NPASS Compound

Structure

CID317781 OpenBabel06191716142D 25 27 0 0 1 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -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 -1.7321 -2.0000 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 4 7 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 8 1 0 0 0 0 6 18 2 0 0 0 0 7 24 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 11 2 0 0 0 0 9 25 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 13 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 23 1 0 0 0 0 16 21 1 0 0 0 0 16 25 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.07
Volume:	326.149
LogP:	1.43
LogD:	0.521
LogS:	-3.688
# Rotatable Bonds:	3
TPSA:	130.34
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.484
Synthetic Accessibility Score:	3.422
Fsp3:	0.176
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:	-4.925
MDCK Permeability:	1.0508636478334665e-05
Pgp-inhibitor:	0.956
Pgp-substrate:	0.905
Human Intestinal Absorption (HIA):	0.261
20% Bioavailability (F20%):	0.101
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	79.08324432373047%
Volume Distribution (VD):	0.876
Pgp-substrate:	18.134828567504883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.906
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.499
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.411
CYP2D6-substrate:	0.356
CYP3A4-inhibitor:	0.164
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	0.857
Half-life (T1/2):	0.871

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.707
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.143
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.527
Carcinogencity:	0.041
Eye Corrosion:	0.007
Eye Irritation:	0.603
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC317781

Natural Product ID:	NPC317781
*Common Name:**	Cyathusal B
IUPAC Name:	6,9,10-trihydroxy-8-methoxy-1-oxo-3-[(E)-prop-1-enyl]-6H-pyrano[4,3-c]isochromene-7-carbaldehyde
Synonyms:
Standard InCHIKey:	YLBKRHCXWXNKBF-ONEGZZNKSA-N
Standard InCHI:	InChI=1S/C17H14O8/c1-3-4-7-5-9-11(17(22)24-7)12-10(16(21)25-9)8(6-18)15(23-2)14(20)13(12)19/h3-6,16,19-21H,1-2H3/b4-3+
SMILES:	C/C=C/c1cc2OC(O)c3c(c2c(=O)o1)c(O)c(c(c3C=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228300
PubChem CID:	16737097
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		EC50	=	46010.0	nM	PMID[523787]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	11060.0	nM	PMID[523787]

☑ 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 NPC317781 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	401
0.1-0.2	1891
0.2-0.3	4463
0.3-0.4	9851
0.4-0.5	8296
0.5-0.6	3721
0.6-0.7	5199
0.7-0.8	5528
0.8-0.85	2889
0.85-0.9	443
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC474779
0.9808	High Similarity	NPC327652
0.9745	High Similarity	NPC329119
0.9679	High Similarity	NPC474763
0.961	High Similarity	NPC197751
0.9545	High Similarity	NPC16286
0.9119	High Similarity	NPC315157
0.8896	High Similarity	NPC470772
0.8848	High Similarity	NPC471288
0.8827	High Similarity	NPC470358
0.8812	High Similarity	NPC16082
0.8812	High Similarity	NPC82592
0.8802	High Similarity	NPC260263
0.878	High Similarity	NPC327809
0.8773	High Similarity	NPC471290
0.8758	High Similarity	NPC227062
0.875	High Similarity	NPC281477
0.8735	High Similarity	NPC283041
0.8727	High Similarity	NPC470773
0.8727	High Similarity	NPC191930
0.8704	High Similarity	NPC190020
0.8704	High Similarity	NPC77679
0.8704	High Similarity	NPC84935
0.869	High Similarity	NPC471181
0.8683	High Similarity	NPC471287
0.8675	High Similarity	NPC20237
0.8667	High Similarity	NPC249181
0.8659	High Similarity	NPC470756
0.8655	High Similarity	NPC329161
0.8655	High Similarity	NPC470091
0.8655	High Similarity	NPC240887
0.8642	High Similarity	NPC150227
0.8625	High Similarity	NPC70016
0.8625	High Similarity	NPC215921
0.8623	High Similarity	NPC298847
0.8623	High Similarity	NPC116745
0.8599	High Similarity	NPC471689
0.858	High Similarity	NPC172807
0.858	High Similarity	NPC254540
0.858	High Similarity	NPC79998
0.858	High Similarity	NPC256760
0.858	High Similarity	NPC199926
0.858	High Similarity	NPC471688
0.858	High Similarity	NPC211594
0.8571	High Similarity	NPC295646
0.8571	High Similarity	NPC328321
0.8562	High Similarity	NPC96501
0.8554	High Similarity	NPC94777
0.8547	High Similarity	NPC212290
0.8545	High Similarity	NPC65746
0.8529	High Similarity	NPC208668
0.8529	High Similarity	NPC4390
0.8528	High Similarity	NPC54928
0.8521	High Similarity	NPC78734
0.8521	High Similarity	NPC124470
0.8521	High Similarity	NPC150767
0.8521	High Similarity	NPC109827
0.8519	High Similarity	NPC197188
0.8519	High Similarity	NPC116850
0.8519	High Similarity	NPC43872
0.8519	High Similarity	NPC238672
0.8519	High Similarity	NPC144801
0.8519	High Similarity	NPC291510
0.8514	High Similarity	NPC105591
0.8512	High Similarity	NPC471180
0.8512	High Similarity	NPC229729
0.8512	High Similarity	NPC477502
0.8509	High Similarity	NPC200773
0.8509	High Similarity	NPC240768
0.8509	High Similarity	NPC250488
0.8503	High Similarity	NPC471788
0.8503	High Similarity	NPC165720
0.8503	High Similarity	NPC22832
0.8503	High Similarity	NPC311830
0.8494	Intermediate Similarity	NPC215612
0.8494	Intermediate Similarity	NPC127782
0.8494	Intermediate Similarity	NPC300537
0.8491	Intermediate Similarity	NPC251188
0.8488	Intermediate Similarity	NPC168584
0.8485	Intermediate Similarity	NPC36217
0.8485	Intermediate Similarity	NPC24627
0.8485	Intermediate Similarity	NPC472055
0.848	Intermediate Similarity	NPC199533
0.848	Intermediate Similarity	NPC472607
0.848	Intermediate Similarity	NPC470454
0.848	Intermediate Similarity	NPC477848
0.848	Intermediate Similarity	NPC108202
0.848	Intermediate Similarity	NPC139350
0.8476	Intermediate Similarity	NPC472860
0.8476	Intermediate Similarity	NPC302258
0.8476	Intermediate Similarity	NPC35598
0.8476	Intermediate Similarity	NPC78103
0.8476	Intermediate Similarity	NPC222689
0.8471	Intermediate Similarity	NPC307518
0.8471	Intermediate Similarity	NPC472386
0.8471	Intermediate Similarity	NPC175107
0.8471	Intermediate Similarity	NPC48773
0.8471	Intermediate Similarity	NPC205076
0.8471	Intermediate Similarity	NPC153755
0.8471	Intermediate Similarity	NPC190003
0.8466	Intermediate Similarity	NPC92395
0.8466	Intermediate Similarity	NPC39184
0.8466	Intermediate Similarity	NPC87404
0.8466	Intermediate Similarity	NPC38898
0.8462	Intermediate Similarity	NPC186807
0.8462	Intermediate Similarity	NPC201292
0.8462	Intermediate Similarity	NPC93337
0.8462	Intermediate Similarity	NPC226294
0.8462	Intermediate Similarity	NPC26568
0.8462	Intermediate Similarity	NPC105025
0.8462	Intermediate Similarity	NPC469931
0.8462	Intermediate Similarity	NPC229687
0.8462	Intermediate Similarity	NPC58053
0.8462	Intermediate Similarity	NPC45638
0.8462	Intermediate Similarity	NPC475942
0.8457	Intermediate Similarity	NPC199773
0.8457	Intermediate Similarity	NPC180388
0.8452	Intermediate Similarity	NPC5778
0.8452	Intermediate Similarity	NPC13481
0.8452	Intermediate Similarity	NPC99957
0.8452	Intermediate Similarity	NPC181616
0.8452	Intermediate Similarity	NPC207575
0.8452	Intermediate Similarity	NPC236934
0.8447	Intermediate Similarity	NPC469619
0.8447	Intermediate Similarity	NPC31132
0.8447	Intermediate Similarity	NPC38775
0.8447	Intermediate Similarity	NPC469670
0.8443	Intermediate Similarity	NPC243930
0.8443	Intermediate Similarity	NPC284960
0.8443	Intermediate Similarity	NPC474350
0.8443	Intermediate Similarity	NPC19709
0.8443	Intermediate Similarity	NPC88043
0.8443	Intermediate Similarity	NPC191306
0.8443	Intermediate Similarity	NPC222936
0.8443	Intermediate Similarity	NPC88023
0.8443	Intermediate Similarity	NPC309025
0.8443	Intermediate Similarity	NPC186686
0.8443	Intermediate Similarity	NPC7483
0.8443	Intermediate Similarity	NPC270335
0.8439	Intermediate Similarity	NPC113446
0.8439	Intermediate Similarity	NPC183843
0.8434	Intermediate Similarity	NPC317544
0.8434	Intermediate Similarity	NPC349525
0.8434	Intermediate Similarity	NPC26326
0.8434	Intermediate Similarity	NPC103201
0.8434	Intermediate Similarity	NPC295009
0.8434	Intermediate Similarity	NPC260640
0.8434	Intermediate Similarity	NPC473106
0.843	Intermediate Similarity	NPC233994
0.843	Intermediate Similarity	NPC472385
0.843	Intermediate Similarity	NPC211532
0.843	Intermediate Similarity	NPC198324
0.843	Intermediate Similarity	NPC196771
0.843	Intermediate Similarity	NPC67629
0.843	Intermediate Similarity	NPC79736
0.8428	Intermediate Similarity	NPC260946
0.8424	Intermediate Similarity	NPC470339
0.8421	Intermediate Similarity	NPC88560
0.8421	Intermediate Similarity	NPC172033
0.8421	Intermediate Similarity	NPC472054
0.8421	Intermediate Similarity	NPC472993
0.8421	Intermediate Similarity	NPC175230
0.8421	Intermediate Similarity	NPC181523
0.8415	Intermediate Similarity	NPC301897
0.8412	Intermediate Similarity	NPC244776
0.8412	Intermediate Similarity	NPC246716
0.8412	Intermediate Similarity	NPC116864
0.8412	Intermediate Similarity	NPC218488
0.8412	Intermediate Similarity	NPC105511
0.8412	Intermediate Similarity	NPC183357
0.8412	Intermediate Similarity	NPC155763
0.8412	Intermediate Similarity	NPC204937
0.8412	Intermediate Similarity	NPC149011
0.8412	Intermediate Similarity	NPC22195
0.8412	Intermediate Similarity	NPC298778
0.8412	Intermediate Similarity	NPC235260
0.8412	Intermediate Similarity	NPC231194
0.8412	Intermediate Similarity	NPC20505
0.8412	Intermediate Similarity	NPC224462
0.8412	Intermediate Similarity	NPC212748
0.8412	Intermediate Similarity	NPC21190
0.8412	Intermediate Similarity	NPC10576
0.8412	Intermediate Similarity	NPC51326
0.8412	Intermediate Similarity	NPC1827
0.8409	Intermediate Similarity	NPC73703
0.8408	Intermediate Similarity	NPC82913
0.8405	Intermediate Similarity	NPC192189
0.8402	Intermediate Similarity	NPC58716
0.8402	Intermediate Similarity	NPC45400
0.8402	Intermediate Similarity	NPC146792
0.8402	Intermediate Similarity	NPC45618
0.8397	Intermediate Similarity	NPC187690
0.8395	Intermediate Similarity	NPC228662
0.8395	Intermediate Similarity	NPC99772
0.8395	Intermediate Similarity	NPC256406
0.8395	Intermediate Similarity	NPC204350
0.8393	Intermediate Similarity	NPC472450
0.8393	Intermediate Similarity	NPC7752
0.8393	Intermediate Similarity	NPC303174
0.8393	Intermediate Similarity	NPC239752

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 NPC317781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	996
0.2-0.3	2036
0.3-0.4	2642
0.4-0.5	1741
0.5-0.6	888
0.6-0.7	294
0.7-0.8	123
0.8-0.85	40
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8512	High Similarity	NPD3818	Discontinued
0.8494	Intermediate Similarity	NPD6232	Discontinued
0.8372	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD2533	Approved
0.8365	Intermediate Similarity	NPD2532	Approved
0.8365	Intermediate Similarity	NPD2534	Approved
0.8353	Intermediate Similarity	NPD7054	Approved
0.8343	Intermediate Similarity	NPD7473	Discontinued
0.8304	Intermediate Similarity	NPD7472	Approved
0.8304	Intermediate Similarity	NPD7074	Phase 3
0.8232	Intermediate Similarity	NPD1934	Approved
0.8182	Intermediate Similarity	NPD2801	Approved
0.8182	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6797	Phase 2
0.8133	Intermediate Similarity	NPD3817	Phase 2
0.8103	Intermediate Similarity	NPD7251	Discontinued
0.8101	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7808	Phase 3
0.8036	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD4380	Phase 2
0.7988	Intermediate Similarity	NPD6234	Discontinued
0.7976	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6166	Phase 2
0.7965	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD1465	Phase 2
0.7964	Intermediate Similarity	NPD7819	Suspended
0.7963	Intermediate Similarity	NPD1511	Approved
0.7931	Intermediate Similarity	NPD5844	Phase 1
0.7931	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD37	Approved
0.7874	Intermediate Similarity	NPD7228	Approved
0.787	Intermediate Similarity	NPD4966	Approved
0.787	Intermediate Similarity	NPD4965	Approved
0.787	Intermediate Similarity	NPD3882	Suspended
0.787	Intermediate Similarity	NPD4967	Phase 2
0.7866	Intermediate Similarity	NPD1512	Approved
0.7824	Intermediate Similarity	NPD7075	Discontinued
0.7802	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6801	Discontinued
0.7791	Intermediate Similarity	NPD7199	Phase 2
0.779	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD919	Approved
0.7746	Intermediate Similarity	NPD5711	Approved
0.7746	Intermediate Similarity	NPD5710	Approved
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7697	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1653	Approved
0.7647	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5494	Approved
0.7607	Intermediate Similarity	NPD2800	Approved
0.7605	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5402	Approved
0.76	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7685	Pre-registration
0.7586	Intermediate Similarity	NPD1247	Approved
0.7578	Intermediate Similarity	NPD1510	Phase 2
0.7542	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7411	Suspended
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD920	Approved
0.7486	Intermediate Similarity	NPD6959	Discontinued
0.7485	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8151	Discontinued
0.7455	Intermediate Similarity	NPD3750	Approved
0.7432	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6799	Approved
0.7425	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2935	Discontinued
0.7412	Intermediate Similarity	NPD3226	Approved
0.7403	Intermediate Similarity	NPD7240	Approved
0.7399	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5403	Approved
0.7396	Intermediate Similarity	NPD7435	Discontinued
0.7391	Intermediate Similarity	NPD447	Suspended
0.7381	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5401	Approved
0.7378	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6599	Discontinued
0.7362	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7768	Phase 2
0.7346	Intermediate Similarity	NPD6651	Approved
0.7342	Intermediate Similarity	NPD9494	Approved
0.7333	Intermediate Similarity	NPD1549	Phase 2
0.733	Intermediate Similarity	NPD6776	Approved
0.733	Intermediate Similarity	NPD6779	Approved
0.733	Intermediate Similarity	NPD6780	Approved
0.733	Intermediate Similarity	NPD6781	Approved
0.733	Intermediate Similarity	NPD6778	Approved
0.733	Intermediate Similarity	NPD6777	Approved
0.733	Intermediate Similarity	NPD6782	Approved
0.7329	Intermediate Similarity	NPD943	Approved
0.7329	Intermediate Similarity	NPD1240	Approved
0.7317	Intermediate Similarity	NPD1551	Phase 2
0.7314	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7262	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1607	Approved
0.7222	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7783	Phase 2
0.7212	Intermediate Similarity	NPD2796	Approved
0.7202	Intermediate Similarity	NPD6190	Approved
0.7186	Intermediate Similarity	NPD6674	Discontinued
0.7182	Intermediate Similarity	NPD3751	Discontinued
0.7178	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5124	Phase 1
0.7172	Intermediate Similarity	NPD7874	Approved
0.7172	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7152	Intermediate Similarity	NPD3748	Approved
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7128	Intermediate Similarity	NPD7698	Approved
0.7128	Intermediate Similarity	NPD7696	Phase 3
0.7128	Intermediate Similarity	NPD7697	Approved
0.7117	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1613	Approved
0.7112	Intermediate Similarity	NPD8434	Phase 2
0.7112	Intermediate Similarity	NPD8150	Discontinued
0.7111	Intermediate Similarity	NPD3926	Phase 2
0.7099	Intermediate Similarity	NPD2313	Discontinued
0.7098	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7871	Phase 2
0.7092	Intermediate Similarity	NPD7870	Phase 2
0.7083	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1243	Approved
0.7077	Intermediate Similarity	NPD6823	Phase 2
0.7073	Intermediate Similarity	NPD1933	Approved
0.7071	Intermediate Similarity	NPD7701	Phase 2
0.7066	Intermediate Similarity	NPD7266	Discontinued
0.7065	Intermediate Similarity	NPD5953	Discontinued
0.7056	Intermediate Similarity	NPD3787	Discontinued
0.7047	Intermediate Similarity	NPD7699	Phase 2
0.7047	Intermediate Similarity	NPD7700	Phase 2
0.7045	Intermediate Similarity	NPD8455	Phase 2
0.7041	Intermediate Similarity	NPD7680	Approved
0.7025	Intermediate Similarity	NPD9269	Phase 2
0.7018	Intermediate Similarity	NPD7390	Discontinued
0.7017	Intermediate Similarity	NPD5242	Approved
0.7011	Intermediate Similarity	NPD7458	Discontinued
0.7005	Intermediate Similarity	NPD8319	Approved
0.7005	Intermediate Similarity	NPD8320	Phase 1
0.6994	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7801	Approved
0.6961	Remote Similarity	NPD7229	Phase 3
0.6957	Remote Similarity	NPD7286	Phase 2
0.6946	Remote Similarity	NPD2799	Discontinued
0.6946	Remote Similarity	NPD7930	Approved
0.6941	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7584	Approved
0.6927	Remote Similarity	NPD6212	Phase 3
0.6927	Remote Similarity	NPD6213	Phase 3
0.6927	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5353	Approved
0.6907	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5404	Approved
0.6905	Remote Similarity	NPD5405	Approved
0.6905	Remote Similarity	NPD5406	Approved
0.6905	Remote Similarity	NPD5408	Approved
0.6904	Remote Similarity	NPD5005	Approved
0.6904	Remote Similarity	NPD5006	Approved
0.6898	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7585	Approved
0.6813	Remote Similarity	NPD8127	Discontinued
0.6807	Remote Similarity	NPD4060	Phase 1
0.6788	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3764	Approved
0.6786	Remote Similarity	NPD4420	Approved
0.6772	Remote Similarity	NPD9268	Approved
0.6766	Remote Similarity	NPD7583	Approved
0.6765	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.675	Remote Similarity	NPD422	Phase 1
0.6748	Remote Similarity	NPD2798	Approved
0.6746	Remote Similarity	NPD7033	Discontinued
0.6742	Remote Similarity	NPD6386	Approved
0.6742	Remote Similarity	NPD6385	Approved
0.6722	Remote Similarity	NPD4288	Approved
0.6709	Remote Similarity	NPD9545	Approved
0.6708	Remote Similarity	NPD9717	Approved
0.6706	Remote Similarity	NPD6100	Approved
0.6706	Remote Similarity	NPD6099	Approved
0.6703	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1203	Approved
0.6686	Remote Similarity	NPD1652	Phase 2
0.6686	Remote Similarity	NPD7004	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