660 -5.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 -6.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -4.5981 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 0.8660 -4.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3660 -5.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 -5.8301 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -4.0981 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -1.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 9 2 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 29 1 0 0 0 0 14 21 1 0 0 0 0 14 26 1 0 0 0 0 15 25 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 19 22 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 29 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 25 30 1 0 0 0 0 26 40 1 0 0 0 0 27 28 1 0 0 0 0 27 41 1 0 0 0 0 28 42 1 0 0 0 0 31 43 1 0 0 0 0 32 43 2 0 0 0 0 33 43 2 0 0 0 0 34 44 1 0 0 0 0 35 44 2 0 0 0 0 36 44 2 0 0 0 0 37 45 1 0 0 0 0 38 45 2 0 0 0 0 39 45 2 0 0 0 0 40 43 1 0 0 0 0 41 44 1 0 0 0 0 42 45 1 0 0 0 0 M CHG 3 31 -1 34 -1 37 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	697.24
Volume:	647.629
LogP:	3.802
LogD:	1.979
LogS:	-5.571
# Rotatable Bonds:	11
TPSA:	199.29
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	5.902
Fsp3:	0.933
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:	-4.878
MDCK Permeability:	3.899399234796874e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.254

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	99.12935638427734%
Volume Distribution (VD):	1.445
Pgp-substrate:	2.6924057006835938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.559
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.248

ADMET: Excretion

Clearance (CL):	1.842
Half-life (T1/2):	0.004

ADMET: Toxicity

hERG Blockers:	0.645
Human Hepatotoxicity (H-HT):	0.854
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.979
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.814
Skin Sensitization:	0.989
Carcinogencity:	0.809
Eye Corrosion:	0.987
Eye Irritation:	0.81
Respiratory Toxicity:	0.995

Download Data

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

Natural Product: NPC469878

Natural Product ID:	NPC469878
*Common Name:**	Topsentinol K Trisulfate
IUPAC Name:	trisodium;[(2S,3S,5S,6S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(Z,2R)-6-methyl-5-propan-2-ylhept-3-en-2-yl]-2,3-disulfonatooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl] sulfate
Synonyms:	Topsentinol K Trisulfate
Standard InCHIKey:	SSCIPPUCOPUHPG-CHTCAWNSSA-K
Standard InCHI:	InChI=1S/C30H52O12S3.3Na/c1-17(2)20(18(3)4)9-8-19(5)22-10-11-23-21-14-26(40-43(31,32)33)25-15-27(41-44(34,35)36)28(42-45(37,38)39)16-30(25,7)24(21)12-13-29(22,23)6;;;/h8-9,17-28H,10-16H2,1-7H3,(H,31,32,33)(H,34,35,36)(H,37,38,39);;;/q;3*+1/p-3/b9-8-;;;/t19-,21+,22-,23+,24+,25-,26+,27+,28+,29-,30-;;;/m1.../s1
SMILES:	CC(C(C(C)C)/C=C[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]([C@@H]2[C@]1(C)C[C@H](OS(=O)(=O)[O-])[C@H](C2)OS(=O)(=O)[O-])OS(=O)(=O)[O-])C)C.[Na+].[Na+].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224769
PubChem CID:	46938754
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	At the 20 m depth, the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17190456]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[19653640]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[2045823]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[20806907]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[8145229]

☑ 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	3

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	1200.0	nM	PMID[520185]
NPT2	Others	Unspecified		IC50	=	2700.0	nM	PMID[520185]
NPT2	Others	Unspecified		IC50	=	34600.0	nM	PMID[520185]

☑ 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 NPC469878 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	259
0.1-0.2	1912
0.2-0.3	8602
0.3-0.4	16363
0.4-0.5	6418
0.5-0.6	5952
0.6-0.7	2853
0.7-0.8	287
0.8-0.85	37
0.85-0.9	11
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9268	High Similarity	NPC478094
0.8889	High Similarity	NPC473534
0.8875	High Similarity	NPC474132
0.8571	High Similarity	NPC478102
0.8519	High Similarity	NPC475337
0.8488	Intermediate Similarity	NPC474657
0.8488	Intermediate Similarity	NPC186145
0.8462	Intermediate Similarity	NPC477226
0.8462	Intermediate Similarity	NPC477822
0.8462	Intermediate Similarity	NPC473552
0.8462	Intermediate Similarity	NPC324984
0.8462	Intermediate Similarity	NPC477821
0.8462	Intermediate Similarity	NPC323900
0.8462	Intermediate Similarity	NPC477823
0.8452	Intermediate Similarity	NPC141941
0.8452	Intermediate Similarity	NPC193870
0.8391	Intermediate Similarity	NPC475664
0.8372	Intermediate Similarity	NPC477604
0.8353	Intermediate Similarity	NPC475798
0.8353	Intermediate Similarity	NPC127606
0.8333	Intermediate Similarity	NPC477599
0.8298	Intermediate Similarity	NPC470602
0.8295	Intermediate Similarity	NPC109744
0.8276	Intermediate Similarity	NPC475313
0.8276	Intermediate Similarity	NPC478104
0.8276	Intermediate Similarity	NPC477600
0.8261	Intermediate Similarity	NPC316604
0.8235	Intermediate Similarity	NPC110778
0.8235	Intermediate Similarity	NPC477818
0.8235	Intermediate Similarity	NPC207013
0.8211	Intermediate Similarity	NPC470601
0.8202	Intermediate Similarity	NPC473956
0.8202	Intermediate Similarity	NPC475751
0.8161	Intermediate Similarity	NPC139724
0.8161	Intermediate Similarity	NPC6605
0.8132	Intermediate Similarity	NPC477605
0.8095	Intermediate Similarity	NPC236237
0.8095	Intermediate Similarity	NPC102253
0.8095	Intermediate Similarity	NPC322313
0.809	Intermediate Similarity	NPC477606
0.809	Intermediate Similarity	NPC105495
0.8072	Intermediate Similarity	NPC6978
0.8072	Intermediate Similarity	NPC244385
0.8072	Intermediate Similarity	NPC167037
0.8072	Intermediate Similarity	NPC138621
0.7978	Intermediate Similarity	NPC133588
0.7976	Intermediate Similarity	NPC80530
0.7976	Intermediate Similarity	NPC273410
0.7955	Intermediate Similarity	NPC24277
0.7955	Intermediate Similarity	NPC71520
0.7955	Intermediate Similarity	NPC269058
0.7955	Intermediate Similarity	NPC201273
0.7949	Intermediate Similarity	NPC475172
0.7931	Intermediate Similarity	NPC124172
0.7927	Intermediate Similarity	NPC103822
0.7912	Intermediate Similarity	NPC275671
0.7882	Intermediate Similarity	NPC13554
0.7882	Intermediate Similarity	NPC236112
0.7857	Intermediate Similarity	NPC285761
0.7831	Intermediate Similarity	NPC473916
0.7831	Intermediate Similarity	NPC477601
0.7831	Intermediate Similarity	NPC477602
0.7831	Intermediate Similarity	NPC237460
0.7826	Intermediate Similarity	NPC478129
0.7816	Intermediate Similarity	NPC211135
0.7816	Intermediate Similarity	NPC85095
0.7816	Intermediate Similarity	NPC216420
0.7816	Intermediate Similarity	NPC113978
0.7791	Intermediate Similarity	NPC474531
0.7778	Intermediate Similarity	NPC474668
0.7766	Intermediate Similarity	NPC475178
0.7766	Intermediate Similarity	NPC471903
0.7765	Intermediate Similarity	NPC472463
0.7753	Intermediate Similarity	NPC94462
0.7753	Intermediate Similarity	NPC299068
0.7753	Intermediate Similarity	NPC261266
0.7727	Intermediate Similarity	NPC209802
0.7727	Intermediate Similarity	NPC474493
0.7727	Intermediate Similarity	NPC255882
0.7717	Intermediate Similarity	NPC41554
0.7717	Intermediate Similarity	NPC97404
0.7701	Intermediate Similarity	NPC30166
0.7701	Intermediate Similarity	NPC1272
0.7701	Intermediate Similarity	NPC218616
0.7701	Intermediate Similarity	NPC296701
0.7701	Intermediate Similarity	NPC470614
0.7701	Intermediate Similarity	NPC248886
0.7692	Intermediate Similarity	NPC477603
0.7684	Intermediate Similarity	NPC474994
0.7684	Intermediate Similarity	NPC476040
0.7684	Intermediate Similarity	NPC476021
0.7674	Intermediate Similarity	NPC287749
0.7674	Intermediate Similarity	NPC71535
0.7674	Intermediate Similarity	NPC78545
0.7667	Intermediate Similarity	NPC470620
0.7647	Intermediate Similarity	NPC477817
0.7647	Intermediate Similarity	NPC85346
0.7647	Intermediate Similarity	NPC148977
0.7647	Intermediate Similarity	NPC302041
0.7647	Intermediate Similarity	NPC477819
0.7647	Intermediate Similarity	NPC65897
0.7647	Intermediate Similarity	NPC87604
0.764	Intermediate Similarity	NPC470360
0.7634	Intermediate Similarity	NPC473678
0.7619	Intermediate Similarity	NPC134330
0.7619	Intermediate Similarity	NPC129165
0.7619	Intermediate Similarity	NPC189883
0.7614	Intermediate Similarity	NPC82623
0.7614	Intermediate Similarity	NPC470558
0.7614	Intermediate Similarity	NPC134481
0.7609	Intermediate Similarity	NPC291484
0.7609	Intermediate Similarity	NPC80561
0.7609	Intermediate Similarity	NPC329596
0.7609	Intermediate Similarity	NPC3345
0.7609	Intermediate Similarity	NPC204188
0.7609	Intermediate Similarity	NPC11216
0.759	Intermediate Similarity	NPC472503
0.759	Intermediate Similarity	NPC308440
0.7586	Intermediate Similarity	NPC470383
0.7582	Intermediate Similarity	NPC67872
0.7582	Intermediate Similarity	NPC475605
0.7582	Intermediate Similarity	NPC4574
0.7582	Intermediate Similarity	NPC470542
0.7582	Intermediate Similarity	NPC212596
0.7561	Intermediate Similarity	NPC478103
0.7558	Intermediate Similarity	NPC1319
0.7556	Intermediate Similarity	NPC237344
0.7556	Intermediate Similarity	NPC121981
0.7556	Intermediate Similarity	NPC6391
0.7529	Intermediate Similarity	NPC471798
0.7529	Intermediate Similarity	NPC130136
0.7529	Intermediate Similarity	NPC214570
0.7529	Intermediate Similarity	NPC202540
0.7527	Intermediate Similarity	NPC210268
0.75	Intermediate Similarity	NPC3403
0.75	Intermediate Similarity	NPC257347
0.75	Intermediate Similarity	NPC141071
0.75	Intermediate Similarity	NPC7988
0.75	Intermediate Similarity	NPC101886
0.75	Intermediate Similarity	NPC470361
0.75	Intermediate Similarity	NPC50964
0.75	Intermediate Similarity	NPC471723
0.7473	Intermediate Similarity	NPC304083
0.7471	Intermediate Similarity	NPC475679
0.7471	Intermediate Similarity	NPC26117
0.7447	Intermediate Similarity	NPC475255
0.7444	Intermediate Similarity	NPC478127
0.7444	Intermediate Similarity	NPC318390
0.7444	Intermediate Similarity	NPC22133
0.7442	Intermediate Similarity	NPC275910
0.7442	Intermediate Similarity	NPC301707
0.7442	Intermediate Similarity	NPC31828
0.7442	Intermediate Similarity	NPC11908
0.7442	Intermediate Similarity	NPC102708
0.7442	Intermediate Similarity	NPC312328
0.7419	Intermediate Similarity	NPC295668
0.7416	Intermediate Similarity	NPC253402
0.7416	Intermediate Similarity	NPC159168
0.7416	Intermediate Similarity	NPC139206
0.7416	Intermediate Similarity	NPC317458
0.7416	Intermediate Similarity	NPC232023
0.7412	Intermediate Similarity	NPC113733
0.7412	Intermediate Similarity	NPC474231
0.7412	Intermediate Similarity	NPC321381
0.7412	Intermediate Similarity	NPC14112
0.7412	Intermediate Similarity	NPC470362
0.7412	Intermediate Similarity	NPC107059
0.7412	Intermediate Similarity	NPC321016
0.7412	Intermediate Similarity	NPC240604
0.7412	Intermediate Similarity	NPC73875
0.7412	Intermediate Similarity	NPC202642
0.7412	Intermediate Similarity	NPC46160
0.7412	Intermediate Similarity	NPC300324
0.7412	Intermediate Similarity	NPC91573
0.7412	Intermediate Similarity	NPC86305
0.7404	Intermediate Similarity	NPC475312
0.74	Intermediate Similarity	NPC312774
0.7396	Intermediate Similarity	NPC288970
0.7391	Intermediate Similarity	NPC280556
0.7391	Intermediate Similarity	NPC470613
0.7391	Intermediate Similarity	NPC470612
0.7391	Intermediate Similarity	NPC193360
0.7386	Intermediate Similarity	NPC476646
0.7386	Intermediate Similarity	NPC209620
0.7386	Intermediate Similarity	NPC23852
0.7386	Intermediate Similarity	NPC70927
0.7368	Intermediate Similarity	NPC127718
0.7368	Intermediate Similarity	NPC65402
0.7356	Intermediate Similarity	NPC475727
0.7356	Intermediate Similarity	NPC472742
0.7356	Intermediate Similarity	NPC30986
0.7356	Intermediate Similarity	NPC328714
0.7356	Intermediate Similarity	NPC209430
0.7356	Intermediate Similarity	NPC80297
0.7356	Intermediate Similarity	NPC24504
0.7356	Intermediate Similarity	NPC116119
0.7349	Intermediate Similarity	NPC111234
0.7347	Intermediate Similarity	NPC208358
0.7347	Intermediate Similarity	NPC473200
0.7347	Intermediate Similarity	NPC7341

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 NPC469878 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	2070
0.2-0.3	4651
0.3-0.4	1636
0.4-0.5	261
0.5-0.6	198
0.6-0.7	143
0.7-0.8	3
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
0.8095	Intermediate Similarity	NPD7525	Registered
0.7294	Intermediate Similarity	NPD7339	Approved
0.7294	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD3668	Phase 3
0.7011	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7645	Phase 2
0.6818	Remote Similarity	NPD6933	Approved
0.6804	Remote Similarity	NPD6079	Approved
0.6782	Remote Similarity	NPD6926	Approved
0.6782	Remote Similarity	NPD6924	Approved
0.6782	Remote Similarity	NPD4784	Approved
0.6782	Remote Similarity	NPD4785	Approved
0.6778	Remote Similarity	NPD6929	Approved
0.6774	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4786	Approved
0.6771	Remote Similarity	NPD5328	Approved
0.6744	Remote Similarity	NPD4243	Approved
0.6744	Remote Similarity	NPD7150	Approved
0.6744	Remote Similarity	NPD7152	Approved
0.6744	Remote Similarity	NPD7151	Approved
0.6742	Remote Similarity	NPD6932	Approved
0.6737	Remote Similarity	NPD7524	Approved
0.6737	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7638	Approved
0.6706	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6931	Approved
0.6703	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6632	Remote Similarity	NPD3618	Phase 1
0.6628	Remote Similarity	NPD7144	Approved
0.6628	Remote Similarity	NPD7143	Approved
0.6566	Remote Similarity	NPD4202	Approved
0.6566	Remote Similarity	NPD6399	Phase 3
0.6559	Remote Similarity	NPD3667	Approved
0.6556	Remote Similarity	NPD6925	Approved
0.6556	Remote Similarity	NPD5776	Phase 2
0.6535	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5222	Approved
0.6535	Remote Similarity	NPD5221	Approved
0.6526	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7514	Phase 3
0.6522	Remote Similarity	NPD7509	Discontinued
0.6512	Remote Similarity	NPD6923	Approved
0.6512	Remote Similarity	NPD6922	Approved
0.6505	Remote Similarity	NPD5285	Approved
0.6505	Remote Similarity	NPD5286	Approved
0.6505	Remote Similarity	NPD4696	Approved
0.6471	Remote Similarity	NPD4755	Approved
0.6471	Remote Similarity	NPD5173	Approved
0.6465	Remote Similarity	NPD8034	Phase 2
0.6465	Remote Similarity	NPD8035	Phase 2
0.6452	Remote Similarity	NPD6902	Approved
0.6442	Remote Similarity	NPD5223	Approved
0.6429	Remote Similarity	NPD6051	Approved
0.6422	Remote Similarity	NPD4634	Approved
0.6413	Remote Similarity	NPD4195	Approved
0.6413	Remote Similarity	NPD6683	Phase 2
0.6408	Remote Similarity	NPD5290	Discontinued
0.6404	Remote Similarity	NPD7516	Approved
0.6392	Remote Similarity	NPD7750	Discontinued
0.6381	Remote Similarity	NPD5225	Approved
0.6381	Remote Similarity	NPD4633	Approved
0.6381	Remote Similarity	NPD5226	Approved
0.6381	Remote Similarity	NPD5224	Approved
0.6381	Remote Similarity	NPD5211	Phase 2
0.6373	Remote Similarity	NPD4697	Phase 3
0.6355	Remote Similarity	NPD6008	Approved
0.6354	Remote Similarity	NPD6893	Approved
0.6346	Remote Similarity	NPD4700	Approved
0.6344	Remote Similarity	NPD4748	Discontinued
0.6344	Remote Similarity	NPD7332	Phase 2
0.6337	Remote Similarity	NPD7900	Approved
0.6337	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5275	Approved
0.6333	Remote Similarity	NPD4190	Phase 3
0.6327	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6672	Approved
0.6327	Remote Similarity	NPD5737	Approved
0.6321	Remote Similarity	NPD5175	Approved
0.6321	Remote Similarity	NPD4754	Approved
0.6321	Remote Similarity	NPD5174	Approved
0.6316	Remote Similarity	NPD7328	Approved
0.6316	Remote Similarity	NPD7327	Approved
0.6306	Remote Similarity	NPD8297	Approved
0.6304	Remote Similarity	NPD6115	Approved
0.6304	Remote Similarity	NPD6118	Approved
0.6304	Remote Similarity	NPD6114	Approved
0.6304	Remote Similarity	NPD6697	Approved
0.63	Remote Similarity	NPD7515	Phase 2
0.6289	Remote Similarity	NPD6409	Approved
0.6289	Remote Similarity	NPD7334	Approved
0.6289	Remote Similarity	NPD5330	Approved
0.6289	Remote Similarity	NPD7146	Approved
0.6289	Remote Similarity	NPD6684	Approved
0.6289	Remote Similarity	NPD7521	Approved
0.6262	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD3133	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD4729	Approved
0.6239	Remote Similarity	NPD4730	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.6216	Remote Similarity	NPD6649	Approved
0.6216	Remote Similarity	NPD6650	Approved
0.6207	Remote Similarity	NPD8377	Approved
0.6207	Remote Similarity	NPD8294	Approved
0.6204	Remote Similarity	NPD4768	Approved
0.6204	Remote Similarity	NPD7128	Approved
0.6204	Remote Similarity	NPD4767	Approved
0.6204	Remote Similarity	NPD6675	Approved
0.6204	Remote Similarity	NPD5739	Approved
0.6204	Remote Similarity	NPD6402	Approved
0.62	Remote Similarity	NPD7136	Phase 2
0.6196	Remote Similarity	NPD6116	Phase 1
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.6176	Remote Similarity	NPD7748	Approved
0.6162	Remote Similarity	NPD6903	Approved
0.6161	Remote Similarity	NPD6882	Approved
0.6154	Remote Similarity	NPD8380	Approved
0.6154	Remote Similarity	NPD8379	Approved
0.6154	Remote Similarity	NPD8335	Approved
0.6154	Remote Similarity	NPD7902	Approved
0.6154	Remote Similarity	NPD8033	Approved
0.6154	Remote Similarity	NPD8378	Approved
0.6154	Remote Similarity	NPD8296	Approved
0.6147	Remote Similarity	NPD5697	Approved
0.6139	Remote Similarity	NPD7087	Discontinued
0.6129	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5135	Approved
0.6126	Remote Similarity	NPD6883	Approved
0.6126	Remote Similarity	NPD5249	Phase 3
0.6126	Remote Similarity	NPD5250	Approved
0.6126	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7102	Approved
0.6126	Remote Similarity	NPD5248	Approved
0.6126	Remote Similarity	NPD5251	Approved
0.6126	Remote Similarity	NPD7290	Approved
0.6126	Remote Similarity	NPD5247	Approved
0.6117	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6898	Phase 1
0.61	Remote Similarity	NPD4753	Phase 2
0.6091	Remote Similarity	NPD6011	Approved
0.6091	Remote Similarity	NPD7320	Approved
0.6087	Remote Similarity	NPD6009	Approved
0.6087	Remote Similarity	NPD6117	Approved
0.6075	Remote Similarity	NPD7632	Discontinued
0.6071	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD6617	Approved
0.6071	Remote Similarity	NPD8130	Phase 1
0.6071	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6847	Approved
0.6068	Remote Similarity	NPD6054	Approved
0.6068	Remote Similarity	NPD6319	Approved
0.6067	Remote Similarity	NPD4787	Phase 1
0.6042	Remote Similarity	NPD4221	Approved
0.6042	Remote Similarity	NPD4223	Phase 3
0.604	Remote Similarity	NPD6700	Approved
0.604	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6012	Approved
0.6036	Remote Similarity	NPD6014	Approved
0.6036	Remote Similarity	NPD6013	Approved
0.602	Remote Similarity	NPD5329	Approved
0.6017	Remote Similarity	NPD7503	Approved
0.6	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD6928	Phase 2
0.6	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5169	Approved
0.598	Remote Similarity	NPD7637	Suspended
0.598	Remote Similarity	NPD6703	Approved
0.598	Remote Similarity	NPD6702	Approved
0.5979	Remote Similarity	NPD4788	Approved
0.5978	Remote Similarity	NPD3703	Phase 2
0.5978	Remote Similarity	NPD8264	Approved
0.5966	Remote Similarity	NPD6370	Approved
0.5962	Remote Similarity	NPD5210	Approved
0.5962	Remote Similarity	NPD4629	Approved
0.596	Remote Similarity	NPD6098	Approved
0.596	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5279	Phase 3
0.5957	Remote Similarity	NPD5364	Discontinued
0.595	Remote Similarity	NPD7507	Approved
0.5946	Remote Similarity	NPD5128	Approved
0.5946	Remote Similarity	NPD5168	Approved
0.5941	Remote Similarity	NPD6904	Approved
0.5941	Remote Similarity	NPD6080	Approved
0.5941	Remote Similarity	NPD6673	Approved
0.5932	Remote Similarity	NPD6059	Approved
0.5929	Remote Similarity	NPD5216	Approved
0.5929	Remote Similarity	NPD5217	Approved
0.5929	Remote Similarity	NPD5215	Approved
0.5929	Remote Similarity	NPD5127	Approved
0.5918	Remote Similarity	NPD4197	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