NPASS Compound

Structure

CID197751 OpenBabel06191715582D 24 26 0 0 0 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 -3.5000 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 -1.7321 -3.0000 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 -2.0000 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 -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 -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 -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 -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 3 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 4 8 1 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 18 2 0 0 0 0 7 10 1 0 0 0 0 7 23 1 0 0 0 0 8 24 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 12 2 0 0 0 0 11 13 2 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 17 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.07
Volume:	317.359
LogP:	1.526
LogD:	0.716
LogS:	-3.399
# Rotatable Bonds:	3
TPSA:	106.2
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	3.497
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.842
MDCK Permeability:	1.141893972089747e-05
Pgp-inhibitor:	0.079
Pgp-substrate:	0.068
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.78

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	94.90233612060547%
Volume Distribution (VD):	0.611
Pgp-substrate:	5.017863750457764%

ADMET: Metabolism

CYP1A2-inhibitor:	0.609
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.205
CYP2C9-inhibitor:	0.375
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.468
CYP3A4-inhibitor:	0.266
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	1.005
Half-life (T1/2):	0.558

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.676
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.124
Rat Oral Acute Toxicity:	0.3
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.379
Carcinogencity:	0.091
Eye Corrosion:	0.004
Eye Irritation:	0.603
Respiratory Toxicity:	0.21

Download Data

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

Natural Product: NPC197751

Natural Product ID:	NPC197751
*Common Name:**	Cyathusal A
IUPAC Name:	9,10-dihydroxy-8-methoxy-1-oxo-3-[(E)-prop-1-enyl]-6H-pyrano[4,3-c]isochromene-7-carbaldehyde
Synonyms:
Standard InCHIKey:	SHZXMBWJQUATLH-ONEGZZNKSA-N
Standard InCHI:	InChI=1S/C17H14O7/c1-3-4-8-5-11-13(17(21)24-8)12-10(7-23-11)9(6-18)16(22-2)15(20)14(12)19/h3-6,19-20H,7H2,1-2H3/b4-3+
SMILES:	C/C=C/c1cc2OCc3c(c2c(=O)o1)c(O)c(c(c3C=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL375925
PubChem CID:	16737098
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
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	7860.0	nM	PMID[474643]
NPT1	Others	Radical scavenging activity		EC50	=	41590.0	nM	PMID[474643]

☑ 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 NPC197751 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	379
0.1-0.2	1861
0.2-0.3	4589
0.3-0.4	10027
0.4-0.5	7832
0.5-0.6	3661
0.6-0.7	5026
0.7-0.8	5424
0.8-0.85	2774
0.85-0.9	1085
0.9-0.95	32
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC16286
0.961	High Similarity	NPC317781
0.9548	High Similarity	NPC327652
0.9487	High Similarity	NPC329119
0.9481	High Similarity	NPC474779
0.9419	High Similarity	NPC474763
0.9351	High Similarity	NPC315157
0.9097	High Similarity	NPC227062
0.9032	High Similarity	NPC82592
0.9032	High Similarity	NPC16082
0.8974	High Similarity	NPC150227
0.8968	High Similarity	NPC281477
0.8938	High Similarity	NPC191930
0.8917	High Similarity	NPC77679
0.8917	High Similarity	NPC84935
0.8917	High Similarity	NPC190020
0.891	High Similarity	NPC79998
0.891	High Similarity	NPC199926
0.8903	High Similarity	NPC295646
0.8896	High Similarity	NPC96501
0.8875	High Similarity	NPC249181
0.8827	High Similarity	NPC283041
0.8824	High Similarity	NPC251188
0.8805	High Similarity	NPC36217
0.879	High Similarity	NPC39184
0.879	High Similarity	NPC38898
0.8782	High Similarity	NPC199773
0.8774	High Similarity	NPC31132
0.8765	High Similarity	NPC20237
0.8758	High Similarity	NPC186686
0.8758	High Similarity	NPC260946
0.8734	High Similarity	NPC54928
0.8733	High Similarity	NPC187690
0.8726	High Similarity	NPC192189
0.872	High Similarity	NPC109827
0.872	High Similarity	NPC124470
0.8718	High Similarity	NPC204350
0.8718	High Similarity	NPC70016
0.8718	High Similarity	NPC215921
0.8718	High Similarity	NPC256406
0.8716	High Similarity	NPC471690
0.871	High Similarity	NPC69430
0.871	High Similarity	NPC264550
0.871	High Similarity	NPC142876
0.871	High Similarity	NPC139293
0.871	High Similarity	NPC40290
0.871	High Similarity	NPC264289
0.871	High Similarity	NPC200060
0.871	High Similarity	NPC333691
0.871	High Similarity	NPC195763
0.8704	High Similarity	NPC275780
0.8704	High Similarity	NPC303174
0.8704	High Similarity	NPC239752
0.8704	High Similarity	NPC472450
0.8701	High Similarity	NPC137296
0.8696	High Similarity	NPC474162
0.8696	High Similarity	NPC294965
0.8696	High Similarity	NPC201800
0.8696	High Similarity	NPC474150
0.8693	High Similarity	NPC75694
0.8688	High Similarity	NPC200594
0.8688	High Similarity	NPC471973
0.8688	High Similarity	NPC228785
0.8688	High Similarity	NPC292415
0.8688	High Similarity	NPC56085
0.8688	High Similarity	NPC14353
0.8679	High Similarity	NPC136674
0.8679	High Similarity	NPC222689
0.8679	High Similarity	NPC302258
0.8679	High Similarity	NPC178976
0.8679	High Similarity	NPC35598
0.8675	High Similarity	NPC139350
0.8671	High Similarity	NPC134287
0.8671	High Similarity	NPC130589
0.8671	High Similarity	NPC20541
0.8662	High Similarity	NPC471982
0.8662	High Similarity	NPC209487
0.8662	High Similarity	NPC131266
0.8662	High Similarity	NPC216769
0.8662	High Similarity	NPC100263
0.8662	High Similarity	NPC245382
0.8662	High Similarity	NPC180388
0.8662	High Similarity	NPC181209
0.8662	High Similarity	NPC35763
0.8662	High Similarity	NPC100971
0.8662	High Similarity	NPC121522
0.8662	High Similarity	NPC269451
0.8662	High Similarity	NPC291802
0.8659	High Similarity	NPC163130
0.8659	High Similarity	NPC165979
0.8659	High Similarity	NPC26568
0.8654	High Similarity	NPC85131
0.865	High Similarity	NPC472452
0.865	High Similarity	NPC39091
0.865	High Similarity	NPC43319
0.8645	High Similarity	NPC254702
0.8645	High Similarity	NPC80710
0.8645	High Similarity	NPC194653
0.8645	High Similarity	NPC139364
0.8645	High Similarity	NPC203747
0.8642	High Similarity	NPC7483
0.8642	High Similarity	NPC234004
0.8642	High Similarity	NPC270837
0.8642	High Similarity	NPC470772
0.8642	High Similarity	NPC220313
0.8642	High Similarity	NPC474350
0.8642	High Similarity	NPC23298
0.8642	High Similarity	NPC189473
0.8642	High Similarity	NPC101769
0.8636	High Similarity	NPC32058
0.8636	High Similarity	NPC85734
0.8636	High Similarity	NPC138978
0.8634	High Similarity	NPC349525
0.8634	High Similarity	NPC40491
0.8634	High Similarity	NPC311740
0.8634	High Similarity	NPC473106
0.8634	High Similarity	NPC61010
0.8634	High Similarity	NPC474187
0.8634	High Similarity	NPC278052
0.8634	High Similarity	NPC103201
0.8631	High Similarity	NPC113446
0.8627	High Similarity	NPC257025
0.8625	High Similarity	NPC235448
0.8625	High Similarity	NPC95936
0.8625	High Similarity	NPC210459
0.8625	High Similarity	NPC100123
0.8625	High Similarity	NPC470339
0.8625	High Similarity	NPC74178
0.8625	High Similarity	NPC250214
0.8625	High Similarity	NPC184755
0.8625	High Similarity	NPC45846
0.8618	High Similarity	NPC299154
0.8618	High Similarity	NPC82913
0.8618	High Similarity	NPC314271
0.8616	High Similarity	NPC14561
0.8616	High Similarity	NPC472455
0.8616	High Similarity	NPC195796
0.8616	High Similarity	NPC291878
0.8616	High Similarity	NPC5379
0.8616	High Similarity	NPC278778
0.8616	High Similarity	NPC35038
0.8616	High Similarity	NPC471985
0.8616	High Similarity	NPC77807
0.8614	High Similarity	NPC233956
0.8614	High Similarity	NPC181523
0.8608	High Similarity	NPC144801
0.8608	High Similarity	NPC291510
0.8608	High Similarity	NPC116850
0.8608	High Similarity	NPC197188
0.8608	High Similarity	NPC238672
0.8608	High Similarity	NPC43872
0.8608	High Similarity	NPC298802
0.8608	High Similarity	NPC93552
0.8608	High Similarity	NPC124714
0.8606	High Similarity	NPC20543
0.8606	High Similarity	NPC246716
0.8606	High Similarity	NPC239440
0.8606	High Similarity	NPC1827
0.8606	High Similarity	NPC10576
0.8599	High Similarity	NPC19980
0.8599	High Similarity	NPC200773
0.8599	High Similarity	NPC240768
0.8599	High Similarity	NPC45291
0.8598	High Similarity	NPC218226
0.8598	High Similarity	NPC272485
0.8598	High Similarity	NPC234331
0.8598	High Similarity	NPC471288
0.8598	High Similarity	NPC292788
0.859	High Similarity	NPC137062
0.859	High Similarity	NPC183950
0.859	High Similarity	NPC171916
0.859	High Similarity	NPC287101
0.859	High Similarity	NPC223579
0.859	High Similarity	NPC52005
0.859	High Similarity	NPC38545
0.8589	High Similarity	NPC85057
0.8589	High Similarity	NPC326520
0.8589	High Similarity	NPC471788
0.8589	High Similarity	NPC293319
0.8589	High Similarity	NPC130920
0.8589	High Similarity	NPC470773
0.8581	High Similarity	NPC8817
0.8581	High Similarity	NPC476463
0.8581	High Similarity	NPC125449
0.8581	High Similarity	NPC188074
0.858	High Similarity	NPC261470
0.858	High Similarity	NPC8300
0.858	High Similarity	NPC229632
0.8571	High Similarity	NPC84571
0.8571	High Similarity	NPC474287
0.8571	High Similarity	NPC472055
0.8571	High Similarity	NPC321399
0.8571	High Similarity	NPC476980
0.8571	High Similarity	NPC139036
0.8571	High Similarity	NPC24627
0.8571	High Similarity	NPC299436
0.8571	High Similarity	NPC118256
0.8571	High Similarity	NPC475886
0.8571	High Similarity	NPC474960
0.8571	High Similarity	NPC119209

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 NPC197751 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	993
0.2-0.3	1940
0.3-0.4	2633
0.4-0.5	1749
0.5-0.6	927
0.6-0.7	373
0.7-0.8	112
0.8-0.85	42
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD6232	Discontinued
0.8693	High Similarity	NPD2533	Approved
0.8693	High Similarity	NPD2532	Approved
0.8693	High Similarity	NPD2534	Approved
0.8544	High Similarity	NPD1934	Approved
0.8537	High Similarity	NPD7473	Discontinued
0.8491	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD2801	Approved
0.8421	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8269	Intermediate Similarity	NPD1511	Approved
0.8165	Intermediate Similarity	NPD1512	Approved
0.816	Intermediate Similarity	NPD3882	Suspended
0.816	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD3818	Discontinued
0.8148	Intermediate Similarity	NPD1465	Phase 2
0.8148	Intermediate Similarity	NPD7819	Suspended
0.8107	Intermediate Similarity	NPD5844	Phase 1
0.8075	Intermediate Similarity	NPD4380	Phase 2
0.8061	Intermediate Similarity	NPD919	Approved
0.8036	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6166	Phase 2
0.8026	Intermediate Similarity	NPD230	Phase 1
0.8024	Intermediate Similarity	NPD5711	Approved
0.8024	Intermediate Similarity	NPD5710	Approved
0.8023	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD7075	Discontinued
0.7987	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7472	Approved
0.7953	Intermediate Similarity	NPD7074	Phase 3
0.7927	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD5494	Approved
0.7898	Intermediate Similarity	NPD2800	Approved
0.7871	Intermediate Similarity	NPD1510	Phase 2
0.7866	Intermediate Similarity	NPD6801	Discontinued
0.7857	Intermediate Similarity	NPD1247	Approved
0.7844	Intermediate Similarity	NPD6234	Discontinued
0.7803	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD920	Approved
0.7759	Intermediate Similarity	NPD7251	Discontinued
0.7753	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD3750	Approved
0.7714	Intermediate Similarity	NPD7808	Phase 3
0.7707	Intermediate Similarity	NPD2935	Discontinued
0.7702	Intermediate Similarity	NPD6799	Approved
0.7697	Intermediate Similarity	NPD7411	Suspended
0.7679	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD447	Suspended
0.7665	Intermediate Similarity	NPD5402	Approved
0.7658	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6559	Discontinued
0.7654	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD37	Approved
0.7647	Intermediate Similarity	NPD6959	Discontinued
0.7643	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6599	Discontinued
0.7632	Intermediate Similarity	NPD9494	Approved
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4965	Approved
0.7619	Intermediate Similarity	NPD4967	Phase 2
0.7619	Intermediate Similarity	NPD4966	Approved
0.7619	Intermediate Similarity	NPD7768	Phase 2
0.7613	Intermediate Similarity	NPD943	Approved
0.7613	Intermediate Similarity	NPD1240	Approved
0.761	Intermediate Similarity	NPD1549	Phase 2
0.76	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1551	Phase 2
0.7586	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3226	Approved
0.7574	Intermediate Similarity	NPD3749	Approved
0.756	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2346	Discontinued
0.7546	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7199	Phase 2
0.7531	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7228	Approved
0.7516	Intermediate Similarity	NPD6651	Approved
0.7516	Intermediate Similarity	NPD1607	Approved
0.7514	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2796	Approved
0.7473	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5403	Approved
0.7455	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5401	Approved
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3748	Approved
0.7389	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7346	Intermediate Similarity	NPD1243	Approved
0.7346	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5124	Phase 1
0.7308	Intermediate Similarity	NPD3027	Phase 3
0.7305	Intermediate Similarity	NPD1653	Approved
0.7303	Intermediate Similarity	NPD9269	Phase 2
0.7301	Intermediate Similarity	NPD4628	Phase 3
0.7287	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1613	Approved
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.7261	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD3926	Phase 2
0.7257	Intermediate Similarity	NPD5242	Approved
0.7256	Intermediate Similarity	NPD6190	Approved
0.7244	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5953	Discontinued
0.7205	Intermediate Similarity	NPD2799	Discontinued
0.72	Intermediate Similarity	NPD7229	Phase 3
0.7195	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7286	Phase 2
0.7182	Intermediate Similarity	NPD8313	Approved
0.7182	Intermediate Similarity	NPD8312	Approved
0.7179	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7390	Discontinued
0.7165	Intermediate Similarity	NPD8151	Discontinued
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.716	Intermediate Similarity	NPD5404	Approved
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7151	Intermediate Similarity	NPD5353	Approved
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7125	Intermediate Similarity	NPD1933	Approved
0.7083	Intermediate Similarity	NPD7435	Discontinued
0.7072	Intermediate Similarity	NPD7240	Approved
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7049	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3764	Approved
0.7039	Intermediate Similarity	NPD9268	Approved
0.7033	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6778	Approved
0.7016	Intermediate Similarity	NPD6782	Approved
0.7016	Intermediate Similarity	NPD6780	Approved
0.7016	Intermediate Similarity	NPD6777	Approved
0.7016	Intermediate Similarity	NPD6776	Approved
0.7016	Intermediate Similarity	NPD6779	Approved
0.7016	Intermediate Similarity	NPD6781	Approved
0.7013	Intermediate Similarity	NPD422	Phase 1
0.7012	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3787	Discontinued
0.6977	Remote Similarity	NPD6386	Approved
0.6977	Remote Similarity	NPD6385	Approved
0.6974	Remote Similarity	NPD9545	Approved
0.6968	Remote Similarity	NPD9717	Approved
0.6959	Remote Similarity	NPD7458	Discontinued
0.6959	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4288	Approved
0.6951	Remote Similarity	NPD6100	Approved
0.6951	Remote Similarity	NPD6099	Approved
0.6947	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1203	Approved
0.6928	Remote Similarity	NPD6674	Discontinued
0.6919	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7783	Phase 2
0.6914	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2344	Approved
0.689	Remote Similarity	NPD7033	Discontinued
0.6886	Remote Similarity	NPD7003	Approved
0.6886	Remote Similarity	NPD8166	Discontinued
0.6883	Remote Similarity	NPD4626	Approved
0.6879	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1283	Approved
0.6869	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7874	Approved
0.6859	Remote Similarity	NPD1608	Approved
0.6856	Remote Similarity	NPD5005	Approved
0.6856	Remote Similarity	NPD5006	Approved
0.6854	Remote Similarity	NPD8127	Discontinued
0.6842	Remote Similarity	NPD6534	Approved
0.6842	Remote Similarity	NPD9493	Approved
0.6842	Remote Similarity	NPD6535	Approved
0.6836	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2797	Approved
0.6835	Remote Similarity	NPD1470	Approved
0.6832	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD411	Approved
0.6832	Remote Similarity	NPD3268	Approved
0.6826	Remote Similarity	NPD1652	Phase 2
0.6824	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7698	Approved
0.6821	Remote Similarity	NPD7697	Approved
0.6821	Remote Similarity	NPD7696	Phase 3
0.6818	Remote Similarity	NPD5691	Approved
0.6815	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6832	Phase 2
0.6809	Remote Similarity	NPD4287	Approved
0.6795	Remote Similarity	NPD1201	Approved
0.6792	Remote Similarity	NPD2798	Approved
0.6788	Remote Similarity	NPD4308	Phase 3
0.6788	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7871	Phase 2
0.6786	Remote Similarity	NPD7870	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data