NPASS Compound

Structure

CID202495 OpenBabel06191715592D 25 28 0 0 0 0 0 0 0 0999 V2000 5.2177 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 -0.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 -0.0211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5454 -0.0211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9602 -0.1009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 2.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2007 2.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5454 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2007 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 4.8065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2007 3.8410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 5.2892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 5.2892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 4.3237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 4.3237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3816 1.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3529 0.7811 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 23 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 8 1 0 0 0 0 4 12 2 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 24 1 0 0 0 0 7 25 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 23 1 0 0 0 0 13 16 2 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 25 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.06
Volume:	323.462
LogP:	3.807
LogD:	4.192
LogS:	-3.714
# Rotatable Bonds:	3
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.706
Synthetic Accessibility Score:	2.448
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.391
MDCK Permeability:	6.8844715315208305e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	91.1546401977539%
Volume Distribution (VD):	0.59
Pgp-substrate:	7.140044212341309%

ADMET: Metabolism

CYP1A2-inhibitor:	0.388
CYP1A2-substrate:	0.285
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.409
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.418
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.014

ADMET: Excretion

Clearance (CL):	1.565
Half-life (T1/2):	0.782

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.257
Drug-inuced Liver Injury (DILI):	0.991
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.601
Carcinogencity:	0.736
Eye Corrosion:	0.004
Eye Irritation:	0.647
Respiratory Toxicity:	0.877

Download Data

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

Natural Product: NPC202495

Natural Product ID:	NPC202495
*Common Name:**	Papilistatin
IUPAC Name:	8-methoxynaphtho[2,1-g][1,3]benzodioxole-5,6-dicarboxylic acid
Synonyms:	Papilistatin
Standard InCHIKey:	KTEBZKXXNMHJFH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12O7/c1-23-12-4-2-3-8-9(12)5-10(17(19)20)14-11(18(21)22)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20)(H,21,22)
SMILES:	COc1cccc2c1cc(c1c(cc3c(c21)OCO3)C(=O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087295
PubChem CID:	46184319
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes 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
NPO40717	Atrophaneura polyeuctes termessus	Strain	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20085286]

☑ 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
GI50	2
MIC	5

Activity Type	# Activity
Cell Line	2
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	=	0.096	ug.mL-1	PMID[478979]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.093	ug.mL-1	PMID[478979]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	32.0	ug.mL-1	PMID[478979]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	16.0	ug.mL-1	PMID[478979]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[478979]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	16.0	ug.mL-1	PMID[478979]
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	8.0	ug.mL-1	PMID[478979]

☑ 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 NPC202495 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	370
0.1-0.2	1706
0.2-0.3	3401
0.3-0.4	9042
0.4-0.5	9651
0.5-0.6	3311
0.6-0.7	6748
0.7-0.8	7972
0.8-0.85	440
0.85-0.9	41
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC109765
0.9664	High Similarity	NPC118332
0.929	High Similarity	NPC125713
0.9236	High Similarity	NPC116838
0.9236	High Similarity	NPC22130
0.9226	High Similarity	NPC296044
0.9226	High Similarity	NPC167098
0.9145	High Similarity	NPC300983
0.9114	High Similarity	NPC198796
0.9038	High Similarity	NPC239113
0.9038	High Similarity	NPC115123
0.9032	High Similarity	NPC54179
0.8981	High Similarity	NPC19600
0.8981	High Similarity	NPC143328
0.8944	High Similarity	NPC474042
0.8944	High Similarity	NPC174734
0.894	High Similarity	NPC471305
0.8909	High Similarity	NPC196771
0.8868	High Similarity	NPC78944
0.8854	High Similarity	NPC472835
0.8834	High Similarity	NPC117911
0.8831	High Similarity	NPC127827
0.8812	High Similarity	NPC15212
0.8805	High Similarity	NPC68619
0.878	High Similarity	NPC52598
0.8774	High Similarity	NPC475722
0.8774	High Similarity	NPC261322
0.8774	High Similarity	NPC37220
0.875	High Similarity	NPC474770
0.8735	High Similarity	NPC193377
0.8727	High Similarity	NPC471920
0.8727	High Similarity	NPC292712
0.8727	High Similarity	NPC312006
0.8727	High Similarity	NPC20114
0.8727	High Similarity	NPC129930
0.8727	High Similarity	NPC474075
0.8727	High Similarity	NPC114550
0.8727	High Similarity	NPC471921
0.8727	High Similarity	NPC471922
0.871	High Similarity	NPC24193
0.8688	High Similarity	NPC474043
0.8684	High Similarity	NPC86455
0.8684	High Similarity	NPC137920
0.8684	High Similarity	NPC125134
0.8675	High Similarity	NPC184624
0.8662	High Similarity	NPC124842
0.8662	High Similarity	NPC473201
0.8662	High Similarity	NPC302783
0.865	High Similarity	NPC474301
0.8645	High Similarity	NPC181464
0.8634	High Similarity	NPC47623
0.8616	High Similarity	NPC234730
0.8598	High Similarity	NPC471923
0.8571	High Similarity	NPC229787
0.8563	High Similarity	NPC316539
0.8562	High Similarity	NPC261090
0.8562	High Similarity	NPC261484
0.8562	High Similarity	NPC473900
0.8553	High Similarity	NPC62051
0.8545	High Similarity	NPC471180
0.8545	High Similarity	NPC473531
0.8545	High Similarity	NPC311912
0.8545	High Similarity	NPC475453
0.8544	High Similarity	NPC104353
0.8544	High Similarity	NPC78505
0.8528	High Similarity	NPC19948
0.8528	High Similarity	NPC144843
0.8523	High Similarity	NPC45404
0.8521	High Similarity	NPC35266
0.8509	High Similarity	NPC76458
0.8509	High Similarity	NPC82733
0.8506	High Similarity	NPC50954
0.85	High Similarity	NPC80489
0.8494	Intermediate Similarity	NPC88557
0.8491	Intermediate Similarity	NPC137125
0.8491	Intermediate Similarity	NPC3744
0.8485	Intermediate Similarity	NPC118162
0.8485	Intermediate Similarity	NPC83049
0.8485	Intermediate Similarity	NPC320471
0.8476	Intermediate Similarity	NPC100420
0.8471	Intermediate Similarity	NPC275690
0.8471	Intermediate Similarity	NPC161609
0.8466	Intermediate Similarity	NPC131905
0.8466	Intermediate Similarity	NPC469889
0.8466	Intermediate Similarity	NPC99968
0.8462	Intermediate Similarity	NPC58752
0.8462	Intermediate Similarity	NPC39361
0.8457	Intermediate Similarity	NPC15764
0.8452	Intermediate Similarity	NPC275278
0.8452	Intermediate Similarity	NPC477881
0.8452	Intermediate Similarity	NPC199357
0.8452	Intermediate Similarity	NPC260152
0.8447	Intermediate Similarity	NPC301897
0.8447	Intermediate Similarity	NPC213401
0.8434	Intermediate Similarity	NPC79322
0.8434	Intermediate Similarity	NPC234331
0.8431	Intermediate Similarity	NPC28398
0.8428	Intermediate Similarity	NPC220577
0.8428	Intermediate Similarity	NPC472838
0.8428	Intermediate Similarity	NPC70320
0.8428	Intermediate Similarity	NPC306011
0.8428	Intermediate Similarity	NPC267091
0.8424	Intermediate Similarity	NPC477884
0.8424	Intermediate Similarity	NPC26386
0.8421	Intermediate Similarity	NPC53680
0.8421	Intermediate Similarity	NPC208797
0.8412	Intermediate Similarity	NPC47191
0.8408	Intermediate Similarity	NPC470757
0.8405	Intermediate Similarity	NPC65784
0.8405	Intermediate Similarity	NPC139876
0.8395	Intermediate Similarity	NPC474990
0.8395	Intermediate Similarity	NPC178976
0.8393	Intermediate Similarity	NPC473697
0.8393	Intermediate Similarity	NPC469506
0.8393	Intermediate Similarity	NPC471181
0.8391	Intermediate Similarity	NPC205721
0.8387	Intermediate Similarity	NPC46880
0.8385	Intermediate Similarity	NPC3273
0.8375	Intermediate Similarity	NPC245948
0.8373	Intermediate Similarity	NPC29160
0.8365	Intermediate Similarity	NPC243891
0.8364	Intermediate Similarity	NPC45943
0.8364	Intermediate Similarity	NPC475865
0.8364	Intermediate Similarity	NPC477689
0.8354	Intermediate Similarity	NPC475848
0.8354	Intermediate Similarity	NPC296540
0.8354	Intermediate Similarity	NPC258322
0.8354	Intermediate Similarity	NPC109238
0.8354	Intermediate Similarity	NPC319749
0.8354	Intermediate Similarity	NPC311740
0.8354	Intermediate Similarity	NPC309335
0.8354	Intermediate Similarity	NPC191352
0.8354	Intermediate Similarity	NPC474306
0.8353	Intermediate Similarity	NPC67629
0.8353	Intermediate Similarity	NPC79736
0.8344	Intermediate Similarity	NPC45846
0.8344	Intermediate Similarity	NPC153620
0.8344	Intermediate Similarity	NPC325122
0.8344	Intermediate Similarity	NPC24257
0.8344	Intermediate Similarity	NPC62518
0.8344	Intermediate Similarity	NPC215375
0.8344	Intermediate Similarity	NPC245891
0.8344	Intermediate Similarity	NPC104876
0.8333	Intermediate Similarity	NPC77807
0.8333	Intermediate Similarity	NPC472836
0.8333	Intermediate Similarity	NPC14561
0.8333	Intermediate Similarity	NPC477883
0.8333	Intermediate Similarity	NPC91694
0.8333	Intermediate Similarity	NPC5379
0.8333	Intermediate Similarity	NPC300603
0.8324	Intermediate Similarity	NPC114120
0.8324	Intermediate Similarity	NPC167045
0.8323	Intermediate Similarity	NPC141817
0.8323	Intermediate Similarity	NPC229218
0.8323	Intermediate Similarity	NPC176030
0.8323	Intermediate Similarity	NPC192597
0.8323	Intermediate Similarity	NPC169214
0.8314	Intermediate Similarity	NPC475996
0.8313	Intermediate Similarity	NPC41689
0.8313	Intermediate Similarity	NPC75377
0.8313	Intermediate Similarity	NPC118427
0.8312	Intermediate Similarity	NPC327187
0.8304	Intermediate Similarity	NPC267549
0.8304	Intermediate Similarity	NPC477880
0.8304	Intermediate Similarity	NPC477882
0.8303	Intermediate Similarity	NPC280778
0.8302	Intermediate Similarity	NPC474305
0.8293	Intermediate Similarity	NPC21046
0.8293	Intermediate Similarity	NPC84571
0.8291	Intermediate Similarity	NPC52692
0.8291	Intermediate Similarity	NPC58373
0.8284	Intermediate Similarity	NPC157522
0.8282	Intermediate Similarity	NPC226759
0.8282	Intermediate Similarity	NPC37543
0.8282	Intermediate Similarity	NPC167595
0.8282	Intermediate Similarity	NPC199463
0.8282	Intermediate Similarity	NPC19947
0.8282	Intermediate Similarity	NPC207584
0.828	Intermediate Similarity	NPC75295
0.828	Intermediate Similarity	NPC160777
0.828	Intermediate Similarity	NPC73416
0.8274	Intermediate Similarity	NPC165979
0.8274	Intermediate Similarity	NPC163130
0.8274	Intermediate Similarity	NPC49487
0.8274	Intermediate Similarity	NPC99613
0.8272	Intermediate Similarity	NPC38898
0.8272	Intermediate Similarity	NPC268008
0.8263	Intermediate Similarity	NPC255787
0.8261	Intermediate Similarity	NPC104728
0.8261	Intermediate Similarity	NPC60211
0.8261	Intermediate Similarity	NPC131121
0.8261	Intermediate Similarity	NPC295646
0.8261	Intermediate Similarity	NPC164912
0.8261	Intermediate Similarity	NPC35544
0.8256	Intermediate Similarity	NPC329161
0.8256	Intermediate Similarity	NPC470091
0.8256	Intermediate Similarity	NPC240887
0.8255	Intermediate Similarity	NPC285776
0.8253	Intermediate Similarity	NPC100425
0.8253	Intermediate Similarity	NPC308156

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 NPC202495 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	961
0.2-0.3	1527
0.3-0.4	2628
0.4-0.5	1991
0.5-0.6	1050
0.6-0.7	478
0.7-0.8	165
0.8-0.85	5
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8758	High Similarity	NPD6232	Discontinued
0.8693	High Similarity	NPD6143	Clinical (unspecified phase)
0.8598	High Similarity	NPD7473	Discontinued
0.8494	Intermediate Similarity	NPD5844	Phase 1
0.8408	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD37	Approved
0.8324	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD4967	Phase 2
0.8221	Intermediate Similarity	NPD4966	Approved
0.8221	Intermediate Similarity	NPD4965	Approved
0.8187	Intermediate Similarity	NPD7458	Discontinued
0.8187	Intermediate Similarity	NPD3226	Approved
0.8121	Intermediate Similarity	NPD6234	Discontinued
0.8077	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7003	Approved
0.8024	Intermediate Similarity	NPD7199	Phase 2
0.7943	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3764	Approved
0.7895	Intermediate Similarity	NPD3818	Discontinued
0.7892	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1465	Phase 2
0.7834	Intermediate Similarity	NPD2346	Discontinued
0.7826	Intermediate Similarity	NPD2533	Approved
0.7826	Intermediate Similarity	NPD2534	Approved
0.7826	Intermediate Similarity	NPD2532	Approved
0.7816	Intermediate Similarity	NPD6559	Discontinued
0.7799	Intermediate Similarity	NPD4628	Phase 3
0.7791	Intermediate Similarity	NPD7228	Approved
0.7733	Intermediate Similarity	NPD1283	Approved
0.7727	Intermediate Similarity	NPD8313	Approved
0.7727	Intermediate Similarity	NPD8312	Approved
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7819	Suspended
0.7658	Intermediate Similarity	NPD2935	Discontinued
0.7647	Intermediate Similarity	NPD5494	Approved
0.7636	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3749	Approved
0.7614	Intermediate Similarity	NPD7685	Pre-registration
0.7605	Intermediate Similarity	NPD1934	Approved
0.7597	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7177	Discontinued
0.7574	Intermediate Similarity	NPD3882	Suspended
0.756	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2801	Approved
0.7547	Intermediate Similarity	NPD5406	Approved
0.7547	Intermediate Similarity	NPD5405	Approved
0.7547	Intermediate Similarity	NPD5404	Approved
0.7547	Intermediate Similarity	NPD5408	Approved
0.7545	Intermediate Similarity	NPD7411	Suspended
0.7533	Intermediate Similarity	NPD1281	Approved
0.7515	Intermediate Similarity	NPD3817	Phase 2
0.7514	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD6959	Discontinued
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7028	Phase 2
0.7485	Intermediate Similarity	NPD919	Approved
0.7472	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3750	Approved
0.7457	Intermediate Similarity	NPD7229	Phase 3
0.7456	Intermediate Similarity	NPD8455	Phase 2
0.7453	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7054	Approved
0.7405	Intermediate Similarity	NPD1933	Approved
0.7405	Intermediate Similarity	NPD447	Suspended
0.7401	Intermediate Similarity	NPD7472	Approved
0.74	Intermediate Similarity	NPD4626	Approved
0.7399	Intermediate Similarity	NPD1247	Approved
0.7399	Intermediate Similarity	NPD8127	Discontinued
0.7396	Intermediate Similarity	NPD8151	Discontinued
0.7391	Intermediate Similarity	NPD2344	Approved
0.7375	Intermediate Similarity	NPD2799	Discontinued
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6166	Phase 2
0.7371	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7768	Phase 2
0.736	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1607	Approved
0.7355	Intermediate Similarity	NPD9494	Approved
0.7353	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6273	Approved
0.7342	Intermediate Similarity	NPD2979	Phase 3
0.7337	Intermediate Similarity	NPD6385	Approved
0.7337	Intermediate Similarity	NPD6386	Approved
0.7333	Intermediate Similarity	NPD1511	Approved
0.7326	Intermediate Similarity	NPD7075	Discontinued
0.7326	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2313	Discontinued
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7314	Intermediate Similarity	NPD3926	Phase 2
0.7303	Intermediate Similarity	NPD3705	Approved
0.7301	Intermediate Similarity	NPD6674	Discontinued
0.7296	Intermediate Similarity	NPD230	Phase 1
0.7293	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3751	Discontinued
0.7278	Intermediate Similarity	NPD7808	Phase 3
0.7278	Intermediate Similarity	NPD4380	Phase 2
0.7278	Intermediate Similarity	NPD6599	Discontinued
0.7267	Intermediate Similarity	NPD3748	Approved
0.7267	Intermediate Similarity	NPD1510	Phase 2
0.7263	Intermediate Similarity	NPD6797	Phase 2
0.7257	Intermediate Similarity	NPD5710	Approved
0.7257	Intermediate Similarity	NPD5711	Approved
0.7255	Intermediate Similarity	NPD1608	Approved
0.7249	Intermediate Similarity	NPD6776	Approved
0.7249	Intermediate Similarity	NPD6778	Approved
0.7249	Intermediate Similarity	NPD6782	Approved
0.7249	Intermediate Similarity	NPD6780	Approved
0.7249	Intermediate Similarity	NPD6781	Approved
0.7249	Intermediate Similarity	NPD6777	Approved
0.7249	Intermediate Similarity	NPD6779	Approved
0.7246	Intermediate Similarity	NPD1512	Approved
0.7233	Intermediate Similarity	NPD1240	Approved
0.7231	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7783	Phase 2
0.7229	Intermediate Similarity	NPD7390	Discontinued
0.7226	Intermediate Similarity	NPD1470	Approved
0.7222	Intermediate Similarity	NPD7038	Approved
0.7222	Intermediate Similarity	NPD7039	Approved
0.7222	Intermediate Similarity	NPD2438	Suspended
0.7222	Intermediate Similarity	NPD7251	Discontinued
0.7219	Intermediate Similarity	NPD1651	Approved
0.7213	Intermediate Similarity	NPD8434	Phase 2
0.7212	Intermediate Similarity	NPD2309	Approved
0.7212	Intermediate Similarity	NPD6190	Approved
0.7209	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD920	Approved
0.7193	Intermediate Similarity	NPD6801	Discontinued
0.7191	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7186	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD4308	Phase 3
0.7152	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3972	Approved
0.7135	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD7697	Approved
0.7135	Intermediate Similarity	NPD7698	Approved
0.7126	Intermediate Similarity	NPD6799	Approved
0.7125	Intermediate Similarity	NPD4060	Phase 1
0.712	Intermediate Similarity	NPD8150	Discontinued
0.7119	Intermediate Similarity	NPD5242	Approved
0.7107	Intermediate Similarity	NPD6798	Discontinued
0.7105	Intermediate Similarity	NPD5691	Approved
0.7097	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7874	Approved
0.7091	Intermediate Similarity	NPD1243	Approved
0.7083	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1201	Approved
0.7073	Intermediate Similarity	NPD1471	Phase 3
0.7073	Intermediate Similarity	NPD7266	Discontinued
0.7062	Intermediate Similarity	NPD3787	Discontinued
0.7062	Intermediate Similarity	NPD7999	Approved
0.7059	Intermediate Similarity	NPD17	Approved
0.7053	Intermediate Similarity	NPD4420	Approved
0.7051	Intermediate Similarity	NPD1876	Approved
0.7048	Intermediate Similarity	NPD8166	Discontinued
0.7048	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4110	Phase 3
0.7048	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7680	Approved
0.7039	Intermediate Similarity	NPD9545	Approved
0.7035	Intermediate Similarity	NPD6873	Phase 2
0.703	Intermediate Similarity	NPD1549	Phase 2
0.7019	Intermediate Similarity	NPD943	Approved
0.7016	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2531	Phase 2
0.7012	Intermediate Similarity	NPD1551	Phase 2
0.7011	Intermediate Similarity	NPD5978	Approved
0.7011	Intermediate Similarity	NPD5977	Approved
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3268	Approved
0.6995	Remote Similarity	NPD6823	Phase 2
0.699	Remote Similarity	NPD7701	Phase 2
0.6988	Remote Similarity	NPD2800	Approved
0.6984	Remote Similarity	NPD6535	Approved
0.6984	Remote Similarity	NPD6534	Approved
0.6975	Remote Similarity	NPD6355	Discontinued
0.6974	Remote Similarity	NPD5536	Phase 2
0.697	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1611	Approved
0.6964	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1653	Approved
0.6937	Remote Similarity	NPD7008	Discontinued
0.6923	Remote Similarity	NPD8319	Approved
0.6923	Remote Similarity	NPD8320	Phase 1
0.6914	Remote Similarity	NPD4307	Phase 2
0.6914	Remote Similarity	NPD5402	Approved
0.6909	Remote Similarity	NPD2796	Approved
0.6909	Remote Similarity	NPD4476	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