NPASS Compound

Structure

CID327652 OpenBabel06191716192D 26 28 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 -1.7321 -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 -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 -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 4 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 5 8 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 19 2 0 0 0 0 8 25 1 0 0 0 0 9 11 1 0 0 0 0 9 16 2 0 0 0 0 10 12 2 0 0 0 0 10 26 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 22 2 0 0 0 0 17 25 1 0 0 0 0 18 24 1 0 0 0 0 18 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.08
Volume:	343.445
LogP:	1.128
LogD:	0.772
LogS:	-3.577
# Rotatable Bonds:	4
TPSA:	115.43
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	4.047
Fsp3:	0.222
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:	-4.871
MDCK Permeability:	8.700470971234608e-06
Pgp-inhibitor:	0.497
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.339

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	88.87776947021484%
Volume Distribution (VD):	0.668
Pgp-substrate:	8.137803077697754%

ADMET: Metabolism

CYP1A2-inhibitor:	0.154
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.624
CYP2C9-inhibitor:	0.162
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.381
CYP3A4-inhibitor:	0.229
CYP3A4-substrate:	0.172

ADMET: Excretion

Clearance (CL):	0.9
Half-life (T1/2):	0.242

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.852
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.185
Rat Oral Acute Toxicity:	0.299
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.538
Carcinogencity:	0.275
Eye Corrosion:	0.004
Eye Irritation:	0.666
Respiratory Toxicity:	0.39

Download Data

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

Natural Product: NPC327652

Natural Product ID:	NPC327652
*Common Name:**	Pulvinatal
IUPAC Name:	9,10-dihydroxy-6,8-dimethoxy-1-oxo-3-[(E)-prop-1-enyl]-6H-pyrano[4,3-c]isochromene-7-carbaldehyde
Synonyms:	Pulvinatal
Standard InCHIKey:	LNBDQNHIHNAAHW-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C18H16O8/c1-4-5-8-6-10-12(17(22)25-8)13-11(18(24-3)26-10)9(7-19)16(23-2)15(21)14(13)20/h4-7,18,20-21H,1-3H3/b5-4+
SMILES:	CC=CC1=CC2=C(C3=C(C(=C(C(=C3C(O2)OC)C=O)OC)O)O)C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL375926
PubChem CID:	44424646
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]
NPO31218	Nidularia pulvinata	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9232889]
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	=	28590.0	nM	PMID[476802]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	8360.0	nM	PMID[476802]

☑ 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 NPC327652 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	1970
0.2-0.3	4570
0.3-0.4	9994
0.4-0.5	8037
0.5-0.6	3692
0.6-0.7	5297
0.7-0.8	5463
0.8-0.85	2857
0.85-0.9	398
0.9-0.95	6
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC329119
0.9871	High Similarity	NPC474763
0.9808	High Similarity	NPC317781
0.9679	High Similarity	NPC474779
0.9548	High Similarity	NPC197751
0.9484	High Similarity	NPC16286
0.9182	High Similarity	NPC315157
0.8902	High Similarity	NPC470773
0.8889	High Similarity	NPC470358
0.8855	High Similarity	NPC471287
0.8841	High Similarity	NPC327809
0.8788	High Similarity	NPC191930
0.8758	High Similarity	NPC16082
0.8758	High Similarity	NPC82592
0.875	High Similarity	NPC471181
0.8727	High Similarity	NPC470772
0.8727	High Similarity	NPC249181
0.872	High Similarity	NPC65746
0.872	High Similarity	NPC470756
0.8704	High Similarity	NPC227062
0.8704	High Similarity	NPC150227
0.8696	High Similarity	NPC281477
0.8683	High Similarity	NPC283041
0.8683	High Similarity	NPC116745
0.8683	High Similarity	NPC471288
0.8683	High Similarity	NPC298847
0.8662	High Similarity	NPC471689
0.865	High Similarity	NPC84935
0.865	High Similarity	NPC77679
0.865	High Similarity	NPC190020
0.8647	High Similarity	NPC108202
0.8642	High Similarity	NPC79998
0.8642	High Similarity	NPC199926
0.8639	High Similarity	NPC172807
0.8639	High Similarity	NPC254540
0.8639	High Similarity	NPC260263
0.8639	High Similarity	NPC256760
0.8639	High Similarity	NPC211594
0.8639	High Similarity	NPC471688
0.8623	High Similarity	NPC20237
0.8614	High Similarity	NPC94777
0.8606	High Similarity	NPC471290
0.8605	High Similarity	NPC212290
0.8596	High Similarity	NPC196771
0.8589	High Similarity	NPC54928
0.8588	High Similarity	NPC208668
0.8588	High Similarity	NPC4390
0.858	High Similarity	NPC150767
0.858	High Similarity	NPC78734
0.858	High Similarity	NPC109827
0.858	High Similarity	NPC124470
0.8571	High Similarity	NPC471180
0.8571	High Similarity	NPC215921
0.8571	High Similarity	NPC229729
0.8571	High Similarity	NPC105591
0.8571	High Similarity	NPC70016
0.8571	High Similarity	NPC250488
0.8571	High Similarity	NPC477502
0.8563	High Similarity	NPC165720
0.8563	High Similarity	NPC22832
0.8563	High Similarity	NPC311830
0.8554	High Similarity	NPC127782
0.8554	High Similarity	NPC300537
0.8547	High Similarity	NPC168584
0.8545	High Similarity	NPC36217
0.8538	High Similarity	NPC139350
0.8538	High Similarity	NPC472607
0.8538	High Similarity	NPC199533
0.8538	High Similarity	NPC477848
0.8538	High Similarity	NPC470454
0.8537	High Similarity	NPC222689
0.8537	High Similarity	NPC35598
0.8537	High Similarity	NPC472860
0.8529	High Similarity	NPC307518
0.8529	High Similarity	NPC153755
0.8529	High Similarity	NPC48773
0.8529	High Similarity	NPC190003
0.8529	High Similarity	NPC472386
0.8529	High Similarity	NPC175107
0.8529	High Similarity	NPC205076
0.8521	High Similarity	NPC475942
0.8521	High Similarity	NPC93337
0.8521	High Similarity	NPC469931
0.8521	High Similarity	NPC45638
0.8521	High Similarity	NPC186807
0.8521	High Similarity	NPC328321
0.8521	High Similarity	NPC105025
0.8521	High Similarity	NPC58053
0.8521	High Similarity	NPC201292
0.8521	High Similarity	NPC226294
0.8521	High Similarity	NPC229687
0.8521	High Similarity	NPC117911
0.8519	High Similarity	NPC295646
0.8519	High Similarity	NPC199773
0.8512	High Similarity	NPC236934
0.8512	High Similarity	NPC5778
0.8512	High Similarity	NPC99957
0.8512	High Similarity	NPC181616
0.8509	High Similarity	NPC31132
0.8509	High Similarity	NPC96501
0.8509	High Similarity	NPC38775
0.8503	High Similarity	NPC309025
0.8503	High Similarity	NPC222936
0.8503	High Similarity	NPC186686
0.8503	High Similarity	NPC19709
0.8503	High Similarity	NPC284960
0.8503	High Similarity	NPC243930
0.8503	High Similarity	NPC191306
0.8503	High Similarity	NPC474350
0.8503	High Similarity	NPC88023
0.8503	High Similarity	NPC270335
0.8503	High Similarity	NPC88043
0.8497	Intermediate Similarity	NPC240887
0.8497	Intermediate Similarity	NPC470091
0.8497	Intermediate Similarity	NPC113446
0.8497	Intermediate Similarity	NPC329161
0.8494	Intermediate Similarity	NPC295009
0.8494	Intermediate Similarity	NPC260640
0.8488	Intermediate Similarity	NPC472385
0.8488	Intermediate Similarity	NPC233994
0.8488	Intermediate Similarity	NPC79736
0.8488	Intermediate Similarity	NPC198324
0.8488	Intermediate Similarity	NPC211532
0.8488	Intermediate Similarity	NPC67629
0.848	Intermediate Similarity	NPC181523
0.848	Intermediate Similarity	NPC88560
0.848	Intermediate Similarity	NPC175230
0.848	Intermediate Similarity	NPC472993
0.848	Intermediate Similarity	NPC172033
0.8476	Intermediate Similarity	NPC301897
0.8471	Intermediate Similarity	NPC116864
0.8471	Intermediate Similarity	NPC244776
0.8471	Intermediate Similarity	NPC218488
0.8471	Intermediate Similarity	NPC246716
0.8471	Intermediate Similarity	NPC21190
0.8471	Intermediate Similarity	NPC298778
0.8471	Intermediate Similarity	NPC155763
0.8471	Intermediate Similarity	NPC149011
0.8471	Intermediate Similarity	NPC105511
0.8471	Intermediate Similarity	NPC235260
0.8471	Intermediate Similarity	NPC204937
0.8471	Intermediate Similarity	NPC212748
0.8471	Intermediate Similarity	NPC231194
0.8471	Intermediate Similarity	NPC224462
0.8471	Intermediate Similarity	NPC20505
0.8471	Intermediate Similarity	NPC22195
0.8471	Intermediate Similarity	NPC51326
0.8471	Intermediate Similarity	NPC183357
0.8466	Intermediate Similarity	NPC291510
0.8466	Intermediate Similarity	NPC43872
0.8466	Intermediate Similarity	NPC238672
0.8466	Intermediate Similarity	NPC73703
0.8466	Intermediate Similarity	NPC144801
0.8466	Intermediate Similarity	NPC116850
0.8466	Intermediate Similarity	NPC197188
0.8462	Intermediate Similarity	NPC45400
0.8462	Intermediate Similarity	NPC146792
0.8462	Intermediate Similarity	NPC45618
0.8462	Intermediate Similarity	NPC58716
0.8457	Intermediate Similarity	NPC240768
0.8457	Intermediate Similarity	NPC200773
0.8457	Intermediate Similarity	NPC256406
0.8452	Intermediate Similarity	NPC472450
0.8452	Intermediate Similarity	NPC275780
0.8452	Intermediate Similarity	NPC7752
0.8452	Intermediate Similarity	NPC471788
0.8452	Intermediate Similarity	NPC88243
0.8452	Intermediate Similarity	NPC303174
0.8452	Intermediate Similarity	NPC239752
0.8443	Intermediate Similarity	NPC77660
0.8443	Intermediate Similarity	NPC474150
0.8443	Intermediate Similarity	NPC22324
0.8443	Intermediate Similarity	NPC215612
0.8443	Intermediate Similarity	NPC189142
0.8443	Intermediate Similarity	NPC474162
0.8443	Intermediate Similarity	NPC201800
0.8443	Intermediate Similarity	NPC473043
0.8439	Intermediate Similarity	NPC469600
0.8439	Intermediate Similarity	NPC267549
0.8438	Intermediate Similarity	NPC137296
0.8438	Intermediate Similarity	NPC251188
0.8434	Intermediate Similarity	NPC285973
0.8434	Intermediate Similarity	NPC292415
0.8434	Intermediate Similarity	NPC228785
0.8434	Intermediate Similarity	NPC24627
0.8434	Intermediate Similarity	NPC56085
0.8434	Intermediate Similarity	NPC225624
0.8434	Intermediate Similarity	NPC203020
0.8434	Intermediate Similarity	NPC14353
0.8434	Intermediate Similarity	NPC471973
0.8434	Intermediate Similarity	NPC472055
0.8434	Intermediate Similarity	NPC239966
0.843	Intermediate Similarity	NPC264735
0.843	Intermediate Similarity	NPC68381
0.843	Intermediate Similarity	NPC49344
0.843	Intermediate Similarity	NPC101191
0.843	Intermediate Similarity	NPC469354
0.843	Intermediate Similarity	NPC146803
0.843	Intermediate Similarity	NPC237435
0.843	Intermediate Similarity	NPC135277

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 NPC327652 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	389
0.1-0.2	1009
0.2-0.3	2045
0.3-0.4	2652
0.4-0.5	1733
0.5-0.6	870
0.6-0.7	289
0.7-0.8	121
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
0.8571	High Similarity	NPD3818	Discontinued
0.8554	High Similarity	NPD6232	Discontinued
0.843	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD2533	Approved
0.8428	Intermediate Similarity	NPD2532	Approved
0.8428	Intermediate Similarity	NPD2534	Approved
0.8412	Intermediate Similarity	NPD7054	Approved
0.8402	Intermediate Similarity	NPD7473	Discontinued
0.8363	Intermediate Similarity	NPD7074	Phase 3
0.8363	Intermediate Similarity	NPD7472	Approved
0.8242	Intermediate Similarity	NPD2801	Approved
0.8242	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD6797	Phase 2
0.8193	Intermediate Similarity	NPD3817	Phase 2
0.8182	Intermediate Similarity	NPD1934	Approved
0.8161	Intermediate Similarity	NPD7251	Discontinued
0.8155	Intermediate Similarity	NPD6234	Discontinued
0.8114	Intermediate Similarity	NPD7808	Phase 3
0.8095	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD6559	Discontinued
0.805	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7819	Suspended
0.7989	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD37	Approved
0.7952	Intermediate Similarity	NPD4380	Phase 2
0.7944	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7228	Approved
0.7929	Intermediate Similarity	NPD4966	Approved
0.7929	Intermediate Similarity	NPD3882	Suspended
0.7929	Intermediate Similarity	NPD4967	Phase 2
0.7929	Intermediate Similarity	NPD4965	Approved
0.7919	Intermediate Similarity	NPD6166	Phase 2
0.7919	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1465	Phase 2
0.7914	Intermediate Similarity	NPD1511	Approved
0.7886	Intermediate Similarity	NPD5844	Phase 1
0.7882	Intermediate Similarity	NPD7075	Discontinued
0.7857	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7199	Phase 2
0.7818	Intermediate Similarity	NPD1512	Approved
0.7803	Intermediate Similarity	NPD5711	Approved
0.7803	Intermediate Similarity	NPD5710	Approved
0.7771	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6801	Discontinued
0.7733	Intermediate Similarity	NPD919	Approved
0.7725	Intermediate Similarity	NPD1653	Approved
0.7706	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5494	Approved
0.7673	Intermediate Similarity	NPD230	Phase 1
0.7654	Intermediate Similarity	NPD7685	Pre-registration
0.7622	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7411	Suspended
0.7582	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8313	Approved
0.7569	Intermediate Similarity	NPD8312	Approved
0.7561	Intermediate Similarity	NPD2800	Approved
0.7558	Intermediate Similarity	NPD5402	Approved
0.7545	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD1247	Approved
0.7543	Intermediate Similarity	NPD6959	Discontinued
0.7531	Intermediate Similarity	NPD1510	Phase 2
0.7526	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6799	Approved
0.7485	Intermediate Similarity	NPD2935	Discontinued
0.7459	Intermediate Similarity	NPD7240	Approved
0.7457	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD920	Approved
0.7448	Intermediate Similarity	NPD7435	Discontinued
0.744	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6599	Discontinued
0.7416	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7768	Phase 2
0.741	Intermediate Similarity	NPD3750	Approved
0.7407	Intermediate Similarity	NPD6651	Approved
0.7382	Intermediate Similarity	NPD6781	Approved
0.7382	Intermediate Similarity	NPD6778	Approved
0.7382	Intermediate Similarity	NPD6779	Approved
0.7382	Intermediate Similarity	NPD6776	Approved
0.7382	Intermediate Similarity	NPD6780	Approved
0.7382	Intermediate Similarity	NPD6777	Approved
0.7382	Intermediate Similarity	NPD6782	Approved
0.7368	Intermediate Similarity	NPD3226	Approved
0.7353	Intermediate Similarity	NPD5403	Approved
0.7346	Intermediate Similarity	NPD447	Suspended
0.7337	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD9494	Approved
0.7289	Intermediate Similarity	NPD1549	Phase 2
0.7284	Intermediate Similarity	NPD943	Approved
0.7284	Intermediate Similarity	NPD1240	Approved
0.7273	Intermediate Similarity	NPD2796	Approved
0.7273	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD7783	Phase 2
0.7246	Intermediate Similarity	NPD6674	Discontinued
0.7243	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5401	Approved
0.7229	Intermediate Similarity	NPD2346	Discontinued
0.7222	Intermediate Similarity	NPD7874	Approved
0.7222	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6535	Approved
0.7211	Intermediate Similarity	NPD6534	Approved
0.7202	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1607	Approved
0.7179	Intermediate Similarity	NPD7697	Approved
0.7179	Intermediate Similarity	NPD7696	Phase 3
0.7179	Intermediate Similarity	NPD7698	Approved
0.7168	Intermediate Similarity	NPD7458	Discontinued
0.7167	Intermediate Similarity	NPD3926	Phase 2
0.716	Intermediate Similarity	NPD6190	Approved
0.715	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7134	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5124	Phase 1
0.7134	Intermediate Similarity	NPD1933	Approved
0.7128	Intermediate Similarity	NPD6823	Phase 2
0.7126	Intermediate Similarity	NPD7266	Discontinued
0.7121	Intermediate Similarity	NPD7701	Phase 2
0.712	Intermediate Similarity	NPD5953	Discontinued
0.7111	Intermediate Similarity	NPD3787	Discontinued
0.7108	Intermediate Similarity	NPD3748	Approved
0.7108	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD8455	Phase 2
0.7101	Intermediate Similarity	NPD4628	Phase 3
0.7099	Intermediate Similarity	NPD3027	Phase 3
0.7098	Intermediate Similarity	NPD7700	Phase 2
0.7098	Intermediate Similarity	NPD7699	Phase 2
0.7092	Intermediate Similarity	NPD7680	Approved
0.7076	Intermediate Similarity	NPD7390	Discontinued
0.7074	Intermediate Similarity	NPD8150	Discontinued
0.7074	Intermediate Similarity	NPD8434	Phase 2
0.7072	Intermediate Similarity	NPD5242	Approved
0.7056	Intermediate Similarity	NPD8320	Phase 1
0.7056	Intermediate Similarity	NPD8319	Approved
0.7055	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7041	Intermediate Similarity	NPD5006	Approved
0.7041	Intermediate Similarity	NPD5005	Approved
0.7041	Intermediate Similarity	NPD1243	Approved
0.7017	Intermediate Similarity	NPD7229	Phase 3
0.7015	Intermediate Similarity	NPD7801	Approved
0.7011	Intermediate Similarity	NPD7286	Phase 2
0.7006	Intermediate Similarity	NPD2799	Discontinued
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7930	Approved
0.6985	Remote Similarity	NPD7584	Approved
0.6981	Remote Similarity	NPD9269	Phase 2
0.6979	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6213	Phase 3
0.6979	Remote Similarity	NPD6212	Phase 3
0.6971	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1613	Approved
0.6966	Remote Similarity	NPD5353	Approved
0.6964	Remote Similarity	NPD5408	Approved
0.6964	Remote Similarity	NPD5404	Approved
0.6964	Remote Similarity	NPD5406	Approved
0.6964	Remote Similarity	NPD5405	Approved
0.6933	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4420	Approved
0.6875	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4060	Phase 1
0.6866	Remote Similarity	NPD7585	Approved
0.6862	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7583	Approved
0.6813	Remote Similarity	NPD3705	Approved
0.681	Remote Similarity	NPD2798	Approved
0.6798	Remote Similarity	NPD6386	Approved
0.6798	Remote Similarity	NPD6385	Approved
0.678	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD8127	Discontinued
0.6766	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6099	Approved
0.6765	Remote Similarity	NPD6100	Approved
0.6758	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3764	Approved
0.673	Remote Similarity	NPD9268	Approved
0.6727	Remote Similarity	NPD6832	Phase 2
0.6725	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD8366	Approved
0.6708	Remote Similarity	NPD422	Phase 1
0.6706	Remote Similarity	NPD7033	Discontinued
0.6705	Remote Similarity	NPD7003	Approved
0.6705	Remote Similarity	NPD8166	Discontinued

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