NPASS Compound

Structure

NPC109827 OpenBabel07101718302D 30 32 0 0 0 0 0 0 0 0999 V2000 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 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 0.8660 -1.5000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 2.5981 -3.5000 0.0000 C 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 3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 8 2 0 0 0 0 4 9 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 13 2 0 0 0 0 8 29 1 0 0 0 0 9 14 1 0 0 0 0 10 27 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 16 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 23 1 0 0 0 0 17 30 1 0 0 0 0 18 24 2 0 0 0 0 18 28 1 0 0 0 0 19 25 2 0 0 0 0 19 29 1 0 0 0 0 20 26 2 0 0 0 0 20 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.07
Volume:	390.344
LogP:	3.884
LogD:	2.223
LogS:	-3.975
# Rotatable Bonds:	6
TPSA:	152.73
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	2.866
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.031
MDCK Permeability:	1.7990965716307983e-05
Pgp-inhibitor:	0.159
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.757
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.883

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	90.93045043945312%
Volume Distribution (VD):	0.564
Pgp-substrate:	12.450294494628906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.925
CYP1A2-substrate:	0.917
CYP2C19-inhibitor:	0.737
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.812
CYP2C9-substrate:	0.877
CYP2D6-inhibitor:	0.505
CYP2D6-substrate:	0.261
CYP3A4-inhibitor:	0.464
CYP3A4-substrate:	0.093

ADMET: Excretion

Clearance (CL):	5.485
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.032
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.614
Skin Sensitization:	0.593
Carcinogencity:	0.013
Eye Corrosion:	0.004
Eye Irritation:	0.894
Respiratory Toxicity:	0.091

Download Data

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

Natural Product: NPC109827

Natural Product ID:	NPC109827
*Common Name:**	Cercophorin C
IUPAC Name:	(2-hydroxy-4-methoxy-6-methoxycarbonylphenyl) 6,8-dihydroxy-3-methyl-1-oxoisochromene-7-carboxylate
Synonyms:	Cercophorin C
Standard InCHIKey:	FYRHLZVZOQUTTL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16O10/c1-8-4-9-5-12(21)15(16(23)14(9)19(25)29-8)20(26)30-17-11(18(24)28-3)6-10(27-2)7-13(17)22/h4-7,21-23H,1-3H3
SMILES:	Cc1cc2cc(c(c(c2c(=O)o1)O)C(=O)Oc1c(cc(cc1O)OC)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516835
PubChem CID:	10341838
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001890] Isocoumarins and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10303	Cercophora areolata	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792624]
NPO10303	Cercophora areolata	Species	Lasiosphaeriaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3095	Organism	Sordaria fimicola	Sordaria fimicola	Activity	=	51.0	%	PMID[490627]

☑ 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 NPC109827 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	423
0.1-0.2	2022
0.2-0.3	4612
0.3-0.4	10196
0.4-0.5	7671
0.5-0.6	3802
0.6-0.7	5136
0.7-0.8	5224
0.8-0.85	2190
0.85-0.9	1223
0.9-0.95	192
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC124470
0.9691	High Similarity	NPC158226
0.9568	High Similarity	NPC99613
0.9568	High Similarity	NPC165979
0.9568	High Similarity	NPC163130
0.9568	High Similarity	NPC49487
0.9455	High Similarity	NPC139350
0.9444	High Similarity	NPC29160
0.9441	High Similarity	NPC270837
0.9441	High Similarity	NPC474350
0.9401	High Similarity	NPC113446
0.9394	High Similarity	NPC181523
0.939	High Similarity	NPC246716
0.939	High Similarity	NPC10576
0.9387	High Similarity	NPC234331
0.9379	High Similarity	NPC294965
0.9329	High Similarity	NPC26568
0.9325	High Similarity	NPC20216
0.9321	High Similarity	NPC477689
0.9321	High Similarity	NPC236132
0.9321	High Similarity	NPC156082
0.9317	High Similarity	NPC66288
0.9313	High Similarity	NPC45846
0.9308	High Similarity	NPC54928
0.9273	High Similarity	NPC17219
0.9273	High Similarity	NPC239440
0.9273	High Similarity	NPC1827
0.9273	High Similarity	NPC20543
0.9268	High Similarity	NPC272485
0.9268	High Similarity	NPC292788
0.9264	High Similarity	NPC8070
0.9264	High Similarity	NPC112981
0.9259	High Similarity	NPC108767
0.9255	High Similarity	NPC56085
0.9255	High Similarity	NPC14353
0.9255	High Similarity	NPC228785
0.9226	High Similarity	NPC207467
0.9222	High Similarity	NPC289147
0.9207	High Similarity	NPC37870
0.9202	High Similarity	NPC234004
0.9202	High Similarity	NPC300984
0.9198	High Similarity	NPC278052
0.9198	High Similarity	NPC61010
0.9198	High Similarity	NPC258331
0.9198	High Similarity	NPC40491
0.9193	High Similarity	NPC83763
0.9193	High Similarity	NPC168616
0.9193	High Similarity	NPC238381
0.9193	High Similarity	NPC100123
0.9146	High Similarity	NPC267153
0.9146	High Similarity	NPC239752
0.9146	High Similarity	NPC275780
0.9146	High Similarity	NPC472450
0.9141	High Similarity	NPC93739
0.9141	High Similarity	NPC470694
0.9141	High Similarity	NPC8300
0.9141	High Similarity	NPC144843
0.9136	High Similarity	NPC119224
0.9136	High Similarity	NPC84571
0.9136	High Similarity	NPC476980
0.9136	High Similarity	NPC320359
0.9136	High Similarity	NPC143050
0.9133	High Similarity	NPC295436
0.913	High Similarity	NPC262286
0.913	High Similarity	NPC165977
0.913	High Similarity	NPC217677
0.913	High Similarity	NPC300727
0.913	High Similarity	NPC241904
0.913	High Similarity	NPC36852
0.9125	High Similarity	NPC208197
0.9119	High Similarity	NPC289968
0.9118	High Similarity	NPC265795
0.9107	High Similarity	NPC245975
0.9091	High Similarity	NPC472452
0.9091	High Similarity	NPC39091
0.9085	High Similarity	NPC284007
0.9085	High Similarity	NPC207690
0.9085	High Similarity	NPC220313
0.9085	High Similarity	NPC189473
0.9085	High Similarity	NPC152659
0.9085	High Similarity	NPC197168
0.9085	High Similarity	NPC236521
0.9085	High Similarity	NPC7483
0.9085	High Similarity	NPC248638
0.9085	High Similarity	NPC23298
0.908	High Similarity	NPC311740
0.908	High Similarity	NPC303565
0.9074	High Similarity	NPC476242
0.9074	High Similarity	NPC315157
0.9068	High Similarity	NPC142339
0.9068	High Similarity	NPC274730
0.9068	High Similarity	NPC146211
0.9068	High Similarity	NPC138243
0.9062	High Similarity	NPC75279
0.9062	High Similarity	NPC276409
0.9062	High Similarity	NPC250822
0.9059	High Similarity	NPC473785
0.9057	High Similarity	NPC133856
0.903	High Similarity	NPC130920
0.903	High Similarity	NPC326520
0.903	High Similarity	NPC85057
0.903	High Similarity	NPC25361
0.903	High Similarity	NPC303174
0.9024	High Similarity	NPC229632
0.9024	High Similarity	NPC329760
0.9024	High Similarity	NPC472448
0.9024	High Similarity	NPC81679
0.9024	High Similarity	NPC25152
0.9024	High Similarity	NPC83922
0.9018	High Similarity	NPC474287
0.9018	High Similarity	NPC130955
0.9018	High Similarity	NPC475886
0.9018	High Similarity	NPC246478
0.9018	High Similarity	NPC47623
0.9017	High Similarity	NPC174486
0.9012	High Similarity	NPC263483
0.9012	High Similarity	NPC476981
0.9012	High Similarity	NPC78225
0.9012	High Similarity	NPC37543
0.9012	High Similarity	NPC236796
0.9012	High Similarity	NPC78103
0.9012	High Similarity	NPC199463
0.9006	High Similarity	NPC128863
0.9006	High Similarity	NPC256612
0.9006	High Similarity	NPC138360
0.9006	High Similarity	NPC280339
0.9006	High Similarity	NPC113906
0.9006	High Similarity	NPC50715
0.9006	High Similarity	NPC20830
0.9006	High Similarity	NPC183597
0.9006	High Similarity	NPC196439
0.9006	High Similarity	NPC163780
0.9006	High Similarity	NPC134287
0.9006	High Similarity	NPC167815
0.9006	High Similarity	NPC227325
0.9006	High Similarity	NPC471800
0.9006	High Similarity	NPC4455
0.9006	High Similarity	NPC20541
0.9006	High Similarity	NPC92659
0.9006	High Similarity	NPC2476
0.9006	High Similarity	NPC201136
0.9006	High Similarity	NPC146165
0.9006	High Similarity	NPC130589
0.9	High Similarity	NPC175978
0.9	High Similarity	NPC471982
0.8982	High Similarity	NPC280493
0.8982	High Similarity	NPC476637
0.8976	High Similarity	NPC472449
0.8976	High Similarity	NPC30027
0.8976	High Similarity	NPC207575
0.8976	High Similarity	NPC13481
0.8976	High Similarity	NPC43319
0.8976	High Similarity	NPC170245
0.897	High Similarity	NPC470459
0.897	High Similarity	NPC41301
0.8963	High Similarity	NPC474351
0.8963	High Similarity	NPC32694
0.8963	High Similarity	NPC259456
0.8963	High Similarity	NPC475883
0.8963	High Similarity	NPC167678
0.8963	High Similarity	NPC29876
0.8963	High Similarity	NPC278427
0.8963	High Similarity	NPC266314
0.8963	High Similarity	NPC474187
0.8963	High Similarity	NPC474186
0.8957	High Similarity	NPC85121
0.8957	High Similarity	NPC40702
0.8957	High Similarity	NPC267627
0.8957	High Similarity	NPC37502
0.8951	High Similarity	NPC5379
0.8951	High Similarity	NPC474520
0.8951	High Similarity	NPC68093
0.8951	High Similarity	NPC14561
0.8951	High Similarity	NPC191146
0.8951	High Similarity	NPC472456
0.8951	High Similarity	NPC77807
0.8951	High Similarity	NPC472455
0.8947	High Similarity	NPC470091
0.8947	High Similarity	NPC240887
0.8947	High Similarity	NPC329161
0.8944	High Similarity	NPC231018
0.8944	High Similarity	NPC250557
0.8944	High Similarity	NPC176775
0.8944	High Similarity	NPC274327
0.8944	High Similarity	NPC183878
0.8944	High Similarity	NPC22519
0.8944	High Similarity	NPC69394
0.8944	High Similarity	NPC89474
0.8944	High Similarity	NPC475895
0.8944	High Similarity	NPC255350
0.8944	High Similarity	NPC93552
0.8944	High Similarity	NPC145379
0.8944	High Similarity	NPC47781
0.8944	High Similarity	NPC160951
0.8944	High Similarity	NPC280937
0.8941	High Similarity	NPC216307
0.8931	High Similarity	NPC106334
0.8931	High Similarity	NPC285527
0.8931	High Similarity	NPC233267
0.8931	High Similarity	NPC291049

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 NPC109827 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	1035
0.2-0.3	1970
0.3-0.4	2655
0.4-0.5	1739
0.5-0.6	871
0.6-0.7	314
0.7-0.8	129
0.8-0.85	29
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9024	High Similarity	NPD6232	Discontinued
0.8944	High Similarity	NPD2801	Approved
0.8869	High Similarity	NPD5844	Phase 1
0.8862	High Similarity	NPD7473	Discontinued
0.8712	High Similarity	NPD1465	Phase 2
0.8606	High Similarity	NPD4868	Clinical (unspecified phase)
0.8598	High Similarity	NPD2393	Clinical (unspecified phase)
0.8545	High Similarity	NPD3817	Phase 2
0.8537	High Similarity	NPD1934	Approved
0.8485	Intermediate Similarity	NPD7819	Suspended
0.848	Intermediate Similarity	NPD3818	Discontinued
0.8448	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD1511	Approved
0.8383	Intermediate Similarity	NPD3882	Suspended
0.8371	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD3226	Approved
0.8343	Intermediate Similarity	NPD5494	Approved
0.8333	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD2533	Approved
0.8333	Intermediate Similarity	NPD2534	Approved
0.8282	Intermediate Similarity	NPD1512	Approved
0.8256	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6166	Phase 2
0.8221	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD7054	Approved
0.8204	Intermediate Similarity	NPD6801	Discontinued
0.8193	Intermediate Similarity	NPD4380	Phase 2
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.8187	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7472	Approved
0.8171	Intermediate Similarity	NPD7074	Phase 3
0.8155	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7411	Suspended
0.8107	Intermediate Similarity	NPD5402	Approved
0.8084	Intermediate Similarity	NPD6599	Discontinued
0.807	Intermediate Similarity	NPD6234	Discontinued
0.8063	Intermediate Similarity	NPD2935	Discontinued
0.8023	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6797	Phase 2
0.8012	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7251	Discontinued
0.7978	Intermediate Similarity	NPD6559	Discontinued
0.7977	Intermediate Similarity	NPD1247	Approved
0.7975	Intermediate Similarity	NPD3750	Approved
0.7965	Intermediate Similarity	NPD919	Approved
0.7943	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6799	Approved
0.7933	Intermediate Similarity	NPD7808	Phase 3
0.7907	Intermediate Similarity	NPD3749	Approved
0.7901	Intermediate Similarity	NPD2346	Discontinued
0.7895	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD37	Approved
0.7849	Intermediate Similarity	NPD4965	Approved
0.7849	Intermediate Similarity	NPD7768	Phase 2
0.7849	Intermediate Similarity	NPD4966	Approved
0.7849	Intermediate Similarity	NPD4967	Phase 2
0.7812	Intermediate Similarity	NPD447	Suspended
0.7812	Intermediate Similarity	NPD230	Phase 1
0.7809	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1510	Phase 2
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.7764	Intermediate Similarity	NPD1607	Approved
0.7758	Intermediate Similarity	NPD4628	Phase 3
0.7753	Intermediate Similarity	NPD7228	Approved
0.7751	Intermediate Similarity	NPD1653	Approved
0.7744	Intermediate Similarity	NPD1549	Phase 2
0.773	Intermediate Similarity	NPD1551	Phase 2
0.773	Intermediate Similarity	NPD2796	Approved
0.7727	Intermediate Similarity	NPD5710	Approved
0.7727	Intermediate Similarity	NPD5711	Approved
0.7705	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1243	Approved
0.7697	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8312	Approved
0.7692	Intermediate Similarity	NPD8313	Approved
0.7692	Intermediate Similarity	NPD920	Approved
0.7692	Intermediate Similarity	NPD5403	Approved
0.7692	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD3926	Phase 2
0.7684	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3748	Approved
0.7651	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD943	Approved
0.764	Intermediate Similarity	NPD1240	Approved
0.7619	Intermediate Similarity	NPD7390	Discontinued
0.759	Intermediate Similarity	NPD2800	Approved
0.7574	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5401	Approved
0.7568	Intermediate Similarity	NPD8150	Discontinued
0.7568	Intermediate Similarity	NPD8434	Phase 2
0.7565	Intermediate Similarity	NPD7435	Discontinued
0.7563	Intermediate Similarity	NPD7783	Phase 2
0.7563	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2799	Discontinued
0.7551	Intermediate Similarity	NPD8151	Discontinued
0.7527	Intermediate Similarity	NPD5953	Discontinued
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.7456	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7286	Phase 2
0.7412	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5406	Approved
0.741	Intermediate Similarity	NPD5405	Approved
0.741	Intermediate Similarity	NPD5404	Approved
0.741	Intermediate Similarity	NPD6100	Approved
0.741	Intermediate Similarity	NPD5408	Approved
0.741	Intermediate Similarity	NPD6099	Approved
0.7407	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7685	Pre-registration
0.7391	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1933	Approved
0.7363	Intermediate Similarity	NPD3751	Discontinued
0.7349	Intermediate Similarity	NPD4308	Phase 3
0.7337	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7874	Approved
0.7337	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7229	Phase 3
0.7317	Intermediate Similarity	NPD1613	Approved
0.7317	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1203	Approved
0.7301	Intermediate Similarity	NPD3268	Approved
0.7301	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7240	Approved
0.7296	Intermediate Similarity	NPD7697	Approved
0.7296	Intermediate Similarity	NPD7696	Phase 3
0.7296	Intermediate Similarity	NPD7698	Approved
0.7293	Intermediate Similarity	NPD5242	Approved
0.7284	Intermediate Similarity	NPD6832	Phase 2
0.7278	Intermediate Similarity	NPD8127	Discontinued
0.7259	Intermediate Similarity	NPD7870	Phase 2
0.7259	Intermediate Similarity	NPD7871	Phase 2
0.7254	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6823	Phase 2
0.724	Intermediate Similarity	NPD6535	Approved
0.724	Intermediate Similarity	NPD6534	Approved
0.7239	Intermediate Similarity	NPD3027	Phase 3
0.7239	Intermediate Similarity	NPD4625	Phase 3
0.7238	Intermediate Similarity	NPD3787	Discontinued
0.7236	Intermediate Similarity	NPD7701	Phase 2
0.7235	Intermediate Similarity	NPD7003	Approved
0.7233	Intermediate Similarity	NPD9269	Phase 2
0.7229	Intermediate Similarity	NPD6651	Approved
0.7212	Intermediate Similarity	NPD4060	Phase 1
0.7205	Intermediate Similarity	NPD2797	Approved
0.72	Intermediate Similarity	NPD7458	Discontinued
0.7195	Intermediate Similarity	NPD411	Approved
0.7191	Intermediate Similarity	NPD4288	Approved
0.7181	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8285	Discontinued
0.7174	Intermediate Similarity	NPD7177	Discontinued
0.7169	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7549	Discontinued
0.716	Intermediate Similarity	NPD2344	Approved
0.7129	Intermediate Similarity	NPD7801	Approved
0.7128	Intermediate Similarity	NPD7700	Phase 2
0.7128	Intermediate Similarity	NPD7699	Phase 2
0.7126	Intermediate Similarity	NPD6273	Approved
0.7126	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD9717	Approved
0.7117	Intermediate Similarity	NPD9494	Approved
0.7108	Intermediate Similarity	NPD4307	Phase 2
0.7095	Intermediate Similarity	NPD5353	Approved
0.7091	Intermediate Similarity	NPD3764	Approved
0.7063	Intermediate Similarity	NPD422	Phase 1
0.7041	Intermediate Similarity	NPD7033	Discontinued
0.7037	Intermediate Similarity	NPD3225	Approved
0.7037	Intermediate Similarity	NPD1283	Approved
0.7031	Intermediate Similarity	NPD4287	Approved
0.7022	Intermediate Similarity	NPD6386	Approved
0.7022	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6385	Approved
0.7021	Intermediate Similarity	NPD7039	Approved
0.7021	Intermediate Similarity	NPD7038	Approved
0.7019	Intermediate Similarity	NPD1608	Approved
0.701	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6213	Phase 3
0.701	Intermediate Similarity	NPD6212	Phase 3
0.7005	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8319	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