NPASS Compound

Structure

NPC470384 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 2 0 0 0 0 8 20 1 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 2 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:	444.36
Volume:	497.012
LogP:	4.801
LogD:	4.629
LogS:	-4.751
# 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:	0.489
Synthetic Accessibility Score:	5.091
Fsp3:	0.862
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:	-4.876
MDCK Permeability:	1.54103781824233e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.163
20% Bioavailability (F20%):	0.929
30% Bioavailability (F30%):	0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.298
Plasma Protein Binding (PPB):	97.82257843017578%
Volume Distribution (VD):	1.055
Pgp-substrate:	1.8226841688156128%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.351
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.223
CYP2C9-substrate:	0.17
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.743
CYP3A4-substrate:	0.859

ADMET: Excretion

Clearance (CL):	13.489
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.885
Human Hepatotoxicity (H-HT):	0.389
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.958
Carcinogencity:	0.154
Eye Corrosion:	0.005
Eye Irritation:	0.012
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC470384

Natural Product ID:	NPC470384
*Common Name:**	Haloxysterol B
IUPAC Name:	(1S,3S,10R,13S,17R)-17-[(2S,3R,5R)-5-ethyl-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-1,3-diol
Synonyms:
Standard InCHIKey:	MVMHIMFXUANMIR-IWAMNEIESA-N
Standard InCHI:	InChI=1S/C29H48O3/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/h8-9,15,17-19,21-27,30-32H,7,10-14,16H2,1-6H3/t18-,19+,21+,22?,23+,24?,25?,26+,27-,28+,29-/m0/s1
SMILES:	CC[C@@H](C(C)C)C[C@H]([C@H]([C@H]1CCC2[C@]1(C)CCC1C2C=CC2=C[C@H](C[C@@H]([C@]12C)O)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL202223
PubChem CID:	11690845
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	=	890.0	nM	PMID[497213]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Ki	=	850.0	nM	PMID[497213]
NPT2569	Individual Protein	Butyrylcholinesterase	Equus caballus	IC50	=	2300.0	nM	PMID[497213]
NPT2569	Individual Protein	Butyrylcholinesterase	Equus caballus	Ki	=	2500.0	nM	PMID[497213]

☑ 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 NPC470384 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	149
0.1-0.2	1074
0.2-0.3	4780
0.3-0.4	15184
0.4-0.5	10089
0.5-0.6	6959
0.6-0.7	3388
0.7-0.8	900
0.8-0.85	118
0.85-0.9	49
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC238485
0.9375	High Similarity	NPC231310
0.9367	High Similarity	NPC202389
0.9125	High Similarity	NPC87489
0.9114	High Similarity	NPC234193
0.9	High Similarity	NPC264245
0.8987	High Similarity	NPC143182
0.8987	High Similarity	NPC84694
0.8987	High Similarity	NPC28862
0.8987	High Similarity	NPC30986
0.8987	High Similarity	NPC47982
0.8987	High Similarity	NPC109546
0.8987	High Similarity	NPC209430
0.8987	High Similarity	NPC81306
0.8961	High Similarity	NPC471468
0.8953	High Similarity	NPC310013
0.8902	High Similarity	NPC205845
0.8889	High Similarity	NPC101462
0.8889	High Similarity	NPC50964
0.8889	High Similarity	NPC49964
0.8889	High Similarity	NPC201852
0.8875	High Similarity	NPC209944
0.8875	High Similarity	NPC241290
0.8875	High Similarity	NPC164840
0.8861	High Similarity	NPC18603
0.8861	High Similarity	NPC186191
0.8861	High Similarity	NPC275910
0.8861	High Similarity	NPC307965
0.8861	High Similarity	NPC205455
0.8861	High Similarity	NPC76931
0.8861	High Similarity	NPC474216
0.8846	High Similarity	NPC244488
0.8846	High Similarity	NPC470362
0.8846	High Similarity	NPC247325
0.878	High Similarity	NPC317458
0.8765	High Similarity	NPC209620
0.8765	High Similarity	NPC47761
0.8765	High Similarity	NPC23852
0.8734	High Similarity	NPC91594
0.8734	High Similarity	NPC214570
0.869	High Similarity	NPC261266
0.869	High Similarity	NPC6391
0.8675	High Similarity	NPC185568
0.8659	High Similarity	NPC189972
0.8659	High Similarity	NPC218616
0.8659	High Similarity	NPC296701
0.8625	High Similarity	NPC473943
0.8625	High Similarity	NPC318136
0.8608	High Similarity	NPC73875
0.8608	High Similarity	NPC321381
0.8608	High Similarity	NPC129165
0.8608	High Similarity	NPC134330
0.8608	High Similarity	NPC107059
0.8608	High Similarity	NPC202642
0.8608	High Similarity	NPC46160
0.8608	High Similarity	NPC321016
0.8608	High Similarity	NPC113733
0.8588	High Similarity	NPC149224
0.8571	High Similarity	NPC266511
0.8571	High Similarity	NPC470360
0.8571	High Similarity	NPC274448
0.8554	High Similarity	NPC474634
0.8554	High Similarity	NPC475789
0.8537	High Similarity	NPC82986
0.8537	High Similarity	NPC474759
0.8537	High Similarity	NPC6707
0.8537	High Similarity	NPC474683
0.8537	High Similarity	NPC474731
0.8537	High Similarity	NPC474752
0.8537	High Similarity	NPC7505
0.8523	High Similarity	NPC472942
0.8506	High Similarity	NPC291484
0.8506	High Similarity	NPC270511
0.8506	High Similarity	NPC11216
0.8506	High Similarity	NPC470390
0.8506	High Similarity	NPC69622
0.8506	High Similarity	NPC192437
0.8506	High Similarity	NPC329596
0.8506	High Similarity	NPC245410
0.8506	High Similarity	NPC3345
0.8506	High Similarity	NPC204188
0.8506	High Similarity	NPC80561
0.85	High Similarity	NPC155986
0.85	High Similarity	NPC318495
0.85	High Similarity	NPC198968
0.8488	Intermediate Similarity	NPC2158
0.8488	Intermediate Similarity	NPC280556
0.8481	Intermediate Similarity	NPC162742
0.8481	Intermediate Similarity	NPC257347
0.8481	Intermediate Similarity	NPC322353
0.8481	Intermediate Similarity	NPC171148
0.8481	Intermediate Similarity	NPC471723
0.8481	Intermediate Similarity	NPC134847
0.8481	Intermediate Similarity	NPC22105
0.8481	Intermediate Similarity	NPC69383
0.8481	Intermediate Similarity	NPC136188
0.8481	Intermediate Similarity	NPC304309
0.8481	Intermediate Similarity	NPC285893
0.8481	Intermediate Similarity	NPC313179
0.8481	Intermediate Similarity	NPC118508
0.8481	Intermediate Similarity	NPC28657
0.8481	Intermediate Similarity	NPC230301
0.8481	Intermediate Similarity	NPC121744
0.8481	Intermediate Similarity	NPC288035
0.8481	Intermediate Similarity	NPC141071
0.8471	Intermediate Similarity	NPC299068
0.8471	Intermediate Similarity	NPC152808
0.8471	Intermediate Similarity	NPC293287
0.8462	Intermediate Similarity	NPC130665
0.8462	Intermediate Similarity	NPC474140
0.8452	Intermediate Similarity	NPC470077
0.8452	Intermediate Similarity	NPC474047
0.8442	Intermediate Similarity	NPC34834
0.8434	Intermediate Similarity	NPC20853
0.8434	Intermediate Similarity	NPC470049
0.8415	Intermediate Similarity	NPC324772
0.8409	Intermediate Similarity	NPC471453
0.8409	Intermediate Similarity	NPC212948
0.8409	Intermediate Similarity	NPC41554
0.8409	Intermediate Similarity	NPC97404
0.8395	Intermediate Similarity	NPC83351
0.8395	Intermediate Similarity	NPC477522
0.8395	Intermediate Similarity	NPC167891
0.8395	Intermediate Similarity	NPC87604
0.8395	Intermediate Similarity	NPC477514
0.8391	Intermediate Similarity	NPC470361
0.8375	Intermediate Similarity	NPC240604
0.8375	Intermediate Similarity	NPC189883
0.8375	Intermediate Similarity	NPC300324
0.8375	Intermediate Similarity	NPC265588
0.8372	Intermediate Similarity	NPC271967
0.8354	Intermediate Similarity	NPC471797
0.8354	Intermediate Similarity	NPC27395
0.8354	Intermediate Similarity	NPC469534
0.8354	Intermediate Similarity	NPC469593
0.8354	Intermediate Similarity	NPC329090
0.8354	Intermediate Similarity	NPC469533
0.8353	Intermediate Similarity	NPC157257
0.8353	Intermediate Similarity	NPC318390
0.8353	Intermediate Similarity	NPC474083
0.8333	Intermediate Similarity	NPC237795
0.8333	Intermediate Similarity	NPC82623
0.8333	Intermediate Similarity	NPC242001
0.8333	Intermediate Similarity	NPC82538
0.8315	Intermediate Similarity	NPC214697
0.8313	Intermediate Similarity	NPC470383
0.8313	Intermediate Similarity	NPC474531
0.8313	Intermediate Similarity	NPC320525
0.8313	Intermediate Similarity	NPC476646
0.8312	Intermediate Similarity	NPC471560
0.8295	Intermediate Similarity	NPC295668
0.8295	Intermediate Similarity	NPC14380
0.8293	Intermediate Similarity	NPC328714
0.8293	Intermediate Similarity	NPC1319
0.8276	Intermediate Similarity	NPC470542
0.8276	Intermediate Similarity	NPC133588
0.8276	Intermediate Similarity	NPC474668
0.8276	Intermediate Similarity	NPC67872
0.8272	Intermediate Similarity	NPC34019
0.825	Intermediate Similarity	NPC328104
0.825	Intermediate Similarity	NPC319090
0.8235	Intermediate Similarity	NPC474493
0.8228	Intermediate Similarity	NPC201373
0.8228	Intermediate Similarity	NPC471799
0.8222	Intermediate Similarity	NPC469406
0.8214	Intermediate Similarity	NPC30166
0.8205	Intermediate Similarity	NPC49422
0.8205	Intermediate Similarity	NPC9161
0.8205	Intermediate Similarity	NPC145498
0.8193	Intermediate Similarity	NPC236112
0.8193	Intermediate Similarity	NPC96362
0.8193	Intermediate Similarity	NPC26117
0.8182	Intermediate Similarity	NPC477606
0.8182	Intermediate Similarity	NPC216460
0.8171	Intermediate Similarity	NPC11908
0.8171	Intermediate Similarity	NPC285761
0.8171	Intermediate Similarity	NPC167037
0.8171	Intermediate Similarity	NPC138621
0.8171	Intermediate Similarity	NPC476314
0.8171	Intermediate Similarity	NPC6978
0.8171	Intermediate Similarity	NPC244385
0.8161	Intermediate Similarity	NPC470620
0.8161	Intermediate Similarity	NPC475772
0.8152	Intermediate Similarity	NPC261807
0.8152	Intermediate Similarity	NPC141401
0.8148	Intermediate Similarity	NPC96319
0.8148	Intermediate Similarity	NPC315261
0.8148	Intermediate Similarity	NPC253190
0.8148	Intermediate Similarity	NPC106432
0.8148	Intermediate Similarity	NPC237460
0.814	Intermediate Similarity	NPC471224
0.8125	Intermediate Similarity	NPC91858
0.8125	Intermediate Similarity	NPC477138
0.8125	Intermediate Similarity	NPC243342
0.8118	Intermediate Similarity	NPC134481
0.8118	Intermediate Similarity	NPC320548
0.8118	Intermediate Similarity	NPC470558
0.8101	Intermediate Similarity	NPC110799
0.8095	Intermediate Similarity	NPC249423
0.809	Intermediate Similarity	NPC107189

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 NPC470384 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1214
0.2-0.3	4023
0.3-0.4	2612
0.4-0.5	709
0.5-0.6	221
0.6-0.7	166
0.7-0.8	37
0.8-0.85	20
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD6929	Approved
0.8481	Intermediate Similarity	NPD7339	Approved
0.8481	Intermediate Similarity	NPD6942	Approved
0.8481	Intermediate Similarity	NPD8264	Approved
0.8415	Intermediate Similarity	NPD7514	Phase 3
0.8415	Intermediate Similarity	NPD6931	Approved
0.8415	Intermediate Similarity	NPD6930	Phase 2
0.8395	Intermediate Similarity	NPD7145	Approved
0.8354	Intermediate Similarity	NPD6926	Approved
0.8354	Intermediate Similarity	NPD6924	Approved
0.8313	Intermediate Similarity	NPD6902	Approved
0.8272	Intermediate Similarity	NPD5776	Phase 2
0.8272	Intermediate Similarity	NPD6925	Approved
0.8205	Intermediate Similarity	NPD7144	Approved
0.8205	Intermediate Similarity	NPD7143	Approved
0.8193	Intermediate Similarity	NPD7332	Phase 2
0.8171	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6933	Approved
0.8118	Intermediate Similarity	NPD6695	Phase 3
0.8101	Intermediate Similarity	NPD7151	Approved
0.8101	Intermediate Similarity	NPD7150	Approved
0.8101	Intermediate Similarity	NPD7152	Approved
0.8077	Intermediate Similarity	NPD6922	Approved
0.8077	Intermediate Similarity	NPD6923	Approved
0.8049	Intermediate Similarity	NPD6932	Approved
0.8023	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7525	Registered
0.7955	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6893	Approved
0.7901	Intermediate Similarity	NPD4785	Approved
0.7901	Intermediate Similarity	NPD4784	Approved
0.7816	Intermediate Similarity	NPD4786	Approved
0.7765	Intermediate Similarity	NPD7509	Discontinued
0.7765	Intermediate Similarity	NPD4748	Discontinued
0.7753	Intermediate Similarity	NPD7750	Discontinued
0.7753	Intermediate Similarity	NPD7524	Approved
0.7674	Intermediate Similarity	NPD6898	Phase 1
0.7654	Intermediate Similarity	NPD4243	Approved
0.7647	Intermediate Similarity	NPD6683	Phase 2
0.7647	Intermediate Similarity	NPD7645	Phase 2
0.764	Intermediate Similarity	NPD5279	Phase 3
0.7586	Intermediate Similarity	NPD3667	Approved
0.7419	Intermediate Similarity	NPD7087	Discontinued
0.7419	Intermediate Similarity	NPD6079	Approved
0.7419	Intermediate Similarity	NPD7637	Suspended
0.7391	Intermediate Similarity	NPD5328	Approved
0.7253	Intermediate Similarity	NPD3618	Phase 1
0.7241	Intermediate Similarity	NPD4195	Approved
0.7222	Intermediate Similarity	NPD3133	Approved
0.7222	Intermediate Similarity	NPD3666	Approved
0.7222	Intermediate Similarity	NPD3665	Phase 1
0.7176	Intermediate Similarity	NPD4190	Phase 3
0.7176	Intermediate Similarity	NPD5275	Approved
0.7128	Intermediate Similarity	NPD7136	Phase 2
0.71	Intermediate Similarity	NPD5211	Phase 2
0.7065	Intermediate Similarity	NPD5280	Approved
0.7065	Intermediate Similarity	NPD4694	Approved
0.7053	Intermediate Similarity	NPD6411	Approved
0.7021	Intermediate Similarity	NPD4753	Phase 2
0.6979	Remote Similarity	NPD6399	Phase 3
0.6979	Remote Similarity	NPD5779	Approved
0.6979	Remote Similarity	NPD5778	Approved
0.6979	Remote Similarity	NPD4202	Approved
0.6961	Remote Similarity	NPD5141	Approved
0.6939	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5222	Approved
0.6939	Remote Similarity	NPD5221	Approved
0.69	Remote Similarity	NPD5285	Approved
0.69	Remote Similarity	NPD4696	Approved
0.69	Remote Similarity	NPD7640	Approved
0.69	Remote Similarity	NPD7639	Approved
0.69	Remote Similarity	NPD5286	Approved
0.6882	Remote Similarity	NPD5690	Phase 2
0.6875	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD5281	Approved
0.6869	Remote Similarity	NPD4755	Approved
0.6869	Remote Similarity	NPD5173	Approved
0.6848	Remote Similarity	NPD3668	Phase 3
0.6842	Remote Similarity	NPD6051	Approved
0.6842	Remote Similarity	NPD6101	Approved
0.6842	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4629	Approved
0.6837	Remote Similarity	NPD5210	Approved
0.6813	Remote Similarity	NPD4223	Phase 3
0.6813	Remote Similarity	NPD4221	Approved
0.68	Remote Similarity	NPD7638	Approved
0.6774	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5329	Approved
0.6768	Remote Similarity	NPD4697	Phase 3
0.6765	Remote Similarity	NPD5225	Approved
0.6765	Remote Similarity	NPD5224	Approved
0.6765	Remote Similarity	NPD4633	Approved
0.6765	Remote Similarity	NPD5226	Approved
0.6753	Remote Similarity	NPD4219	Approved
0.675	Remote Similarity	NPD368	Approved
0.6744	Remote Similarity	NPD4732	Discontinued
0.6742	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4518	Approved
0.6733	Remote Similarity	NPD4700	Approved
0.6733	Remote Similarity	NPD6404	Discontinued
0.6727	Remote Similarity	NPD7115	Discovery
0.6702	Remote Similarity	NPD4623	Approved
0.6702	Remote Similarity	NPD4519	Discontinued
0.67	Remote Similarity	NPD6084	Phase 2
0.67	Remote Similarity	NPD6083	Phase 2
0.6699	Remote Similarity	NPD5175	Approved
0.6699	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6634	Remote Similarity	NPD5290	Discontinued
0.6623	Remote Similarity	NPD342	Phase 1
0.6604	Remote Similarity	NPD6881	Approved
0.6604	Remote Similarity	NPD6899	Approved
0.6598	Remote Similarity	NPD4096	Approved
0.6598	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1696	Phase 3
0.6593	Remote Similarity	NPD4819	Approved
0.6593	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4822	Approved
0.6593	Remote Similarity	NPD4821	Approved
0.6593	Remote Similarity	NPD4820	Approved
0.6588	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7128	Approved
0.6571	Remote Similarity	NPD6675	Approved
0.6571	Remote Similarity	NPD5739	Approved
0.6571	Remote Similarity	NPD6402	Approved
0.6559	Remote Similarity	NPD5362	Discontinued
0.6559	Remote Similarity	NPD5332	Approved
0.6559	Remote Similarity	NPD4788	Approved
0.6559	Remote Similarity	NPD5331	Approved
0.6556	Remote Similarity	NPD4271	Approved
0.6556	Remote Similarity	NPD4268	Approved
0.6531	Remote Similarity	NPD7515	Phase 2
0.6526	Remote Similarity	NPD5330	Approved
0.6526	Remote Similarity	NPD4138	Approved
0.6526	Remote Similarity	NPD7521	Approved
0.6526	Remote Similarity	NPD6684	Approved
0.6526	Remote Similarity	NPD7146	Approved
0.6526	Remote Similarity	NPD4690	Approved
0.6526	Remote Similarity	NPD4693	Phase 3
0.6526	Remote Similarity	NPD7334	Approved
0.6526	Remote Similarity	NPD4688	Approved
0.6526	Remote Similarity	NPD5205	Approved
0.6526	Remote Similarity	NPD4689	Approved
0.6526	Remote Similarity	NPD6409	Approved
0.6522	Remote Similarity	NPD4692	Approved
0.6522	Remote Similarity	NPD4139	Approved
0.6522	Remote Similarity	NPD4790	Discontinued
0.6509	Remote Similarity	NPD5697	Approved
0.6505	Remote Similarity	NPD4159	Approved
0.6491	Remote Similarity	NPD7503	Approved
0.6481	Remote Similarity	NPD7102	Approved
0.6481	Remote Similarity	NPD7290	Approved
0.6481	Remote Similarity	NPD6883	Approved
0.6471	Remote Similarity	NPD4225	Approved
0.6465	Remote Similarity	NPD5133	Approved
0.6449	Remote Similarity	NPD4729	Approved
0.6449	Remote Similarity	NPD4730	Approved
0.6449	Remote Similarity	NPD7320	Approved
0.6437	Remote Similarity	NPD5276	Approved
0.6429	Remote Similarity	NPD5207	Approved
0.6422	Remote Similarity	NPD8130	Phase 1
0.6422	Remote Similarity	NPD6650	Approved
0.6422	Remote Similarity	NPD6649	Approved
0.6422	Remote Similarity	NPD6847	Approved
0.6422	Remote Similarity	NPD6617	Approved
0.6422	Remote Similarity	NPD6869	Approved
0.6415	Remote Similarity	NPD4768	Approved
0.6415	Remote Similarity	NPD4767	Approved
0.6415	Remote Similarity	NPD7333	Discontinued
0.6415	Remote Similarity	NPD6640	Phase 3
0.6413	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7741	Discontinued
0.6392	Remote Similarity	NPD4723	Approved
0.6392	Remote Similarity	NPD6903	Approved
0.6392	Remote Similarity	NPD6672	Approved
0.6392	Remote Similarity	NPD5737	Approved
0.6392	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4722	Approved
0.6389	Remote Similarity	NPD6373	Approved
0.6389	Remote Similarity	NPD6013	Approved
0.6389	Remote Similarity	NPD6372	Approved
0.6389	Remote Similarity	NPD6012	Approved
0.6389	Remote Similarity	NPD6014	Approved
0.6381	Remote Similarity	NPD4754	Approved
0.6374	Remote Similarity	NPD3617	Approved
0.6364	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD6050	Approved
0.6364	Remote Similarity	NPD5694	Approved
0.6355	Remote Similarity	NPD5701	Approved
0.6354	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5250	Approved
0.633	Remote Similarity	NPD5248	Approved
0.633	Remote Similarity	NPD4634	Approved
0.633	Remote Similarity	NPD5247	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