NPASS Compound

Structure

NPC118332 OpenBabel07101718332D 23 26 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 0.6581 -5.4781 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 -4.5380 -1.4781 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 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 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 11 1 0 0 0 0 5 14 2 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 22 1 0 0 0 0 9 23 1 0 0 0 0 10 11 2 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 17 23 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.08
Volume:	308.518
LogP:	4.497
LogD:	3.838
LogS:	-6.863
# Rotatable Bonds:	3
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.535
Synthetic Accessibility Score:	2.264
Fsp3:	0.167
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:	-4.773
MDCK Permeability:	5.8837442338699475e-05
Pgp-inhibitor:	0.273
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.346
Plasma Protein Binding (PPB):	91.92269897460938%
Volume Distribution (VD):	0.639
Pgp-substrate:	2.7544212341308594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.688
CYP2C19-inhibitor:	0.974
CYP2C19-substrate:	0.278
CYP2C9-inhibitor:	0.866
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.924
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	13.322
Half-life (T1/2):	0.161

ADMET: Toxicity

hERG Blockers:	0.199
Human Hepatotoxicity (H-HT):	0.102
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.815
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.304
Skin Sensitization:	0.828
Carcinogencity:	0.943
Eye Corrosion:	0.012
Eye Irritation:	0.751
Respiratory Toxicity:	0.78

Download Data

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

Natural Product: NPC118332

Natural Product ID:	NPC118332
*Common Name:**	Methyl Aristolate
IUPAC Name:	methyl 8-methoxynaphtho[2,1-g][1,3]benzodioxole-5-carboxylate
Synonyms:	Methyl Aristolate
Standard InCHIKey:	LBBQPQFZUZOHTO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14O5/c1-20-14-5-3-4-11-10(14)6-7-12-13(18(19)21-2)8-15-17(16(11)12)23-9-22-15/h3-8H,9H2,1-2H3
SMILES:	COc1cccc2c1ccc1c(cc3c(c21)OCO3)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520680
PubChem CID:	160246
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
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[12880323]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20097074]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21353775]
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]
NPO18443	Aristolochia manshuriensis	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]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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
IC50	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[519480]

☑ 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 NPC118332 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	450
0.1-0.2	1820
0.2-0.3	3933
0.3-0.4	9863
0.4-0.5	8510
0.5-0.6	3450
0.6-0.7	7761
0.7-0.8	6577
0.8-0.85	267
0.85-0.9	50
0.9-0.95	12
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.973	High Similarity	NPC109765
0.9664	High Similarity	NPC202495
0.96	High Similarity	NPC125713
0.9338	High Similarity	NPC115123
0.9338	High Similarity	NPC239113
0.9333	High Similarity	NPC54179
0.9324	High Similarity	NPC300983
0.9276	High Similarity	NPC19600
0.9156	High Similarity	NPC78944
0.9128	High Similarity	NPC127827
0.9097	High Similarity	NPC15212
0.9067	High Similarity	NPC475722
0.9038	High Similarity	NPC116838
0.9038	High Similarity	NPC22130
0.9	High Similarity	NPC24193
0.898	High Similarity	NPC125134
0.898	High Similarity	NPC137920
0.898	High Similarity	NPC86455
0.8968	High Similarity	NPC474043
0.8933	High Similarity	NPC181464
0.8917	High Similarity	NPC198796
0.8903	High Similarity	NPC296044
0.8903	High Similarity	NPC167098
0.8896	High Similarity	NPC234730
0.8868	High Similarity	NPC471923
0.8859	High Similarity	NPC229787
0.8839	High Similarity	NPC261484
0.8839	High Similarity	NPC473900
0.8824	High Similarity	NPC104353
0.8812	High Similarity	NPC475453
0.8812	High Similarity	NPC473531
0.8797	High Similarity	NPC19948
0.8782	High Similarity	NPC76458
0.8782	High Similarity	NPC143328
0.8782	High Similarity	NPC82733
0.875	High Similarity	NPC474042
0.875	High Similarity	NPC174734
0.8733	High Similarity	NPC471305
0.8726	High Similarity	NPC68619
0.8726	High Similarity	NPC15764
0.872	High Similarity	NPC196771
0.8718	High Similarity	NPC301897
0.8704	High Similarity	NPC52598
0.8701	High Similarity	NPC220577
0.8688	High Similarity	NPC477884
0.8671	High Similarity	NPC139876
0.8671	High Similarity	NPC65784
0.8654	High Similarity	NPC472835
0.8654	High Similarity	NPC3273
0.865	High Similarity	NPC474075
0.865	High Similarity	NPC20114
0.865	High Similarity	NPC114550
0.865	High Similarity	NPC471922
0.865	High Similarity	NPC292712
0.865	High Similarity	NPC473697
0.865	High Similarity	NPC312006
0.865	High Similarity	NPC471921
0.865	High Similarity	NPC129930
0.865	High Similarity	NPC471920
0.8642	High Similarity	NPC117911
0.8627	High Similarity	NPC475848
0.8627	High Similarity	NPC474306
0.8618	High Similarity	NPC24257
0.8618	High Similarity	NPC153620
0.8616	High Similarity	NPC309335
0.8616	High Similarity	NPC258322
0.8616	High Similarity	NPC191352
0.8616	High Similarity	NPC319749
0.8616	High Similarity	NPC296540
0.8609	High Similarity	NPC472836
0.8608	High Similarity	NPC325122
0.8598	High Similarity	NPC184624
0.8571	High Similarity	NPC474305
0.8571	High Similarity	NPC37220
0.8571	High Similarity	NPC261322
0.8562	High Similarity	NPC280778
0.8553	High Similarity	NPC474770
0.8545	High Similarity	NPC193377
0.8523	High Similarity	NPC223336
0.8503	High Similarity	NPC88065
0.8503	High Similarity	NPC89504
0.8503	High Similarity	NPC95485
0.85	High Similarity	NPC209411
0.85	High Similarity	NPC239890
0.85	High Similarity	NPC109238
0.8487	Intermediate Similarity	NPC308006
0.8481	Intermediate Similarity	NPC261090
0.8471	Intermediate Similarity	NPC273578
0.8462	Intermediate Similarity	NPC302783
0.8462	Intermediate Similarity	NPC474414
0.8462	Intermediate Similarity	NPC124842
0.8462	Intermediate Similarity	NPC473201
0.8457	Intermediate Similarity	NPC474301
0.8443	Intermediate Similarity	NPC35266
0.8438	Intermediate Similarity	NPC47623
0.8431	Intermediate Similarity	NPC224687
0.8418	Intermediate Similarity	NPC478238
0.8408	Intermediate Similarity	NPC308555
0.8408	Intermediate Similarity	NPC153008
0.8408	Intermediate Similarity	NPC148497
0.8405	Intermediate Similarity	NPC118162
0.8405	Intermediate Similarity	NPC320471
0.8405	Intermediate Similarity	NPC83049
0.8393	Intermediate Similarity	NPC275690
0.8393	Intermediate Similarity	NPC161609
0.8387	Intermediate Similarity	NPC472839
0.8385	Intermediate Similarity	NPC99968
0.8373	Intermediate Similarity	NPC316539
0.8373	Intermediate Similarity	NPC477881
0.8365	Intermediate Similarity	NPC477380
0.8354	Intermediate Similarity	NPC62051
0.8354	Intermediate Similarity	NPC471180
0.8354	Intermediate Similarity	NPC311912
0.8354	Intermediate Similarity	NPC478213
0.8354	Intermediate Similarity	NPC79322
0.8344	Intermediate Similarity	NPC78505
0.8333	Intermediate Similarity	NPC108767
0.8333	Intermediate Similarity	NPC149505
0.8333	Intermediate Similarity	NPC61141
0.8333	Intermediate Similarity	NPC144843
0.8313	Intermediate Similarity	NPC477885
0.8313	Intermediate Similarity	NPC310206
0.8312	Intermediate Similarity	NPC87295
0.8312	Intermediate Similarity	NPC296575
0.8311	Intermediate Similarity	NPC45404
0.8303	Intermediate Similarity	NPC88557
0.8302	Intermediate Similarity	NPC80489
0.8302	Intermediate Similarity	NPC254163
0.8301	Intermediate Similarity	NPC474036
0.8301	Intermediate Similarity	NPC50954
0.8291	Intermediate Similarity	NPC144162
0.8291	Intermediate Similarity	NPC3744
0.8291	Intermediate Similarity	NPC137125
0.8282	Intermediate Similarity	NPC100420
0.828	Intermediate Similarity	NPC210642
0.828	Intermediate Similarity	NPC13985
0.8272	Intermediate Similarity	NPC131905
0.8272	Intermediate Similarity	NPC469889
0.8264	Intermediate Similarity	NPC154275
0.8263	Intermediate Similarity	NPC199357
0.8263	Intermediate Similarity	NPC72455
0.8258	Intermediate Similarity	NPC104024
0.8258	Intermediate Similarity	NPC80230
0.8258	Intermediate Similarity	NPC65574
0.8258	Intermediate Similarity	NPC58752
0.8258	Intermediate Similarity	NPC101755
0.8258	Intermediate Similarity	NPC304687
0.8258	Intermediate Similarity	NPC39361
0.8253	Intermediate Similarity	NPC477883
0.825	Intermediate Similarity	NPC155063
0.825	Intermediate Similarity	NPC213401
0.8247	Intermediate Similarity	NPC275278
0.8246	Intermediate Similarity	NPC114120
0.8246	Intermediate Similarity	NPC167045
0.8242	Intermediate Similarity	NPC234331
0.8239	Intermediate Similarity	NPC348849
0.8239	Intermediate Similarity	NPC244371
0.8239	Intermediate Similarity	NPC57211
0.8239	Intermediate Similarity	NPC178195
0.8235	Intermediate Similarity	NPC208797
0.8235	Intermediate Similarity	NPC53680
0.8232	Intermediate Similarity	NPC41689
0.8232	Intermediate Similarity	NPC26386
0.8228	Intermediate Similarity	NPC279061
0.8228	Intermediate Similarity	NPC267091
0.8228	Intermediate Similarity	NPC70320
0.8228	Intermediate Similarity	NPC306011
0.8228	Intermediate Similarity	NPC472838
0.8225	Intermediate Similarity	NPC477882
0.8225	Intermediate Similarity	NPC47191
0.8225	Intermediate Similarity	NPC477880
0.8224	Intermediate Similarity	NPC162851
0.8224	Intermediate Similarity	NPC246474
0.8224	Intermediate Similarity	NPC218092
0.8224	Intermediate Similarity	NPC28398
0.8212	Intermediate Similarity	NPC470962
0.8212	Intermediate Similarity	NPC233780
0.8208	Intermediate Similarity	NPC205721
0.8207	Intermediate Similarity	NPC286683
0.8207	Intermediate Similarity	NPC100129
0.8205	Intermediate Similarity	NPC40654
0.8205	Intermediate Similarity	NPC470757
0.8205	Intermediate Similarity	NPC262804
0.8204	Intermediate Similarity	NPC471181
0.8204	Intermediate Similarity	NPC469506
0.82	Intermediate Similarity	NPC160425
0.8199	Intermediate Similarity	NPC474990
0.8199	Intermediate Similarity	NPC178976
0.8193	Intermediate Similarity	NPC41853
0.8188	Intermediate Similarity	NPC1249
0.8188	Intermediate Similarity	NPC311339
0.8187	Intermediate Similarity	NPC474009
0.8182	Intermediate Similarity	NPC46880
0.8182	Intermediate Similarity	NPC29160
0.8176	Intermediate Similarity	NPC68882
0.8176	Intermediate Similarity	NPC183103
0.8176	Intermediate Similarity	NPC245948
0.8176	Intermediate Similarity	NPC52623
0.8176	Intermediate Similarity	NPC60211
0.8176	Intermediate Similarity	NPC477377

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 NPC118332 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	985
0.2-0.3	1530
0.3-0.4	2712
0.4-0.5	1930
0.5-0.6	1012
0.6-0.7	438
0.7-0.8	142
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD6980	Clinical (unspecified phase)
0.8562	High Similarity	NPD6232	Discontinued
0.8487	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7473	Discontinued
0.8303	Intermediate Similarity	NPD5844	Phase 1
0.8176	Intermediate Similarity	NPD37	Approved
0.814	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4965	Approved
0.8025	Intermediate Similarity	NPD4967	Phase 2
0.8025	Intermediate Similarity	NPD4966	Approved
0.7987	Intermediate Similarity	NPD7458	Discontinued
0.7939	Intermediate Similarity	NPD7199	Phase 2
0.7927	Intermediate Similarity	NPD6234	Discontinued
0.7879	Intermediate Similarity	NPD5494	Approved
0.7875	Intermediate Similarity	NPD3226	Approved
0.7844	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7003	Approved
0.7793	Intermediate Similarity	NPD1281	Approved
0.7759	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2346	Discontinued
0.7711	Intermediate Similarity	NPD919	Approved
0.7706	Intermediate Similarity	NPD3818	Discontinued
0.7697	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1465	Phase 2
0.7682	Intermediate Similarity	NPD3764	Approved
0.7647	Intermediate Similarity	NPD1933	Approved
0.7635	Intermediate Similarity	NPD1283	Approved
0.763	Intermediate Similarity	NPD6559	Discontinued
0.7625	Intermediate Similarity	NPD2533	Approved
0.7625	Intermediate Similarity	NPD2534	Approved
0.7625	Intermediate Similarity	NPD2532	Approved
0.7602	Intermediate Similarity	NPD7228	Approved
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7582	Intermediate Similarity	NPD2979	Phase 3
0.7576	Intermediate Similarity	NPD7819	Suspended
0.7561	Intermediate Similarity	NPD6386	Approved
0.7561	Intermediate Similarity	NPD6385	Approved
0.7551	Intermediate Similarity	NPD3705	Approved
0.7543	Intermediate Similarity	NPD8313	Approved
0.7543	Intermediate Similarity	NPD8312	Approved
0.7542	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3817	Phase 2
0.7529	Intermediate Similarity	NPD3926	Phase 2
0.7515	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD3748	Approved
0.7466	Intermediate Similarity	NPD1651	Approved
0.7452	Intermediate Similarity	NPD2438	Suspended
0.7452	Intermediate Similarity	NPD2935	Discontinued
0.744	Intermediate Similarity	NPD3749	Approved
0.7439	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7685	Pre-registration
0.7429	Intermediate Similarity	NPD7240	Approved
0.7423	Intermediate Similarity	NPD920	Approved
0.741	Intermediate Similarity	NPD1934	Approved
0.7405	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7177	Discontinued
0.7394	Intermediate Similarity	NPD7028	Phase 2
0.7386	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD3972	Approved
0.7381	Intermediate Similarity	NPD3882	Suspended
0.7368	Intermediate Similarity	NPD7229	Phase 3
0.7365	Intermediate Similarity	NPD8455	Phase 2
0.7365	Intermediate Similarity	NPD2801	Approved
0.7365	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5691	Approved
0.7342	Intermediate Similarity	NPD5404	Approved
0.7342	Intermediate Similarity	NPD5405	Approved
0.7342	Intermediate Similarity	NPD5406	Approved
0.7342	Intermediate Similarity	NPD5408	Approved
0.7326	Intermediate Similarity	NPD5242	Approved
0.7314	Intermediate Similarity	NPD7074	Phase 3
0.7312	Intermediate Similarity	NPD1243	Approved
0.731	Intermediate Similarity	NPD8127	Discontinued
0.731	Intermediate Similarity	NPD6959	Discontinued
0.7301	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4626	Approved
0.7297	Intermediate Similarity	NPD17	Approved
0.7289	Intermediate Similarity	NPD6599	Discontinued
0.7288	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1876	Approved
0.7278	Intermediate Similarity	NPD2799	Discontinued
0.7267	Intermediate Similarity	NPD3750	Approved
0.7262	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7054	Approved
0.7256	Intermediate Similarity	NPD6273	Approved
0.725	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6873	Phase 2
0.7246	Intermediate Similarity	NPD7411	Suspended
0.7243	Intermediate Similarity	NPD4420	Approved
0.7233	Intermediate Similarity	NPD2531	Phase 2
0.7226	Intermediate Similarity	NPD2313	Discontinued
0.7225	Intermediate Similarity	NPD8151	Discontinued
0.7219	Intermediate Similarity	NPD5978	Approved
0.7219	Intermediate Similarity	NPD5977	Approved
0.7216	Intermediate Similarity	NPD7472	Approved
0.7211	Intermediate Similarity	NPD5536	Phase 2
0.7205	Intermediate Similarity	NPD6674	Discontinued
0.72	Intermediate Similarity	NPD1611	Approved
0.7197	Intermediate Similarity	NPD447	Suspended
0.719	Intermediate Similarity	NPD2798	Approved
0.7188	Intermediate Similarity	NPD1471	Phase 3
0.7188	Intermediate Similarity	NPD2344	Approved
0.7184	Intermediate Similarity	NPD6166	Phase 2
0.7184	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7768	Phase 2
0.7175	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD1607	Approved
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD9494	Approved
0.7135	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7075	Discontinued
0.7134	Intermediate Similarity	NPD1511	Approved
0.7134	Intermediate Similarity	NPD4307	Phase 2
0.7134	Intermediate Similarity	NPD6799	Approved
0.7125	Intermediate Similarity	NPD2796	Approved
0.7111	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3751	Discontinued
0.7101	Intermediate Similarity	NPD6801	Discontinued
0.7095	Intermediate Similarity	NPD7808	Phase 3
0.7091	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5006	Approved
0.709	Intermediate Similarity	NPD5005	Approved
0.7089	Intermediate Similarity	NPD230	Phase 1
0.7086	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4380	Phase 2
0.7079	Intermediate Similarity	NPD6797	Phase 2
0.7074	Intermediate Similarity	NPD6782	Approved
0.7074	Intermediate Similarity	NPD6779	Approved
0.7074	Intermediate Similarity	NPD6777	Approved
0.7074	Intermediate Similarity	NPD6778	Approved
0.7074	Intermediate Similarity	NPD6780	Approved
0.7074	Intermediate Similarity	NPD6781	Approved
0.7074	Intermediate Similarity	NPD6776	Approved
0.707	Intermediate Similarity	NPD8032	Phase 2
0.7069	Intermediate Similarity	NPD5710	Approved
0.7069	Intermediate Similarity	NPD5711	Approved
0.7063	Intermediate Similarity	NPD1510	Phase 2
0.7062	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7783	Phase 2
0.7055	Intermediate Similarity	NPD5283	Phase 1
0.7048	Intermediate Similarity	NPD1512	Approved
0.7039	Intermediate Similarity	NPD7251	Discontinued
0.7039	Intermediate Similarity	NPD7038	Approved
0.7039	Intermediate Similarity	NPD7039	Approved
0.703	Intermediate Similarity	NPD7390	Discontinued
0.7025	Intermediate Similarity	NPD1240	Approved
0.7018	Intermediate Similarity	NPD5353	Approved
0.7018	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7870	Phase 2
0.7016	Intermediate Similarity	NPD7871	Phase 2
0.7013	Intermediate Similarity	NPD1470	Approved
0.7012	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6190	Approved
0.7012	Intermediate Similarity	NPD2309	Approved
0.7006	Intermediate Similarity	NPD6798	Discontinued
0.6988	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7999	Approved
0.6971	Remote Similarity	NPD3787	Discontinued
0.6966	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7696	Phase 3
0.6963	Remote Similarity	NPD7698	Approved
0.6963	Remote Similarity	NPD7697	Approved
0.6957	Remote Similarity	NPD4308	Phase 3
0.6951	Remote Similarity	NPD4110	Phase 3
0.6951	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.694	Remote Similarity	NPD8434	Phase 2
0.694	Remote Similarity	NPD8150	Discontinued
0.6923	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7874	Approved
0.6919	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4060	Phase 1
0.6903	Remote Similarity	NPD3266	Approved
0.6903	Remote Similarity	NPD3267	Approved
0.6899	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4107	Approved
0.6883	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6832	Phase 2
0.6875	Remote Similarity	NPD6355	Discontinued
0.6875	Remote Similarity	NPD7680	Approved
0.6871	Remote Similarity	NPD7266	Discontinued
0.6871	Remote Similarity	NPD2353	Approved
0.6871	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1201	Approved
0.6848	Remote Similarity	NPD8166	Discontinued
0.6848	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1549	Phase 2
0.6823	Remote Similarity	NPD6823	Phase 2

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