NPASS Compound

Structure

NPC470361 OpenBabel07101718242D 32 35 0 0 1 0 0 0 0 0999 V2000 8.1309 2.8975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1235 5.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7707 4.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 4.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 3.4135 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 7.1527 2.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 3.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5054 3.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.1910 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 0.8660 2.5000 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 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7926 4.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 3.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4836 3.4328 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 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 3.5491 2.8090 0.0000 C 0 0 2 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 0.8660 1.5000 0.0000 C 0 0 1 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 2.5981 2.5000 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 0.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 6 28 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 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 23 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 22 2 0 0 0 0 16 26 1 0 0 0 0 17 21 1 0 0 0 0 17 29 1 0 0 0 0 18 20 1 0 0 0 0 19 4 1 6 0 0 0 19 23 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 27 1 1 0 0 0 24 27 1 1 0 0 0 25 28 1 1 0 0 0 26 29 1 0 0 0 0 26 31 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.38
Volume:	499.648
LogP:	6.037
LogD:	5.683
LogS:	-5.144
# 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:	0.431
Synthetic Accessibility Score:	4.827
Fsp3:	0.931
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.757
MDCK Permeability:	5.545239764614962e-05
Pgp-inhibitor:	0.103
Pgp-substrate:	0.612
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.919
30% Bioavailability (F30%):	0.558

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	95.74291229248047%
Volume Distribution (VD):	1.149
Pgp-substrate:	1.6064802408218384%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.333
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.246
CYP2C9-substrate:	0.237
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.271
CYP3A4-inhibitor:	0.68
CYP3A4-substrate:	0.611

ADMET: Excretion

Clearance (CL):	9.929
Half-life (T1/2):	0.051

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.61
Skin Sensitization:	0.035
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.045
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC470361

Natural Product ID:	NPC470361
*Common Name:**	24-Ethyl-Cholest-7-Ene-3,5,6-Triol
IUPAC Name:	(3S,9S,10R,13R,14R,17R)-17-[(2R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,5,6-triol
Synonyms:
Standard InCHIKey:	OZIAZQBXQMKSLA-XMWGPCPVSA-N
Standard InCHI:	InChI=1S/C29H50O3/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-16-26(31)29(32)17-21(30)12-15-28(29,6)25(22)13-14-27(23,24)5/h16,18-21,23-26,30-32H,7-15,17H2,1-6H3/t19-,20?,21+,23-,24+,25+,26?,27-,28-,29?/m1/s1
SMILES:	CCC(C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1C2=CC(C2([C@]1(C)CC[C@@H](C2)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL201951
PubChem CID:	44407137
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	=	13700.0	nM	PMID[513086]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Ki	=	12600.0	nM	PMID[513086]
NPT2569	Individual Protein	Butyrylcholinesterase	Equus caballus	IC50	=	2000.0	nM	PMID[513086]
NPT2569	Individual Protein	Butyrylcholinesterase	Equus caballus	Ki	=	2500.0	nM	PMID[513086]

☑ 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 NPC470361 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	179
0.1-0.2	1433
0.2-0.3	4992
0.3-0.4	13019
0.4-0.5	10260
0.5-0.6	5752
0.6-0.7	5123
0.7-0.8	1556
0.8-0.85	270
0.85-0.9	83
0.9-0.95	20
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC291484
0.9881	High Similarity	NPC11216
0.9881	High Similarity	NPC80561
0.9881	High Similarity	NPC329596
0.9881	High Similarity	NPC204188
0.9881	High Similarity	NPC3345
0.9765	High Similarity	NPC97404
0.9765	High Similarity	NPC41554
0.9425	High Similarity	NPC310013
0.9412	High Similarity	NPC133588
0.9412	High Similarity	NPC474668
0.9405	High Similarity	NPC6391
0.9405	High Similarity	NPC299068
0.9326	High Similarity	NPC288970
0.9318	High Similarity	NPC127718
0.9318	High Similarity	NPC65402
0.9286	High Similarity	NPC470360
0.9213	High Similarity	NPC8774
0.9176	High Similarity	NPC261266
0.9167	High Similarity	NPC185568
0.9111	High Similarity	NPC12103
0.9111	High Similarity	NPC227583
0.9111	High Similarity	NPC98457
0.9048	High Similarity	NPC317458
0.9048	High Similarity	NPC474634
0.9036	High Similarity	NPC23852
0.9036	High Similarity	NPC209620
0.9036	High Similarity	NPC470383
0.9011	High Similarity	NPC261807
0.8977	High Similarity	NPC470390
0.8977	High Similarity	NPC245410
0.8977	High Similarity	NPC270511
0.8977	High Similarity	NPC14380
0.8977	High Similarity	NPC192437
0.8966	High Similarity	NPC67872
0.8953	High Similarity	NPC293287
0.8953	High Similarity	NPC94462
0.8953	High Similarity	NPC152808
0.8941	High Similarity	NPC205845
0.8929	High Similarity	NPC101462
0.8929	High Similarity	NPC50964
0.8929	High Similarity	NPC30166
0.8929	High Similarity	NPC49964
0.8901	High Similarity	NPC210717
0.8901	High Similarity	NPC103165
0.8889	High Similarity	NPC477605
0.8876	High Similarity	NPC275671
0.8864	High Similarity	NPC101886
0.8851	High Similarity	NPC470620
0.881	High Similarity	NPC476646
0.881	High Similarity	NPC264245
0.881	High Similarity	NPC474531
0.881	High Similarity	NPC249423
0.8804	High Similarity	NPC476893
0.8795	High Similarity	NPC328714
0.8795	High Similarity	NPC47982
0.8795	High Similarity	NPC209430
0.8795	High Similarity	NPC81306
0.8795	High Similarity	NPC84694
0.8795	High Similarity	NPC109546
0.8795	High Similarity	NPC30986
0.8795	High Similarity	NPC143182
0.8795	High Similarity	NPC28862
0.8778	High Similarity	NPC137461
0.8764	High Similarity	NPC473956
0.8764	High Similarity	NPC295668
0.8764	High Similarity	NPC475751
0.875	High Similarity	NPC280556
0.875	High Similarity	NPC4574
0.875	High Similarity	NPC212596
0.8736	High Similarity	NPC269058
0.8736	High Similarity	NPC71520
0.8736	High Similarity	NPC201273
0.8721	High Similarity	NPC124172
0.871	High Similarity	NPC476895
0.8706	High Similarity	NPC296701
0.8706	High Similarity	NPC87489
0.8706	High Similarity	NPC218616
0.8696	High Similarity	NPC72204
0.869	High Similarity	NPC236112
0.869	High Similarity	NPC241290
0.869	High Similarity	NPC164840
0.869	High Similarity	NPC234193
0.869	High Similarity	NPC209944
0.869	High Similarity	NPC96362
0.869	High Similarity	NPC13554
0.8681	High Similarity	NPC144202
0.8675	High Similarity	NPC87604
0.8675	High Similarity	NPC474216
0.8667	High Similarity	NPC114389
0.8667	High Similarity	NPC210268
0.8652	High Similarity	NPC109744
0.8652	High Similarity	NPC105495
0.8652	High Similarity	NPC138974
0.8652	High Similarity	NPC259875
0.8652	High Similarity	NPC187785
0.8636	High Similarity	NPC304083
0.8636	High Similarity	NPC149224
0.8621	High Similarity	NPC266511
0.8621	High Similarity	NPC274448
0.8605	High Similarity	NPC211135
0.8605	High Similarity	NPC85095
0.8605	High Similarity	NPC216420
0.8605	High Similarity	NPC475789
0.8605	High Similarity	NPC113978
0.8605	High Similarity	NPC320548
0.8605	High Similarity	NPC207013
0.8602	High Similarity	NPC477226
0.8588	High Similarity	NPC47761
0.8587	High Similarity	NPC476894
0.8571	High Similarity	NPC27531
0.8571	High Similarity	NPC80530
0.8571	High Similarity	NPC273410
0.8554	High Similarity	NPC155986
0.8554	High Similarity	NPC198968
0.8554	High Similarity	NPC318495
0.8554	High Similarity	NPC130136
0.8539	High Similarity	NPC475605
0.8539	High Similarity	NPC475664
0.8526	High Similarity	NPC476896
0.8523	High Similarity	NPC6605
0.8523	High Similarity	NPC139724
0.8523	High Similarity	NPC125399
0.8523	High Similarity	NPC24277
0.8523	High Similarity	NPC121981
0.8506	High Similarity	NPC238485
0.8506	High Similarity	NPC470077
0.8506	High Similarity	NPC474047
0.8506	High Similarity	NPC209802
0.8506	High Similarity	NPC231310
0.8488	Intermediate Similarity	NPC189972
0.8488	Intermediate Similarity	NPC470049
0.8488	Intermediate Similarity	NPC7988
0.8488	Intermediate Similarity	NPC202389
0.8488	Intermediate Similarity	NPC470614
0.8488	Intermediate Similarity	NPC248886
0.8488	Intermediate Similarity	NPC1272
0.8471	Intermediate Similarity	NPC102253
0.8471	Intermediate Similarity	NPC236237
0.8471	Intermediate Similarity	NPC26117
0.8471	Intermediate Similarity	NPC287749
0.8471	Intermediate Similarity	NPC324772
0.8471	Intermediate Similarity	NPC322313
0.8452	Intermediate Similarity	NPC285761
0.8452	Intermediate Similarity	NPC275910
0.8452	Intermediate Similarity	NPC167891
0.8452	Intermediate Similarity	NPC244385
0.8452	Intermediate Similarity	NPC473943
0.8452	Intermediate Similarity	NPC6978
0.8452	Intermediate Similarity	NPC83351
0.8452	Intermediate Similarity	NPC138621
0.8452	Intermediate Similarity	NPC31828
0.8452	Intermediate Similarity	NPC167037
0.8444	Intermediate Similarity	NPC477606
0.8434	Intermediate Similarity	NPC107059
0.8434	Intermediate Similarity	NPC244488
0.8434	Intermediate Similarity	NPC300324
0.8434	Intermediate Similarity	NPC240604
0.8434	Intermediate Similarity	NPC321016
0.8434	Intermediate Similarity	NPC321381
0.8434	Intermediate Similarity	NPC189883
0.8434	Intermediate Similarity	NPC247325
0.8427	Intermediate Similarity	NPC186145
0.8427	Intermediate Similarity	NPC475313
0.8427	Intermediate Similarity	NPC474657
0.8409	Intermediate Similarity	NPC318390
0.8409	Intermediate Similarity	NPC157257
0.8391	Intermediate Similarity	NPC477818
0.8391	Intermediate Similarity	NPC232023
0.8391	Intermediate Similarity	NPC110778
0.8391	Intermediate Similarity	NPC470384
0.8391	Intermediate Similarity	NPC82623
0.8384	Intermediate Similarity	NPC472219
0.8384	Intermediate Similarity	NPC472218
0.8384	Intermediate Similarity	NPC472217
0.8372	Intermediate Similarity	NPC82986
0.8372	Intermediate Similarity	NPC474752
0.8372	Intermediate Similarity	NPC7505
0.8372	Intermediate Similarity	NPC474731
0.8372	Intermediate Similarity	NPC320525
0.8372	Intermediate Similarity	NPC474759
0.8372	Intermediate Similarity	NPC6707
0.8372	Intermediate Similarity	NPC474683
0.837	Intermediate Similarity	NPC98193
0.837	Intermediate Similarity	NPC119379
0.8353	Intermediate Similarity	NPC472463
0.8353	Intermediate Similarity	NPC1319
0.8333	Intermediate Similarity	NPC470542
0.8333	Intermediate Similarity	NPC471952
0.8333	Intermediate Similarity	NPC477924
0.8333	Intermediate Similarity	NPC470711
0.8333	Intermediate Similarity	NPC470758
0.8333	Intermediate Similarity	NPC214570
0.8333	Intermediate Similarity	NPC471798
0.8333	Intermediate Similarity	NPC475617
0.8333	Intermediate Similarity	NPC91594
0.8315	Intermediate Similarity	NPC237344
0.8313	Intermediate Similarity	NPC257347
0.8313	Intermediate Similarity	NPC288035
0.8313	Intermediate Similarity	NPC230301

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 NPC470361 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1654
0.2-0.3	4190
0.3-0.4	2119
0.4-0.5	572
0.5-0.6	176
0.6-0.7	176
0.7-0.8	69
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8471	Intermediate Similarity	NPD7525	Registered
0.8471	Intermediate Similarity	NPD6930	Phase 2
0.8471	Intermediate Similarity	NPD6931	Approved
0.8427	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD6929	Approved
0.8313	Intermediate Similarity	NPD7339	Approved
0.8313	Intermediate Similarity	NPD6942	Approved
0.8295	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7514	Phase 3
0.8222	Intermediate Similarity	NPD7524	Approved
0.8182	Intermediate Similarity	NPD6695	Phase 3
0.8118	Intermediate Similarity	NPD5776	Phase 2
0.8118	Intermediate Similarity	NPD6925	Approved
0.8046	Intermediate Similarity	NPD7332	Phase 2
0.8023	Intermediate Similarity	NPD7145	Approved
0.8	Intermediate Similarity	NPD6933	Approved
0.8	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6893	Approved
0.7955	Intermediate Similarity	NPD6902	Approved
0.7907	Intermediate Similarity	NPD6932	Approved
0.7826	Intermediate Similarity	NPD7750	Discontinued
0.7765	Intermediate Similarity	NPD6924	Approved
0.7765	Intermediate Similarity	NPD6926	Approved
0.7753	Intermediate Similarity	NPD6898	Phase 1
0.7727	Intermediate Similarity	NPD7645	Phase 2
0.7727	Intermediate Similarity	NPD6683	Phase 2
0.7692	Intermediate Similarity	NPD4786	Approved
0.7558	Intermediate Similarity	NPD4785	Approved
0.7558	Intermediate Similarity	NPD4784	Approved
0.7529	Intermediate Similarity	NPD4243	Approved
0.75	Intermediate Similarity	NPD7087	Discontinued
0.7474	Intermediate Similarity	NPD5328	Approved
0.7473	Intermediate Similarity	NPD3667	Approved
0.7444	Intermediate Similarity	NPD7509	Discontinued
0.7444	Intermediate Similarity	NPD4748	Discontinued
0.7423	Intermediate Similarity	NPD4202	Approved
0.7416	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5211	Phase 2
0.734	Intermediate Similarity	NPD3618	Phase 1
0.7327	Intermediate Similarity	NPD7639	Approved
0.7327	Intermediate Similarity	NPD7640	Approved
0.7326	Intermediate Similarity	NPD7151	Approved
0.7326	Intermediate Similarity	NPD7152	Approved
0.7326	Intermediate Similarity	NPD7150	Approved
0.732	Intermediate Similarity	NPD6079	Approved
0.73	Intermediate Similarity	NPD4755	Approved
0.7294	Intermediate Similarity	NPD6922	Approved
0.7294	Intermediate Similarity	NPD6923	Approved
0.7294	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8264	Approved
0.7255	Intermediate Similarity	NPD4159	Approved
0.7228	Intermediate Similarity	NPD7638	Approved
0.7212	Intermediate Similarity	NPD5141	Approved
0.7209	Intermediate Similarity	NPD7144	Approved
0.7209	Intermediate Similarity	NPD7143	Approved
0.7207	Intermediate Similarity	NPD7328	Approved
0.7207	Intermediate Similarity	NPD7327	Approved
0.7196	Intermediate Similarity	NPD4634	Approved
0.7157	Intermediate Similarity	NPD5285	Approved
0.7157	Intermediate Similarity	NPD4700	Approved
0.7157	Intermediate Similarity	NPD5286	Approved
0.7157	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD7637	Suspended
0.7143	Intermediate Similarity	NPD7516	Approved
0.7117	Intermediate Similarity	NPD7115	Discovery
0.7079	Intermediate Similarity	NPD4190	Phase 3
0.7079	Intermediate Similarity	NPD5275	Approved
0.7071	Intermediate Similarity	NPD6399	Phase 3
0.7019	Intermediate Similarity	NPD5225	Approved
0.7019	Intermediate Similarity	NPD5226	Approved
0.7019	Intermediate Similarity	NPD4633	Approved
0.7019	Intermediate Similarity	NPD5224	Approved
0.7018	Intermediate Similarity	NPD8296	Approved
0.7018	Intermediate Similarity	NPD8378	Approved
0.7018	Intermediate Similarity	NPD8033	Approved
0.7018	Intermediate Similarity	NPD8335	Approved
0.7018	Intermediate Similarity	NPD8380	Approved
0.7018	Intermediate Similarity	NPD8379	Approved
0.6981	Remote Similarity	NPD5739	Approved
0.6981	Remote Similarity	NPD7128	Approved
0.6981	Remote Similarity	NPD6675	Approved
0.6981	Remote Similarity	NPD6402	Approved
0.6957	Remote Similarity	NPD4195	Approved
0.6952	Remote Similarity	NPD5175	Approved
0.6952	Remote Similarity	NPD5174	Approved
0.6947	Remote Similarity	NPD3133	Approved
0.6947	Remote Similarity	NPD3665	Phase 1
0.6947	Remote Similarity	NPD3666	Approved
0.6939	Remote Similarity	NPD4753	Phase 2
0.693	Remote Similarity	NPD8377	Approved
0.693	Remote Similarity	NPD8294	Approved
0.6923	Remote Similarity	NPD5223	Approved
0.6893	Remote Similarity	NPD4225	Approved
0.6875	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7503	Approved
0.6869	Remote Similarity	NPD7136	Phase 2
0.6867	Remote Similarity	NPD368	Approved
0.6863	Remote Similarity	NPD5221	Approved
0.6863	Remote Similarity	NPD4697	Phase 3
0.6863	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5222	Approved
0.6852	Remote Similarity	NPD7320	Approved
0.6852	Remote Similarity	NPD6881	Approved
0.6852	Remote Similarity	NPD6899	Approved
0.6847	Remote Similarity	NPD4632	Approved
0.6822	Remote Similarity	NPD4767	Approved
0.6822	Remote Similarity	NPD4768	Approved
0.6796	Remote Similarity	NPD5173	Approved
0.6792	Remote Similarity	NPD4754	Approved
0.6789	Remote Similarity	NPD6372	Approved
0.6789	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6373	Approved
0.6771	Remote Similarity	NPD3668	Phase 3
0.6768	Remote Similarity	NPD6051	Approved
0.6762	Remote Similarity	NPD5344	Discontinued
0.6759	Remote Similarity	NPD5701	Approved
0.6759	Remote Similarity	NPD5697	Approved
0.6759	Remote Similarity	NPD6412	Phase 2
0.6757	Remote Similarity	NPD8297	Approved
0.6737	Remote Similarity	NPD4221	Approved
0.6737	Remote Similarity	NPD4223	Phase 3
0.6727	Remote Similarity	NPD7102	Approved
0.6727	Remote Similarity	NPD7290	Approved
0.6727	Remote Similarity	NPD6883	Approved
0.6701	Remote Similarity	NPD5329	Approved
0.6698	Remote Similarity	NPD7632	Discontinued
0.6697	Remote Similarity	NPD4730	Approved
0.6697	Remote Similarity	NPD4729	Approved
0.6697	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD6640	Phase 3
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD7507	Approved
0.6638	Remote Similarity	NPD6059	Approved
0.6638	Remote Similarity	NPD6319	Approved
0.6638	Remote Similarity	NPD6054	Approved
0.6636	Remote Similarity	NPD6013	Approved
0.6636	Remote Similarity	NPD6014	Approved
0.6636	Remote Similarity	NPD6012	Approved
0.6635	Remote Similarity	NPD6083	Phase 2
0.6635	Remote Similarity	NPD6084	Phase 2
0.6634	Remote Similarity	NPD7515	Phase 2
0.6633	Remote Similarity	NPD5279	Phase 3
0.6612	Remote Similarity	NPD7319	Approved
0.6607	Remote Similarity	NPD6882	Approved
0.6602	Remote Similarity	NPD5210	Approved
0.6602	Remote Similarity	NPD4629	Approved
0.6598	Remote Similarity	NPD4197	Approved
0.6577	Remote Similarity	NPD5250	Approved
0.6577	Remote Similarity	NPD5248	Approved
0.6577	Remote Similarity	NPD5251	Approved
0.6577	Remote Similarity	NPD5247	Approved
0.6577	Remote Similarity	NPD5249	Phase 3
0.6571	Remote Similarity	NPD5290	Discontinued
0.6545	Remote Similarity	NPD6011	Approved
0.6525	Remote Similarity	NPD6370	Approved
0.6522	Remote Similarity	NPD6009	Approved
0.6518	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5215	Approved
0.6518	Remote Similarity	NPD5217	Approved
0.6518	Remote Similarity	NPD5216	Approved
0.6514	Remote Similarity	NPD6008	Approved
0.6495	Remote Similarity	NPD4788	Approved
0.6484	Remote Similarity	NPD4732	Discontinued
0.6471	Remote Similarity	NPD8035	Phase 2
0.6471	Remote Similarity	NPD8034	Phase 2
0.6465	Remote Similarity	NPD4688	Approved
0.6465	Remote Similarity	NPD4689	Approved
0.6465	Remote Similarity	NPD4693	Phase 3
0.6465	Remote Similarity	NPD4690	Approved
0.6465	Remote Similarity	NPD4623	Approved
0.6465	Remote Similarity	NPD5205	Approved
0.6465	Remote Similarity	NPD4519	Discontinued
0.6465	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4138	Approved
0.6444	Remote Similarity	NPD4787	Phase 1
0.6441	Remote Similarity	NPD6016	Approved
0.6441	Remote Similarity	NPD6015	Approved
0.6429	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5135	Approved
0.6429	Remote Similarity	NPD5169	Approved
0.6417	Remote Similarity	NPD7492	Approved
0.6396	Remote Similarity	NPD6686	Approved
0.6387	Remote Similarity	NPD5988	Approved
0.6372	Remote Similarity	NPD5127	Approved
0.6364	Remote Similarity	NPD7333	Discontinued
0.6364	Remote Similarity	NPD6616	Approved
0.6356	Remote Similarity	NPD7741	Discontinued
0.6355	Remote Similarity	NPD6648	Approved
0.6354	Remote Similarity	NPD4820	Approved
0.6354	Remote Similarity	NPD4821	Approved
0.6354	Remote Similarity	NPD4819	Approved
0.6354	Remote Similarity	NPD4822	Approved
0.6346	Remote Similarity	NPD7748	Approved
0.6337	Remote Similarity	NPD4723	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