NPASS Compound

Structure

NPC268607 OpenBabel07101719512D 38 41 0 0 1 0 0 0 0 0999 V2000 -3.5890 0.1543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6667 1.8846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0028 -2.1902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0118 -3.6107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1309 1.9137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0172 3.6420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9405 1.7265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2554 0.6530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3969 1.1659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2404 -0.3469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5235 0.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3670 -0.8339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1294 1.0868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5910 0.2440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2771 -2.0422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4227 2.6794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3624 -1.0459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8648 1.7824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2508 -0.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1284 1.0419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0972 -2.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4249 2.7450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5086 -0.3210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5920 0.2889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7767 -0.2951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6352 -0.8080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1602 -0.7020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8429 0.4406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4577 -0.4738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6202 -1.8079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2945 -1.6930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7792 0.7920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9326 -0.3609 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 21 2 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 23 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 24 2 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 22 2 0 0 0 0 16 18 1 0 0 0 0 16 23 2 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 25 1 0 0 0 0 19 31 1 0 0 0 0 20 30 1 0 0 0 0 20 32 1 0 0 0 0 24 27 1 0 0 0 0 25 30 1 1 0 0 0 26 27 2 0 0 0 0 26 28 1 0 0 0 0 26 29 1 0 0 0 0 27 34 1 0 0 0 0 28 31 1 0 0 0 0 28 35 2 0 0 0 0 29 32 1 0 0 0 0 29 36 2 0 0 0 0 30 7 1 6 0 0 0 30 38 1 0 0 0 0 31 33 1 6 0 0 0 32 33 1 6 0 0 0 33 37 1 6 0 0 0 33 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	518.3
Volume:	565.321
LogP:	7.028
LogD:	4.328
LogS:	-4.361
# Rotatable Bonds:	9
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.227
Synthetic Accessibility Score:	5.807
Fsp3:	0.545
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:	-4.955
MDCK Permeability:	2.7961739760939963e-05
Pgp-inhibitor:	0.647
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.101
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.688

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	97.66710662841797%
Volume Distribution (VD):	2.255
Pgp-substrate:	4.8912672996521%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.351
CYP2C19-inhibitor:	0.746
CYP2C19-substrate:	0.869
CYP2C9-inhibitor:	0.826
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.132
CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.931
CYP3A4-substrate:	0.87

ADMET: Excretion

Clearance (CL):	9.068
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.71
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.677
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.268
Skin Sensitization:	0.162
Carcinogencity:	0.651
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC268607

Natural Product ID:	NPC268607
*Common Name:**	Xerophenone A
IUPAC Name:	n.a.
Synonyms:	Xerophenone A
Standard InCHIKey:	YSWMOTQKYHHEFG-VQSSYIAGSA-N
Standard InCHI:	InChI=1S/C33H42O5/c1-21(2)13-14-25-19-31(17-15-22(3)4)28(35)26(27(34)24-11-9-8-10-12-24)29(36)32(18-16-23(5)6)20-30(25,7)38-33(31,32)37/h8-12,15-16,25,34,37H,1,13-14,17-20H2,2-7H3/b27-26+/t25-,30-,31-,32+,33-/m1/s1
SMILES:	C=C(C)CC[C@@H]1C[C@]2(CC=C(C)C)C(=O)/C(=C(/c3ccccc3)O)/C(=O)[C@]3(CC=C(C)C)C[C@@]1(C)O[C@]23O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2147808
PubChem CID:	71461868
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002012] Oxanes

*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
NPO32914	Garcinia propinqua	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[22963193]
NPO32914	Garcinia propinqua	Species	Clusiaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28489373]

☑ 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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[504533]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128.0	ug.mL-1	PMID[504533]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	128.0	ug.mL-1	PMID[504533]

☑ 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 NPC268607 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	271
0.1-0.2	1165
0.2-0.3	2027
0.3-0.4	4844
0.4-0.5	10815
0.5-0.6	14936
0.6-0.7	8022
0.7-0.8	612
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8692	High Similarity	NPC472682
0.8692	High Similarity	NPC472692
0.845	Intermediate Similarity	NPC470649
0.845	Intermediate Similarity	NPC478107
0.8	Intermediate Similarity	NPC294458
0.7868	Intermediate Similarity	NPC471334
0.7836	Intermediate Similarity	NPC146239
0.782	Intermediate Similarity	NPC478108
0.7794	Intermediate Similarity	NPC471832
0.7794	Intermediate Similarity	NPC25736
0.7778	Intermediate Similarity	NPC51448
0.7778	Intermediate Similarity	NPC316553
0.7778	Intermediate Similarity	NPC115797
0.7778	Intermediate Similarity	NPC477475
0.7778	Intermediate Similarity	NPC477476
0.7754	Intermediate Similarity	NPC144257
0.7752	Intermediate Similarity	NPC268930
0.7744	Intermediate Similarity	NPC85511
0.7742	Intermediate Similarity	NPC469511
0.773	Intermediate Similarity	NPC118366
0.7727	Intermediate Similarity	NPC269923
0.7727	Intermediate Similarity	NPC167323
0.7717	Intermediate Similarity	NPC234637
0.7717	Intermediate Similarity	NPC130591
0.771	Intermediate Similarity	NPC475804
0.771	Intermediate Similarity	NPC474222
0.771	Intermediate Similarity	NPC475827
0.771	Intermediate Similarity	NPC474223
0.7687	Intermediate Similarity	NPC472693
0.7687	Intermediate Similarity	NPC472694
0.7669	Intermediate Similarity	NPC474159
0.7669	Intermediate Similarity	NPC474254
0.7643	Intermediate Similarity	NPC212207
0.7638	Intermediate Similarity	NPC471481
0.763	Intermediate Similarity	NPC294050
0.763	Intermediate Similarity	NPC328997
0.7622	Intermediate Similarity	NPC77493
0.7603	Intermediate Similarity	NPC145301
0.7603	Intermediate Similarity	NPC469513
0.7603	Intermediate Similarity	NPC8493
0.7603	Intermediate Similarity	NPC469375
0.7603	Intermediate Similarity	NPC294679
0.7603	Intermediate Similarity	NPC144247
0.7597	Intermediate Similarity	NPC260886
0.7576	Intermediate Similarity	NPC476225
0.7574	Intermediate Similarity	NPC474106
0.7559	Intermediate Similarity	NPC218855
0.7536	Intermediate Similarity	NPC262819
0.7532	Intermediate Similarity	NPC314795
0.7521	Intermediate Similarity	NPC54647
0.7518	Intermediate Similarity	NPC477893
0.7518	Intermediate Similarity	NPC475088
0.7518	Intermediate Similarity	NPC477896
0.7517	Intermediate Similarity	NPC51602
0.75	Intermediate Similarity	NPC470816
0.75	Intermediate Similarity	NPC469417
0.75	Intermediate Similarity	NPC470818
0.75	Intermediate Similarity	NPC294330
0.75	Intermediate Similarity	NPC470330
0.7483	Intermediate Similarity	NPC21410
0.7483	Intermediate Similarity	NPC473670
0.7481	Intermediate Similarity	NPC61651
0.7481	Intermediate Similarity	NPC138798
0.7481	Intermediate Similarity	NPC94425
0.7467	Intermediate Similarity	NPC472548
0.7467	Intermediate Similarity	NPC477905
0.7466	Intermediate Similarity	NPC80895
0.7466	Intermediate Similarity	NPC471912
0.7465	Intermediate Similarity	NPC309056
0.7463	Intermediate Similarity	NPC369
0.7463	Intermediate Similarity	NPC293831
0.7462	Intermediate Similarity	NPC471616
0.7447	Intermediate Similarity	NPC136994
0.7447	Intermediate Similarity	NPC88255
0.7447	Intermediate Similarity	NPC329913
0.7447	Intermediate Similarity	NPC310662
0.7445	Intermediate Similarity	NPC169913
0.7431	Intermediate Similarity	NPC5014
0.7431	Intermediate Similarity	NPC114333
0.7431	Intermediate Similarity	NPC473779
0.7431	Intermediate Similarity	NPC28592
0.7431	Intermediate Similarity	NPC46242
0.7431	Intermediate Similarity	NPC289358
0.7431	Intermediate Similarity	NPC51531
0.7431	Intermediate Similarity	NPC245760
0.7431	Intermediate Similarity	NPC469857
0.7431	Intermediate Similarity	NPC149773
0.7431	Intermediate Similarity	NPC42384
0.7431	Intermediate Similarity	NPC79921
0.7431	Intermediate Similarity	NPC473479
0.7431	Intermediate Similarity	NPC23667
0.7431	Intermediate Similarity	NPC91887
0.7431	Intermediate Similarity	NPC165191
0.7431	Intermediate Similarity	NPC157284
0.7431	Intermediate Similarity	NPC50615
0.7431	Intermediate Similarity	NPC297797
0.7431	Intermediate Similarity	NPC477849
0.7431	Intermediate Similarity	NPC473622
0.7429	Intermediate Similarity	NPC209851
0.7424	Intermediate Similarity	NPC472697
0.7424	Intermediate Similarity	NPC472698
0.7417	Intermediate Similarity	NPC469477
0.7417	Intermediate Similarity	NPC133430
0.7415	Intermediate Similarity	NPC301946
0.7415	Intermediate Similarity	NPC277053
0.7415	Intermediate Similarity	NPC127857
0.7413	Intermediate Similarity	NPC475955
0.7413	Intermediate Similarity	NPC474726
0.7405	Intermediate Similarity	NPC105141
0.7405	Intermediate Similarity	NPC190298
0.7405	Intermediate Similarity	NPC242764
0.7405	Intermediate Similarity	NPC102465
0.74	Intermediate Similarity	NPC471103
0.74	Intermediate Similarity	NPC132810
0.74	Intermediate Similarity	NPC473719
0.7397	Intermediate Similarity	NPC95449
0.7394	Intermediate Similarity	NPC471864
0.7385	Intermediate Similarity	NPC469509
0.7379	Intermediate Similarity	NPC242355
0.7379	Intermediate Similarity	NPC471862
0.7376	Intermediate Similarity	NPC15850
0.7372	Intermediate Similarity	NPC100402
0.7372	Intermediate Similarity	NPC79608
0.7372	Intermediate Similarity	NPC9180
0.7372	Intermediate Similarity	NPC275576
0.7368	Intermediate Similarity	NPC472549
0.7368	Intermediate Similarity	NPC282239
0.7365	Intermediate Similarity	NPC169942
0.7365	Intermediate Similarity	NPC477737
0.7365	Intermediate Similarity	NPC170668
0.7364	Intermediate Similarity	NPC469547
0.7357	Intermediate Similarity	NPC60825
0.7357	Intermediate Similarity	NPC291419
0.7353	Intermediate Similarity	NPC12881
0.7353	Intermediate Similarity	NPC472681
0.7353	Intermediate Similarity	NPC77691
0.7353	Intermediate Similarity	NPC140118
0.7353	Intermediate Similarity	NPC325740
0.7351	Intermediate Similarity	NPC35160
0.7351	Intermediate Similarity	NPC162569
0.7351	Intermediate Similarity	NPC474310
0.7344	Intermediate Similarity	NPC95126
0.7344	Intermediate Similarity	NPC475002
0.7343	Intermediate Similarity	NPC279463
0.7343	Intermediate Similarity	NPC477596
0.7338	Intermediate Similarity	NPC229894
0.7338	Intermediate Similarity	NPC469399
0.7338	Intermediate Similarity	NPC49297
0.7333	Intermediate Similarity	NPC7095
0.7333	Intermediate Similarity	NPC112216
0.7329	Intermediate Similarity	NPC172311
0.7329	Intermediate Similarity	NPC63737
0.7329	Intermediate Similarity	NPC473527
0.7325	Intermediate Similarity	NPC477627
0.7324	Intermediate Similarity	NPC126516
0.732	Intermediate Similarity	NPC106895
0.732	Intermediate Similarity	NPC217091
0.7319	Intermediate Similarity	NPC253681
0.7319	Intermediate Similarity	NPC473751
0.7319	Intermediate Similarity	NPC470648
0.7319	Intermediate Similarity	NPC48992
0.7315	Intermediate Similarity	NPC208293
0.7313	Intermediate Similarity	NPC234337
0.7313	Intermediate Similarity	NPC133389
0.7313	Intermediate Similarity	NPC183339
0.731	Intermediate Similarity	NPC477904
0.731	Intermediate Similarity	NPC183270
0.7305	Intermediate Similarity	NPC469499
0.7305	Intermediate Similarity	NPC471880
0.7303	Intermediate Similarity	NPC146310
0.7297	Intermediate Similarity	NPC471107
0.7297	Intermediate Similarity	NPC471100
0.7292	Intermediate Similarity	NPC243893
0.7292	Intermediate Similarity	NPC472308
0.7292	Intermediate Similarity	NPC474311
0.7292	Intermediate Similarity	NPC7464
0.7292	Intermediate Similarity	NPC262324
0.729	Intermediate Similarity	NPC471968
0.7286	Intermediate Similarity	NPC117899
0.7286	Intermediate Similarity	NPC49272
0.7286	Intermediate Similarity	NPC147561
0.7286	Intermediate Similarity	NPC472388
0.7285	Intermediate Similarity	NPC46549
0.7285	Intermediate Similarity	NPC101043
0.7285	Intermediate Similarity	NPC264229
0.7285	Intermediate Similarity	NPC197037
0.7285	Intermediate Similarity	NPC306799
0.7279	Intermediate Similarity	NPC477894
0.7279	Intermediate Similarity	NPC273336
0.7279	Intermediate Similarity	NPC182333
0.7273	Intermediate Similarity	NPC477594
0.7273	Intermediate Similarity	NPC181924
0.7273	Intermediate Similarity	NPC473216
0.7273	Intermediate Similarity	NPC473399
0.7273	Intermediate Similarity	NPC472393
0.7267	Intermediate Similarity	NPC60509
0.7267	Intermediate Similarity	NPC471970
0.7267	Intermediate Similarity	NPC250046
0.7267	Intermediate Similarity	NPC81698
0.7267	Intermediate Similarity	NPC273798

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 NPC268607 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	710
0.2-0.3	1280
0.3-0.4	2791
0.4-0.5	2553
0.5-0.6	1282
0.6-0.7	267
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.75	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD5909	Discontinued
0.6993	Remote Similarity	NPD3268	Approved
0.6992	Remote Similarity	NPD5951	Approved
0.6992	Remote Similarity	NPD2629	Approved
0.6954	Remote Similarity	NPD7236	Approved
0.695	Remote Similarity	NPD2798	Approved
0.6939	Remote Similarity	NPD7305	Phase 1
0.6934	Remote Similarity	NPD3019	Approved
0.6934	Remote Similarity	NPD2932	Approved
0.6912	Remote Similarity	NPD7741	Discontinued
0.6899	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6099	Approved
0.6892	Remote Similarity	NPD6100	Approved
0.689	Remote Similarity	NPD7799	Discontinued
0.6879	Remote Similarity	NPD1470	Approved
0.6875	Remote Similarity	NPD3764	Approved
0.6867	Remote Similarity	NPD2800	Approved
0.6835	Remote Similarity	NPD1201	Approved
0.6829	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2066	Phase 3
0.6822	Remote Similarity	NPD5048	Discontinued
0.6821	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3317	Approved
0.6797	Remote Similarity	NPD6647	Phase 2
0.6797	Remote Similarity	NPD1929	Approved
0.6797	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1930	Approved
0.6795	Remote Similarity	NPD3226	Approved
0.6767	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2313	Discontinued
0.6755	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD2344	Approved
0.6733	Remote Similarity	NPD2346	Discontinued
0.6731	Remote Similarity	NPD7239	Suspended
0.6725	Remote Similarity	NPD8434	Phase 2
0.6716	Remote Similarity	NPD7094	Approved
0.6716	Remote Similarity	NPD6858	Approved
0.6713	Remote Similarity	NPD6085	Phase 2
0.6713	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7961	Discontinued
0.6712	Remote Similarity	NPD6663	Approved
0.6711	Remote Similarity	NPD8166	Discontinued
0.6711	Remote Similarity	NPD2799	Discontinued
0.6711	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8407	Phase 2
0.6691	Remote Similarity	NPD5126	Approved
0.6691	Remote Similarity	NPD5125	Phase 3
0.6691	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD5736	Approved
0.6645	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2797	Approved
0.6643	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3267	Approved
0.6643	Remote Similarity	NPD3023	Approved
0.6643	Remote Similarity	NPD3266	Approved
0.6643	Remote Similarity	NPD3026	Approved
0.6627	Remote Similarity	NPD8368	Discontinued
0.6625	Remote Similarity	NPD7819	Suspended
0.6623	Remote Similarity	NPD1471	Phase 3
0.6619	Remote Similarity	NPD3025	Approved
0.6619	Remote Similarity	NPD3024	Approved
0.6604	Remote Similarity	NPD7411	Suspended
0.66	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7033	Discontinued
0.6599	Remote Similarity	NPD7715	Approved
0.6599	Remote Similarity	NPD7714	Approved
0.6594	Remote Similarity	NPD7610	Discontinued
0.6581	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.657	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4198	Discontinued
0.6567	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD2309	Approved
0.6549	Remote Similarity	NPD4878	Approved
0.6549	Remote Similarity	NPD1608	Approved
0.6544	Remote Similarity	NPD6010	Discontinued
0.6538	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5760	Phase 2
0.6522	Remote Similarity	NPD5761	Phase 2
0.6516	Remote Similarity	NPD3300	Phase 2
0.6515	Remote Similarity	NPD6685	Approved
0.6513	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD1693	Approved
0.6503	Remote Similarity	NPD3749	Approved
0.6494	Remote Similarity	NPD4628	Phase 3
0.6493	Remote Similarity	NPD2067	Discontinued
0.6489	Remote Similarity	NPD1237	Approved
0.6486	Remote Similarity	NPD8032	Phase 2
0.648	Remote Similarity	NPD1088	Approved
0.6479	Remote Similarity	NPD4807	Approved
0.6479	Remote Similarity	NPD4806	Approved
0.6474	Remote Similarity	NPD7390	Discontinued
0.6467	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6651	Approved
0.6463	Remote Similarity	NPD7008	Discontinued
0.6457	Remote Similarity	NPD8361	Approved
0.6457	Remote Similarity	NPD8360	Approved
0.6454	Remote Similarity	NPD5305	Approved
0.6454	Remote Similarity	NPD5306	Approved
0.645	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5404	Approved
0.6447	Remote Similarity	NPD5408	Approved
0.6447	Remote Similarity	NPD5406	Approved
0.6447	Remote Similarity	NPD5405	Approved
0.6443	Remote Similarity	NPD943	Approved
0.6438	Remote Similarity	NPD4380	Phase 2
0.6438	Remote Similarity	NPD7028	Phase 2
0.6434	Remote Similarity	NPD3972	Approved
0.6433	Remote Similarity	NPD2533	Approved
0.6433	Remote Similarity	NPD2534	Approved
0.6433	Remote Similarity	NPD2532	Approved
0.6429	Remote Similarity	NPD7009	Phase 2
0.6424	Remote Similarity	NPD7097	Phase 1
0.642	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD2182	Approved
0.6405	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6002	Phase 3
0.6405	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6005	Phase 3
0.6405	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6004	Phase 3
0.6403	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7075	Discontinued
0.6389	Remote Similarity	NPD1755	Approved
0.6383	Remote Similarity	NPD4105	Approved
0.6383	Remote Similarity	NPD4102	Approved
0.6382	Remote Similarity	NPD1510	Phase 2
0.6364	Remote Similarity	NPD6287	Discontinued
0.6364	Remote Similarity	NPD8435	Approved
0.6364	Remote Similarity	NPD1549	Phase 2
0.6343	Remote Similarity	NPD8150	Discontinued
0.6341	Remote Similarity	NPD7057	Phase 3
0.6341	Remote Similarity	NPD7058	Phase 2
0.634	Remote Similarity	NPD2935	Discontinued
0.6338	Remote Similarity	NPD17	Approved
0.6336	Remote Similarity	NPD1932	Approved
0.6333	Remote Similarity	NPD1240	Approved
0.6331	Remote Similarity	NPD7473	Discontinued
0.6329	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5494	Approved
0.6324	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.632	Remote Similarity	NPD1090	Approved
0.632	Remote Similarity	NPD1089	Approved
0.632	Remote Similarity	NPD1086	Approved
0.6312	Remote Similarity	NPD9545	Approved
0.6309	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD3020	Approved
0.6304	Remote Similarity	NPD2652	Approved
0.6304	Remote Similarity	NPD2650	Approved
0.6301	Remote Similarity	NPD1164	Approved
0.6296	Remote Similarity	NPD2329	Discontinued
0.6294	Remote Similarity	NPD4136	Approved
0.6294	Remote Similarity	NPD3818	Discontinued
0.6294	Remote Similarity	NPD4135	Approved
0.6294	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4106	Approved
0.6292	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD6355	Discontinued
0.6288	Remote Similarity	NPD5765	Approved
0.6288	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD8127	Discontinued
0.6284	Remote Similarity	NPD2613	Approved
0.6282	Remote Similarity	NPD2575	Approved
0.6282	Remote Similarity	NPD7003	Approved
0.6282	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8312	Approved
0.6264	Remote Similarity	NPD8313	Approved
0.6259	Remote Similarity	NPD4980	Approved
0.6258	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD37	Approved
0.6258	Remote Similarity	NPD1934	Approved
0.6257	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.625	Remote Similarity	NPD688	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1607	Approved
0.6242	Remote Similarity	NPD6190	Approved
0.6242	Remote Similarity	NPD7095	Approved
0.6242	Remote Similarity	NPD4967	Phase 2
0.6242	Remote Similarity	NPD4965	Approved
0.6242	Remote Similarity	NPD7768	Phase 2
0.6242	Remote Similarity	NPD4966	Approved
0.6241	Remote Similarity	NPD164	Approved
0.624	Remote Similarity	NPD5346	Phase 2
0.624	Remote Similarity	NPD800	Approved
0.624	Remote Similarity	NPD5347	Phase 2

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