NPASS Compound

Structure

NPC470383 OpenBabel07101718192D 32 35 0 0 1 0 0 0 0 0999 V2000 6.1235 4.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7633 5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1161 6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4980 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 4.7852 5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 2.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4762 4.6622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.1890 3.5032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2109 3.2953 0.0000 O 0 0 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 7 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 8 9 1 0 0 0 0 8 20 2 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 19 1 0 0 0 0 14 26 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 21 1 0 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 18 4 1 1 0 0 0 18 23 1 0 0 0 0 18 26 1 0 0 0 0 19 7 1 6 0 0 0 20 29 1 0 0 0 0 21 30 1 1 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 28 1 1 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 26 31 1 6 0 0 0 27 29 1 6 0 0 0 27 32 1 0 0 0 0 28 5 1 1 0 0 0 29 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.38
Volume:	499.648
LogP:	5.416
LogD:	4.787
LogS:	-5.696
# Rotatable Bonds:	6
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.441
Synthetic Accessibility Score:	4.828
Fsp3:	0.931
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.772
MDCK Permeability:	7.821147846698295e-06
Pgp-inhibitor:	0.825
Pgp-substrate:	0.913
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.042

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	97.56307220458984%
Volume Distribution (VD):	1.229
Pgp-substrate:	1.5906907320022583%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.453
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.902
CYP2C9-inhibitor:	0.183
CYP2C9-substrate:	0.248
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.357
CYP3A4-substrate:	0.775

ADMET: Excretion

Clearance (CL):	12.187
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.839
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.065
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.354
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.716
Carcinogencity:	0.073
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.87

Download Data

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

Natural Product: NPC470383

Natural Product ID:	NPC470383
*Common Name:**	Haloxysterol A
IUPAC Name:	(1S,3R,10R,13S,17R)-17-[(2S,3R,5R)-5-ethyl-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-1,3-diol
Synonyms:
Standard InCHIKey:	UNBKHVKAEFBHAN-IWAMNEIESA-N
Standard InCHI:	InChI=1S/C29H50O3/c1-7-19(17(2)3)14-26(31)18(4)23-10-11-24-22-9-8-20-15-21(30)16-27(32)29(20,6)25(22)12-13-28(23,24)5/h8,17-19,21-27,30-32H,7,9-16H2,1-6H3/t18-,19+,21+,22?,23+,24?,25?,26+,27-,28+,29-/m0/s1
SMILES:	CCC(CC(C(C)C1CCC2C1(CCC3C2CC=C4C3(C(CC(C4)O)O)C)C)O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL202221
PubChem CID:	44407168
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
NPO14224	Haloxylon recurvum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16274989]
NPO14224	Haloxylon recurvum	Species	Chenopodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16651755]
NPO14224	Haloxylon recurvum	Species	Chenopodiaceae	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	2
Ki	2

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	8300.0	nM	PMID[453431]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Ki	=	7600.0	nM	PMID[453431]
NPT2569	Individual Protein	Butyrylcholinesterase	Equus caballus	IC50	=	4700.0	nM	PMID[453431]
NPT2569	Individual Protein	Butyrylcholinesterase	Equus caballus	Ki	=	4500.0	nM	PMID[453431]

☑ 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 NPC470383 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	157
0.1-0.2	1362
0.2-0.3	5722
0.3-0.4	15739
0.4-0.5	7945
0.5-0.6	5490
0.6-0.7	4629
0.7-0.8	1260
0.8-0.85	240
0.85-0.9	104
0.9-0.95	47
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC87604
0.9351	High Similarity	NPC26117
0.9333	High Similarity	NPC300324
0.9333	High Similarity	NPC107059
0.9333	High Similarity	NPC240604
0.9333	High Similarity	NPC321381
0.9333	High Similarity	NPC321016
0.9259	High Similarity	NPC475313
0.9241	High Similarity	NPC113978
0.9231	High Similarity	NPC209620
0.9231	High Similarity	NPC23852
0.9211	High Similarity	NPC155986
0.9211	High Similarity	NPC198968
0.9211	High Similarity	NPC318495
0.92	High Similarity	NPC288035
0.92	High Similarity	NPC134847
0.92	High Similarity	NPC285893
0.92	High Similarity	NPC28657
0.92	High Similarity	NPC136188
0.92	High Similarity	NPC304309
0.92	High Similarity	NPC22105
0.92	High Similarity	NPC230301
0.92	High Similarity	NPC162742
0.9136	High Similarity	NPC6391
0.9125	High Similarity	NPC124172
0.9125	High Similarity	NPC209802
0.9114	High Similarity	NPC1272
0.9114	High Similarity	NPC101462
0.9114	High Similarity	NPC248886
0.9114	High Similarity	NPC50964
0.9114	High Similarity	NPC470614
0.9091	High Similarity	NPC477522
0.9091	High Similarity	NPC275910
0.9091	High Similarity	NPC473943
0.9091	High Similarity	NPC474216
0.9079	High Similarity	NPC189883
0.9079	High Similarity	NPC113733
0.9036	High Similarity	NPC470361
0.9012	High Similarity	NPC470360
0.8987	High Similarity	NPC474531
0.8974	High Similarity	NPC328714
0.8974	High Similarity	NPC84694
0.8974	High Similarity	NPC109546
0.8974	High Similarity	NPC1319
0.8974	High Similarity	NPC472463
0.8974	High Similarity	NPC81306
0.8974	High Similarity	NPC28862
0.8974	High Similarity	NPC143182
0.8974	High Similarity	NPC47982
0.8961	High Similarity	NPC471798
0.8961	High Similarity	NPC214570
0.8961	High Similarity	NPC34019
0.8947	High Similarity	NPC257347
0.8947	High Similarity	NPC141071
0.8947	High Similarity	NPC471723
0.8929	High Similarity	NPC80561
0.8929	High Similarity	NPC329596
0.8929	High Similarity	NPC204188
0.8929	High Similarity	NPC3345
0.8929	High Similarity	NPC291484
0.8929	High Similarity	NPC11216
0.8902	High Similarity	NPC293287
0.8902	High Similarity	NPC201273
0.8902	High Similarity	NPC24277
0.8902	High Similarity	NPC94462
0.8902	High Similarity	NPC269058
0.8902	High Similarity	NPC152808
0.8902	High Similarity	NPC299068
0.8902	High Similarity	NPC71520
0.8902	High Similarity	NPC261266
0.8889	High Similarity	NPC185568
0.8889	High Similarity	NPC205845
0.8875	High Similarity	NPC49964
0.8875	High Similarity	NPC30166
0.8861	High Similarity	NPC164840
0.8861	High Similarity	NPC234193
0.8861	High Similarity	NPC236112
0.8861	High Similarity	NPC209944
0.8861	High Similarity	NPC241290
0.8846	High Similarity	NPC138621
0.8846	High Similarity	NPC244385
0.8846	High Similarity	NPC18603
0.8846	High Similarity	NPC307965
0.8846	High Similarity	NPC285761
0.8846	High Similarity	NPC76931
0.8846	High Similarity	NPC6978
0.8846	High Similarity	NPC31828
0.8846	High Similarity	NPC167037
0.8831	High Similarity	NPC134330
0.8831	High Similarity	NPC73875
0.8831	High Similarity	NPC129165
0.8831	High Similarity	NPC237460
0.8831	High Similarity	NPC46160
0.8831	High Similarity	NPC96319
0.8831	High Similarity	NPC202642
0.8824	High Similarity	NPC97404
0.8824	High Similarity	NPC41554
0.8816	High Similarity	NPC471797
0.878	High Similarity	NPC266511
0.8765	High Similarity	NPC110778
0.8765	High Similarity	NPC477818
0.875	High Similarity	NPC474752
0.875	High Similarity	NPC82986
0.875	High Similarity	NPC474759
0.875	High Similarity	NPC474731
0.875	High Similarity	NPC242350
0.875	High Similarity	NPC474683
0.875	High Similarity	NPC47761
0.875	High Similarity	NPC264245
0.875	High Similarity	NPC7505
0.8734	High Similarity	NPC475727
0.8734	High Similarity	NPC116119
0.8734	High Similarity	NPC30986
0.8734	High Similarity	NPC80297
0.8734	High Similarity	NPC273410
0.8734	High Similarity	NPC209430
0.8734	High Similarity	NPC472742
0.8734	High Similarity	NPC80530
0.8706	High Similarity	NPC245410
0.8706	High Similarity	NPC192437
0.8706	High Similarity	NPC270511
0.8706	High Similarity	NPC14380
0.8706	High Similarity	NPC470390
0.8701	High Similarity	NPC118508
0.8701	High Similarity	NPC121744
0.8701	High Similarity	NPC322353
0.869	High Similarity	NPC470542
0.8684	High Similarity	NPC474140
0.8684	High Similarity	NPC471799
0.8675	High Similarity	NPC6605
0.8659	High Similarity	NPC475798
0.8659	High Similarity	NPC127606
0.8659	High Similarity	NPC474493
0.8642	High Similarity	NPC470049
0.8642	High Similarity	NPC189972
0.8642	High Similarity	NPC201852
0.8642	High Similarity	NPC5985
0.8625	High Similarity	NPC236237
0.8625	High Similarity	NPC13554
0.8625	High Similarity	NPC475679
0.8625	High Similarity	NPC322313
0.8625	High Similarity	NPC324772
0.8625	High Similarity	NPC102253
0.8621	High Similarity	NPC127718
0.8621	High Similarity	NPC65402
0.8608	High Similarity	NPC148977
0.8608	High Similarity	NPC65897
0.8608	High Similarity	NPC85346
0.8608	High Similarity	NPC186191
0.8608	High Similarity	NPC477514
0.8608	High Similarity	NPC205455
0.8608	High Similarity	NPC302041
0.859	High Similarity	NPC470362
0.859	High Similarity	NPC244488
0.859	High Similarity	NPC247325
0.8588	High Similarity	NPC101886
0.8588	High Similarity	NPC105495
0.8571	High Similarity	NPC308440
0.8571	High Similarity	NPC91858
0.8571	High Similarity	NPC149224
0.8571	High Similarity	NPC477138
0.8571	High Similarity	NPC243342
0.8571	High Similarity	NPC472503
0.8554	High Similarity	NPC474189
0.8554	High Similarity	NPC474349
0.8554	High Similarity	NPC274448
0.8554	High Similarity	NPC157257
0.8537	High Similarity	NPC193870
0.8537	High Similarity	NPC141941
0.8537	High Similarity	NPC474634
0.8537	High Similarity	NPC232023
0.8537	High Similarity	NPC317458
0.8537	High Similarity	NPC475789
0.8523	High Similarity	NPC8774
0.8519	High Similarity	NPC320525
0.8519	High Similarity	NPC476646
0.8519	High Similarity	NPC249423
0.8506	High Similarity	NPC310013
0.85	High Similarity	NPC53744
0.8488	Intermediate Similarity	NPC473956
0.8488	Intermediate Similarity	NPC475751
0.8488	Intermediate Similarity	NPC295668
0.8481	Intermediate Similarity	NPC130136
0.8481	Intermediate Similarity	NPC202540
0.8481	Intermediate Similarity	NPC477924
0.8471	Intermediate Similarity	NPC474668
0.8471	Intermediate Similarity	NPC212596
0.8471	Intermediate Similarity	NPC133588
0.8471	Intermediate Similarity	NPC4574
0.8471	Intermediate Similarity	NPC475664
0.8471	Intermediate Similarity	NPC2158
0.8462	Intermediate Similarity	NPC291503
0.8462	Intermediate Similarity	NPC477923
0.8462	Intermediate Similarity	NPC66566
0.8462	Intermediate Similarity	NPC103822
0.8452	Intermediate Similarity	NPC125399
0.8452	Intermediate Similarity	NPC474970
0.8442	Intermediate Similarity	NPC182717
0.8442	Intermediate Similarity	NPC201373
0.8434	Intermediate Similarity	NPC59453

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 NPC470383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1620
0.2-0.3	4383
0.3-0.4	2128
0.4-0.5	432
0.5-0.6	158
0.6-0.7	171
0.7-0.8	68
0.8-0.85	23
0.85-0.9	8
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.92	High Similarity	NPD6942	Approved
0.92	High Similarity	NPD7339	Approved
0.8831	High Similarity	NPD3701	Clinical (unspecified phase)
0.8734	High Similarity	NPD6929	Approved
0.8625	High Similarity	NPD7525	Registered
0.8625	High Similarity	NPD6930	Phase 2
0.8625	High Similarity	NPD6931	Approved
0.8481	Intermediate Similarity	NPD6925	Approved
0.8481	Intermediate Similarity	NPD6932	Approved
0.8481	Intermediate Similarity	NPD5776	Phase 2
0.8434	Intermediate Similarity	NPD4786	Approved
0.8375	Intermediate Similarity	NPD7145	Approved
0.8353	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6924	Approved
0.8333	Intermediate Similarity	NPD6926	Approved
0.8313	Intermediate Similarity	NPD6695	Phase 3
0.8272	Intermediate Similarity	NPD6683	Phase 2
0.8272	Intermediate Similarity	NPD7645	Phase 2
0.8214	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD3667	Approved
0.8171	Intermediate Similarity	NPD7514	Phase 3
0.8125	Intermediate Similarity	NPD6933	Approved
0.8118	Intermediate Similarity	NPD6893	Approved
0.8101	Intermediate Similarity	NPD4784	Approved
0.8101	Intermediate Similarity	NPD4785	Approved
0.8077	Intermediate Similarity	NPD7150	Approved
0.8077	Intermediate Similarity	NPD4243	Approved
0.8077	Intermediate Similarity	NPD7152	Approved
0.8077	Intermediate Similarity	NPD7151	Approved
0.8072	Intermediate Similarity	NPD6902	Approved
0.8052	Intermediate Similarity	NPD6923	Approved
0.8052	Intermediate Similarity	NPD6922	Approved
0.7955	Intermediate Similarity	NPD5328	Approved
0.7952	Intermediate Similarity	NPD7332	Phase 2
0.7949	Intermediate Similarity	NPD7144	Approved
0.7949	Intermediate Similarity	NPD7143	Approved
0.7931	Intermediate Similarity	NPD7750	Discontinued
0.7931	Intermediate Similarity	NPD7524	Approved
0.7857	Intermediate Similarity	NPD6898	Phase 1
0.7816	Intermediate Similarity	NPD3618	Phase 1
0.7778	Intermediate Similarity	NPD6079	Approved
0.7738	Intermediate Similarity	NPD4748	Discontinued
0.7586	Intermediate Similarity	NPD3665	Phase 1
0.7586	Intermediate Similarity	NPD3666	Approved
0.7586	Intermediate Similarity	NPD3133	Approved
0.7582	Intermediate Similarity	NPD7087	Discontinued
0.7561	Intermediate Similarity	NPD4190	Phase 3
0.7561	Intermediate Similarity	NPD5275	Approved
0.7529	Intermediate Similarity	NPD7509	Discontinued
0.75	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD6399	Phase 3
0.7412	Intermediate Similarity	NPD4195	Approved
0.7386	Intermediate Similarity	NPD3668	Phase 3
0.7368	Intermediate Similarity	NPD4755	Approved
0.7363	Intermediate Similarity	NPD4753	Phase 2
0.7303	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7638	Approved
0.7263	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5222	Approved
0.7263	Intermediate Similarity	NPD4697	Phase 3
0.7263	Intermediate Similarity	NPD5221	Approved
0.7222	Intermediate Similarity	NPD5279	Phase 3
0.7216	Intermediate Similarity	NPD7639	Approved
0.7216	Intermediate Similarity	NPD5286	Approved
0.7216	Intermediate Similarity	NPD5285	Approved
0.7216	Intermediate Similarity	NPD4700	Approved
0.7216	Intermediate Similarity	NPD4696	Approved
0.7216	Intermediate Similarity	NPD7640	Approved
0.7204	Intermediate Similarity	NPD7637	Suspended
0.7188	Intermediate Similarity	NPD5173	Approved
0.716	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4223	Phase 3
0.7159	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD8264	Approved
0.7111	Intermediate Similarity	NPD5329	Approved
0.7097	Intermediate Similarity	NPD7136	Phase 2
0.7071	Intermediate Similarity	NPD5211	Phase 2
0.7071	Intermediate Similarity	NPD4633	Approved
0.7071	Intermediate Similarity	NPD5225	Approved
0.7071	Intermediate Similarity	NPD5226	Approved
0.7071	Intermediate Similarity	NPD5224	Approved
0.703	Intermediate Similarity	NPD6402	Approved
0.703	Intermediate Similarity	NPD5739	Approved
0.703	Intermediate Similarity	NPD6675	Approved
0.703	Intermediate Similarity	NPD7128	Approved
0.7021	Intermediate Similarity	NPD7515	Phase 2
0.701	Intermediate Similarity	NPD6083	Phase 2
0.701	Intermediate Similarity	NPD6084	Phase 2
0.7	Intermediate Similarity	NPD5174	Approved
0.7	Intermediate Similarity	NPD4197	Approved
0.7	Intermediate Similarity	NPD5175	Approved
0.6979	Remote Similarity	NPD5210	Approved
0.6979	Remote Similarity	NPD4629	Approved
0.697	Remote Similarity	NPD5223	Approved
0.6939	Remote Similarity	NPD5290	Discontinued
0.6931	Remote Similarity	NPD5141	Approved
0.6923	Remote Similarity	NPD4634	Approved
0.6893	Remote Similarity	NPD6881	Approved
0.6893	Remote Similarity	NPD6899	Approved
0.6893	Remote Similarity	NPD7320	Approved
0.6889	Remote Similarity	NPD4788	Approved
0.6863	Remote Similarity	NPD4767	Approved
0.6863	Remote Similarity	NPD4768	Approved
0.6848	Remote Similarity	NPD5330	Approved
0.6848	Remote Similarity	NPD5205	Approved
0.6848	Remote Similarity	NPD4138	Approved
0.6848	Remote Similarity	NPD7521	Approved
0.6848	Remote Similarity	NPD4689	Approved
0.6848	Remote Similarity	NPD4688	Approved
0.6848	Remote Similarity	NPD6684	Approved
0.6848	Remote Similarity	NPD4690	Approved
0.6848	Remote Similarity	NPD7146	Approved
0.6848	Remote Similarity	NPD4693	Phase 3
0.6848	Remote Similarity	NPD7334	Approved
0.6848	Remote Similarity	NPD6409	Approved
0.6832	Remote Similarity	NPD4754	Approved
0.6827	Remote Similarity	NPD6373	Approved
0.6827	Remote Similarity	NPD6372	Approved
0.6809	Remote Similarity	NPD6051	Approved
0.68	Remote Similarity	NPD4159	Approved
0.6796	Remote Similarity	NPD6412	Phase 2
0.6796	Remote Similarity	NPD5701	Approved
0.6796	Remote Similarity	NPD5697	Approved
0.6762	Remote Similarity	NPD7290	Approved
0.6762	Remote Similarity	NPD7102	Approved
0.6762	Remote Similarity	NPD6883	Approved
0.6731	Remote Similarity	NPD5128	Approved
0.6731	Remote Similarity	NPD4730	Approved
0.6731	Remote Similarity	NPD4729	Approved
0.6705	Remote Similarity	NPD6118	Approved
0.6705	Remote Similarity	NPD3617	Approved
0.6705	Remote Similarity	NPD6114	Approved
0.6705	Remote Similarity	NPD6115	Approved
0.6705	Remote Similarity	NPD6697	Approved
0.6702	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4723	Approved
0.6702	Remote Similarity	NPD5737	Approved
0.6702	Remote Similarity	NPD6903	Approved
0.6702	Remote Similarity	NPD4722	Approved
0.6702	Remote Similarity	NPD6672	Approved
0.6701	Remote Similarity	NPD7748	Approved
0.6698	Remote Similarity	NPD6847	Approved
0.6698	Remote Similarity	NPD6650	Approved
0.6698	Remote Similarity	NPD6617	Approved
0.6698	Remote Similarity	NPD6869	Approved
0.6698	Remote Similarity	NPD6649	Approved
0.6698	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7327	Approved
0.6636	Remote Similarity	NPD7328	Approved
0.6636	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6633	Remote Similarity	NPD5695	Phase 3
0.6604	Remote Similarity	NPD5251	Approved
0.6604	Remote Similarity	NPD5250	Approved
0.6604	Remote Similarity	NPD5249	Phase 3
0.6604	Remote Similarity	NPD5247	Approved
0.6604	Remote Similarity	NPD5248	Approved
0.66	Remote Similarity	NPD5696	Approved
0.6588	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7516	Approved
0.6574	Remote Similarity	NPD4632	Approved
0.6571	Remote Similarity	NPD6011	Approved
0.6571	Remote Similarity	NPD5168	Approved
0.6569	Remote Similarity	NPD7632	Discontinued
0.6556	Remote Similarity	NPD4695	Discontinued
0.6552	Remote Similarity	NPD3703	Phase 2
0.6545	Remote Similarity	NPD7115	Discovery
0.6542	Remote Similarity	NPD5215	Approved
0.6542	Remote Similarity	NPD5216	Approved
0.6542	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5217	Approved
0.6538	Remote Similarity	NPD7333	Discontinued
0.6538	Remote Similarity	NPD6008	Approved
0.6518	Remote Similarity	NPD6059	Approved
0.6518	Remote Similarity	NPD6054	Approved
0.65	Remote Similarity	NPD7902	Approved
0.65	Remote Similarity	NPD368	Approved
0.6489	Remote Similarity	NPD6098	Approved
0.6484	Remote Similarity	NPD4692	Approved
0.6484	Remote Similarity	NPD4139	Approved
0.6477	Remote Similarity	NPD6117	Approved
0.6471	Remote Similarity	NPD4747	Approved
0.646	Remote Similarity	NPD8378	Approved
0.646	Remote Similarity	NPD8335	Approved
0.646	Remote Similarity	NPD8296	Approved
0.646	Remote Similarity	NPD8033	Approved
0.646	Remote Similarity	NPD8380	Approved
0.646	Remote Similarity	NPD8379	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