NPASS Compound

Structure

NPC470710 OpenBabel07101718282D 36 39 0 0 0 0 0 0 0 0999 V2000 4.0247 2.3946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9543 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7953 0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7953 0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9543 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0032 -0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0032 -0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5385 1.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6974 -0.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6974 -0.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5385 1.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 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 -1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4895 0.7473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4895 0.7473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -4.5388 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.3305 2.0345 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -5.6485 -0.5398 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.6485 -0.5398 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.3305 2.0345 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -5.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 -2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2327 1.4164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2327 1.4164 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 35 1 0 0 0 0 2 3 2 0 0 0 0 2 11 1 0 0 0 0 3 18 1 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 10 1 0 0 0 0 5 17 2 0 0 0 0 6 10 1 0 0 0 0 6 19 2 3 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 15 2 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 18 2 0 0 0 0 13 26 1 0 0 0 0 14 23 2 0 0 0 0 14 27 1 0 0 0 0 15 23 1 0 0 0 0 15 28 1 0 0 0 0 16 24 2 0 0 0 0 16 29 1 0 0 0 0 17 24 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 36 1 0 0 0 0 20 21 2 0 0 0 0 21 22 1 0 0 0 0 21 25 1 0 0 0 0 22 32 2 0 0 0 0 23 33 1 0 0 0 0 24 35 1 0 0 0 0 25 34 2 0 0 0 0 25 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	803.66
Volume:	521.616
LogP:	6.483
LogD:	2.412
LogS:	-4.278
# Rotatable Bonds:	5
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.154
Synthetic Accessibility Score:	3.183
Fsp3:	0.04
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:	-6.146
MDCK Permeability:	1.3620361642097123e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.872
20% Bioavailability (F20%):	0.585
30% Bioavailability (F30%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	108.29926300048828%
Volume Distribution (VD):	0.414
Pgp-substrate:	5.127119541168213%

ADMET: Metabolism

CYP1A2-inhibitor:	0.765
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.777
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.651
CYP2C9-substrate:	0.299
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	0.037
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.102
Human Hepatotoxicity (H-HT):	0.387
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.888
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.334
Carcinogencity:	0.121
Eye Corrosion:	0.003
Eye Irritation:	0.651
Respiratory Toxicity:	0.097

Download Data

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

Natural Product: NPC470710

Natural Product ID:	NPC470710
*Common Name:**	Cadiolide F
IUPAC Name:	4-(3-bromo-4-hydroxyphenyl)-3-(3,5-dibromo-4-hydroxybenzoyl)-5-[(3,5-dibromo-4-methoxyphenyl)methylidene]furan-2-one
Synonyms:	Cadiolide F
Standard InCHIKey:	UIMMZOZDZSRXGB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H13Br5O6/c1-35-24-16(29)4-10(5-17(24)30)6-19-20(11-2-3-18(31)13(26)7-11)21(25(34)36-19)22(32)12-8-14(27)23(33)15(28)9-12/h2-9,31,33H,1H3
SMILES:	COc1c(Br)cc(cc1Br)C=C1OC(=O)C(=C1c1ccc(c(c1)Br)O)C(=O)c1cc(Br)c(c(c1)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204153
PubChem CID:	73345227
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids 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
NPO33352	pseudodistoma antinboja	Species	Pseudodistomidae	Eukaryota	n.a.	Korean	n.a.	PMID[23145884]

☑ 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	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.0	ug.mL-1	PMID[535773]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[535773]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[535773]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug.mL-1	PMID[535773]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	3.1	ug.mL-1	PMID[535773]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	6.3	ug.mL-1	PMID[535773]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[535773]

☑ 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 NPC470710 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	363
0.1-0.2	1947
0.2-0.3	5540
0.3-0.4	12310
0.4-0.5	5558
0.5-0.6	7510
0.6-0.7	8663
0.7-0.8	769
0.8-0.85	14
0.85-0.9	14
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9577	High Similarity	NPC270848
0.9577	High Similarity	NPC272868
0.9577	High Similarity	NPC122599
0.9437	High Similarity	NPC147137
0.9155	High Similarity	NPC471236
0.9155	High Similarity	NPC197766
0.9085	High Similarity	NPC177967
0.9085	High Similarity	NPC471237
0.8958	High Similarity	NPC81137
0.8933	High Similarity	NPC235033
0.8933	High Similarity	NPC73132
0.8933	High Similarity	NPC471235
0.8662	High Similarity	NPC11449
0.8451	Intermediate Similarity	NPC78061
0.8451	Intermediate Similarity	NPC159987
0.8451	Intermediate Similarity	NPC122359
0.8239	Intermediate Similarity	NPC213414
0.8169	Intermediate Similarity	NPC105999
0.8099	Intermediate Similarity	NPC116562
0.8099	Intermediate Similarity	NPC296202
0.8028	Intermediate Similarity	NPC7830
0.7959	Intermediate Similarity	NPC478071
0.7891	Intermediate Similarity	NPC2596
0.7762	Intermediate Similarity	NPC180207
0.7568	Intermediate Similarity	NPC4164
0.7566	Intermediate Similarity	NPC262359
0.7562	Intermediate Similarity	NPC178097
0.7562	Intermediate Similarity	NPC25844
0.7546	Intermediate Similarity	NPC135103
0.7535	Intermediate Similarity	NPC296526
0.7533	Intermediate Similarity	NPC196034
0.7516	Intermediate Similarity	NPC87231
0.7516	Intermediate Similarity	NPC257756
0.7516	Intermediate Similarity	NPC129132
0.7516	Intermediate Similarity	NPC205468
0.7516	Intermediate Similarity	NPC212631
0.75	Intermediate Similarity	NPC250266
0.75	Intermediate Similarity	NPC266597
0.7485	Intermediate Similarity	NPC470566
0.7483	Intermediate Similarity	NPC128249
0.7483	Intermediate Similarity	NPC19290
0.7468	Intermediate Similarity	NPC188646
0.7468	Intermediate Similarity	NPC175098
0.7468	Intermediate Similarity	NPC242294
0.7468	Intermediate Similarity	NPC56031
0.7468	Intermediate Similarity	NPC263670
0.7468	Intermediate Similarity	NPC472365
0.7468	Intermediate Similarity	NPC192304
0.7468	Intermediate Similarity	NPC312318
0.7468	Intermediate Similarity	NPC139813
0.7468	Intermediate Similarity	NPC184632
0.7468	Intermediate Similarity	NPC337373
0.7452	Intermediate Similarity	NPC243528
0.7452	Intermediate Similarity	NPC251681
0.7452	Intermediate Similarity	NPC99333
0.7452	Intermediate Similarity	NPC280284
0.7452	Intermediate Similarity	NPC188947
0.7452	Intermediate Similarity	NPC112789
0.7452	Intermediate Similarity	NPC19622
0.7451	Intermediate Similarity	NPC308037
0.7451	Intermediate Similarity	NPC64359
0.7448	Intermediate Similarity	NPC61779
0.7448	Intermediate Similarity	NPC100395
0.7442	Intermediate Similarity	NPC470567
0.7438	Intermediate Similarity	NPC470216
0.7436	Intermediate Similarity	NPC234133
0.7436	Intermediate Similarity	NPC231772
0.7436	Intermediate Similarity	NPC473887
0.7436	Intermediate Similarity	NPC124784
0.7436	Intermediate Similarity	NPC127447
0.7436	Intermediate Similarity	NPC29353
0.7436	Intermediate Similarity	NPC47815
0.7436	Intermediate Similarity	NPC194281
0.7434	Intermediate Similarity	NPC247779
0.7432	Intermediate Similarity	NPC473942
0.7431	Intermediate Similarity	NPC469954
0.7419	Intermediate Similarity	NPC286336
0.741	Intermediate Similarity	NPC474535
0.7405	Intermediate Similarity	NPC275903
0.7391	Intermediate Similarity	NPC469953
0.7389	Intermediate Similarity	NPC181124
0.7389	Intermediate Similarity	NPC303644
0.7389	Intermediate Similarity	NPC7013
0.7389	Intermediate Similarity	NPC162680
0.7389	Intermediate Similarity	NPC209560
0.7389	Intermediate Similarity	NPC188879
0.7389	Intermediate Similarity	NPC290291
0.7389	Intermediate Similarity	NPC275055
0.7389	Intermediate Similarity	NPC294409
0.7389	Intermediate Similarity	NPC116632
0.7383	Intermediate Similarity	NPC221798
0.7379	Intermediate Similarity	NPC311091
0.7379	Intermediate Similarity	NPC471033
0.7372	Intermediate Similarity	NPC131039
0.7365	Intermediate Similarity	NPC68167
0.7365	Intermediate Similarity	NPC475697
0.7365	Intermediate Similarity	NPC69403
0.7365	Intermediate Similarity	NPC291189
0.7358	Intermediate Similarity	NPC269652
0.7358	Intermediate Similarity	NPC281207
0.7355	Intermediate Similarity	NPC144051
0.7355	Intermediate Similarity	NPC28753
0.7355	Intermediate Similarity	NPC159623
0.7355	Intermediate Similarity	NPC20560
0.7355	Intermediate Similarity	NPC204960
0.7355	Intermediate Similarity	NPC18877
0.7355	Intermediate Similarity	NPC82225
0.7355	Intermediate Similarity	NPC294593
0.7351	Intermediate Similarity	NPC22783
0.7342	Intermediate Similarity	NPC278323
0.7342	Intermediate Similarity	NPC309154
0.7342	Intermediate Similarity	NPC279668
0.7342	Intermediate Similarity	NPC124269
0.7342	Intermediate Similarity	NPC90665
0.7342	Intermediate Similarity	NPC12175
0.7342	Intermediate Similarity	NPC55162
0.7338	Intermediate Similarity	NPC128348
0.7338	Intermediate Similarity	NPC66384
0.7338	Intermediate Similarity	NPC112192
0.7338	Intermediate Similarity	NPC189106
0.7338	Intermediate Similarity	NPC309717
0.7338	Intermediate Similarity	NPC313618
0.7338	Intermediate Similarity	NPC164236
0.7329	Intermediate Similarity	NPC264976
0.7329	Intermediate Similarity	NPC302181
0.7325	Intermediate Similarity	NPC168105
0.7325	Intermediate Similarity	NPC150399
0.7325	Intermediate Similarity	NPC13408
0.7325	Intermediate Similarity	NPC12165
0.7325	Intermediate Similarity	NPC240593
0.7325	Intermediate Similarity	NPC274109
0.7325	Intermediate Similarity	NPC472367
0.7325	Intermediate Similarity	NPC213603
0.7325	Intermediate Similarity	NPC41461
0.7325	Intermediate Similarity	NPC1486
0.7325	Intermediate Similarity	NPC25287
0.7325	Intermediate Similarity	NPC472364
0.7325	Intermediate Similarity	NPC477244
0.7325	Intermediate Similarity	NPC473391
0.7325	Intermediate Similarity	NPC249606
0.7325	Intermediate Similarity	NPC476333
0.7325	Intermediate Similarity	NPC98115
0.7325	Intermediate Similarity	NPC66349
0.7325	Intermediate Similarity	NPC477243
0.7325	Intermediate Similarity	NPC477242
0.7325	Intermediate Similarity	NPC186838
0.732	Intermediate Similarity	NPC66905
0.732	Intermediate Similarity	NPC42292
0.732	Intermediate Similarity	NPC307732
0.7312	Intermediate Similarity	NPC110969
0.7312	Intermediate Similarity	NPC3188
0.7312	Intermediate Similarity	NPC136840
0.7312	Intermediate Similarity	NPC26238
0.7308	Intermediate Similarity	NPC66705
0.7308	Intermediate Similarity	NPC172262
0.7296	Intermediate Similarity	NPC241838
0.7296	Intermediate Similarity	NPC250597
0.7296	Intermediate Similarity	NPC143799
0.7296	Intermediate Similarity	NPC310135
0.7296	Intermediate Similarity	NPC295384
0.7296	Intermediate Similarity	NPC222342
0.7296	Intermediate Similarity	NPC265871
0.7296	Intermediate Similarity	NPC78913
0.7296	Intermediate Similarity	NPC261234
0.7296	Intermediate Similarity	NPC18260
0.7296	Intermediate Similarity	NPC274784
0.7296	Intermediate Similarity	NPC20709
0.7296	Intermediate Similarity	NPC329203
0.7296	Intermediate Similarity	NPC225153
0.7296	Intermediate Similarity	NPC152042
0.7296	Intermediate Similarity	NPC150648
0.729	Intermediate Similarity	NPC287533
0.7285	Intermediate Similarity	NPC475236
0.7284	Intermediate Similarity	NPC230943
0.7278	Intermediate Similarity	NPC317119
0.7278	Intermediate Similarity	NPC153979
0.7278	Intermediate Similarity	NPC472419
0.7278	Intermediate Similarity	NPC228661
0.7278	Intermediate Similarity	NPC284409
0.7273	Intermediate Similarity	NPC125153
0.7273	Intermediate Similarity	NPC243891
0.7273	Intermediate Similarity	NPC295036
0.7273	Intermediate Similarity	NPC151973
0.7267	Intermediate Similarity	NPC53192
0.7267	Intermediate Similarity	NPC202981
0.7267	Intermediate Similarity	NPC226636
0.7267	Intermediate Similarity	NPC193805
0.7267	Intermediate Similarity	NPC11561
0.7267	Intermediate Similarity	NPC271451
0.7267	Intermediate Similarity	NPC36181
0.7262	Intermediate Similarity	NPC471787
0.7261	Intermediate Similarity	NPC9985
0.7261	Intermediate Similarity	NPC156092
0.7261	Intermediate Similarity	NPC13575
0.7261	Intermediate Similarity	NPC324929
0.7261	Intermediate Similarity	NPC234560
0.7261	Intermediate Similarity	NPC39426
0.7261	Intermediate Similarity	NPC239495
0.7261	Intermediate Similarity	NPC163029
0.726	Intermediate Similarity	NPC27633

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 NPC470710 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	1017
0.2-0.3	1603
0.3-0.4	2872
0.4-0.5	2006
0.5-0.6	1004
0.6-0.7	270
0.7-0.8	37
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8526	High Similarity	NPD2296	Approved
0.7919	Intermediate Similarity	NPD4287	Approved
0.7628	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4288	Approved
0.7528	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2344	Approved
0.7338	Intermediate Similarity	NPD1240	Approved
0.7333	Intermediate Similarity	NPD1203	Approved
0.7333	Intermediate Similarity	NPD7411	Suspended
0.7325	Intermediate Similarity	NPD2935	Discontinued
0.732	Intermediate Similarity	NPD3764	Approved
0.7312	Intermediate Similarity	NPD2309	Approved
0.7261	Intermediate Similarity	NPD2799	Discontinued
0.7261	Intermediate Similarity	NPD1510	Phase 2
0.726	Intermediate Similarity	NPD9545	Approved
0.7248	Intermediate Similarity	NPD3972	Approved
0.7244	Intermediate Similarity	NPD1607	Approved
0.7233	Intermediate Similarity	NPD1549	Phase 2
0.7222	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2313	Discontinued
0.7178	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7133	Intermediate Similarity	NPD9717	Approved
0.7118	Intermediate Similarity	NPD3749	Approved
0.7117	Intermediate Similarity	NPD6799	Approved
0.7091	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6832	Phase 2
0.7073	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2798	Approved
0.7055	Intermediate Similarity	NPD7440	Discontinued
0.7039	Intermediate Similarity	NPD1876	Approved
0.7037	Intermediate Similarity	NPD7003	Approved
0.7037	Intermediate Similarity	NPD3750	Approved
0.702	Intermediate Similarity	NPD1481	Phase 2
0.7019	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7075	Discontinued
0.7007	Intermediate Similarity	NPD9493	Approved
0.7006	Intermediate Similarity	NPD7458	Discontinued
0.6994	Remote Similarity	NPD2354	Approved
0.6987	Remote Similarity	NPD6798	Discontinued
0.6987	Remote Similarity	NPD3268	Approved
0.6971	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7768	Phase 2
0.6957	Remote Similarity	NPD2346	Discontinued
0.6954	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1535	Discovery
0.6943	Remote Similarity	NPD6233	Phase 2
0.6941	Remote Similarity	NPD7819	Suspended
0.6941	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4308	Phase 3
0.6918	Remote Similarity	NPD1241	Discontinued
0.6913	Remote Similarity	NPD1894	Discontinued
0.6905	Remote Similarity	NPD3226	Approved
0.6901	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2796	Approved
0.6894	Remote Similarity	NPD1551	Phase 2
0.6886	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD2797	Approved
0.6882	Remote Similarity	NPD6801	Discontinued
0.6879	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4380	Phase 2
0.6864	Remote Similarity	NPD6599	Discontinued
0.6855	Remote Similarity	NPD1933	Approved
0.6852	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2353	Approved
0.6832	Remote Similarity	NPD7033	Discontinued
0.6829	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6273	Approved
0.6807	Remote Similarity	NPD1511	Approved
0.6797	Remote Similarity	NPD1608	Approved
0.6788	Remote Similarity	NPD3887	Approved
0.6784	Remote Similarity	NPD1934	Approved
0.6776	Remote Similarity	NPD3847	Discontinued
0.6774	Remote Similarity	NPD3267	Approved
0.6774	Remote Similarity	NPD3266	Approved
0.6763	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3882	Suspended
0.6761	Remote Similarity	NPD6232	Discontinued
0.6753	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2801	Approved
0.6742	Remote Similarity	NPD7473	Discontinued
0.6736	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5535	Approved
0.6728	Remote Similarity	NPD3748	Approved
0.6726	Remote Similarity	NPD1512	Approved
0.6724	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.671	Remote Similarity	NPD3225	Approved
0.671	Remote Similarity	NPD1283	Approved
0.6709	Remote Similarity	NPD9718	Approved
0.6705	Remote Similarity	NPD3817	Phase 2
0.6688	Remote Similarity	NPD9494	Approved
0.6687	Remote Similarity	NPD4307	Phase 2
0.6686	Remote Similarity	NPD7577	Discontinued
0.6686	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD411	Approved
0.6667	Remote Similarity	NPD1243	Approved
0.6646	Remote Similarity	NPD447	Suspended
0.6646	Remote Similarity	NPD6355	Discontinued
0.6646	Remote Similarity	NPD1471	Phase 3
0.6625	Remote Similarity	NPD4062	Phase 3
0.6624	Remote Similarity	NPD1019	Discontinued
0.6608	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD17	Approved
0.6592	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6166	Phase 2
0.6588	Remote Similarity	NPD920	Approved
0.6584	Remote Similarity	NPD3140	Approved
0.6584	Remote Similarity	NPD3142	Approved
0.6573	Remote Similarity	NPD6808	Phase 2
0.6568	Remote Similarity	NPD2532	Approved
0.6568	Remote Similarity	NPD2534	Approved
0.6568	Remote Similarity	NPD2533	Approved
0.6568	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2800	Approved
0.6561	Remote Similarity	NPD1164	Approved
0.6552	Remote Similarity	NPD3134	Approved
0.6548	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD230	Phase 1
0.6534	Remote Similarity	NPD6971	Discontinued
0.6529	Remote Similarity	NPD5049	Phase 3
0.6519	Remote Similarity	NPD3818	Discontinued
0.6519	Remote Similarity	NPD5647	Approved
0.6517	Remote Similarity	NPD6959	Discontinued
0.6516	Remote Similarity	NPD1281	Approved
0.6513	Remote Similarity	NPD5536	Phase 2
0.6507	Remote Similarity	NPD1358	Approved
0.6506	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6651	Approved
0.6503	Remote Similarity	NPD5953	Discontinued
0.65	Remote Similarity	NPD7095	Approved
0.6494	Remote Similarity	NPD6279	Approved
0.6494	Remote Similarity	NPD6280	Approved
0.6485	Remote Similarity	NPD5404	Approved
0.6485	Remote Similarity	NPD5406	Approved
0.6485	Remote Similarity	NPD5408	Approved
0.6485	Remote Similarity	NPD5405	Approved
0.6484	Remote Similarity	NPD5844	Phase 1
0.6484	Remote Similarity	NPD7286	Phase 2
0.6471	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6559	Discontinued
0.6463	Remote Similarity	NPD9266	Approved
0.6463	Remote Similarity	NPD74	Approved
0.6456	Remote Similarity	NPD1470	Approved
0.6446	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2614	Approved
0.6429	Remote Similarity	NPD8166	Discontinued
0.6429	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD690	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5402	Approved
0.642	Remote Similarity	NPD8032	Phase 2
0.6413	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.641	Remote Similarity	NPD1201	Approved
0.641	Remote Similarity	NPD422	Phase 1
0.6402	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD9267	Approved
0.6395	Remote Similarity	NPD9263	Approved
0.6395	Remote Similarity	NPD9264	Approved
0.6393	Remote Similarity	NPD7054	Approved
0.6393	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6190	Approved
0.6386	Remote Similarity	NPD4476	Approved
0.6386	Remote Similarity	NPD4477	Approved
0.638	Remote Similarity	NPD943	Approved
0.638	Remote Similarity	NPD2979	Phase 3
0.6369	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1238	Approved
0.6359	Remote Similarity	NPD7472	Approved
0.6359	Remote Similarity	NPD7074	Phase 3
0.6359	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5889	Approved
0.6343	Remote Similarity	NPD6385	Approved
0.6343	Remote Similarity	NPD5890	Approved
0.6343	Remote Similarity	NPD6386	Approved
0.6339	Remote Similarity	NPD7177	Discontinued
0.6329	Remote Similarity	NPD6583	Phase 3
0.6329	Remote Similarity	NPD6582	Phase 2
0.6324	Remote Similarity	NPD6797	Phase 2
0.6323	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD1651	Approved
0.6322	Remote Similarity	NPD3455	Phase 2
0.6319	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD919	Approved
0.6309	Remote Similarity	NPD5451	Approved
0.6307	Remote Similarity	NPD6844	Discontinued
0.6301	Remote Similarity	NPD1670	Discontinued
0.629	Remote Similarity	NPD7251	Discontinued
0.629	Remote Similarity	NPD7685	Pre-registration
0.629	Remote Similarity	NPD1298	Discontinued
0.6289	Remote Similarity	NPD8090	Clinical (unspecified phase)

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