NPASS Compound

Structure

CID171882 OpenBabel06191715542D 24 27 0 0 0 0 0 0 0 0999 V2000 3.5409 0.9432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5409 -0.0211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7058 2.3896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8707 -0.0211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6346 2.3896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9590 -0.1008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7058 1.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7058 -0.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8707 0.9432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2005 2.8718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8707 2.8718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6346 1.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0356 2.3896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0356 1.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2005 0.9432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2005 4.8004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8707 3.8361 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7058 -1.4675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0356 5.2825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6346 5.2825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7058 4.3182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0356 4.3182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3512 0.7801 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 2 2 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 7 2 0 0 0 0 3 11 1 0 0 0 0 4 8 2 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 23 1 0 0 0 0 6 24 1 0 0 0 0 7 9 1 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 10 13 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 15 2 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 24 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 17 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	327.04
Volume:	299.867
LogP:	3.395
LogD:	1.704
LogS:	-4.152
# Rotatable Bonds:	2
TPSA:	119.13
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.422
Synthetic Accessibility Score:	2.698
Fsp3:	0.062
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:	-4.858
MDCK Permeability:	2.769527600321453e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.137

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	97.63884735107422%
Volume Distribution (VD):	0.477
Pgp-substrate:	3.2266836166381836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.868
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.137
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.575
CYP2C9-substrate:	0.318
CYP2D6-inhibitor:	0.787
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.209
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	5.198
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.46
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.925
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.63
Skin Sensitization:	0.873
Carcinogencity:	0.906
Eye Corrosion:	0.009
Eye Irritation:	0.726
Respiratory Toxicity:	0.89

Download Data

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

Natural Product: NPC171882

Natural Product ID:	NPC171882
*Common Name:**	Aristolochic Acid C
IUPAC Name:	10-hydroxy-6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid
Synonyms:	Aristolochic Acid C; Aristolochic acid-IIIa
Standard InCHIKey:	NBFGYDJKTHENDP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H9NO7/c18-8-2-1-7-3-11(17(21)22)13-10(16(19)20)5-12-15(24-6-23-12)14(13)9(7)4-8/h1-5,18H,6H2,(H,19,20)
SMILES:	Oc1ccc2c(c1)c1c3OCOc3cc(c1c(c2)N(=O)=O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL603494
PubChem CID:	165274
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0002664] Aristolochic acids 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]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1431939]
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]
NPO320	Coffea canephora	Species	Rubiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14814	Aristolochia contorta	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]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO320	Coffea canephora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24916	Aristolochia debilis	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]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10238	Erysimum rhaeticum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29226	Ficus cordata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO320	Coffea canephora	Species	Rubiaceae	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	3

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	=	30000.0	nM	PMID[488791]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[488792]

☑ 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 NPC171882 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	483
0.1-0.2	2413
0.2-0.3	6595
0.3-0.4	11154
0.4-0.5	5134
0.5-0.6	11110
0.6-0.7	5700
0.7-0.8	86
0.8-0.85	6
0.85-0.9	2
0.9-0.95	7
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC121510
0.9946	High Similarity	NPC46679
0.9892	High Similarity	NPC85661
0.9735	High Similarity	NPC91234
0.9677	High Similarity	NPC38961
0.9583	High Similarity	NPC240684
0.9531	High Similarity	NPC290227
0.9375	High Similarity	NPC61731
0.9375	High Similarity	NPC186569
0.9278	High Similarity	NPC124658
0.9278	High Similarity	NPC227361
0.9045	High Similarity	NPC256422
0.845	Intermediate Similarity	NPC90185
0.8103	Intermediate Similarity	NPC112676
0.8088	Intermediate Similarity	NPC207873
0.8088	Intermediate Similarity	NPC100573
0.801	Intermediate Similarity	NPC296742
0.8	Intermediate Similarity	NPC69213
0.7959	Intermediate Similarity	NPC224293
0.7943	Intermediate Similarity	NPC55470
0.7903	Intermediate Similarity	NPC109765
0.7861	Intermediate Similarity	NPC202495
0.7795	Intermediate Similarity	NPC192939
0.7795	Intermediate Similarity	NPC215747
0.7773	Intermediate Similarity	NPC298449
0.7761	Intermediate Similarity	NPC29472
0.7744	Intermediate Similarity	NPC260118
0.7716	Intermediate Similarity	NPC28425
0.7692	Intermediate Similarity	NPC265383
0.7688	Intermediate Similarity	NPC118332
0.7665	Intermediate Similarity	NPC119579
0.7638	Intermediate Similarity	NPC180253
0.7638	Intermediate Similarity	NPC219170
0.7614	Intermediate Similarity	NPC311936
0.7608	Intermediate Similarity	NPC308943
0.7608	Intermediate Similarity	NPC222561
0.7548	Intermediate Similarity	NPC159101
0.7538	Intermediate Similarity	NPC276060
0.7513	Intermediate Similarity	NPC116838
0.7513	Intermediate Similarity	NPC22130
0.7513	Intermediate Similarity	NPC198796
0.7512	Intermediate Similarity	NPC22928
0.7476	Intermediate Similarity	NPC23080
0.7476	Intermediate Similarity	NPC193906
0.7475	Intermediate Similarity	NPC312531
0.7475	Intermediate Similarity	NPC474904
0.7464	Intermediate Similarity	NPC207971
0.7453	Intermediate Similarity	NPC46990
0.7448	Intermediate Similarity	NPC125713
0.744	Intermediate Similarity	NPC5374
0.7396	Intermediate Similarity	NPC167098
0.7396	Intermediate Similarity	NPC296044
0.7366	Intermediate Similarity	NPC254957
0.7363	Intermediate Similarity	NPC249405
0.7346	Intermediate Similarity	NPC268077
0.733	Intermediate Similarity	NPC54179
0.7317	Intermediate Similarity	NPC294244
0.7313	Intermediate Similarity	NPC196771
0.731	Intermediate Similarity	NPC474042
0.731	Intermediate Similarity	NPC174734
0.7308	Intermediate Similarity	NPC71124
0.7308	Intermediate Similarity	NPC17677
0.7306	Intermediate Similarity	NPC143328
0.7264	Intermediate Similarity	NPC193377
0.7261	Intermediate Similarity	NPC210296
0.7255	Intermediate Similarity	NPC474009
0.7255	Intermediate Similarity	NPC320088
0.7254	Intermediate Similarity	NPC239113
0.7254	Intermediate Similarity	NPC115123
0.7236	Intermediate Similarity	NPC117911
0.7216	Intermediate Similarity	NPC19600
0.7212	Intermediate Similarity	NPC227033
0.7212	Intermediate Similarity	NPC162653
0.7211	Intermediate Similarity	NPC37220
0.7211	Intermediate Similarity	NPC300983
0.7209	Intermediate Similarity	NPC477825
0.7202	Intermediate Similarity	NPC472835
0.7161	Intermediate Similarity	NPC183537
0.7157	Intermediate Similarity	NPC276674
0.7157	Intermediate Similarity	NPC33902
0.7143	Intermediate Similarity	NPC78944
0.7143	Intermediate Similarity	NPC179704
0.7129	Intermediate Similarity	NPC470023
0.7129	Intermediate Similarity	NPC190461
0.7129	Intermediate Similarity	NPC114364
0.7129	Intermediate Similarity	NPC320223
0.7128	Intermediate Similarity	NPC471305
0.7123	Intermediate Similarity	NPC471489
0.7122	Intermediate Similarity	NPC18306
0.712	Intermediate Similarity	NPC261322
0.7115	Intermediate Similarity	NPC78284
0.7114	Intermediate Similarity	NPC52598
0.711	Intermediate Similarity	NPC477826
0.711	Intermediate Similarity	NPC477827
0.7107	Intermediate Similarity	NPC15212
0.7097	Intermediate Similarity	NPC25961
0.7095	Intermediate Similarity	NPC470021
0.7092	Intermediate Similarity	NPC68619
0.7085	Intermediate Similarity	NPC474301
0.7079	Intermediate Similarity	NPC292712
0.7079	Intermediate Similarity	NPC98416
0.7079	Intermediate Similarity	NPC20114
0.7079	Intermediate Similarity	NPC474075
0.7079	Intermediate Similarity	NPC312006
0.7079	Intermediate Similarity	NPC471920
0.7079	Intermediate Similarity	NPC114550
0.7079	Intermediate Similarity	NPC471921
0.7079	Intermediate Similarity	NPC471922
0.7079	Intermediate Similarity	NPC129930
0.7079	Intermediate Similarity	NPC287588
0.7068	Intermediate Similarity	NPC127827
0.7068	Intermediate Similarity	NPC24193
0.7067	Intermediate Similarity	NPC226708
0.7056	Intermediate Similarity	NPC474770
0.7056	Intermediate Similarity	NPC47623
0.7056	Intermediate Similarity	NPC189903
0.7056	Intermediate Similarity	NPC182907
0.7048	Intermediate Similarity	NPC33256
0.7047	Intermediate Similarity	NPC302783
0.7047	Intermediate Similarity	NPC124842
0.7047	Intermediate Similarity	NPC473201
0.7044	Intermediate Similarity	NPC316539
0.7044	Intermediate Similarity	NPC184624
0.7039	Intermediate Similarity	NPC53680
0.7039	Intermediate Similarity	NPC208797
0.7031	Intermediate Similarity	NPC475722
0.703	Intermediate Similarity	NPC477558
0.703	Intermediate Similarity	NPC229166
0.703	Intermediate Similarity	NPC128560
0.703	Intermediate Similarity	NPC199465
0.7026	Intermediate Similarity	NPC80489
0.7024	Intermediate Similarity	NPC116284
0.7017	Intermediate Similarity	NPC77878
0.7016	Intermediate Similarity	NPC181464
0.7015	Intermediate Similarity	NPC311912
0.7013	Intermediate Similarity	NPC108342
0.7005	Intermediate Similarity	NPC474043
0.7	Intermediate Similarity	NPC469816
0.7	Intermediate Similarity	NPC469815
0.6995	Remote Similarity	NPC85613
0.6995	Remote Similarity	NPC283810
0.6995	Remote Similarity	NPC5167
0.699	Remote Similarity	NPC135772
0.699	Remote Similarity	NPC261090
0.6985	Remote Similarity	NPC144843
0.6982	Remote Similarity	NPC477828
0.698	Remote Similarity	NPC9475
0.698	Remote Similarity	NPC285941
0.698	Remote Similarity	NPC88557
0.6974	Remote Similarity	NPC62051
0.6967	Remote Similarity	NPC125924
0.6965	Remote Similarity	NPC471923
0.6961	Remote Similarity	NPC199357
0.6959	Remote Similarity	NPC78505
0.6952	Remote Similarity	NPC302001
0.6952	Remote Similarity	NPC205721
0.695	Remote Similarity	NPC247389
0.695	Remote Similarity	NPC298979
0.695	Remote Similarity	NPC100420
0.6949	Remote Similarity	NPC124313
0.6947	Remote Similarity	NPC229787
0.6944	Remote Similarity	NPC244606
0.6944	Remote Similarity	NPC156728
0.6942	Remote Similarity	NPC47191
0.6942	Remote Similarity	NPC35266
0.6942	Remote Similarity	NPC248642
0.6939	Remote Similarity	NPC234730
0.6935	Remote Similarity	NPC131905
0.6935	Remote Similarity	NPC469889
0.6931	Remote Similarity	NPC303581
0.6931	Remote Similarity	NPC234331
0.6931	Remote Similarity	NPC86455
0.6931	Remote Similarity	NPC471180
0.6931	Remote Similarity	NPC475453
0.6931	Remote Similarity	NPC137920
0.6931	Remote Similarity	NPC473531
0.6931	Remote Similarity	NPC227683
0.6931	Remote Similarity	NPC125134
0.6931	Remote Similarity	NPC67978
0.6926	Remote Similarity	NPC22481
0.6923	Remote Similarity	NPC137125
0.6923	Remote Similarity	NPC162694
0.6923	Remote Similarity	NPC3744
0.6915	Remote Similarity	NPC26386
0.6912	Remote Similarity	NPC469506
0.6912	Remote Similarity	NPC471181
0.6912	Remote Similarity	NPC475768
0.6909	Remote Similarity	NPC295479
0.6909	Remote Similarity	NPC220241
0.6908	Remote Similarity	NPC161609
0.6908	Remote Similarity	NPC275690
0.6908	Remote Similarity	NPC156576
0.6904	Remote Similarity	NPC473900
0.6904	Remote Similarity	NPC261484
0.6904	Remote Similarity	NPC213401
0.69	Remote Similarity	NPC476432
0.69	Remote Similarity	NPC24264
0.69	Remote Similarity	NPC19948
0.69	Remote Similarity	NPC219341
0.6895	Remote Similarity	NPC50954

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 NPC171882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	909
0.2-0.3	1158
0.3-0.4	2472
0.4-0.5	2532
0.5-0.6	1416
0.6-0.7	302
0.7-0.8	15
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7534	Intermediate Similarity	NPD6723	Discontinued
0.7358	Intermediate Similarity	NPD6296	Discontinued
0.7268	Intermediate Similarity	NPD3252	Approved
0.726	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD1221	Approved
0.7231	Intermediate Similarity	NPD710	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8067	Phase 3
0.7172	Intermediate Similarity	NPD1220	Phase 1
0.7157	Intermediate Similarity	NPD6232	Discontinued
0.7107	Intermediate Similarity	NPD2821	Approved
0.7056	Intermediate Similarity	NPD3251	Approved
0.705	Intermediate Similarity	NPD7473	Discontinued
0.7009	Intermediate Similarity	NPD5848	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4859	Phase 1
0.6926	Remote Similarity	NPD7922	Phase 1
0.6916	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5844	Phase 1
0.6893	Remote Similarity	NPD7546	Discontinued
0.689	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4420	Approved
0.6781	Remote Similarity	NPD6625	Approved
0.6762	Remote Similarity	NPD3398	Discontinued
0.6753	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD37	Approved
0.6725	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5006	Approved
0.6697	Remote Similarity	NPD5005	Approved
0.6683	Remote Similarity	NPD7177	Discontinued
0.6682	Remote Similarity	NPD1898	Discontinued
0.6667	Remote Similarity	NPD6234	Discontinued
0.6652	Remote Similarity	NPD7827	Phase 1
0.6651	Remote Similarity	NPD7476	Discontinued
0.665	Remote Similarity	NPD4965	Approved
0.665	Remote Similarity	NPD4966	Approved
0.665	Remote Similarity	NPD4967	Phase 2
0.6636	Remote Similarity	NPD6212	Phase 3
0.6636	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6213	Phase 3
0.6626	Remote Similarity	NPD8367	Approved
0.6624	Remote Similarity	NPD4846	Phase 2
0.6623	Remote Similarity	NPD5519	Discontinued
0.6622	Remote Similarity	NPD5950	Discontinued
0.6618	Remote Similarity	NPD5242	Approved
0.6616	Remote Similarity	NPD6385	Approved
0.6616	Remote Similarity	NPD6386	Approved
0.6607	Remote Similarity	NPD7783	Phase 2
0.6607	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4107	Approved
0.6602	Remote Similarity	NPD3818	Discontinued
0.6599	Remote Similarity	NPD7458	Discontinued
0.6588	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3452	Approved
0.6575	Remote Similarity	NPD3450	Approved
0.6567	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7039	Approved
0.6555	Remote Similarity	NPD7038	Approved
0.655	Remote Similarity	NPD1465	Phase 2
0.655	Remote Similarity	NPD2899	Discontinued
0.6545	Remote Similarity	NPD3057	Approved
0.6545	Remote Similarity	NPD3448	Approved
0.654	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD6997	Phase 2
0.6533	Remote Similarity	NPD683	Approved
0.6533	Remote Similarity	NPD2672	Discontinued
0.653	Remote Similarity	NPD3290	Approved
0.653	Remote Similarity	NPD3289	Phase 3
0.6528	Remote Similarity	NPD7256	Discontinued
0.652	Remote Similarity	NPD7199	Phase 2
0.6518	Remote Similarity	NPD8492	Approved
0.6518	Remote Similarity	NPD8151	Discontinued
0.6517	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3226	Approved
0.6513	Remote Similarity	NPD3752	Phase 2
0.6513	Remote Similarity	NPD1543	Discontinued
0.6507	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2494	Approved
0.65	Remote Similarity	NPD4482	Phase 3
0.65	Remote Similarity	NPD2493	Approved
0.6498	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5928	Phase 1
0.6494	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD8312	Approved
0.6493	Remote Similarity	NPD8313	Approved
0.6491	Remote Similarity	NPD8149	Discontinued
0.6489	Remote Similarity	NPD5914	Approved
0.6489	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7891	Discontinued
0.6485	Remote Similarity	NPD5805	Approved
0.6484	Remote Similarity	NPD6874	Approved
0.6482	Remote Similarity	NPD3684	Discontinued
0.6476	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6559	Discontinued
0.6471	Remote Similarity	NPD2972	Approved
0.6471	Remote Similarity	NPD2491	Approved
0.6471	Remote Similarity	NPD3533	Approved
0.6471	Remote Similarity	NPD3764	Approved
0.6468	Remote Similarity	NPD7654	Discontinued
0.6468	Remote Similarity	NPD2974	Approved
0.6468	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD2973	Approved
0.6468	Remote Similarity	NPD2975	Approved
0.6465	Remote Similarity	NPD2488	Approved
0.6465	Remote Similarity	NPD2490	Approved
0.6456	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6779	Approved
0.6455	Remote Similarity	NPD6778	Approved
0.6455	Remote Similarity	NPD6782	Approved
0.6455	Remote Similarity	NPD6776	Approved
0.6455	Remote Similarity	NPD6781	Approved
0.6455	Remote Similarity	NPD6780	Approved
0.6455	Remote Similarity	NPD6777	Approved
0.6454	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD955	Approved
0.6453	Remote Similarity	NPD3453	Discontinued
0.645	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD2792	Approved
0.6443	Remote Similarity	NPD7003	Approved
0.6442	Remote Similarity	NPD7228	Approved
0.6441	Remote Similarity	NPD4002	Approved
0.6441	Remote Similarity	NPD4004	Approved
0.6439	Remote Similarity	NPD8127	Discontinued
0.6438	Remote Similarity	NPD5071	Phase 2
0.6436	Remote Similarity	NPD5978	Approved
0.6436	Remote Similarity	NPD5977	Approved
0.6435	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6184	Discontinued
0.6422	Remote Similarity	NPD7907	Approved
0.6422	Remote Similarity	NPD5582	Discontinued
0.6419	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5025	Approved
0.6413	Remote Similarity	NPD7870	Phase 2
0.6413	Remote Similarity	NPD4582	Approved
0.6413	Remote Similarity	NPD4583	Approved
0.6413	Remote Similarity	NPD7871	Phase 2
0.6407	Remote Similarity	NPD4111	Phase 1
0.6407	Remote Similarity	NPD4665	Approved
0.64	Remote Similarity	NPD7585	Approved
0.6396	Remote Similarity	NPD2532	Approved
0.6396	Remote Similarity	NPD2534	Approved
0.6396	Remote Similarity	NPD2533	Approved
0.6392	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5641	Discontinued
0.6384	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD7999	Approved
0.638	Remote Similarity	NPD4580	Approved
0.6379	Remote Similarity	NPD3437	Discontinued
0.6379	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3749	Approved
0.6368	Remote Similarity	NPD7697	Approved
0.6368	Remote Similarity	NPD7696	Phase 3
0.6368	Remote Similarity	NPD7698	Approved
0.6368	Remote Similarity	NPD7279	Phase 2
0.6368	Remote Similarity	NPD7278	Phase 2
0.6368	Remote Similarity	NPD7435	Discontinued
0.6364	Remote Similarity	NPD7395	Discontinued
0.6359	Remote Similarity	NPD1196	Approved
0.6359	Remote Similarity	NPD6457	Approved
0.6356	Remote Similarity	NPD7583	Approved
0.6356	Remote Similarity	NPD7584	Approved
0.635	Remote Similarity	NPD5811	Approved
0.6347	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7874	Approved
0.6344	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD2968	Approved
0.6338	Remote Similarity	NPD7280	Phase 3
0.6338	Remote Similarity	NPD7281	Phase 3
0.6338	Remote Similarity	NPD2971	Approved
0.6337	Remote Similarity	NPD7417	Discontinued
0.6333	Remote Similarity	NPD3965	Phase 1
0.6323	Remote Similarity	NPD7627	Approved
0.6323	Remote Similarity	NPD7626	Approved
0.6321	Remote Similarity	NPD5637	Discontinued
0.6321	Remote Similarity	NPD7685	Pre-registration
0.6316	Remote Similarity	NPD2979	Phase 3
0.6316	Remote Similarity	NPD5676	Approved
0.6313	Remote Similarity	NPD5871	Discontinued
0.6308	Remote Similarity	NPD1195	Approved
0.6304	Remote Similarity	NPD7930	Approved
0.6301	Remote Similarity	NPD5488	Discontinued
0.6298	Remote Similarity	NPD3912	Discontinued
0.6293	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1891	Discontinued
0.6289	Remote Similarity	NPD2346	Discontinued
0.6287	Remote Similarity	NPD2366	Approved
0.628	Remote Similarity	NPD2247	Approved
0.628	Remote Similarity	NPD2249	Approved
0.6277	Remote Similarity	NPD7047	Phase 3
0.6277	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD4628	Phase 3

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