NPASS Compound

Structure

NPC474763 OpenBabel07101719132D 27 29 0 0 1 0 0 0 0 0999 V2000 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 4 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 5 2 0 0 0 0 5 7 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 26 1 0 0 0 0 8 9 2 0 0 0 0 8 27 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 11 2 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 14 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 24 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 18 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.08
Volume:	352.235
LogP:	0.867
LogD:	0.086
LogS:	-3.019
# Rotatable Bonds:	4
TPSA:	135.66
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	3.946
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.228
MDCK Permeability:	7.658291906409431e-06
Pgp-inhibitor:	0.032
Pgp-substrate:	0.253
Human Intestinal Absorption (HIA):	0.263
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.757

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	85.43145751953125%
Volume Distribution (VD):	0.609
Pgp-substrate:	11.16448974609375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.145
CYP2C9-substrate:	0.363
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.05

ADMET: Excretion

Clearance (CL):	0.878
Half-life (T1/2):	0.528

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.902
Drug-inuced Liver Injury (DILI):	0.995
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.408
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.235
Carcinogencity:	0.135
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.177

Download Data

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

Natural Product: NPC474763

Natural Product ID:	NPC474763
*Common Name:**	Cyathuscavin B
IUPAC Name:	9,10-dihydroxy-6,8-dimethoxy-1-oxo-3-[(E)-prop-1-enyl]-6H-pyrano[4,3-c]isochromene-7-carboxylic acid
Synonyms:	cyathuscavin B
Standard InCHIKey:	ZORZPKUBRKXKSU-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C18H16O9/c1-4-5-7-6-8-9(17(23)26-7)10-11(18(25-3)27-8)12(16(21)22)15(24-2)14(20)13(10)19/h4-6,18-20H,1-3H3,(H,21,22)/b5-4+
SMILES:	C/C=C/c1cc2OC(OC)c3c(c2c(=O)o1)c(O)c(c(c3C(=O)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481769
PubChem CID:	24894009
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002344] Methoxybenzoic acids and derivatives [CHEMONTID:0002345] O-methoxybenzoic 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
NPO28590	Cyathus stercoreus	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17511503]
NPO28590	Cyathus stercoreus	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18565749]
NPO28590	Cyathus stercoreus	Species	Nidulariaceae	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
EC50	3
Others	1

Activity Type	# Activity
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		EC50	=	13920.0	nM	PMID[540259]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	9840.0	nM	PMID[540259]
NPT2	Others	Unspecified		Activity	=	90.0	%	PMID[540259]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	25120.0	nM	PMID[540259]

☑ 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 NPC474763 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	408
0.1-0.2	1921
0.2-0.3	4456
0.3-0.4	9751
0.4-0.5	8238
0.5-0.6	3752
0.6-0.7	5111
0.7-0.8	5440
0.8-0.85	2931
0.85-0.9	659
0.9-0.95	23
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9871	High Similarity	NPC327652
0.9808	High Similarity	NPC329119
0.9805	High Similarity	NPC474779
0.9679	High Similarity	NPC317781
0.9608	High Similarity	NPC16286
0.9419	High Similarity	NPC197751
0.9299	High Similarity	NPC315157
0.9012	High Similarity	NPC470773
0.9	High Similarity	NPC470358
0.8963	High Similarity	NPC471287
0.8951	High Similarity	NPC327809
0.8896	High Similarity	NPC191930
0.8868	High Similarity	NPC16082
0.8868	High Similarity	NPC82592
0.8855	High Similarity	NPC471181
0.8834	High Similarity	NPC249181
0.8834	High Similarity	NPC470772
0.8827	High Similarity	NPC470756
0.8827	High Similarity	NPC65746
0.8812	High Similarity	NPC227062
0.8812	High Similarity	NPC150227
0.8805	High Similarity	NPC281477
0.8788	High Similarity	NPC116745
0.8788	High Similarity	NPC471288
0.8788	High Similarity	NPC283041
0.8788	High Similarity	NPC298847
0.8774	High Similarity	NPC471689
0.8758	High Similarity	NPC84935
0.8758	High Similarity	NPC190020
0.8758	High Similarity	NPC77679
0.875	High Similarity	NPC108202
0.875	High Similarity	NPC79998
0.875	High Similarity	NPC199926
0.8743	High Similarity	NPC211594
0.8743	High Similarity	NPC260263
0.8743	High Similarity	NPC254540
0.8743	High Similarity	NPC172807
0.8743	High Similarity	NPC256760
0.8727	High Similarity	NPC20237
0.872	High Similarity	NPC94777
0.8712	High Similarity	NPC471290
0.8706	High Similarity	NPC212290
0.8698	High Similarity	NPC196771
0.8696	High Similarity	NPC54928
0.869	High Similarity	NPC208668
0.869	High Similarity	NPC4390
0.8683	High Similarity	NPC109827
0.8683	High Similarity	NPC78734
0.8683	High Similarity	NPC124470
0.8683	High Similarity	NPC150767
0.8679	High Similarity	NPC215921
0.8679	High Similarity	NPC70016
0.8675	High Similarity	NPC471180
0.8675	High Similarity	NPC229729
0.8675	High Similarity	NPC477502
0.8671	High Similarity	NPC105591
0.8667	High Similarity	NPC22832
0.8667	High Similarity	NPC165720
0.8667	High Similarity	NPC311830
0.8659	High Similarity	NPC300537
0.8659	High Similarity	NPC127782
0.865	High Similarity	NPC36217
0.8647	High Similarity	NPC168584
0.8642	High Similarity	NPC35598
0.8642	High Similarity	NPC472860
0.8642	High Similarity	NPC222689
0.8639	High Similarity	NPC472607
0.8639	High Similarity	NPC199533
0.8639	High Similarity	NPC477848
0.8639	High Similarity	NPC470454
0.8631	High Similarity	NPC175107
0.8631	High Similarity	NPC153755
0.8631	High Similarity	NPC48773
0.8631	High Similarity	NPC205076
0.8631	High Similarity	NPC190003
0.8631	High Similarity	NPC307518
0.8631	High Similarity	NPC472386
0.8625	High Similarity	NPC199773
0.8625	High Similarity	NPC295646
0.8623	High Similarity	NPC186807
0.8623	High Similarity	NPC469931
0.8623	High Similarity	NPC117911
0.8623	High Similarity	NPC45638
0.8623	High Similarity	NPC226294
0.8623	High Similarity	NPC58053
0.8623	High Similarity	NPC201292
0.8623	High Similarity	NPC93337
0.8623	High Similarity	NPC328321
0.8623	High Similarity	NPC105025
0.8623	High Similarity	NPC229687
0.8623	High Similarity	NPC475942
0.8616	High Similarity	NPC31132
0.8616	High Similarity	NPC38775
0.8616	High Similarity	NPC96501
0.8614	High Similarity	NPC236934
0.8614	High Similarity	NPC5778
0.8614	High Similarity	NPC99957
0.8614	High Similarity	NPC181616
0.8606	High Similarity	NPC243930
0.8606	High Similarity	NPC474350
0.8606	High Similarity	NPC309025
0.8606	High Similarity	NPC88023
0.8606	High Similarity	NPC186686
0.8606	High Similarity	NPC191306
0.8606	High Similarity	NPC19709
0.8606	High Similarity	NPC270335
0.8606	High Similarity	NPC284960
0.8606	High Similarity	NPC88043
0.8606	High Similarity	NPC222936
0.8598	High Similarity	NPC295009
0.8598	High Similarity	NPC260640
0.8588	High Similarity	NPC233994
0.8588	High Similarity	NPC79736
0.8588	High Similarity	NPC472385
0.8588	High Similarity	NPC211532
0.8588	High Similarity	NPC198324
0.8588	High Similarity	NPC67629
0.858	High Similarity	NPC472993
0.858	High Similarity	NPC172033
0.858	High Similarity	NPC88560
0.858	High Similarity	NPC175230
0.858	High Similarity	NPC301897
0.8571	High Similarity	NPC43872
0.8571	High Similarity	NPC235260
0.8571	High Similarity	NPC291510
0.8571	High Similarity	NPC20505
0.8571	High Similarity	NPC149011
0.8571	High Similarity	NPC21190
0.8571	High Similarity	NPC116850
0.8571	High Similarity	NPC212748
0.8571	High Similarity	NPC224462
0.8571	High Similarity	NPC155763
0.8571	High Similarity	NPC238672
0.8571	High Similarity	NPC183357
0.8571	High Similarity	NPC105511
0.8571	High Similarity	NPC231194
0.8571	High Similarity	NPC204937
0.8571	High Similarity	NPC51326
0.8571	High Similarity	NPC244776
0.8571	High Similarity	NPC144801
0.8571	High Similarity	NPC298778
0.8571	High Similarity	NPC22195
0.8571	High Similarity	NPC218488
0.8571	High Similarity	NPC116864
0.8571	High Similarity	NPC197188
0.8563	High Similarity	NPC58716
0.8563	High Similarity	NPC45618
0.8563	High Similarity	NPC45400
0.8563	High Similarity	NPC146792
0.8562	High Similarity	NPC256406
0.8562	High Similarity	NPC200773
0.8562	High Similarity	NPC240768
0.8554	High Similarity	NPC275780
0.8554	High Similarity	NPC472450
0.8554	High Similarity	NPC303174
0.8554	High Similarity	NPC471788
0.8554	High Similarity	NPC7752
0.8554	High Similarity	NPC239752
0.8554	High Similarity	NPC88243
0.8545	High Similarity	NPC189142
0.8545	High Similarity	NPC22324
0.8545	High Similarity	NPC474150
0.8545	High Similarity	NPC77660
0.8545	High Similarity	NPC215612
0.8545	High Similarity	NPC474162
0.8545	High Similarity	NPC201800
0.8545	High Similarity	NPC473043
0.8544	High Similarity	NPC137296
0.8544	High Similarity	NPC251188
0.8538	High Similarity	NPC267549
0.8537	High Similarity	NPC472055
0.8537	High Similarity	NPC239966
0.8537	High Similarity	NPC56085
0.8537	High Similarity	NPC14353
0.8537	High Similarity	NPC471973
0.8537	High Similarity	NPC285973
0.8537	High Similarity	NPC24627
0.8537	High Similarity	NPC225624
0.8537	High Similarity	NPC292415
0.8537	High Similarity	NPC228785
0.8537	High Similarity	NPC203020
0.8535	High Similarity	NPC75694
0.8529	High Similarity	NPC115760
0.8529	High Similarity	NPC43211
0.8529	High Similarity	NPC294629
0.8529	High Similarity	NPC264735
0.8529	High Similarity	NPC49344
0.8529	High Similarity	NPC210094
0.8529	High Similarity	NPC237435
0.8529	High Similarity	NPC135277
0.8529	High Similarity	NPC101191
0.8529	High Similarity	NPC68381
0.8529	High Similarity	NPC146803
0.8529	High Similarity	NPC63105
0.8529	High Similarity	NPC469354
0.8528	High Similarity	NPC136674
0.8528	High Similarity	NPC302258
0.8528	High Similarity	NPC78103
0.8523	High Similarity	NPC264302
0.8521	High Similarity	NPC475825

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 NPC474763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	1001
0.2-0.3	2017
0.3-0.4	2668
0.4-0.5	1731
0.5-0.6	872
0.6-0.7	306
0.7-0.8	127
0.8-0.85	41
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8675	High Similarity	NPD3818	Discontinued
0.8659	High Similarity	NPD6232	Discontinued
0.8535	High Similarity	NPD2532	Approved
0.8535	High Similarity	NPD2534	Approved
0.8535	High Similarity	NPD2533	Approved
0.8529	High Similarity	NPD4338	Clinical (unspecified phase)
0.8512	High Similarity	NPD7054	Approved
0.8503	High Similarity	NPD7473	Discontinued
0.8462	Intermediate Similarity	NPD7074	Phase 3
0.8462	Intermediate Similarity	NPD7472	Approved
0.8344	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2801	Approved
0.8304	Intermediate Similarity	NPD6797	Phase 2
0.8293	Intermediate Similarity	NPD3817	Phase 2
0.8282	Intermediate Similarity	NPD1934	Approved
0.8256	Intermediate Similarity	NPD7251	Discontinued
0.8253	Intermediate Similarity	NPD6234	Discontinued
0.8208	Intermediate Similarity	NPD7808	Phase 3
0.8193	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7819	Suspended
0.8081	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD37	Approved
0.8049	Intermediate Similarity	NPD4380	Phase 2
0.8034	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD3882	Suspended
0.8024	Intermediate Similarity	NPD4965	Approved
0.8024	Intermediate Similarity	NPD4967	Phase 2
0.8024	Intermediate Similarity	NPD4966	Approved
0.8023	Intermediate Similarity	NPD7228	Approved
0.8012	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD1511	Approved
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.8012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD5844	Phase 1
0.7976	Intermediate Similarity	NPD7075	Discontinued
0.7944	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6559	Discontinued
0.7941	Intermediate Similarity	NPD7199	Phase 2
0.7914	Intermediate Similarity	NPD1512	Approved
0.7895	Intermediate Similarity	NPD5711	Approved
0.7895	Intermediate Similarity	NPD5710	Approved
0.7866	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6801	Discontinued
0.7818	Intermediate Similarity	NPD1653	Approved
0.7798	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5494	Approved
0.7771	Intermediate Similarity	NPD230	Phase 1
0.774	Intermediate Similarity	NPD7685	Pre-registration
0.7716	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7411	Suspended
0.7667	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8313	Approved
0.7654	Intermediate Similarity	NPD2800	Approved
0.7654	Intermediate Similarity	NPD8312	Approved
0.7647	Intermediate Similarity	NPD5402	Approved
0.7636	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6959	Discontinued
0.7625	Intermediate Similarity	NPD1510	Phase 2
0.7616	Intermediate Similarity	NPD919	Approved
0.7604	Intermediate Similarity	NPD8151	Discontinued
0.7584	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2935	Discontinued
0.7576	Intermediate Similarity	NPD6799	Approved
0.7544	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7240	Approved
0.7526	Intermediate Similarity	NPD7435	Discontinued
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.746	Intermediate Similarity	NPD6780	Approved
0.746	Intermediate Similarity	NPD6779	Approved
0.746	Intermediate Similarity	NPD6777	Approved
0.746	Intermediate Similarity	NPD6782	Approved
0.746	Intermediate Similarity	NPD6776	Approved
0.746	Intermediate Similarity	NPD6778	Approved
0.746	Intermediate Similarity	NPD6781	Approved
0.7456	Intermediate Similarity	NPD3226	Approved
0.744	Intermediate Similarity	NPD5403	Approved
0.7438	Intermediate Similarity	NPD447	Suspended
0.7429	Intermediate Similarity	NPD1247	Approved
0.7423	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1549	Phase 2
0.7375	Intermediate Similarity	NPD943	Approved
0.7375	Intermediate Similarity	NPD1240	Approved
0.7362	Intermediate Similarity	NPD2796	Approved
0.7356	Intermediate Similarity	NPD3749	Approved
0.7347	Intermediate Similarity	NPD7783	Phase 2
0.7347	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD920	Approved
0.7333	Intermediate Similarity	NPD6674	Discontinued
0.7322	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5401	Approved
0.7321	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2346	Discontinued
0.7296	Intermediate Similarity	NPD7874	Approved
0.7296	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6535	Approved
0.7287	Intermediate Similarity	NPD6534	Approved
0.7284	Intermediate Similarity	NPD1607	Approved
0.7277	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7696	Phase 3
0.7254	Intermediate Similarity	NPD7697	Approved
0.7254	Intermediate Similarity	NPD7698	Approved
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.7247	Intermediate Similarity	NPD3926	Phase 2
0.7246	Intermediate Similarity	NPD6190	Approved
0.7229	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3751	Discontinued
0.7222	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5124	Phase 1
0.7222	Intermediate Similarity	NPD1933	Approved
0.7219	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7870	Phase 2
0.7216	Intermediate Similarity	NPD7871	Phase 2
0.7212	Intermediate Similarity	NPD7266	Discontinued
0.7202	Intermediate Similarity	NPD6823	Phase 2
0.7198	Intermediate Similarity	NPD5953	Discontinued
0.7195	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3748	Approved
0.7194	Intermediate Similarity	NPD7701	Phase 2
0.7191	Intermediate Similarity	NPD3787	Discontinued
0.7188	Intermediate Similarity	NPD3027	Phase 3
0.7186	Intermediate Similarity	NPD4628	Phase 3
0.7184	Intermediate Similarity	NPD8455	Phase 2
0.7173	Intermediate Similarity	NPD7699	Phase 2
0.7173	Intermediate Similarity	NPD7700	Phase 2
0.717	Intermediate Similarity	NPD9494	Approved
0.7165	Intermediate Similarity	NPD7680	Approved
0.716	Intermediate Similarity	NPD7390	Discontinued
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7151	Intermediate Similarity	NPD5242	Approved
0.7151	Intermediate Similarity	NPD8150	Discontinued
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7128	Intermediate Similarity	NPD8320	Phase 1
0.7128	Intermediate Similarity	NPD8319	Approved
0.7126	Intermediate Similarity	NPD1243	Approved
0.7113	Intermediate Similarity	NPD5005	Approved
0.7113	Intermediate Similarity	NPD5006	Approved
0.7101	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7229	Phase 3
0.7091	Intermediate Similarity	NPD2799	Discontinued
0.7088	Intermediate Similarity	NPD7286	Phase 2
0.7085	Intermediate Similarity	NPD7801	Approved
0.7083	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD9269	Phase 2
0.7065	Intermediate Similarity	NPD7930	Approved
0.7056	Intermediate Similarity	NPD7584	Approved
0.7055	Intermediate Similarity	NPD1613	Approved
0.7055	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6213	Phase 3
0.7053	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6212	Phase 3
0.7048	Intermediate Similarity	NPD5406	Approved
0.7048	Intermediate Similarity	NPD5404	Approved
0.7048	Intermediate Similarity	NPD5405	Approved
0.7048	Intermediate Similarity	NPD5408	Approved
0.7045	Intermediate Similarity	NPD5353	Approved
0.7019	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4420	Approved
0.6968	Remote Similarity	NPD8434	Phase 2
0.6957	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4060	Phase 1
0.6943	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7585	Approved
0.6935	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3705	Approved
0.6894	Remote Similarity	NPD2798	Approved
0.6884	Remote Similarity	NPD7583	Approved
0.6875	Remote Similarity	NPD6385	Approved
0.6875	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6386	Approved
0.6857	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD8127	Discontinued
0.6845	Remote Similarity	NPD6099	Approved
0.6845	Remote Similarity	NPD6100	Approved
0.6834	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3764	Approved
0.6815	Remote Similarity	NPD9268	Approved
0.681	Remote Similarity	NPD6832	Phase 2
0.6792	Remote Similarity	NPD422	Phase 1
0.6786	Remote Similarity	NPD7033	Discontinued
0.6784	Remote Similarity	NPD8166	Discontinued
0.6784	Remote Similarity	NPD7003	Approved
0.678	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD8366	Approved
0.6772	Remote Similarity	NPD4626	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data