NPASS Compound

Structure

CID284007 OpenBabel06191716092D 37 39 0 0 0 0 0 0 0 0999 V2000 7.2626 1.0521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8162 -6.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6993 1.8783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8162 -5.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7021 1.8036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9502 -4.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2682 0.9026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9502 -3.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2710 0.8279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0842 -3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8399 -0.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9693 -1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 -3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5382 -2.8507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 -0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4060 -1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8371 -0.0731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -3.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 -2.7760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 -2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4088 -1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 -2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4004 -0.8993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -4.6235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0988 -3.6022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 -0.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 -3.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2459 -1.6235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5984 0.5593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.2470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 29 2 0 0 0 0 18 30 2 0 0 0 0 19 31 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 21 32 1 0 0 0 0 22 24 2 0 0 0 0 22 36 1 0 0 0 0 23 26 2 0 0 0 0 23 37 1 0 0 0 0 24 28 1 0 0 0 0 25 27 1 0 0 0 0 26 36 1 0 0 0 0 27 33 2 0 0 0 0 27 34 1 0 0 0 0 28 35 2 0 0 0 0 28 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.2
Volume:	519.922
LogP:	5.498
LogD:	2.929
LogS:	-3.617
# Rotatable Bonds:	13
TPSA:	147.43
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.18
Synthetic Accessibility Score:	3.197
Fsp3:	0.429
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.768
MDCK Permeability:	2.5984727471950464e-05
Pgp-inhibitor:	0.135
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.892

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	97.2669448852539%
Volume Distribution (VD):	0.302
Pgp-substrate:	1.1937440633773804%

ADMET: Metabolism

CYP1A2-inhibitor:	0.262
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.131
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.785
CYP2C9-substrate:	0.654
CYP2D6-inhibitor:	0.302
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.163
CYP3A4-substrate:	0.037

ADMET: Excretion

Clearance (CL):	6.31
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.227
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.567
Maximum Recommended Daily Dose:	0.836
Skin Sensitization:	0.832
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.073
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC284007

Natural Product ID:	NPC284007
*Common Name:**	Alpha-Alectoronic Acid
IUPAC Name:	3,9-dihydroxy-6-oxo-1,7-bis(2-oxoheptyl)benzo[b][1,4]benzodioxepine-2-carboxylic acid
Synonyms:	Alpha-Alectoronic Acid
Standard InCHIKey:	ZDIOCINAHISORH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H32O9/c1-3-5-7-9-17(29)11-16-12-19(31)14-22-24(16)28(35)37-23-15-21(32)25(27(33)34)20(26(23)36-22)13-18(30)10-8-6-4-2/h12,14-15,31-32H,3-11,13H2,1-2H3,(H,33,34)
SMILES:	CCCCCC(=O)Cc1cc(cc2c1C(=O)Oc1cc(c(c(CC(=O)CCCCC)c1O2)C(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL426543
PubChem CID:	15558610
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO10332	Garcinia atroviridis	Species	Clusiaceae	Eukaryota	roots	n.a.	n.a.	PMID[11473441]
NPO16337	Ochrolechia parella	Species	Ochrolechiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17256903]
NPO12221	Acacia saligna	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25183120]
NPO27306	Sterculia urens	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10332	Garcinia atroviridis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12221	Acacia saligna	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16337	Ochrolechia parella	Species	Ochrolechiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13194	Gentiana purpurea	Species	Gentianaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	=	10300.0	nM	PMID[478417]

☑ 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 NPC284007 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	411
0.1-0.2	1775
0.2-0.3	4468
0.3-0.4	10042
0.4-0.5	7938
0.5-0.6	3729
0.6-0.7	5347
0.7-0.8	6179
0.8-0.85	2262
0.85-0.9	492
0.9-0.95	48
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC267153
0.9935	High Similarity	NPC93739
0.9808	High Similarity	NPC8070
0.9618	High Similarity	NPC300984
0.9615	High Similarity	NPC303565
0.9545	High Similarity	NPC471800
0.9371	High Similarity	NPC474350
0.9363	High Similarity	NPC238381
0.9321	High Similarity	NPC20543
0.9321	High Similarity	NPC246716
0.9321	High Similarity	NPC239440
0.9268	High Similarity	NPC139350
0.9259	High Similarity	NPC26568
0.9255	High Similarity	NPC20216
0.925	High Similarity	NPC156082
0.9236	High Similarity	NPC54928
0.9221	High Similarity	NPC6923
0.9207	High Similarity	NPC181523
0.9202	High Similarity	NPC1827
0.9202	High Similarity	NPC17219
0.9202	High Similarity	NPC10576
0.9198	High Similarity	NPC272485
0.9198	High Similarity	NPC292788
0.9193	High Similarity	NPC112981
0.9161	High Similarity	NPC60413
0.9152	High Similarity	NPC289147
0.9141	High Similarity	NPC49487
0.9141	High Similarity	NPC99613
0.9119	High Similarity	NPC83763
0.9119	High Similarity	NPC168616
0.9114	High Similarity	NPC274730
0.9102	High Similarity	NPC113446
0.9085	High Similarity	NPC124470
0.9085	High Similarity	NPC109827
0.9062	High Similarity	NPC320359
0.9062	High Similarity	NPC475886
0.9062	High Similarity	NPC200594
0.9062	High Similarity	NPC474287
0.9057	High Similarity	NPC241904
0.9057	High Similarity	NPC165977
0.9057	High Similarity	NPC217677
0.9057	High Similarity	NPC300727
0.9045	High Similarity	NPC289968
0.903	High Similarity	NPC158226
0.9018	High Similarity	NPC29160
0.9006	High Similarity	NPC474186
0.9006	High Similarity	NPC278052
0.9006	High Similarity	NPC474351
0.9006	High Similarity	NPC474187
0.9006	High Similarity	NPC40491
0.9006	High Similarity	NPC475883
0.9	High Similarity	NPC476242
0.9	High Similarity	NPC100123
0.8987	High Similarity	NPC475895
0.8987	High Similarity	NPC89474
0.8981	High Similarity	NPC474663
0.8963	High Similarity	NPC234331
0.8961	High Similarity	NPC29577
0.8951	High Similarity	NPC8300
0.8944	High Similarity	NPC14353
0.8944	High Similarity	NPC56085
0.8944	High Similarity	NPC200746
0.8944	High Similarity	NPC228785
0.8938	High Similarity	NPC236796
0.8931	High Similarity	NPC38898
0.8917	High Similarity	NPC29056
0.8909	High Similarity	NPC165979
0.8909	High Similarity	NPC163130
0.8903	High Similarity	NPC237208
0.8896	High Similarity	NPC7483
0.8896	High Similarity	NPC234004
0.8896	High Similarity	NPC236132
0.8889	High Similarity	NPC61010
0.8889	High Similarity	NPC66288
0.8876	High Similarity	NPC240887
0.8876	High Similarity	NPC470091
0.8876	High Similarity	NPC329161
0.8875	High Similarity	NPC142339
0.8875	High Similarity	NPC472456
0.8868	High Similarity	NPC250822
0.8868	High Similarity	NPC276409
0.8868	High Similarity	NPC280937
0.8868	High Similarity	NPC75279
0.8861	High Similarity	NPC202157
0.8861	High Similarity	NPC208043
0.8861	High Similarity	NPC198615
0.8861	High Similarity	NPC226973
0.8861	High Similarity	NPC117579
0.8854	High Similarity	NPC328119
0.8841	High Similarity	NPC130920
0.8841	High Similarity	NPC39306
0.8841	High Similarity	NPC85057
0.8839	High Similarity	NPC134621
0.8834	High Similarity	NPC229632
0.8834	High Similarity	NPC108767
0.8834	High Similarity	NPC25152
0.8827	High Similarity	NPC119224
0.8827	High Similarity	NPC143050
0.8827	High Similarity	NPC139036
0.882	High Similarity	NPC181960
0.882	High Similarity	NPC469584
0.882	High Similarity	NPC108456
0.8812	High Similarity	NPC163780
0.8812	High Similarity	NPC183597
0.8812	High Similarity	NPC37392
0.8812	High Similarity	NPC50715
0.8812	High Similarity	NPC201136
0.8812	High Similarity	NPC20541
0.8812	High Similarity	NPC92659
0.8812	High Similarity	NPC128863
0.8812	High Similarity	NPC146165
0.8812	High Similarity	NPC227325
0.8812	High Similarity	NPC196439
0.8812	High Similarity	NPC472909
0.8812	High Similarity	NPC2476
0.8812	High Similarity	NPC167815
0.8812	High Similarity	NPC208197
0.8812	High Similarity	NPC138360
0.8812	High Similarity	NPC280339
0.8812	High Similarity	NPC4455
0.8797	High Similarity	NPC307780
0.8797	High Similarity	NPC306821
0.8797	High Similarity	NPC309979
0.8797	High Similarity	NPC151473
0.8797	High Similarity	NPC179183
0.8788	High Similarity	NPC39091
0.878	High Similarity	NPC475985
0.878	High Similarity	NPC197168
0.878	High Similarity	NPC133065
0.878	High Similarity	NPC23298
0.878	High Similarity	NPC270837
0.878	High Similarity	NPC220313
0.878	High Similarity	NPC248638
0.878	High Similarity	NPC189473
0.878	High Similarity	NPC152659
0.878	High Similarity	NPC236521
0.8774	High Similarity	NPC95123
0.8774	High Similarity	NPC66404
0.8773	High Similarity	NPC258331
0.8766	High Similarity	NPC105648
0.8765	High Similarity	NPC474290
0.8765	High Similarity	NPC329091
0.8758	High Similarity	NPC474520
0.8758	High Similarity	NPC68093
0.8758	High Similarity	NPC472907
0.8758	High Similarity	NPC191146
0.8758	High Similarity	NPC178854
0.8758	High Similarity	NPC138243
0.8758	High Similarity	NPC257277
0.875	High Similarity	NPC145379
0.875	High Similarity	NPC47781
0.875	High Similarity	NPC274327
0.875	High Similarity	NPC186507
0.875	High Similarity	NPC176775
0.875	High Similarity	NPC246204
0.875	High Similarity	NPC183878
0.875	High Similarity	NPC69394
0.875	High Similarity	NPC231018
0.875	High Similarity	NPC22519
0.875	High Similarity	NPC86485
0.875	High Similarity	NPC255350
0.875	High Similarity	NPC160951
0.875	High Similarity	NPC472915
0.8742	High Similarity	NPC308451
0.8742	High Similarity	NPC133856
0.8742	High Similarity	NPC204350
0.8742	High Similarity	NPC149614
0.8734	High Similarity	NPC474648
0.8734	High Similarity	NPC285527
0.8734	High Similarity	NPC106334
0.8727	High Similarity	NPC472450
0.8727	High Similarity	NPC326520
0.8727	High Similarity	NPC275780
0.8727	High Similarity	NPC25361
0.8727	High Similarity	NPC239752
0.8726	High Similarity	NPC93034
0.8726	High Similarity	NPC119660
0.8726	High Similarity	NPC62536
0.8726	High Similarity	NPC12305
0.8726	High Similarity	NPC33265
0.872	High Similarity	NPC52204
0.872	High Similarity	NPC294965
0.8718	High Similarity	NPC312789
0.8712	High Similarity	NPC299436
0.8712	High Similarity	NPC235018
0.8712	High Similarity	NPC45146
0.8712	High Similarity	NPC47623
0.8704	High Similarity	NPC476981
0.8704	High Similarity	NPC475267
0.8704	High Similarity	NPC472910
0.8704	High Similarity	NPC93376
0.8704	High Similarity	NPC472963
0.8704	High Similarity	NPC245758
0.8704	High Similarity	NPC262286
0.8704	High Similarity	NPC48208
0.8704	High Similarity	NPC235215
0.8704	High Similarity	NPC7973
0.8704	High Similarity	NPC472438
0.8704	High Similarity	NPC162869
0.8704	High Similarity	NPC227192

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 NPC284007 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	1021
0.2-0.3	1963
0.3-0.4	2635
0.4-0.5	1708
0.5-0.6	910
0.6-0.7	384
0.7-0.8	134
0.8-0.85	25
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD2801	Approved
0.8675	High Similarity	NPD7473	Discontinued
0.8606	High Similarity	NPD6232	Discontinued
0.8519	High Similarity	NPD1465	Phase 2
0.8466	Intermediate Similarity	NPD3817	Phase 2
0.8457	Intermediate Similarity	NPD1934	Approved
0.8405	Intermediate Similarity	NPD7819	Suspended
0.8353	Intermediate Similarity	NPD5844	Phase 1
0.8303	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD3882	Suspended
0.8302	Intermediate Similarity	NPD1511	Approved
0.8293	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD1512	Approved
0.8198	Intermediate Similarity	NPD7074	Phase 3
0.8187	Intermediate Similarity	NPD3818	Discontinued
0.8176	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6166	Phase 2
0.816	Intermediate Similarity	NPD3226	Approved
0.8155	Intermediate Similarity	NPD5494	Approved
0.8144	Intermediate Similarity	NPD7075	Discontinued
0.814	Intermediate Similarity	NPD7054	Approved
0.8092	Intermediate Similarity	NPD7472	Approved
0.8061	Intermediate Similarity	NPD7411	Suspended
0.8036	Intermediate Similarity	NPD3749	Approved
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8024	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3750	Approved
0.7964	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6799	Approved
0.7955	Intermediate Similarity	NPD7808	Phase 3
0.7949	Intermediate Similarity	NPD447	Suspended
0.7943	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5402	Approved
0.7898	Intermediate Similarity	NPD7251	Discontinued
0.7895	Intermediate Similarity	NPD6959	Discontinued
0.7895	Intermediate Similarity	NPD1247	Approved
0.7892	Intermediate Similarity	NPD6599	Discontinued
0.7889	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7861	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6797	Phase 2
0.7824	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD3926	Phase 2
0.7799	Intermediate Similarity	NPD2799	Discontinued
0.7798	Intermediate Similarity	NPD6801	Discontinued
0.7784	Intermediate Similarity	NPD4380	Phase 2
0.7778	Intermediate Similarity	NPD919	Approved
0.7771	Intermediate Similarity	NPD1240	Approved
0.7764	Intermediate Similarity	NPD1549	Phase 2
0.7716	Intermediate Similarity	NPD2800	Approved
0.7711	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD37	Approved
0.7688	Intermediate Similarity	NPD7199	Phase 2
0.7688	Intermediate Similarity	NPD1510	Phase 2
0.7688	Intermediate Similarity	NPD3748	Approved
0.7674	Intermediate Similarity	NPD6234	Discontinued
0.7673	Intermediate Similarity	NPD1607	Approved
0.7661	Intermediate Similarity	NPD4966	Approved
0.7661	Intermediate Similarity	NPD7768	Phase 2
0.7661	Intermediate Similarity	NPD4965	Approved
0.7661	Intermediate Similarity	NPD4967	Phase 2
0.7658	Intermediate Similarity	NPD943	Approved
0.7643	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2796	Approved
0.7627	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD230	Phase 1
0.7609	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1243	Approved
0.76	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3268	Approved
0.7531	Intermediate Similarity	NPD6100	Approved
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.7531	Intermediate Similarity	NPD6099	Approved
0.7527	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD6559	Discontinued
0.7472	Intermediate Similarity	NPD7228	Approved
0.7469	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4628	Phase 3
0.7455	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5953	Discontinued
0.7443	Intermediate Similarity	NPD5710	Approved
0.7443	Intermediate Similarity	NPD5711	Approved
0.7436	Intermediate Similarity	NPD1203	Approved
0.743	Intermediate Similarity	NPD7286	Phase 2
0.7425	Intermediate Similarity	NPD7390	Discontinued
0.7425	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6832	Phase 2
0.7391	Intermediate Similarity	NPD8434	Phase 2
0.7381	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5401	Approved
0.7378	Intermediate Similarity	NPD2344	Approved
0.7353	Intermediate Similarity	NPD1653	Approved
0.7346	Intermediate Similarity	NPD6651	Approved
0.7342	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8312	Approved
0.7322	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD2313	Discontinued
0.7303	Intermediate Similarity	NPD5242	Approved
0.7296	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1933	Approved
0.7278	Intermediate Similarity	NPD3751	Discontinued
0.7262	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD3787	Discontinued
0.7247	Intermediate Similarity	NPD7229	Phase 3
0.7244	Intermediate Similarity	NPD9717	Approved
0.7244	Intermediate Similarity	NPD1608	Approved
0.7235	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD7435	Discontinued
0.7215	Intermediate Similarity	NPD2797	Approved
0.7215	Intermediate Similarity	NPD3267	Approved
0.7215	Intermediate Similarity	NPD3266	Approved
0.7208	Intermediate Similarity	NPD8151	Discontinued
0.7204	Intermediate Similarity	NPD8150	Discontinued
0.7202	Intermediate Similarity	NPD2309	Approved
0.7202	Intermediate Similarity	NPD6190	Approved
0.72	Intermediate Similarity	NPD5353	Approved
0.7179	Intermediate Similarity	NPD422	Phase 1
0.7178	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7134	Intermediate Similarity	NPD9269	Phase 2
0.7128	Intermediate Similarity	NPD4287	Approved
0.7126	Intermediate Similarity	NPD6386	Approved
0.7126	Intermediate Similarity	NPD6385	Approved
0.712	Intermediate Similarity	NPD7685	Pre-registration
0.712	Intermediate Similarity	NPD7240	Approved
0.7117	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1613	Approved
0.7102	Intermediate Similarity	NPD4288	Approved
0.7099	Intermediate Similarity	NPD3764	Approved
0.7099	Intermediate Similarity	NPD411	Approved
0.7097	Intermediate Similarity	NPD9268	Approved
0.7095	Intermediate Similarity	NPD8127	Discontinued
0.7066	Intermediate Similarity	NPD1471	Phase 3
0.7062	Intermediate Similarity	NPD6776	Approved
0.7062	Intermediate Similarity	NPD6780	Approved
0.7062	Intermediate Similarity	NPD6778	Approved
0.7062	Intermediate Similarity	NPD6782	Approved
0.7062	Intermediate Similarity	NPD6781	Approved
0.7062	Intermediate Similarity	NPD6777	Approved
0.7062	Intermediate Similarity	NPD6779	Approved
0.7051	Intermediate Similarity	NPD17	Approved
0.7048	Intermediate Similarity	NPD4308	Phase 3
0.7044	Intermediate Similarity	NPD3225	Approved
0.7041	Intermediate Similarity	NPD7698	Approved
0.7041	Intermediate Similarity	NPD7696	Phase 3
0.7041	Intermediate Similarity	NPD7697	Approved
0.7012	Intermediate Similarity	NPD4060	Phase 1
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.7005	Intermediate Similarity	NPD7871	Phase 2
0.7005	Intermediate Similarity	NPD7870	Phase 2
0.7	Intermediate Similarity	NPD7874	Approved
0.7	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1296	Phase 2
0.6994	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7549	Discontinued
0.6977	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6355	Discontinued
0.6957	Remote Similarity	NPD2798	Approved
0.6946	Remote Similarity	NPD7033	Discontinued
0.6933	Remote Similarity	NPD4625	Phase 3
0.6932	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8285	Discontinued
0.6918	Remote Similarity	NPD1481	Phase 2
0.6915	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD9494	Approved
0.6914	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7458	Discontinued
0.6905	Remote Similarity	NPD4476	Approved
0.6905	Remote Similarity	NPD4477	Approved
0.6904	Remote Similarity	NPD6823	Phase 2
0.6902	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7701	Phase 2
0.6894	Remote Similarity	NPD1470	Approved
0.6875	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4908	Phase 1

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