NPASS Compound

Structure

CID326065 OpenBabel06191716182D 23 24 0 0 0 0 0 0 0 0999 V2000 -1.7321 -4.0000 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 -1.0000 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 -3.4641 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 0.8660 0.5000 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 1.7321 -0.0000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -2.5981 1.5000 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 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 23 1 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.07
Volume:	308.619
LogP:	3.074
LogD:	5.285
LogS:	-4.056
# Rotatable Bonds:	6
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.835
Synthetic Accessibility Score:	2.013
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.732
MDCK Permeability:	2.9277991416165605e-05
Pgp-inhibitor:	0.049
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.702

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.75
Plasma Protein Binding (PPB):	98.86122131347656%
Volume Distribution (VD):	0.437
Pgp-substrate:	3.581692934036255%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.832
CYP2C19-inhibitor:	0.894
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.791
CYP2C9-substrate:	0.849
CYP2D6-inhibitor:	0.586
CYP2D6-substrate:	0.458
CYP3A4-inhibitor:	0.592
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	12.534
Half-life (T1/2):	0.942

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.8
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.398
Carcinogencity:	0.097
Eye Corrosion:	0.004
Eye Irritation:	0.929
Respiratory Toxicity:	0.164

Download Data

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

Natural Product: NPC326065

Natural Product ID:	NPC326065
*Common Name:**	Cylindol A
IUPAC Name:	methyl 4-hydroxy-3-(2-hydroxy-5-methoxycarbonylphenoxy)benzoate
Synonyms:
Standard InCHIKey:	OEYSNLOOZVNLRA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O7/c1-21-15(19)9-3-5-11(17)13(7-9)23-14-8-10(16(20)22-2)4-6-12(14)18/h3-8,17-18H,1-2H3
SMILES:	COC(=O)C1=CC(=C(C=C1)O)OC2=C(C=CC(=C2)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471083
PubChem CID:	10425993
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499335]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7714541]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760071]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7798964]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964801]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23628	Imperata cylindrica	Species	Poaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT183	Individual Protein	Arachidonate 5-lipoxygenase	Rattus norvegicus	Inhibition	=	64.0	%	PMID[507887]

☑ 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 NPC326065 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	344
0.1-0.2	1581
0.2-0.3	4548
0.3-0.4	9938
0.4-0.5	7628
0.5-0.6	3471
0.6-0.7	5994
0.7-0.8	7548
0.8-0.85	1343
0.85-0.9	271
0.9-0.95	26
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC472969
0.9493	High Similarity	NPC473090
0.9474	High Similarity	NPC159418
0.9474	High Similarity	NPC283823
0.9433	High Similarity	NPC476394
0.9433	High Similarity	NPC98809
0.9398	High Similarity	NPC111888
0.9286	High Similarity	NPC113397
0.9248	High Similarity	NPC285776
0.9236	High Similarity	NPC75695
0.922	High Similarity	NPC287495
0.922	High Similarity	NPC9370
0.9214	High Similarity	NPC134975
0.9173	High Similarity	NPC94810
0.9161	High Similarity	NPC107636
0.911	High Similarity	NPC327032
0.911	High Similarity	NPC191046
0.911	High Similarity	NPC194095
0.9097	High Similarity	NPC473091
0.9078	High Similarity	NPC469615
0.9058	High Similarity	NPC95679
0.9058	High Similarity	NPC112068
0.9058	High Similarity	NPC110899
0.9058	High Similarity	NPC25305
0.9058	High Similarity	NPC125417
0.903	High Similarity	NPC226855
0.9023	High Similarity	NPC158654
0.9014	High Similarity	NPC469683
0.8986	High Similarity	NPC471405
0.898	High Similarity	NPC469888
0.8978	High Similarity	NPC144662
0.8973	High Similarity	NPC134905
0.8973	High Similarity	NPC36130
0.8963	High Similarity	NPC66905
0.8951	High Similarity	NPC262282
0.8947	High Similarity	NPC154275
0.8926	High Similarity	NPC133984
0.8919	High Similarity	NPC10205
0.8904	High Similarity	NPC243891
0.8881	High Similarity	NPC281020
0.8873	High Similarity	NPC312256
0.8867	High Similarity	NPC160780
0.8867	High Similarity	NPC289811
0.8857	High Similarity	NPC207516
0.8857	High Similarity	NPC284409
0.8844	High Similarity	NPC267091
0.8841	High Similarity	NPC155098
0.8824	High Similarity	NPC298268
0.8819	High Similarity	NPC98356
0.8811	High Similarity	NPC46161
0.8811	High Similarity	NPC50954
0.8811	High Similarity	NPC239608
0.8808	High Similarity	NPC203020
0.8808	High Similarity	NPC53889
0.8808	High Similarity	NPC239966
0.8803	High Similarity	NPC110419
0.88	High Similarity	NPC1913
0.8794	High Similarity	NPC289690
0.8794	High Similarity	NPC288452
0.8792	High Similarity	NPC80489
0.8792	High Similarity	NPC145425
0.8784	High Similarity	NPC60972
0.8784	High Similarity	NPC131121
0.8784	High Similarity	NPC289968
0.8784	High Similarity	NPC39732
0.8784	High Similarity	NPC157898
0.8784	High Similarity	NPC137813
0.8777	High Similarity	NPC139519
0.8767	High Similarity	NPC111785
0.8759	High Similarity	NPC165389
0.875	High Similarity	NPC25389
0.875	High Similarity	NPC472859
0.875	High Similarity	NPC241354
0.875	High Similarity	NPC311803
0.875	High Similarity	NPC207732
0.875	High Similarity	NPC275278
0.8742	High Similarity	NPC87317
0.8741	High Similarity	NPC32163
0.8741	High Similarity	NPC16651
0.8733	High Similarity	NPC54928
0.8732	High Similarity	NPC290664
0.8716	High Similarity	NPC31363
0.8714	High Similarity	NPC90431
0.8707	High Similarity	NPC137062
0.8707	High Similarity	NPC183950
0.8707	High Similarity	NPC287101
0.8707	High Similarity	NPC52005
0.8707	High Similarity	NPC205054
0.8707	High Similarity	NPC223579
0.8705	High Similarity	NPC45404
0.8699	High Similarity	NPC139839
0.8693	High Similarity	NPC285108
0.8693	High Similarity	NPC33298
0.869	High Similarity	NPC287275
0.8684	High Similarity	NPC476373
0.8684	High Similarity	NPC166277
0.8684	High Similarity	NPC119125
0.8681	High Similarity	NPC160378
0.8676	High Similarity	NPC2596
0.8675	High Similarity	NPC226759
0.8675	High Similarity	NPC160512
0.8675	High Similarity	NPC38779
0.8675	High Similarity	NPC114179
0.8675	High Similarity	NPC167098
0.8675	High Similarity	NPC68324
0.8675	High Similarity	NPC296044
0.8675	High Similarity	NPC289322
0.8675	High Similarity	NPC156818
0.8675	High Similarity	NPC472860
0.8671	High Similarity	NPC91546
0.8667	High Similarity	NPC20830
0.8667	High Similarity	NPC475236
0.8667	High Similarity	NPC256612
0.8667	High Similarity	NPC180901
0.8667	High Similarity	NPC2928
0.8667	High Similarity	NPC268008
0.8667	High Similarity	NPC300757
0.8658	High Similarity	NPC275836
0.8658	High Similarity	NPC71334
0.8658	High Similarity	NPC100887
0.8658	High Similarity	NPC256283
0.8658	High Similarity	NPC57030
0.8658	High Similarity	NPC293183
0.8658	High Similarity	NPC241498
0.8658	High Similarity	NPC257648
0.8658	High Similarity	NPC120163
0.8658	High Similarity	NPC275722
0.8658	High Similarity	NPC188203
0.8658	High Similarity	NPC162313
0.8658	High Similarity	NPC105827
0.8658	High Similarity	NPC55205
0.8658	High Similarity	NPC310661
0.8658	High Similarity	NPC239128
0.8658	High Similarity	NPC187498
0.8658	High Similarity	NPC198826
0.8658	High Similarity	NPC199773
0.8658	High Similarity	NPC83508
0.8658	High Similarity	NPC222830
0.8658	High Similarity	NPC212678
0.8658	High Similarity	NPC477231
0.8658	High Similarity	NPC131624
0.8658	High Similarity	NPC301323
0.8658	High Similarity	NPC25270
0.8658	High Similarity	NPC156222
0.8658	High Similarity	NPC295646
0.8652	High Similarity	NPC126206
0.8649	High Similarity	NPC29231
0.8643	High Similarity	NPC18646
0.8643	High Similarity	NPC208760
0.8639	High Similarity	NPC120464
0.8636	High Similarity	NPC89131
0.8633	High Similarity	NPC129889
0.8633	High Similarity	NPC304929
0.8633	High Similarity	NPC1321
0.8633	High Similarity	NPC156124
0.8633	High Similarity	NPC307006
0.8627	High Similarity	NPC469889
0.8623	High Similarity	NPC318799
0.8623	High Similarity	NPC264145
0.8621	High Similarity	NPC213900
0.8621	High Similarity	NPC142165
0.8618	High Similarity	NPC37502
0.8618	High Similarity	NPC267627
0.8618	High Similarity	NPC74319
0.8618	High Similarity	NPC287872
0.8618	High Similarity	NPC40702
0.8609	High Similarity	NPC104983
0.8609	High Similarity	NPC291948
0.8609	High Similarity	NPC88803
0.8609	High Similarity	NPC472916
0.8609	High Similarity	NPC265511
0.8609	High Similarity	NPC250436
0.8609	High Similarity	NPC300845
0.8603	High Similarity	NPC5018
0.8603	High Similarity	NPC117237
0.8603	High Similarity	NPC123228
0.8603	High Similarity	NPC276466
0.8603	High Similarity	NPC123722
0.8603	High Similarity	NPC151167
0.8603	High Similarity	NPC203719
0.86	High Similarity	NPC88645
0.86	High Similarity	NPC69394
0.86	High Similarity	NPC298802
0.86	High Similarity	NPC167091
0.86	High Similarity	NPC176775
0.86	High Similarity	NPC47781
0.86	High Similarity	NPC206238
0.86	High Similarity	NPC22519
0.86	High Similarity	NPC292214
0.86	High Similarity	NPC274327
0.86	High Similarity	NPC255350
0.86	High Similarity	NPC271779
0.86	High Similarity	NPC231018
0.86	High Similarity	NPC160951
0.86	High Similarity	NPC183878
0.86	High Similarity	NPC145379
0.8593	High Similarity	NPC289459
0.8592	High Similarity	NPC325625
0.8591	High Similarity	NPC125062
0.8591	High Similarity	NPC200740

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 NPC326065 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	904
0.2-0.3	1738
0.3-0.4	2537
0.4-0.5	1807
0.5-0.6	1090
0.6-0.7	576
0.7-0.8	167
0.8-0.85	20
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8633	High Similarity	NPD230	Phase 1
0.8609	High Similarity	NPD4868	Clinical (unspecified phase)
0.8603	High Similarity	NPD9494	Approved
0.86	High Similarity	NPD2801	Approved
0.8542	High Similarity	NPD4628	Phase 3
0.8533	High Similarity	NPD1934	Approved
0.8487	Intermediate Similarity	NPD3882	Suspended
0.8369	Intermediate Similarity	NPD447	Suspended
0.8367	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1511	Approved
0.8355	Intermediate Similarity	NPD1465	Phase 2
0.8309	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD3817	Phase 2
0.8255	Intermediate Similarity	NPD1512	Approved
0.8235	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD6190	Approved
0.8134	Intermediate Similarity	NPD9545	Approved
0.8125	Intermediate Similarity	NPD3818	Discontinued
0.8105	Intermediate Similarity	NPD6385	Approved
0.8105	Intermediate Similarity	NPD6386	Approved
0.8102	Intermediate Similarity	NPD1608	Approved
0.8095	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7685	Pre-registration
0.8	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6232	Discontinued
0.7975	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD9269	Phase 2
0.7963	Intermediate Similarity	NPD7054	Approved
0.7963	Intermediate Similarity	NPD5844	Phase 1
0.7961	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7472	Approved
0.7914	Intermediate Similarity	NPD7074	Phase 3
0.7891	Intermediate Similarity	NPD2935	Discontinued
0.7883	Intermediate Similarity	NPD17	Approved
0.7862	Intermediate Similarity	NPD1933	Approved
0.7848	Intermediate Similarity	NPD7075	Discontinued
0.784	Intermediate Similarity	NPD7473	Discontinued
0.7801	Intermediate Similarity	NPD1203	Approved
0.78	Intermediate Similarity	NPD3750	Approved
0.7794	Intermediate Similarity	NPD5536	Phase 2
0.7785	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3764	Approved
0.7771	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1551	Phase 2
0.7758	Intermediate Similarity	NPD6797	Phase 2
0.7748	Intermediate Similarity	NPD2354	Approved
0.7742	Intermediate Similarity	NPD3226	Approved
0.7714	Intermediate Similarity	NPD1481	Phase 2
0.7712	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7251	Discontinued
0.7708	Intermediate Similarity	NPD3027	Phase 3
0.7703	Intermediate Similarity	NPD2799	Discontinued
0.7692	Intermediate Similarity	NPD6599	Discontinued
0.7681	Intermediate Similarity	NPD9268	Approved
0.7671	Intermediate Similarity	NPD1240	Approved
0.7671	Intermediate Similarity	NPD943	Approved
0.7667	Intermediate Similarity	NPD1549	Phase 2
0.7665	Intermediate Similarity	NPD7808	Phase 3
0.7658	Intermediate Similarity	NPD7819	Suspended
0.7655	Intermediate Similarity	NPD2313	Discontinued
0.7643	Intermediate Similarity	NPD1535	Discovery
0.764	Intermediate Similarity	NPD5494	Approved
0.7639	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3455	Phase 2
0.7625	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD228	Approved
0.761	Intermediate Similarity	NPD5402	Approved
0.761	Intermediate Similarity	NPD5353	Approved
0.7607	Intermediate Similarity	NPD5242	Approved
0.7605	Intermediate Similarity	NPD7039	Approved
0.7605	Intermediate Similarity	NPD7038	Approved
0.7603	Intermediate Similarity	NPD6233	Phase 2
0.7602	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2344	Approved
0.76	Intermediate Similarity	NPD7266	Discontinued
0.76	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2346	Discontinued
0.76	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6801	Discontinued
0.7589	Intermediate Similarity	NPD9717	Approved
0.7584	Intermediate Similarity	NPD1510	Phase 2
0.758	Intermediate Similarity	NPD4380	Phase 2
0.7578	Intermediate Similarity	NPD6234	Discontinued
0.7578	Intermediate Similarity	NPD919	Approved
0.7569	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1607	Approved
0.7566	Intermediate Similarity	NPD4110	Phase 3
0.7566	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1653	Approved
0.7551	Intermediate Similarity	NPD1613	Approved
0.7551	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6798	Discontinued
0.7532	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD6355	Discontinued
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7484	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3146	Approved
0.7483	Intermediate Similarity	NPD4062	Phase 3
0.7483	Intermediate Similarity	NPD2353	Approved
0.7483	Intermediate Similarity	NPD3225	Approved
0.7483	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1894	Discontinued
0.7467	Intermediate Similarity	NPD4308	Phase 3
0.7467	Intermediate Similarity	NPD3748	Approved
0.7466	Intermediate Similarity	NPD7095	Approved
0.7444	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4060	Phase 1
0.7432	Intermediate Similarity	NPD1558	Phase 1
0.7417	Intermediate Similarity	NPD2796	Approved
0.7415	Intermediate Similarity	NPD411	Approved
0.7407	Intermediate Similarity	NPD3749	Approved
0.7405	Intermediate Similarity	NPD824	Approved
0.7403	Intermediate Similarity	NPD3887	Approved
0.7403	Intermediate Similarity	NPD2309	Approved
0.7397	Intermediate Similarity	NPD6832	Phase 2
0.7394	Intermediate Similarity	NPD3926	Phase 2
0.7394	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5403	Approved
0.7378	Intermediate Similarity	NPD1247	Approved
0.7378	Intermediate Similarity	NPD8127	Discontinued
0.7376	Intermediate Similarity	NPD1778	Approved
0.7375	Intermediate Similarity	NPD37	Approved
0.7372	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2534	Approved
0.7372	Intermediate Similarity	NPD2532	Approved
0.7372	Intermediate Similarity	NPD2533	Approved
0.7372	Intermediate Similarity	NPD1241	Discontinued
0.7372	Intermediate Similarity	NPD5401	Approved
0.7368	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1283	Approved
0.7355	Intermediate Similarity	NPD7440	Discontinued
0.7346	Intermediate Similarity	NPD4967	Phase 2
0.7346	Intermediate Similarity	NPD7768	Phase 2
0.7346	Intermediate Similarity	NPD4965	Approved
0.7346	Intermediate Similarity	NPD4966	Approved
0.7343	Intermediate Similarity	NPD3972	Approved
0.7338	Intermediate Similarity	NPD8166	Discontinued
0.7338	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6273	Approved
0.731	Intermediate Similarity	NPD2797	Approved
0.7308	Intermediate Similarity	NPD4357	Discontinued
0.7305	Intermediate Similarity	NPD5585	Approved
0.7299	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3268	Approved
0.7296	Intermediate Similarity	NPD7458	Discontinued
0.7294	Intermediate Similarity	NPD6559	Discontinued
0.7278	Intermediate Similarity	NPD920	Approved
0.7273	Intermediate Similarity	NPD2821	Approved
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7267	Intermediate Similarity	NPD4340	Discontinued
0.7262	Intermediate Similarity	NPD7228	Approved
0.7261	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5283	Phase 1
0.7237	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7033	Discontinued
0.7226	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5049	Phase 3
0.7214	Intermediate Similarity	NPD9493	Approved
0.7205	Intermediate Similarity	NPD6873	Phase 2
0.7203	Intermediate Similarity	NPD3496	Discontinued
0.72	Intermediate Similarity	NPD4307	Phase 2
0.7185	Intermediate Similarity	NPD1358	Approved
0.7184	Intermediate Similarity	NPD8434	Phase 2
0.7178	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2800	Approved
0.7161	Intermediate Similarity	NPD1243	Approved
0.716	Intermediate Similarity	NPD3751	Discontinued
0.7153	Intermediate Similarity	NPD1281	Approved
0.7152	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1019	Discontinued
0.7135	Intermediate Similarity	NPD5953	Discontinued
0.7125	Intermediate Similarity	NPD3686	Approved
0.7125	Intermediate Similarity	NPD3687	Approved
0.7123	Intermediate Similarity	NPD1876	Approved
0.7118	Intermediate Similarity	NPD7286	Phase 2
0.7115	Intermediate Similarity	NPD7003	Approved
0.711	Intermediate Similarity	NPD8312	Approved
0.711	Intermediate Similarity	NPD8313	Approved
0.7105	Intermediate Similarity	NPD6653	Approved
0.7097	Intermediate Similarity	NPD4534	Discontinued
0.7091	Intermediate Similarity	NPD6971	Discontinued
0.7086	Intermediate Similarity	NPD2979	Phase 3
0.7083	Intermediate Similarity	NPD3847	Discontinued
0.7081	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6032	Approved
0.7078	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3266	Approved
0.7075	Intermediate Similarity	NPD3267	Approved
0.7066	Intermediate Similarity	NPD6959	Discontinued
0.7059	Intermediate Similarity	NPD2163	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