NPASS Compound

Structure

NPC72696 OpenBabel07101718192D 48 52 0 0 1 0 0 0 0 0999 V2000 7.5266 -1.3058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5788 3.1093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3763 0.1659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0538 -0.0466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9775 5.0716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3236 -2.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8272 -1.3058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6769 0.1659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4285 1.6376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7291 1.6376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5266 3.5999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3991 -2.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3763 2.1282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0726 -1.7460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6769 -0.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5788 2.1282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3763 3.1093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5821 -2.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6769 3.1093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8896 -1.7460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9775 -0.8152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8272 0.6565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4285 0.6565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7291 0.6565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5266 1.6376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5821 -0.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9775 0.1659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5788 0.1659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6769 2.1282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3748 -0.7938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8272 3.5999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8519 -1.7460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1279 0.6565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3991 -0.8963 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2260 3.5999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0726 -3.4454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1279 -1.3058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0313 -1.5229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9775 3.1093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3425 -0.8963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1279 1.6376 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5266 0.6565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0726 -0.0466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8272 4.5810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3425 -2.5957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8272 1.6376 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2782 0.1659 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 42 1 0 0 0 0 4 43 1 0 0 0 0 5 44 1 0 0 0 0 6 45 1 0 0 0 0 7 15 2 0 0 0 0 7 21 1 0 0 0 0 8 15 1 0 0 0 0 8 22 2 0 0 0 0 9 16 2 0 0 0 0 9 23 1 0 0 0 0 10 16 1 0 0 0 0 10 24 2 0 0 0 0 11 17 2 0 0 0 0 11 19 1 0 0 0 0 12 18 1 0 0 0 0 12 20 2 0 0 0 0 13 17 1 0 0 0 0 13 25 2 0 0 0 0 14 18 1 0 0 0 0 14 26 2 0 0 0 0 17 35 1 0 0 0 0 18 36 2 0 0 0 0 19 29 2 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 27 2 0 0 0 0 21 37 1 0 0 0 0 22 27 1 0 0 0 0 22 46 1 0 0 0 0 23 28 2 0 0 0 0 23 47 1 0 0 0 0 24 28 1 0 0 0 0 24 48 1 0 0 0 0 25 29 1 0 0 0 0 25 42 1 0 0 0 0 26 34 1 0 0 0 0 26 43 1 0 0 0 0 27 33 1 0 0 0 0 28 30 1 0 0 0 0 29 46 1 0 0 0 0 30 34 1 0 0 0 0 30 38 2 0 0 0 0 31 39 2 0 0 0 0 31 44 1 0 0 0 0 32 40 2 0 0 0 0 32 45 1 0 0 0 0 33 41 2 0 0 0 0 33 47 1 0 0 0 0 34 20 1 6 0 0 0 34 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	660.15
Volume:	634.717
LogP:	4.303
LogD:	2.723
LogS:	-4.617
# Rotatable Bonds:	11
TPSA:	190.42
# H-Bond Aceptor:	14
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.26
Synthetic Accessibility Score:	4.489
Fsp3:	0.206
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.519
MDCK Permeability:	5.473060082294978e-05
Pgp-inhibitor:	0.957
Pgp-substrate:	0.068
Human Intestinal Absorption (HIA):	0.799
20% Bioavailability (F20%):	0.658
30% Bioavailability (F30%):	0.912

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	90.50623321533203%
Volume Distribution (VD):	0.408
Pgp-substrate:	10.794903755187988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.164
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.913
CYP2C19-substrate:	0.351
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.229
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.83
CYP3A4-substrate:	0.887

ADMET: Excretion

Clearance (CL):	7.011
Half-life (T1/2):	0.605

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.582
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.273
Rat Oral Acute Toxicity:	0.892
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.697
Carcinogencity:	0.204
Eye Corrosion:	0.003
Eye Irritation:	0.221
Respiratory Toxicity:	0.879

Download Data

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

Natural Product: NPC72696

Natural Product ID:	NPC72696
*Common Name:**	Geomycin C
IUPAC Name:	methyl (2R)-4-[2-hydroxy-6-(4-hydroxy-2-methoxy-6-methoxycarbonylphenoxy)-4-methylbenzoyl]oxy-5'-methoxy-6-methyl-3,3'-dioxospiro[1-benzofuran-2,6'-cyclohexa-1,4-diene]-1'-carboxylate
Synonyms:	Geomycin C
Standard InCHIKey:	GNHQZFDQZNRWBS-UUWRZZSWSA-N
Standard InCHI:	InChI=1S/C34H28O14/c1-15-7-21(37)27(22(8-15)46-29-19(31(39)44-5)11-17(35)13-25(29)42-3)33(41)47-23-9-16(2)10-24-28(23)30(38)34(48-24)20(32(40)45-6)12-18(36)14-26(34)43-4/h7-14,35,37H,1-6H3/t34-/m1/s1
SMILES:	COC(=O)C1=CC(=O)C=C([C@@]21Oc1c(C2=O)c(cc(c1)C)OC(=O)c1c(O)cc(cc1Oc1c(OC)cc(cc1C(=O)OC)O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507180
PubChem CID:	25111485
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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
NPO32625	geomyces sp.	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18720971]

☑ 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	3
MIC	3

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	17300.0	nM	PMID[463144]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	75800.0	nM	PMID[463144]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	IC50	=	36200.0	nM	PMID[463144]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	151500.0	nM	PMID[463144]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	=	12900.0	nM	PMID[463144]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	30300.0	nM	PMID[463144]

☑ 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 NPC72696 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	403
0.1-0.2	1715
0.2-0.3	4180
0.3-0.4	9479
0.4-0.5	8995
0.5-0.6	3906
0.6-0.7	6061
0.7-0.8	6369
0.8-0.85	1497
0.85-0.9	89
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9193	High Similarity	NPC287458
0.9136	High Similarity	NPC98892
0.8994	High Similarity	NPC475717
0.8982	High Similarity	NPC280493
0.8931	High Similarity	NPC285527
0.8931	High Similarity	NPC106334
0.8895	High Similarity	NPC47883
0.8889	High Similarity	NPC297807
0.8889	High Similarity	NPC98546
0.8875	High Similarity	NPC164527
0.8875	High Similarity	NPC213382
0.8869	High Similarity	NPC99613
0.8869	High Similarity	NPC49487
0.8851	High Similarity	NPC226725
0.8817	High Similarity	NPC476641
0.8807	High Similarity	NPC295436
0.8793	High Similarity	NPC154527
0.8788	High Similarity	NPC130955
0.8765	High Similarity	NPC158226
0.875	High Similarity	NPC29160
0.8713	High Similarity	NPC473834
0.8713	High Similarity	NPC65885
0.8713	High Similarity	NPC476640
0.8713	High Similarity	NPC216842
0.8713	High Similarity	NPC82217
0.8698	High Similarity	NPC234331
0.8693	High Similarity	NPC248315
0.8693	High Similarity	NPC174486
0.869	High Similarity	NPC280893
0.8686	High Similarity	NPC71260
0.8675	High Similarity	NPC188967
0.8663	High Similarity	NPC287243
0.8655	High Similarity	NPC230619
0.8655	High Similarity	NPC476370
0.8655	High Similarity	NPC54098
0.865	High Similarity	NPC75069
0.8647	High Similarity	NPC476279
0.8647	High Similarity	NPC165979
0.8647	High Similarity	NPC163130
0.8631	High Similarity	NPC300984
0.8614	High Similarity	NPC190487
0.8614	High Similarity	NPC195832
0.8614	High Similarity	NPC154304
0.8613	High Similarity	NPC8127
0.8613	High Similarity	NPC49667
0.8606	High Similarity	NPC178854
0.8605	High Similarity	NPC476374
0.8598	High Similarity	NPC246204
0.8596	High Similarity	NPC19273
0.8596	High Similarity	NPC17884
0.8588	High Similarity	NPC76647
0.858	High Similarity	NPC36320
0.8571	High Similarity	NPC46941
0.8571	High Similarity	NPC108767
0.8555	High Similarity	NPC245975
0.8554	High Similarity	NPC472438
0.8554	High Similarity	NPC29841
0.8554	High Similarity	NPC78302
0.8554	High Similarity	NPC235215
0.8554	High Similarity	NPC7973
0.8545	High Similarity	NPC32557
0.8545	High Similarity	NPC122623
0.8545	High Similarity	NPC189960
0.8545	High Similarity	NPC276059
0.8545	High Similarity	NPC237560
0.8545	High Similarity	NPC241774
0.8545	High Similarity	NPC34725
0.8528	High Similarity	NPC225129
0.8523	High Similarity	NPC182693
0.8521	High Similarity	NPC474350
0.8512	High Similarity	NPC303565
0.8512	High Similarity	NPC476929
0.8503	High Similarity	NPC7846
0.8503	High Similarity	NPC115798
0.8503	High Similarity	NPC143828
0.8503	High Similarity	NPC18772
0.8503	High Similarity	NPC18607
0.8503	High Similarity	NPC288669
0.8503	High Similarity	NPC25495
0.8503	High Similarity	NPC261004
0.8503	High Similarity	NPC130894
0.8503	High Similarity	NPC4481
0.8503	High Similarity	NPC152166
0.8503	High Similarity	NPC300943
0.8503	High Similarity	NPC176300
0.8503	High Similarity	NPC253634
0.8503	High Similarity	NPC152904
0.8503	High Similarity	NPC191459
0.8503	High Similarity	NPC19687
0.8503	High Similarity	NPC22472
0.8503	High Similarity	NPC204854
0.8503	High Similarity	NPC105242
0.8503	High Similarity	NPC193842
0.8503	High Similarity	NPC9609
0.8497	Intermediate Similarity	NPC37606
0.8494	Intermediate Similarity	NPC200388
0.8494	Intermediate Similarity	NPC100916
0.8494	Intermediate Similarity	NPC257277
0.8494	Intermediate Similarity	NPC268161
0.8494	Intermediate Similarity	NPC45131
0.8494	Intermediate Similarity	NPC55619
0.8494	Intermediate Similarity	NPC474520
0.8488	Intermediate Similarity	NPC109827
0.8488	Intermediate Similarity	NPC124470
0.8488	Intermediate Similarity	NPC17219
0.8485	Intermediate Similarity	NPC280937
0.8485	Intermediate Similarity	NPC86485
0.848	Intermediate Similarity	NPC470704
0.848	Intermediate Similarity	NPC86477
0.848	Intermediate Similarity	NPC76482
0.8476	Intermediate Similarity	NPC76376
0.8476	Intermediate Similarity	NPC474663
0.8475	Intermediate Similarity	NPC470416
0.8471	Intermediate Similarity	NPC45449
0.8471	Intermediate Similarity	NPC88243
0.8471	Intermediate Similarity	NPC234052
0.8466	Intermediate Similarity	NPC475996
0.8466	Intermediate Similarity	NPC208069
0.8466	Intermediate Similarity	NPC294502
0.8466	Intermediate Similarity	NPC200221
0.8462	Intermediate Similarity	NPC471745
0.8462	Intermediate Similarity	NPC272722
0.8457	Intermediate Similarity	NPC477683
0.8457	Intermediate Similarity	NPC476773
0.8457	Intermediate Similarity	NPC477682
0.8453	Intermediate Similarity	NPC314020
0.8452	Intermediate Similarity	NPC246478
0.8448	Intermediate Similarity	NPC99591
0.8443	Intermediate Similarity	NPC227192
0.8443	Intermediate Similarity	NPC476981
0.8443	Intermediate Similarity	NPC203891
0.8443	Intermediate Similarity	NPC287979
0.8443	Intermediate Similarity	NPC75215
0.8443	Intermediate Similarity	NPC305663
0.8443	Intermediate Similarity	NPC101830
0.8443	Intermediate Similarity	NPC189179
0.8443	Intermediate Similarity	NPC176665
0.8443	Intermediate Similarity	NPC224137
0.8443	Intermediate Similarity	NPC163524
0.8443	Intermediate Similarity	NPC110070
0.8443	Intermediate Similarity	NPC93376
0.8439	Intermediate Similarity	NPC475669
0.8439	Intermediate Similarity	NPC174700
0.8439	Intermediate Similarity	NPC247964
0.8439	Intermediate Similarity	NPC121333
0.8434	Intermediate Similarity	NPC326910
0.8434	Intermediate Similarity	NPC208197
0.843	Intermediate Similarity	NPC152477
0.843	Intermediate Similarity	NPC242395
0.8424	Intermediate Similarity	NPC134677
0.8424	Intermediate Similarity	NPC289968
0.8424	Intermediate Similarity	NPC301123
0.8421	Intermediate Similarity	NPC113093
0.8418	Intermediate Similarity	NPC475148
0.8418	Intermediate Similarity	NPC475656
0.8418	Intermediate Similarity	NPC36138
0.8415	Intermediate Similarity	NPC179183
0.8415	Intermediate Similarity	NPC219330
0.8415	Intermediate Similarity	NPC29056
0.8412	Intermediate Similarity	NPC470459
0.8412	Intermediate Similarity	NPC1706
0.8412	Intermediate Similarity	NPC1755
0.8412	Intermediate Similarity	NPC39305
0.8412	Intermediate Similarity	NPC41301
0.8412	Intermediate Similarity	NPC263092
0.8412	Intermediate Similarity	NPC59295
0.8402	Intermediate Similarity	NPC112418
0.84	Intermediate Similarity	NPC296018
0.84	Intermediate Similarity	NPC24258
0.84	Intermediate Similarity	NPC472382
0.84	Intermediate Similarity	NPC472384
0.84	Intermediate Similarity	NPC154741
0.84	Intermediate Similarity	NPC164384
0.84	Intermediate Similarity	NPC472380
0.8393	Intermediate Similarity	NPC196879
0.8393	Intermediate Similarity	NPC87317
0.8391	Intermediate Similarity	NPC261471
0.8391	Intermediate Similarity	NPC149846
0.8383	Intermediate Similarity	NPC303255
0.8383	Intermediate Similarity	NPC266960
0.8383	Intermediate Similarity	NPC292107
0.8383	Intermediate Similarity	NPC265511
0.8383	Intermediate Similarity	NPC245546
0.8383	Intermediate Similarity	NPC49824
0.8383	Intermediate Similarity	NPC247017
0.8383	Intermediate Similarity	NPC98661
0.8383	Intermediate Similarity	NPC43243
0.8382	Intermediate Similarity	NPC218533
0.8382	Intermediate Similarity	NPC78830
0.8382	Intermediate Similarity	NPC476365
0.8373	Intermediate Similarity	NPC75279
0.8373	Intermediate Similarity	NPC472915
0.8373	Intermediate Similarity	NPC58382
0.8373	Intermediate Similarity	NPC475895
0.8373	Intermediate Similarity	NPC276409
0.8373	Intermediate Similarity	NPC301233
0.8373	Intermediate Similarity	NPC471981
0.8373	Intermediate Similarity	NPC186507
0.8373	Intermediate Similarity	NPC162351
0.8373	Intermediate Similarity	NPC250822

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 NPC72696 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	978
0.2-0.3	1871
0.3-0.4	2652
0.4-0.5	1888
0.5-0.6	900
0.6-0.7	346
0.7-0.8	135
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
0.8434	Intermediate Similarity	NPD5402	Approved
0.8383	Intermediate Similarity	NPD3882	Suspended
0.8353	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8314	Intermediate Similarity	NPD7473	Discontinued
0.8274	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD2801	Approved
0.8256	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6166	Phase 2
0.8239	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD5844	Phase 1
0.8125	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD3818	Discontinued
0.8023	Intermediate Similarity	NPD5494	Approved
0.8012	Intermediate Similarity	NPD7075	Discontinued
0.8012	Intermediate Similarity	NPD5403	Approved
0.7988	Intermediate Similarity	NPD1934	Approved
0.7978	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7808	Phase 3
0.7917	Intermediate Similarity	NPD3226	Approved
0.7907	Intermediate Similarity	NPD3749	Approved
0.7892	Intermediate Similarity	NPD5401	Approved
0.7886	Intermediate Similarity	NPD3926	Phase 2
0.7877	Intermediate Similarity	NPD6559	Discontinued
0.787	Intermediate Similarity	NPD6599	Discontinued
0.7861	Intermediate Similarity	NPD919	Approved
0.7844	Intermediate Similarity	NPD1512	Approved
0.7836	Intermediate Similarity	NPD1465	Phase 2
0.7836	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6799	Approved
0.7824	Intermediate Similarity	NPD7411	Suspended
0.7821	Intermediate Similarity	NPD6797	Phase 2
0.7812	Intermediate Similarity	NPD447	Suspended
0.7798	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD6801	Discontinued
0.7771	Intermediate Similarity	NPD1247	Approved
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.7746	Intermediate Similarity	NPD7768	Phase 2
0.7733	Intermediate Similarity	NPD7819	Suspended
0.773	Intermediate Similarity	NPD1551	Phase 2
0.7725	Intermediate Similarity	NPD1511	Approved
0.7709	Intermediate Similarity	NPD7054	Approved
0.7705	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6959	Discontinued
0.7667	Intermediate Similarity	NPD7472	Approved
0.7663	Intermediate Similarity	NPD8434	Phase 2
0.7651	Intermediate Similarity	NPD3750	Approved
0.7651	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2935	Discontinued
0.7611	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8312	Approved
0.7596	Intermediate Similarity	NPD8313	Approved
0.7586	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD2533	Approved
0.7574	Intermediate Similarity	NPD2534	Approved
0.7574	Intermediate Similarity	NPD2532	Approved
0.7572	Intermediate Similarity	NPD37	Approved
0.7568	Intermediate Similarity	NPD8150	Discontinued
0.7558	Intermediate Similarity	NPD4380	Phase 2
0.7557	Intermediate Similarity	NPD6234	Discontinued
0.7556	Intermediate Similarity	NPD3751	Discontinued
0.7543	Intermediate Similarity	NPD4965	Approved
0.7543	Intermediate Similarity	NPD4966	Approved
0.7543	Intermediate Similarity	NPD4967	Phase 2
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.747	Intermediate Similarity	NPD2346	Discontinued
0.744	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1607	Approved
0.7425	Intermediate Similarity	NPD1549	Phase 2
0.7412	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6190	Approved
0.7378	Intermediate Similarity	NPD1933	Approved
0.7374	Intermediate Similarity	NPD7199	Phase 2
0.7365	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7228	Approved
0.7349	Intermediate Similarity	NPD4308	Phase 3
0.7349	Intermediate Similarity	NPD3748	Approved
0.7349	Intermediate Similarity	NPD1510	Phase 2
0.7347	Intermediate Similarity	NPD7871	Phase 2
0.7347	Intermediate Similarity	NPD7870	Phase 2
0.7337	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7874	Approved
0.7321	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6776	Approved
0.732	Intermediate Similarity	NPD6779	Approved
0.732	Intermediate Similarity	NPD6781	Approved
0.732	Intermediate Similarity	NPD6780	Approved
0.732	Intermediate Similarity	NPD6778	Approved
0.732	Intermediate Similarity	NPD6782	Approved
0.732	Intermediate Similarity	NPD6777	Approved
0.7317	Intermediate Similarity	NPD1240	Approved
0.7312	Intermediate Similarity	NPD1203	Approved
0.7305	Intermediate Similarity	NPD2796	Approved
0.7301	Intermediate Similarity	NPD2313	Discontinued
0.7296	Intermediate Similarity	NPD7696	Phase 3
0.7296	Intermediate Similarity	NPD7697	Approved
0.7296	Intermediate Similarity	NPD7698	Approved
0.7284	Intermediate Similarity	NPD6832	Phase 2
0.7283	Intermediate Similarity	NPD920	Approved
0.7278	Intermediate Similarity	NPD1243	Approved
0.7278	Intermediate Similarity	NPD2800	Approved
0.7278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1653	Approved
0.7238	Intermediate Similarity	NPD3787	Discontinued
0.7202	Intermediate Similarity	NPD6100	Approved
0.7202	Intermediate Similarity	NPD6099	Approved
0.72	Intermediate Similarity	NPD8151	Discontinued
0.72	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD411	Approved
0.7182	Intermediate Similarity	NPD8127	Discontinued
0.7169	Intermediate Similarity	NPD230	Phase 1
0.7169	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7549	Discontinued
0.716	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7151	Intermediate Similarity	NPD5953	Discontinued
0.715	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7135	Intermediate Similarity	NPD4628	Phase 3
0.7129	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7783	Phase 2
0.7125	Intermediate Similarity	NPD9717	Approved
0.711	Intermediate Similarity	NPD7390	Discontinued
0.7108	Intermediate Similarity	NPD4307	Phase 2
0.7108	Intermediate Similarity	NPD943	Approved
0.7091	Intermediate Similarity	NPD3764	Approved
0.7091	Intermediate Similarity	NPD6798	Discontinued
0.7067	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD2403	Approved
0.7062	Intermediate Similarity	NPD6535	Approved
0.7062	Intermediate Similarity	NPD6534	Approved
0.7059	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5710	Approved
0.7049	Intermediate Similarity	NPD5711	Approved
0.7044	Intermediate Similarity	NPD7801	Approved
0.7041	Intermediate Similarity	NPD7699	Phase 2
0.7041	Intermediate Similarity	NPD7700	Phase 2
0.7031	Intermediate Similarity	NPD4287	Approved
0.7021	Intermediate Similarity	NPD7685	Pre-registration
0.7021	Intermediate Similarity	NPD7240	Approved
0.7021	Intermediate Similarity	NPD7039	Approved
0.7021	Intermediate Similarity	NPD7038	Approved
0.7012	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD8319	Approved
0.7	Intermediate Similarity	NPD8320	Phase 1
0.7	Intermediate Similarity	NPD5406	Approved
0.6994	Remote Similarity	NPD2797	Approved
0.6994	Remote Similarity	NPD2309	Approved
0.6988	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3268	Approved
0.6985	Remote Similarity	NPD6823	Phase 2
0.6978	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4749	Approved
0.6971	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7286	Phase 2
0.6941	Remote Similarity	NPD7033	Discontinued
0.6919	Remote Similarity	NPD8285	Discontinued
0.6905	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1613	Approved
0.689	Remote Similarity	NPD1470	Approved
0.6889	Remote Similarity	NPD6844	Discontinued
0.6884	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4908	Phase 1
0.6865	Remote Similarity	NPD7229	Phase 3
0.6864	Remote Similarity	NPD6355	Discontinued
0.686	Remote Similarity	NPD1471	Phase 3
0.6848	Remote Similarity	NPD2798	Approved
0.6842	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7003	Approved
0.6836	Remote Similarity	NPD6273	Approved
0.6831	Remote Similarity	NPD6971	Discontinued
0.6829	Remote Similarity	NPD3225	Approved
0.6828	Remote Similarity	NPD5242	Approved
0.6826	Remote Similarity	NPD4625	Phase 3
0.6826	Remote Similarity	NPD7095	Approved
0.6826	Remote Similarity	NPD3027	Phase 3
0.6825	Remote Similarity	NPD7907	Approved
0.6824	Remote Similarity	NPD6651	Approved
0.6816	Remote Similarity	NPD7458	Discontinued

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