NPASS Compound

Structure

NPC109765 OpenBabel07101719242D 22 25 0 0 0 0 0 0 0 0999 V2000 5.4041 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 1.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 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 20 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 10 1 0 0 0 0 4 13 2 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 21 1 0 0 0 0 8 22 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 15 2 0 0 0 0 12 17 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.07
Volume:	291.222
LogP:	4.24
LogD:	3.194
LogS:	-3.981
# Rotatable Bonds:	2
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.734
Synthetic Accessibility Score:	2.257
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.786
MDCK Permeability:	2.3020507796900347e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	93.04041290283203%
Volume Distribution (VD):	0.514
Pgp-substrate:	2.6151821613311768%

ADMET: Metabolism

CYP1A2-inhibitor:	0.862
CYP1A2-substrate:	0.465
CYP2C19-inhibitor:	0.129
CYP2C19-substrate:	0.096
CYP2C9-inhibitor:	0.49
CYP2C9-substrate:	0.338
CYP2D6-inhibitor:	0.801
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.353
CYP3A4-substrate:	0.06

ADMET: Excretion

Clearance (CL):	8.177
Half-life (T1/2):	0.374

ADMET: Toxicity

hERG Blockers:	0.161
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.058
Skin Sensitization:	0.671
Carcinogencity:	0.94
Eye Corrosion:	0.007
Eye Irritation:	0.792
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC109765

Natural Product ID:	NPC109765
*Common Name:**	Aristolic Acid
IUPAC Name:	8-methoxynaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid
Synonyms:	Aristolic Acid
Standard InCHIKey:	WNMKOPJJPJHXJX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H12O5/c1-20-13-4-2-3-10-9(13)5-6-11-12(17(18)19)7-14-16(15(10)11)22-8-21-14/h2-7H,8H2,1H3,(H,18,19)
SMILES:	COc1cccc2c1ccc1c2c2OCOc2cc1C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486801
PubChem CID:	119465
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
NPO8725	Aristolochia indica	Species	Aristolochiaceae	Eukaryota	roots	n.a.	n.a.	PMID[6539809]
NPO8725	Aristolochia indica	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8725	Aristolochia indica	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8725	Aristolochia indica	Species	Aristolochiaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	80.0	%	PMID[497611]

☑ 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 NPC109765 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	385
0.1-0.2	1778
0.2-0.3	3553
0.3-0.4	9267
0.4-0.5	9311
0.5-0.6	3295
0.6-0.7	6877
0.7-0.8	7775
0.8-0.85	395
0.85-0.9	46
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC202495
0.973	High Similarity	NPC118332
0.9351	High Similarity	NPC125713
0.9295	High Similarity	NPC116838
0.9295	High Similarity	NPC22130
0.9172	High Similarity	NPC198796
0.9161	High Similarity	NPC167098
0.9161	High Similarity	NPC296044
0.9097	High Similarity	NPC115123
0.9097	High Similarity	NPC239113
0.9091	High Similarity	NPC54179
0.9079	High Similarity	NPC300983
0.9038	High Similarity	NPC19600
0.9038	High Similarity	NPC143328
0.9	High Similarity	NPC474042
0.9	High Similarity	NPC174734
0.9	High Similarity	NPC471305
0.8963	High Similarity	NPC196771
0.8924	High Similarity	NPC78944
0.891	High Similarity	NPC472835
0.8889	High Similarity	NPC127827
0.8889	High Similarity	NPC117911
0.8868	High Similarity	NPC15212
0.8861	High Similarity	NPC68619
0.8834	High Similarity	NPC52598
0.8831	High Similarity	NPC261322
0.8831	High Similarity	NPC475722
0.8831	High Similarity	NPC37220
0.8805	High Similarity	NPC474770
0.8788	High Similarity	NPC193377
0.878	High Similarity	NPC312006
0.878	High Similarity	NPC471921
0.878	High Similarity	NPC129930
0.878	High Similarity	NPC474075
0.878	High Similarity	NPC471920
0.878	High Similarity	NPC20114
0.878	High Similarity	NPC114550
0.878	High Similarity	NPC471922
0.878	High Similarity	NPC292712
0.8766	High Similarity	NPC24193
0.8742	High Similarity	NPC474043
0.8742	High Similarity	NPC125134
0.8742	High Similarity	NPC137920
0.8742	High Similarity	NPC86455
0.8727	High Similarity	NPC184624
0.8718	High Similarity	NPC124842
0.8718	High Similarity	NPC302783
0.8718	High Similarity	NPC473201
0.8704	High Similarity	NPC474301
0.8701	High Similarity	NPC181464
0.8688	High Similarity	NPC47623
0.8671	High Similarity	NPC234730
0.865	High Similarity	NPC471923
0.8627	High Similarity	NPC229787
0.8616	High Similarity	NPC473900
0.8616	High Similarity	NPC261090
0.8616	High Similarity	NPC261484
0.8614	High Similarity	NPC316539
0.8608	High Similarity	NPC62051
0.8599	High Similarity	NPC104353
0.8599	High Similarity	NPC78505
0.8598	High Similarity	NPC473531
0.8598	High Similarity	NPC475453
0.8598	High Similarity	NPC471180
0.8598	High Similarity	NPC311912
0.8581	High Similarity	NPC45404
0.858	High Similarity	NPC144843
0.858	High Similarity	NPC19948
0.8571	High Similarity	NPC35266
0.8562	High Similarity	NPC50954
0.8562	High Similarity	NPC76458
0.8562	High Similarity	NPC82733
0.8553	High Similarity	NPC80489
0.8545	High Similarity	NPC88557
0.8544	High Similarity	NPC3744
0.8544	High Similarity	NPC137125
0.8537	High Similarity	NPC83049
0.8537	High Similarity	NPC118162
0.8537	High Similarity	NPC320471
0.8528	High Similarity	NPC100420
0.8521	High Similarity	NPC275690
0.8521	High Similarity	NPC161609
0.8519	High Similarity	NPC99968
0.8519	High Similarity	NPC131905
0.8519	High Similarity	NPC469889
0.8516	High Similarity	NPC39361
0.8516	High Similarity	NPC58752
0.8509	High Similarity	NPC15764
0.8506	High Similarity	NPC275278
0.8503	High Similarity	NPC199357
0.8503	High Similarity	NPC477881
0.85	High Similarity	NPC213401
0.85	High Similarity	NPC301897
0.8487	Intermediate Similarity	NPC28398
0.8485	Intermediate Similarity	NPC234331
0.8485	Intermediate Similarity	NPC79322
0.8481	Intermediate Similarity	NPC220577
0.8481	Intermediate Similarity	NPC70320
0.8481	Intermediate Similarity	NPC472838
0.8481	Intermediate Similarity	NPC306011
0.8481	Intermediate Similarity	NPC267091
0.8476	Intermediate Similarity	NPC26386
0.8476	Intermediate Similarity	NPC477884
0.8471	Intermediate Similarity	NPC53680
0.8471	Intermediate Similarity	NPC208797
0.8462	Intermediate Similarity	NPC47191
0.8462	Intermediate Similarity	NPC470757
0.8457	Intermediate Similarity	NPC139876
0.8457	Intermediate Similarity	NPC65784
0.8447	Intermediate Similarity	NPC178976
0.8447	Intermediate Similarity	NPC474990
0.8443	Intermediate Similarity	NPC473697
0.8443	Intermediate Similarity	NPC471181
0.8443	Intermediate Similarity	NPC469506
0.8442	Intermediate Similarity	NPC46880
0.8439	Intermediate Similarity	NPC205721
0.8438	Intermediate Similarity	NPC3273
0.8428	Intermediate Similarity	NPC245948
0.8424	Intermediate Similarity	NPC29160
0.8418	Intermediate Similarity	NPC243891
0.8415	Intermediate Similarity	NPC45943
0.8415	Intermediate Similarity	NPC477689
0.8415	Intermediate Similarity	NPC475865
0.8408	Intermediate Similarity	NPC474306
0.8408	Intermediate Similarity	NPC475848
0.8405	Intermediate Similarity	NPC311740
0.8405	Intermediate Similarity	NPC191352
0.8405	Intermediate Similarity	NPC296540
0.8405	Intermediate Similarity	NPC319749
0.8405	Intermediate Similarity	NPC309335
0.8405	Intermediate Similarity	NPC258322
0.8402	Intermediate Similarity	NPC79736
0.8402	Intermediate Similarity	NPC67629
0.8397	Intermediate Similarity	NPC153620
0.8397	Intermediate Similarity	NPC24257
0.8395	Intermediate Similarity	NPC45846
0.8395	Intermediate Similarity	NPC325122
0.8395	Intermediate Similarity	NPC62518
0.8395	Intermediate Similarity	NPC215375
0.8395	Intermediate Similarity	NPC245891
0.8395	Intermediate Similarity	NPC104876
0.8387	Intermediate Similarity	NPC260152
0.8387	Intermediate Similarity	NPC300603
0.8387	Intermediate Similarity	NPC472836
0.8387	Intermediate Similarity	NPC91694
0.8385	Intermediate Similarity	NPC77807
0.8385	Intermediate Similarity	NPC5379
0.8385	Intermediate Similarity	NPC14561
0.8383	Intermediate Similarity	NPC477883
0.8377	Intermediate Similarity	NPC169214
0.8377	Intermediate Similarity	NPC229218
0.8377	Intermediate Similarity	NPC141817
0.8377	Intermediate Similarity	NPC176030
0.8377	Intermediate Similarity	NPC192597
0.8372	Intermediate Similarity	NPC167045
0.8372	Intermediate Similarity	NPC114120
0.8366	Intermediate Similarity	NPC327187
0.8365	Intermediate Similarity	NPC75377
0.8365	Intermediate Similarity	NPC118427
0.8364	Intermediate Similarity	NPC41689
0.8354	Intermediate Similarity	NPC474305
0.8354	Intermediate Similarity	NPC280778
0.8353	Intermediate Similarity	NPC477880
0.8353	Intermediate Similarity	NPC267549
0.8353	Intermediate Similarity	NPC477882
0.8344	Intermediate Similarity	NPC58373
0.8344	Intermediate Similarity	NPC84571
0.8333	Intermediate Similarity	NPC19947
0.8333	Intermediate Similarity	NPC75295
0.8333	Intermediate Similarity	NPC37543
0.8333	Intermediate Similarity	NPC226759
0.8333	Intermediate Similarity	NPC199463
0.8333	Intermediate Similarity	NPC160777
0.8333	Intermediate Similarity	NPC73416
0.8333	Intermediate Similarity	NPC167595
0.8333	Intermediate Similarity	NPC207584
0.8323	Intermediate Similarity	NPC49487
0.8323	Intermediate Similarity	NPC99613
0.8323	Intermediate Similarity	NPC163130
0.8323	Intermediate Similarity	NPC165979
0.8323	Intermediate Similarity	NPC268008
0.8313	Intermediate Similarity	NPC104728
0.8313	Intermediate Similarity	NPC60211
0.8313	Intermediate Similarity	NPC131121
0.8313	Intermediate Similarity	NPC35544
0.8313	Intermediate Similarity	NPC255787
0.8313	Intermediate Similarity	NPC164912
0.8313	Intermediate Similarity	NPC295646
0.8311	Intermediate Similarity	NPC285776
0.8303	Intermediate Similarity	NPC308156
0.8303	Intermediate Similarity	NPC173729
0.8303	Intermediate Similarity	NPC223006
0.8303	Intermediate Similarity	NPC272750
0.8303	Intermediate Similarity	NPC100425
0.8303	Intermediate Similarity	NPC134047
0.8302	Intermediate Similarity	NPC58310
0.8302	Intermediate Similarity	NPC234152
0.8302	Intermediate Similarity	NPC295977
0.8302	Intermediate Similarity	NPC119929
0.8301	Intermediate Similarity	NPC223336

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 NPC109765 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	957
0.2-0.3	1557
0.3-0.4	2651
0.4-0.5	1944
0.5-0.6	1036
0.6-0.7	468
0.7-0.8	162
0.8-0.85	4
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8812	High Similarity	NPD6232	Discontinued
0.875	High Similarity	NPD6143	Clinical (unspecified phase)
0.865	High Similarity	NPD7473	Discontinued
0.8545	High Similarity	NPD5844	Phase 1
0.8462	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD37	Approved
0.8372	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD4967	Phase 2
0.8272	Intermediate Similarity	NPD4965	Approved
0.8272	Intermediate Similarity	NPD4966	Approved
0.8239	Intermediate Similarity	NPD7458	Discontinued
0.8171	Intermediate Similarity	NPD6234	Discontinued
0.8125	Intermediate Similarity	NPD3226	Approved
0.8077	Intermediate Similarity	NPD7003	Approved
0.8072	Intermediate Similarity	NPD7199	Phase 2
0.8013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD3764	Approved
0.7941	Intermediate Similarity	NPD3818	Discontinued
0.7939	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1465	Phase 2
0.7885	Intermediate Similarity	NPD2346	Discontinued
0.7875	Intermediate Similarity	NPD2533	Approved
0.7875	Intermediate Similarity	NPD2532	Approved
0.7875	Intermediate Similarity	NPD2534	Approved
0.7861	Intermediate Similarity	NPD6559	Discontinued
0.7848	Intermediate Similarity	NPD4628	Phase 3
0.7836	Intermediate Similarity	NPD7228	Approved
0.7785	Intermediate Similarity	NPD1283	Approved
0.7771	Intermediate Similarity	NPD8312	Approved
0.7771	Intermediate Similarity	NPD8313	Approved
0.7765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7819	Suspended
0.7707	Intermediate Similarity	NPD2935	Discontinued
0.7692	Intermediate Similarity	NPD5494	Approved
0.7683	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3749	Approved
0.7657	Intermediate Similarity	NPD7685	Pre-registration
0.7651	Intermediate Similarity	NPD1934	Approved
0.7647	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7177	Discontinued
0.7619	Intermediate Similarity	NPD3882	Suspended
0.7605	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD2801	Approved
0.7595	Intermediate Similarity	NPD5408	Approved
0.7595	Intermediate Similarity	NPD5405	Approved
0.7595	Intermediate Similarity	NPD5404	Approved
0.7595	Intermediate Similarity	NPD5406	Approved
0.7584	Intermediate Similarity	NPD1281	Approved
0.756	Intermediate Similarity	NPD3817	Phase 2
0.7557	Intermediate Similarity	NPD7240	Approved
0.7547	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6959	Discontinued
0.7543	Intermediate Similarity	NPD7074	Phase 3
0.753	Intermediate Similarity	NPD7028	Phase 2
0.7529	Intermediate Similarity	NPD919	Approved
0.7516	Intermediate Similarity	NPD3750	Approved
0.7514	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD8455	Phase 2
0.7486	Intermediate Similarity	NPD7054	Approved
0.7485	Intermediate Similarity	NPD7411	Suspended
0.7452	Intermediate Similarity	NPD447	Suspended
0.7452	Intermediate Similarity	NPD1933	Approved
0.745	Intermediate Similarity	NPD4626	Approved
0.7443	Intermediate Similarity	NPD7472	Approved
0.7442	Intermediate Similarity	NPD8127	Discontinued
0.7438	Intermediate Similarity	NPD2344	Approved
0.7435	Intermediate Similarity	NPD8151	Discontinued
0.7421	Intermediate Similarity	NPD2799	Discontinued
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6166	Phase 2
0.7414	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7768	Phase 2
0.7405	Intermediate Similarity	NPD1607	Approved
0.7403	Intermediate Similarity	NPD9494	Approved
0.7401	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6273	Approved
0.7389	Intermediate Similarity	NPD2979	Phase 3
0.7381	Intermediate Similarity	NPD6385	Approved
0.7381	Intermediate Similarity	NPD6386	Approved
0.7378	Intermediate Similarity	NPD1511	Approved
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7368	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7075	Discontinued
0.7356	Intermediate Similarity	NPD3926	Phase 2
0.7354	Intermediate Similarity	NPD7435	Discontinued
0.7351	Intermediate Similarity	NPD3705	Approved
0.7346	Intermediate Similarity	NPD6674	Discontinued
0.7342	Intermediate Similarity	NPD230	Phase 1
0.7341	Intermediate Similarity	NPD1247	Approved
0.7333	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3751	Discontinued
0.7321	Intermediate Similarity	NPD6599	Discontinued
0.7321	Intermediate Similarity	NPD4380	Phase 2
0.7318	Intermediate Similarity	NPD7808	Phase 3
0.7314	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3748	Approved
0.7312	Intermediate Similarity	NPD1510	Phase 2
0.7303	Intermediate Similarity	NPD6797	Phase 2
0.7303	Intermediate Similarity	NPD1608	Approved
0.7299	Intermediate Similarity	NPD5710	Approved
0.7299	Intermediate Similarity	NPD5711	Approved
0.7289	Intermediate Similarity	NPD1512	Approved
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7278	Intermediate Similarity	NPD1240	Approved
0.7273	Intermediate Similarity	NPD1470	Approved
0.7273	Intermediate Similarity	NPD7390	Discontinued
0.7268	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7783	Phase 2
0.7267	Intermediate Similarity	NPD1651	Approved
0.7267	Intermediate Similarity	NPD2438	Suspended
0.7263	Intermediate Similarity	NPD7039	Approved
0.7263	Intermediate Similarity	NPD7038	Approved
0.7263	Intermediate Similarity	NPD7251	Discontinued
0.7256	Intermediate Similarity	NPD2309	Approved
0.7256	Intermediate Similarity	NPD6190	Approved
0.7246	Intermediate Similarity	NPD920	Approved
0.7235	Intermediate Similarity	NPD6801	Discontinued
0.7229	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2798	Approved
0.7225	Intermediate Similarity	NPD7870	Phase 2
0.7225	Intermediate Similarity	NPD7871	Phase 2
0.7205	Intermediate Similarity	NPD4308	Phase 3
0.7195	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3972	Approved
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7698	Approved
0.717	Intermediate Similarity	NPD4060	Phase 1
0.7169	Intermediate Similarity	NPD6799	Approved
0.7159	Intermediate Similarity	NPD5242	Approved
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD5691	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7151	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1243	Approved
0.7128	Intermediate Similarity	NPD7874	Approved
0.7128	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1201	Approved
0.7117	Intermediate Similarity	NPD7266	Discontinued
0.7105	Intermediate Similarity	NPD17	Approved
0.7102	Intermediate Similarity	NPD3787	Discontinued
0.7098	Intermediate Similarity	NPD7999	Approved
0.7097	Intermediate Similarity	NPD1876	Approved
0.7091	Intermediate Similarity	NPD8166	Discontinued
0.7091	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4110	Phase 3
0.709	Intermediate Similarity	NPD4420	Approved
0.7086	Intermediate Similarity	NPD9545	Approved
0.7083	Intermediate Similarity	NPD7680	Approved
0.7076	Intermediate Similarity	NPD6873	Phase 2
0.7073	Intermediate Similarity	NPD1549	Phase 2
0.7063	Intermediate Similarity	NPD943	Approved
0.7055	Intermediate Similarity	NPD1551	Phase 2
0.7055	Intermediate Similarity	NPD2531	Phase 2
0.7053	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5978	Approved
0.7052	Intermediate Similarity	NPD5977	Approved
0.7044	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6823	Phase 2
0.703	Intermediate Similarity	NPD2800	Approved
0.7026	Intermediate Similarity	NPD7701	Phase 2
0.7021	Intermediate Similarity	NPD6534	Approved
0.7021	Intermediate Similarity	NPD6535	Approved
0.702	Intermediate Similarity	NPD5536	Phase 2
0.7019	Intermediate Similarity	NPD6355	Discontinued
0.7013	Intermediate Similarity	NPD1611	Approved
0.7012	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1471	Phase 3
0.7012	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1653	Approved
0.6981	Remote Similarity	NPD7008	Discontinued
0.6959	Remote Similarity	NPD8320	Phase 1
0.6959	Remote Similarity	NPD8319	Approved
0.6957	Remote Similarity	NPD4307	Phase 2
0.6954	Remote Similarity	NPD5402	Approved
0.6951	Remote Similarity	NPD4477	Approved
0.6951	Remote Similarity	NPD4476	Approved
0.6951	Remote Similarity	NPD2796	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