NPASS Compound

Structure

CID329119 OpenBabel06191716202D 28 30 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 -0.0000 -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 -4.3301 -1.5000 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 -2.5981 -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 0.8660 2.5000 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 0.0000 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 -1.7321 1.0000 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 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 -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 -3.4641 -2.0000 0.0000 O 0 0 0 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 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 5 1 0 0 0 0 2 9 1 0 0 0 0 3 9 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 6 10 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 21 2 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 12 14 2 0 0 0 0 12 28 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 26 1 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.12
Volume:	378.037
LogP:	1.748
LogD:	1.424
LogS:	-3.844
# Rotatable Bonds:	5
TPSA:	115.43
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.592
Synthetic Accessibility Score:	4.098
Fsp3:	0.3
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:	-4.847
MDCK Permeability:	1.0911015124293044e-05
Pgp-inhibitor:	0.578
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	90.26251220703125%
Volume Distribution (VD):	0.624
Pgp-substrate:	6.170121192932129%

ADMET: Metabolism

CYP1A2-inhibitor:	0.266
CYP1A2-substrate:	0.92
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.741
CYP2C9-inhibitor:	0.584
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.076
CYP2D6-substrate:	0.484
CYP3A4-inhibitor:	0.323
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	0.795
Half-life (T1/2):	0.286

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.887
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.209
Rat Oral Acute Toxicity:	0.353
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.461
Carcinogencity:	0.728
Eye Corrosion:	0.004
Eye Irritation:	0.362
Respiratory Toxicity:	0.524

Download Data

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

Natural Product: NPC329119

Natural Product ID:	NPC329119
*Common Name:**	Cyathusal C
IUPAC Name:	9,10-dihydroxy-8-methoxy-1-oxo-6-propan-2-yloxy-3-[(E)-prop-1-enyl]-6H-pyrano[4,3-c]isochromene-7-carbaldehyde
Synonyms:	Cyathusal C
Standard InCHIKey:	BNFPYGWOFGPTQR-AATRIKPKSA-N
Standard InCHI:	InChI=1S/C20H20O8/c1-5-6-10-7-12-14(19(24)27-10)15-13(20(28-12)26-9(2)3)11(8-21)18(25-4)17(23)16(15)22/h5-9,20,22-23H,1-4H3/b6-5+
SMILES:	CC=CC1=CC2=C(C3=C(C(=C(C(=C3C(O2)OC(C)C)C=O)OC)O)O)C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228355
PubChem CID:	16737295
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	=	26640.0	nM	PMID[469823]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	9100.0	nM	PMID[469823]

☑ 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 NPC329119 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	406
0.1-0.2	1803
0.2-0.3	4199
0.3-0.4	9591
0.4-0.5	8772
0.5-0.6	3683
0.6-0.7	5131
0.7-0.8	5676
0.8-0.85	2908
0.85-0.9	519
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC327652
0.9808	High Similarity	NPC474763
0.9745	High Similarity	NPC317781
0.9618	High Similarity	NPC474779
0.9487	High Similarity	NPC197751
0.9423	High Similarity	NPC16286
0.9125	High Similarity	NPC315157
0.8951	High Similarity	NPC470358
0.8848	High Similarity	NPC470773
0.8848	High Similarity	NPC191930
0.882	High Similarity	NPC82592
0.882	High Similarity	NPC16082
0.881	High Similarity	NPC471181
0.8802	High Similarity	NPC471287
0.8788	High Similarity	NPC249181
0.8788	High Similarity	NPC327809
0.878	High Similarity	NPC65746
0.8765	High Similarity	NPC227062
0.8765	High Similarity	NPC150227
0.8758	High Similarity	NPC281477
0.8743	High Similarity	NPC283041
0.8743	High Similarity	NPC116745
0.8743	High Similarity	NPC298847
0.8712	High Similarity	NPC84935
0.8712	High Similarity	NPC190020
0.8712	High Similarity	NPC77679
0.8706	High Similarity	NPC108202
0.8704	High Similarity	NPC79998
0.8704	High Similarity	NPC199926
0.8698	High Similarity	NPC172807
0.8698	High Similarity	NPC471688
0.8698	High Similarity	NPC254540
0.8698	High Similarity	NPC211594
0.8698	High Similarity	NPC256760
0.8683	High Similarity	NPC20237
0.8675	High Similarity	NPC94777
0.8675	High Similarity	NPC470772
0.8667	High Similarity	NPC470756
0.8663	High Similarity	NPC212290
0.8647	High Similarity	NPC4390
0.8647	High Similarity	NPC208668
0.8639	High Similarity	NPC78734
0.8639	High Similarity	NPC150767
0.8634	High Similarity	NPC250488
0.8634	High Similarity	NPC70016
0.8634	High Similarity	NPC215921
0.8631	High Similarity	NPC471288
0.8631	High Similarity	NPC229729
0.8631	High Similarity	NPC471180
0.8631	High Similarity	NPC477502
0.8629	High Similarity	NPC105591
0.8623	High Similarity	NPC22832
0.8623	High Similarity	NPC311830
0.8623	High Similarity	NPC165720
0.8614	High Similarity	NPC127782
0.8614	High Similarity	NPC300537
0.8608	High Similarity	NPC471689
0.8606	High Similarity	NPC36217
0.8605	High Similarity	NPC168584
0.8598	High Similarity	NPC472860
0.8596	High Similarity	NPC477848
0.8596	High Similarity	NPC472607
0.8596	High Similarity	NPC199533
0.8596	High Similarity	NPC470454
0.8588	High Similarity	NPC260263
0.8588	High Similarity	NPC205076
0.8588	High Similarity	NPC48773
0.8588	High Similarity	NPC307518
0.8588	High Similarity	NPC153755
0.8588	High Similarity	NPC190003
0.8588	High Similarity	NPC472386
0.8588	High Similarity	NPC175107
0.858	High Similarity	NPC475942
0.858	High Similarity	NPC45638
0.858	High Similarity	NPC186807
0.858	High Similarity	NPC469931
0.858	High Similarity	NPC295646
0.858	High Similarity	NPC58053
0.858	High Similarity	NPC229687
0.858	High Similarity	NPC201292
0.858	High Similarity	NPC226294
0.858	High Similarity	NPC105025
0.858	High Similarity	NPC93337
0.8571	High Similarity	NPC96501
0.8571	High Similarity	NPC5778
0.8571	High Similarity	NPC38775
0.8571	High Similarity	NPC99957
0.8571	High Similarity	NPC181616
0.8571	High Similarity	NPC236934
0.8563	High Similarity	NPC19709
0.8563	High Similarity	NPC88043
0.8563	High Similarity	NPC309025
0.8563	High Similarity	NPC284960
0.8563	High Similarity	NPC243930
0.8563	High Similarity	NPC191306
0.8563	High Similarity	NPC222936
0.8563	High Similarity	NPC186686
0.8563	High Similarity	NPC270335
0.8563	High Similarity	NPC88023
0.8554	High Similarity	NPC471290
0.8547	High Similarity	NPC67629
0.8547	High Similarity	NPC233994
0.8547	High Similarity	NPC196771
0.8547	High Similarity	NPC79736
0.8547	High Similarity	NPC211532
0.8547	High Similarity	NPC198324
0.8547	High Similarity	NPC472385
0.8538	High Similarity	NPC88560
0.8538	High Similarity	NPC472993
0.8538	High Similarity	NPC172033
0.8538	High Similarity	NPC175230
0.8537	High Similarity	NPC54928
0.8537	High Similarity	NPC301897
0.8529	High Similarity	NPC218488
0.8529	High Similarity	NPC183357
0.8529	High Similarity	NPC105511
0.8529	High Similarity	NPC204937
0.8529	High Similarity	NPC298778
0.8529	High Similarity	NPC244776
0.8529	High Similarity	NPC22195
0.8529	High Similarity	NPC116864
0.8529	High Similarity	NPC124470
0.8529	High Similarity	NPC51326
0.8529	High Similarity	NPC155763
0.8529	High Similarity	NPC149011
0.8529	High Similarity	NPC109827
0.8529	High Similarity	NPC235260
0.8529	High Similarity	NPC20505
0.8529	High Similarity	NPC21190
0.8529	High Similarity	NPC212748
0.8529	High Similarity	NPC231194
0.8529	High Similarity	NPC224462
0.8528	High Similarity	NPC238672
0.8528	High Similarity	NPC144801
0.8528	High Similarity	NPC116850
0.8528	High Similarity	NPC197188
0.8528	High Similarity	NPC43872
0.8528	High Similarity	NPC291510
0.8523	High Similarity	NPC73703
0.8521	High Similarity	NPC146792
0.8521	High Similarity	NPC45400
0.8521	High Similarity	NPC58716
0.8521	High Similarity	NPC45618
0.8519	High Similarity	NPC200773
0.8519	High Similarity	NPC240768
0.8512	High Similarity	NPC471788
0.8512	High Similarity	NPC7752
0.8503	High Similarity	NPC201800
0.8503	High Similarity	NPC473043
0.8503	High Similarity	NPC77660
0.8503	High Similarity	NPC22324
0.8503	High Similarity	NPC189142
0.8503	High Similarity	NPC215612
0.8497	Intermediate Similarity	NPC267549
0.8497	Intermediate Similarity	NPC469600
0.8494	Intermediate Similarity	NPC24627
0.8494	Intermediate Similarity	NPC292415
0.8494	Intermediate Similarity	NPC203020
0.8494	Intermediate Similarity	NPC239966
0.8494	Intermediate Similarity	NPC472055
0.8488	Intermediate Similarity	NPC264735
0.8488	Intermediate Similarity	NPC135277
0.8488	Intermediate Similarity	NPC43211
0.8488	Intermediate Similarity	NPC101191
0.8488	Intermediate Similarity	NPC146803
0.8488	Intermediate Similarity	NPC294629
0.8488	Intermediate Similarity	NPC49344
0.8488	Intermediate Similarity	NPC469354
0.8488	Intermediate Similarity	NPC210094
0.8488	Intermediate Similarity	NPC237435
0.8488	Intermediate Similarity	NPC63105
0.8488	Intermediate Similarity	NPC68381
0.8488	Intermediate Similarity	NPC139350
0.8488	Intermediate Similarity	NPC115760
0.8485	Intermediate Similarity	NPC302258
0.8485	Intermediate Similarity	NPC35598
0.8485	Intermediate Similarity	NPC222689
0.8483	Intermediate Similarity	NPC264302
0.848	Intermediate Similarity	NPC476405
0.848	Intermediate Similarity	NPC235575
0.848	Intermediate Similarity	NPC117260
0.8476	Intermediate Similarity	NPC470605
0.8476	Intermediate Similarity	NPC470603
0.8476	Intermediate Similarity	NPC470604
0.8471	Intermediate Similarity	NPC95855
0.8471	Intermediate Similarity	NPC219904
0.8471	Intermediate Similarity	NPC120099
0.8471	Intermediate Similarity	NPC210042
0.8471	Intermediate Similarity	NPC170675
0.8471	Intermediate Similarity	NPC195257
0.8471	Intermediate Similarity	NPC209296
0.8471	Intermediate Similarity	NPC138927
0.8471	Intermediate Similarity	NPC117911
0.8471	Intermediate Similarity	NPC223747
0.8471	Intermediate Similarity	NPC472381
0.8471	Intermediate Similarity	NPC259905
0.8471	Intermediate Similarity	NPC471457
0.8471	Intermediate Similarity	NPC225434
0.8471	Intermediate Similarity	NPC472383
0.8471	Intermediate Similarity	NPC203050

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 NPC329119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	986
0.2-0.3	2023
0.3-0.4	2654
0.4-0.5	1760
0.5-0.6	877
0.6-0.7	304
0.7-0.8	127
0.8-0.85	39
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8631	High Similarity	NPD3818	Discontinued
0.8503	High Similarity	NPD6232	Discontinued
0.8488	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7054	Approved
0.8421	Intermediate Similarity	NPD7074	Phase 3
0.8421	Intermediate Similarity	NPD7472	Approved
0.8375	Intermediate Similarity	NPD2532	Approved
0.8375	Intermediate Similarity	NPD2533	Approved
0.8375	Intermediate Similarity	NPD2534	Approved
0.8353	Intermediate Similarity	NPD7473	Discontinued
0.8303	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD6797	Phase 2
0.8242	Intermediate Similarity	NPD1934	Approved
0.8218	Intermediate Similarity	NPD7251	Discontinued
0.8214	Intermediate Similarity	NPD6234	Discontinued
0.8193	Intermediate Similarity	NPD2801	Approved
0.8171	Intermediate Similarity	NPD7808	Phase 3
0.8155	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD3817	Phase 2
0.8114	Intermediate Similarity	NPD6559	Discontinued
0.8095	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD37	Approved
0.8012	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD4967	Phase 2
0.7988	Intermediate Similarity	NPD4966	Approved
0.7988	Intermediate Similarity	NPD4965	Approved
0.7977	Intermediate Similarity	NPD6166	Phase 2
0.7977	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7819	Suspended
0.7943	Intermediate Similarity	NPD5844	Phase 1
0.7941	Intermediate Similarity	NPD7075	Discontinued
0.7912	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3882	Suspended
0.787	Intermediate Similarity	NPD1465	Phase 2
0.7866	Intermediate Similarity	NPD1511	Approved
0.7811	Intermediate Similarity	NPD6801	Discontinued
0.7803	Intermediate Similarity	NPD7199	Phase 2
0.7784	Intermediate Similarity	NPD1653	Approved
0.7771	Intermediate Similarity	NPD1512	Approved
0.7765	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD5710	Approved
0.7759	Intermediate Similarity	NPD5711	Approved
0.7746	Intermediate Similarity	NPD5494	Approved
0.7725	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7685	Pre-registration
0.7688	Intermediate Similarity	NPD919	Approved
0.7637	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD230	Phase 1
0.7624	Intermediate Similarity	NPD8312	Approved
0.7624	Intermediate Similarity	NPD8313	Approved
0.7616	Intermediate Similarity	NPD5402	Approved
0.76	Intermediate Similarity	NPD6959	Discontinued
0.7577	Intermediate Similarity	NPD8151	Discontinued
0.7576	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7411	Suspended
0.7515	Intermediate Similarity	NPD2800	Approved
0.7514	Intermediate Similarity	NPD7240	Approved
0.7514	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7435	Discontinued
0.7485	Intermediate Similarity	NPD1510	Phase 2
0.744	Intermediate Similarity	NPD6799	Approved
0.7439	Intermediate Similarity	NPD2935	Discontinued
0.7435	Intermediate Similarity	NPD6779	Approved
0.7435	Intermediate Similarity	NPD6776	Approved
0.7435	Intermediate Similarity	NPD6780	Approved
0.7435	Intermediate Similarity	NPD6781	Approved
0.7435	Intermediate Similarity	NPD6782	Approved
0.7435	Intermediate Similarity	NPD6777	Approved
0.7435	Intermediate Similarity	NPD6778	Approved
0.7412	Intermediate Similarity	NPD920	Approved
0.7412	Intermediate Similarity	NPD5403	Approved
0.7396	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6599	Discontinued
0.7374	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7768	Phase 2
0.7365	Intermediate Similarity	NPD3750	Approved
0.7362	Intermediate Similarity	NPD6651	Approved
0.7349	Intermediate Similarity	NPD1549	Phase 2
0.7333	Intermediate Similarity	NPD2796	Approved
0.7326	Intermediate Similarity	NPD3226	Approved
0.7323	Intermediate Similarity	NPD7783	Phase 2
0.7323	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6674	Discontinued
0.7301	Intermediate Similarity	NPD447	Suspended
0.7294	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5401	Approved
0.7273	Intermediate Similarity	NPD7874	Approved
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6535	Approved
0.7263	Intermediate Similarity	NPD6534	Approved
0.725	Intermediate Similarity	NPD9494	Approved
0.7239	Intermediate Similarity	NPD1240	Approved
0.7239	Intermediate Similarity	NPD943	Approved
0.7232	Intermediate Similarity	NPD3749	Approved
0.7231	Intermediate Similarity	NPD7697	Approved
0.7231	Intermediate Similarity	NPD7698	Approved
0.7231	Intermediate Similarity	NPD7696	Phase 3
0.7229	Intermediate Similarity	NPD1551	Phase 2
0.7219	Intermediate Similarity	NPD6190	Approved
0.7204	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD3751	Discontinued
0.7195	Intermediate Similarity	NPD5124	Phase 1
0.7195	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7871	Phase 2
0.7194	Intermediate Similarity	NPD7870	Phase 2
0.7186	Intermediate Similarity	NPD7266	Discontinued
0.7186	Intermediate Similarity	NPD2346	Discontinued
0.7179	Intermediate Similarity	NPD6823	Phase 2
0.7176	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7701	Phase 2
0.7167	Intermediate Similarity	NPD3787	Discontinued
0.7165	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3027	Phase 3
0.716	Intermediate Similarity	NPD4628	Phase 3
0.7159	Intermediate Similarity	NPD8455	Phase 2
0.7152	Intermediate Similarity	NPD1607	Approved
0.715	Intermediate Similarity	NPD7700	Phase 2
0.715	Intermediate Similarity	NPD7699	Phase 2
0.7143	Intermediate Similarity	NPD7680	Approved
0.7128	Intermediate Similarity	NPD8434	Phase 2
0.7128	Intermediate Similarity	NPD8150	Discontinued
0.7127	Intermediate Similarity	NPD3926	Phase 2
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7107	Intermediate Similarity	NPD8319	Approved
0.7107	Intermediate Similarity	NPD8320	Phase 1
0.7101	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5006	Approved
0.7092	Intermediate Similarity	NPD5005	Approved
0.7091	Intermediate Similarity	NPD1933	Approved
0.7081	Intermediate Similarity	NPD5953	Discontinued
0.7066	Intermediate Similarity	NPD3748	Approved
0.7066	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7801	Approved
0.7044	Intermediate Similarity	NPD7930	Approved
0.7035	Intermediate Similarity	NPD7390	Discontinued
0.7035	Intermediate Similarity	NPD7584	Approved
0.7033	Intermediate Similarity	NPD5242	Approved
0.7031	Intermediate Similarity	NPD6213	Phase 3
0.7031	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6212	Phase 3
0.703	Intermediate Similarity	NPD1613	Approved
0.703	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5353	Approved
0.7019	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2313	Discontinued
0.7012	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1243	Approved
0.6978	Remote Similarity	NPD7229	Phase 3
0.6974	Remote Similarity	NPD4420	Approved
0.6973	Remote Similarity	NPD7286	Phase 2
0.6964	Remote Similarity	NPD2799	Discontinued
0.6959	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD9269	Phase 2
0.6923	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5408	Approved
0.6923	Remote Similarity	NPD5404	Approved
0.6923	Remote Similarity	NPD5406	Approved
0.6923	Remote Similarity	NPD5405	Approved
0.6915	Remote Similarity	NPD7585	Approved
0.6909	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7583	Approved
0.6836	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD8127	Discontinued
0.6829	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4060	Phase 1
0.6825	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3705	Approved
0.6768	Remote Similarity	NPD2798	Approved
0.6765	Remote Similarity	NPD7033	Discontinued
0.6762	Remote Similarity	NPD8366	Approved
0.676	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6386	Approved
0.676	Remote Similarity	NPD6385	Approved
0.6725	Remote Similarity	NPD6099	Approved
0.6725	Remote Similarity	NPD6100	Approved
0.6725	Remote Similarity	NPD2438	Suspended
0.6707	Remote Similarity	NPD3764	Approved
0.6705	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1652	Phase 2
0.6687	Remote Similarity	NPD6832	Phase 2
0.6687	Remote Similarity	NPD9268	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