NPASS Compound

Structure

NPC114335 OpenBabel07101719512D 28 31 0 0 0 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 17 1 0 0 0 0 8 19 2 0 0 0 0 9 10 2 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 21 1 0 0 0 0 14 25 2 0 0 0 0 15 22 2 0 0 0 0 15 25 1 0 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 21 1 0 0 0 0 18 24 2 0 0 0 0 19 23 1 0 0 0 0 19 27 1 0 0 0 0 20 23 2 0 0 0 0 20 28 1 0 0 0 0 22 24 1 0 0 0 0 24 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	373.17
Volume:	400.437
LogP:	5.71
LogD:	3.644
LogS:	-4.81
# Rotatable Bonds:	3
TPSA:	51.58
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	2.553
Fsp3:	0.208
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:	-4.973
MDCK Permeability:	2.968711851281114e-05
Pgp-inhibitor:	0.396
Pgp-substrate:	0.885
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.723
30% Bioavailability (F30%):	0.884

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	91.30048370361328%
Volume Distribution (VD):	0.429
Pgp-substrate:	1.9581986665725708%

ADMET: Metabolism

CYP1A2-inhibitor:	0.825
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.657
CYP2C19-substrate:	0.517
CYP2C9-inhibitor:	0.738
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.446
CYP2D6-substrate:	0.946
CYP3A4-inhibitor:	0.323
CYP3A4-substrate:	0.648

ADMET: Excretion

Clearance (CL):	4.456
Half-life (T1/2):	0.125

ADMET: Toxicity

hERG Blockers:	0.553
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.811
Rat Oral Acute Toxicity:	0.611
Maximum Recommended Daily Dose:	0.25
Skin Sensitization:	0.598
Carcinogencity:	0.849
Eye Corrosion:	0.003
Eye Irritation:	0.427
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC114335

Natural Product ID:	NPC114335
*Common Name:**	JTZHYHRJMAAGGY-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	7,1'-Coupled Ent-Dioncophylleine A
Standard InCHIKey:	JTZHYHRJMAAGGY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H23NO3/c1-13-11-20(28-5)23-17(7-6-8-19(23)27-4)21(13)18-10-9-16-12-14(2)25-15(3)22(16)24(18)26/h6-12,26H,1-5H3
SMILES:	COc1cccc2c1c(OC)cc(c2c1ccc2c(c1O)c(C)nc(c2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518407
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002195] Naphthylisoquinolines

*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
NPO32919	ancistrocladus benomensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620251]
NPO32919	ancistrocladus benomensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921410]

☑ 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
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3.9	ug.mL-1	PMID[502750]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	54.0	ug.mL-1	PMID[502750]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	5.6	ug.mL-1	PMID[502750]

☑ 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 NPC114335 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	531
0.1-0.2	2423
0.2-0.3	12210
0.3-0.4	5191
0.4-0.5	9659
0.5-0.6	10360
0.6-0.7	1865
0.7-0.8	426
0.8-0.85	23
0.85-0.9	4
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC280964
1.0	High Similarity	NPC141915
0.9392	High Similarity	NPC137929
0.9392	High Similarity	NPC164374
0.8729	High Similarity	NPC469390
0.8717	High Similarity	NPC469440
0.8715	High Similarity	NPC61350
0.8595	High Similarity	NPC224928
0.8438	Intermediate Similarity	NPC470931
0.8333	Intermediate Similarity	NPC304183
0.8259	Intermediate Similarity	NPC122463
0.8227	Intermediate Similarity	NPC200888
0.8222	Intermediate Similarity	NPC283152
0.8201	Intermediate Similarity	NPC243834
0.8201	Intermediate Similarity	NPC70956
0.8197	Intermediate Similarity	NPC62069
0.8196	Intermediate Similarity	NPC193777
0.8173	Intermediate Similarity	NPC112206
0.8173	Intermediate Similarity	NPC202605
0.8162	Intermediate Similarity	NPC66083
0.8073	Intermediate Similarity	NPC11017
0.8069	Intermediate Similarity	NPC174049
0.8066	Intermediate Similarity	NPC288943
0.806	Intermediate Similarity	NPC473822
0.8054	Intermediate Similarity	NPC42591
0.8011	Intermediate Similarity	NPC312872
0.8	Intermediate Similarity	NPC476581
0.8	Intermediate Similarity	NPC26850
0.8	Intermediate Similarity	NPC36229
0.8	Intermediate Similarity	NPC16452
0.799	Intermediate Similarity	NPC118121
0.799	Intermediate Similarity	NPC475085
0.799	Intermediate Similarity	NPC48353
0.799	Intermediate Similarity	NPC255800
0.799	Intermediate Similarity	NPC96584
0.799	Intermediate Similarity	NPC475112
0.799	Intermediate Similarity	NPC291535
0.7989	Intermediate Similarity	NPC133140
0.7989	Intermediate Similarity	NPC195268
0.7981	Intermediate Similarity	NPC201508
0.798	Intermediate Similarity	NPC469439
0.7958	Intermediate Similarity	NPC473053
0.7949	Intermediate Similarity	NPC223427
0.7938	Intermediate Similarity	NPC267423
0.7931	Intermediate Similarity	NPC473179
0.79	Intermediate Similarity	NPC251160
0.7846	Intermediate Similarity	NPC31930
0.7829	Intermediate Similarity	NPC26872
0.7822	Intermediate Similarity	NPC235076
0.7819	Intermediate Similarity	NPC204385
0.7812	Intermediate Similarity	NPC131017
0.7799	Intermediate Similarity	NPC252251
0.7794	Intermediate Similarity	NPC100079
0.7794	Intermediate Similarity	NPC204446
0.7794	Intermediate Similarity	NPC23614
0.7788	Intermediate Similarity	NPC202503
0.7784	Intermediate Similarity	NPC72211
0.7778	Intermediate Similarity	NPC476106
0.7766	Intermediate Similarity	NPC162484
0.775	Intermediate Similarity	NPC201697
0.7744	Intermediate Similarity	NPC4071
0.7744	Intermediate Similarity	NPC476578
0.7744	Intermediate Similarity	NPC476582
0.7737	Intermediate Similarity	NPC128751
0.7732	Intermediate Similarity	NPC153042
0.7727	Intermediate Similarity	NPC302807
0.7725	Intermediate Similarity	NPC477531
0.7723	Intermediate Similarity	NPC296482
0.7723	Intermediate Similarity	NPC53069
0.7723	Intermediate Similarity	NPC202768
0.7716	Intermediate Similarity	NPC66815
0.7714	Intermediate Similarity	NPC476997
0.7713	Intermediate Similarity	NPC320394
0.7711	Intermediate Similarity	NPC470020
0.7709	Intermediate Similarity	NPC79328
0.7696	Intermediate Similarity	NPC106833
0.7696	Intermediate Similarity	NPC469497
0.7681	Intermediate Similarity	NPC477532
0.768	Intermediate Similarity	NPC70259
0.7678	Intermediate Similarity	NPC476998
0.7678	Intermediate Similarity	NPC476996
0.7678	Intermediate Similarity	NPC209174
0.7672	Intermediate Similarity	NPC94943
0.767	Intermediate Similarity	NPC46451
0.7667	Intermediate Similarity	NPC221864
0.7667	Intermediate Similarity	NPC177404
0.7667	Intermediate Similarity	NPC473185
0.7662	Intermediate Similarity	NPC209769
0.7656	Intermediate Similarity	NPC473449
0.7653	Intermediate Similarity	NPC473182
0.7635	Intermediate Similarity	NPC473180
0.7632	Intermediate Similarity	NPC33902
0.7632	Intermediate Similarity	NPC276674
0.763	Intermediate Similarity	NPC476994
0.7629	Intermediate Similarity	NPC205934
0.7629	Intermediate Similarity	NPC43787
0.7626	Intermediate Similarity	NPC199277
0.7626	Intermediate Similarity	NPC135887
0.7624	Intermediate Similarity	NPC271388
0.7624	Intermediate Similarity	NPC290689
0.7624	Intermediate Similarity	NPC235143
0.7624	Intermediate Similarity	NPC205255
0.7624	Intermediate Similarity	NPC230956
0.7624	Intermediate Similarity	NPC119649
0.7624	Intermediate Similarity	NPC188420
0.7619	Intermediate Similarity	NPC190007
0.7614	Intermediate Similarity	NPC477019
0.7606	Intermediate Similarity	NPC206201
0.7602	Intermediate Similarity	NPC280853
0.7598	Intermediate Similarity	NPC149471
0.7598	Intermediate Similarity	NPC474594
0.7598	Intermediate Similarity	NPC271215
0.7593	Intermediate Similarity	NPC11408
0.7586	Intermediate Similarity	NPC220337
0.7585	Intermediate Similarity	NPC148409
0.7582	Intermediate Similarity	NPC80759
0.7582	Intermediate Similarity	NPC79402
0.7577	Intermediate Similarity	NPC279401
0.7577	Intermediate Similarity	NPC79293
0.7577	Intermediate Similarity	NPC289786
0.7566	Intermediate Similarity	NPC212535
0.7558	Intermediate Similarity	NPC245657
0.7558	Intermediate Similarity	NPC285016
0.7556	Intermediate Similarity	NPC29647
0.7553	Intermediate Similarity	NPC478032
0.7552	Intermediate Similarity	NPC246700
0.7549	Intermediate Similarity	NPC171409
0.7549	Intermediate Similarity	NPC96405
0.7544	Intermediate Similarity	NPC471596
0.7537	Intermediate Similarity	NPC199667
0.7534	Intermediate Similarity	NPC15406
0.7529	Intermediate Similarity	NPC471598
0.7523	Intermediate Similarity	NPC217554
0.7512	Intermediate Similarity	NPC472111
0.7512	Intermediate Similarity	NPC478074
0.75	Intermediate Similarity	NPC209377
0.75	Intermediate Similarity	NPC208284
0.7488	Intermediate Similarity	NPC473181
0.7487	Intermediate Similarity	NPC476565
0.7487	Intermediate Similarity	NPC476044
0.7476	Intermediate Similarity	NPC280272
0.7476	Intermediate Similarity	NPC210434
0.7475	Intermediate Similarity	NPC313189
0.7475	Intermediate Similarity	NPC128823
0.7475	Intermediate Similarity	NPC287437
0.7463	Intermediate Similarity	NPC285558
0.7463	Intermediate Similarity	NPC470930
0.7462	Intermediate Similarity	NPC474188
0.7461	Intermediate Similarity	NPC320088
0.7459	Intermediate Similarity	NPC56887
0.7459	Intermediate Similarity	NPC195392
0.7459	Intermediate Similarity	NPC193853
0.7459	Intermediate Similarity	NPC223077
0.7451	Intermediate Similarity	NPC11464
0.7447	Intermediate Similarity	NPC285941
0.7438	Intermediate Similarity	NPC475910
0.7437	Intermediate Similarity	NPC234197
0.7437	Intermediate Similarity	NPC329747
0.7436	Intermediate Similarity	NPC259350
0.7436	Intermediate Similarity	NPC223236
0.7432	Intermediate Similarity	NPC118511
0.7432	Intermediate Similarity	NPC159319
0.7432	Intermediate Similarity	NPC473057
0.7421	Intermediate Similarity	NPC284141
0.7418	Intermediate Similarity	NPC206736
0.7418	Intermediate Similarity	NPC195766
0.7416	Intermediate Similarity	NPC193267
0.7416	Intermediate Similarity	NPC213530
0.7402	Intermediate Similarity	NPC469589
0.7395	Intermediate Similarity	NPC316065
0.7395	Intermediate Similarity	NPC289905
0.7389	Intermediate Similarity	NPC474595
0.7385	Intermediate Similarity	NPC476995
0.7385	Intermediate Similarity	NPC473183
0.7381	Intermediate Similarity	NPC150239
0.7377	Intermediate Similarity	NPC315214
0.7377	Intermediate Similarity	NPC47298
0.7373	Intermediate Similarity	NPC90875
0.7373	Intermediate Similarity	NPC473184
0.7361	Intermediate Similarity	NPC233334
0.7349	Intermediate Similarity	NPC24019
0.7349	Intermediate Similarity	NPC469792
0.7345	Intermediate Similarity	NPC161292
0.7344	Intermediate Similarity	NPC84478
0.7341	Intermediate Similarity	NPC471594
0.734	Intermediate Similarity	NPC470164
0.734	Intermediate Similarity	NPC323345
0.7337	Intermediate Similarity	NPC32028
0.7333	Intermediate Similarity	NPC474904
0.7333	Intermediate Similarity	NPC183537
0.7323	Intermediate Similarity	NPC472193
0.7321	Intermediate Similarity	NPC314552
0.732	Intermediate Similarity	NPC219170
0.732	Intermediate Similarity	NPC180253
0.7316	Intermediate Similarity	NPC88363
0.7316	Intermediate Similarity	NPC472168
0.7308	Intermediate Similarity	NPC123323
0.7304	Intermediate Similarity	NPC135549
0.7302	Intermediate Similarity	NPC194724
0.7299	Intermediate Similarity	NPC174760

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 NPC114335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	689
0.2-0.3	923
0.3-0.4	1239
0.4-0.5	2638
0.5-0.6	2477
0.6-0.7	735
0.7-0.8	100
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8483	Intermediate Similarity	NPD3920	Phase 2
0.8352	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5530	Phase 1
0.8103	Intermediate Similarity	NPD5429	Discontinued
0.8051	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.801	Intermediate Similarity	NPD7222	Phase 2
0.7989	Intermediate Similarity	NPD3923	Approved
0.7989	Intermediate Similarity	NPD3922	Approved
0.7989	Intermediate Similarity	NPD3921	Approved
0.7989	Intermediate Similarity	NPD3924	Approved
0.7906	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD7069	Discontinued
0.7739	Intermediate Similarity	NPD7452	Approved
0.7739	Intermediate Similarity	NPD7453	Approved
0.7723	Intermediate Similarity	NPD3816	Phase 1
0.7723	Intermediate Similarity	NPD3815	Phase 1
0.7708	Intermediate Similarity	NPD6569	Phase 2
0.7707	Intermediate Similarity	NPD7395	Discontinued
0.77	Intermediate Similarity	NPD7672	Approved
0.77	Intermediate Similarity	NPD7671	Approved
0.767	Intermediate Similarity	NPD3763	Approved
0.7668	Intermediate Similarity	NPD6361	Phase 2
0.766	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6159	Phase 2
0.7632	Intermediate Similarity	NPD4375	Approved
0.7586	Intermediate Similarity	NPD4502	Phase 2
0.757	Intermediate Similarity	NPD6494	Phase 2
0.7568	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5488	Discontinued
0.7538	Intermediate Similarity	NPD6208	Discontinued
0.7538	Intermediate Similarity	NPD6590	Discontinued
0.7538	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4204	Approved
0.7513	Intermediate Similarity	NPD4203	Approved
0.7513	Intermediate Similarity	NPD3386	Phase 2
0.75	Intermediate Similarity	NPD7479	Phase 2
0.75	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6991	Approved
0.75	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4551	Phase 2
0.7475	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD6988	Phase 1
0.7449	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2917	Approved
0.7438	Intermediate Similarity	NPD5658	Approved
0.7427	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6150	Discontinued
0.7424	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5512	Phase 3
0.7407	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4889	Approved
0.7396	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7418	Discontinued
0.7377	Intermediate Similarity	NPD1685	Approved
0.7377	Intermediate Similarity	NPD1684	Approved
0.7363	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4418	Discontinued
0.733	Intermediate Similarity	NPD5936	Approved
0.733	Intermediate Similarity	NPD5939	Approved
0.7323	Intermediate Similarity	NPD6550	Discontinued
0.7321	Intermediate Similarity	NPD5164	Discontinued
0.7302	Intermediate Similarity	NPD7555	Discontinued
0.73	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6158	Phase 2
0.7277	Intermediate Similarity	NPD6975	Discontinued
0.7273	Intermediate Similarity	NPD7474	Suspended
0.7268	Intermediate Similarity	NPD5256	Discontinued
0.7233	Intermediate Similarity	NPD4437	Phase 3
0.7231	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7417	Discontinued
0.7206	Intermediate Similarity	NPD4035	Approved
0.7206	Intermediate Similarity	NPD32	Approved
0.7206	Intermediate Similarity	NPD4033	Approved
0.7206	Intermediate Similarity	NPD31	Approved
0.7206	Intermediate Similarity	NPD4122	Approved
0.7206	Intermediate Similarity	NPD4037	Approved
0.7206	Intermediate Similarity	NPD4036	Approved
0.7206	Intermediate Similarity	NPD4034	Approved
0.7206	Intermediate Similarity	NPD4039	Approved
0.7206	Intermediate Similarity	NPD4038	Approved
0.7184	Intermediate Similarity	NPD2916	Discontinued
0.7178	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6327	Phase 1
0.7176	Intermediate Similarity	NPD6326	Phase 2
0.7171	Intermediate Similarity	NPD3003	Approved
0.7169	Intermediate Similarity	NPD7558	Phase 2
0.7164	Intermediate Similarity	NPD2727	Phase 2
0.7163	Intermediate Similarity	NPD3925	Approved
0.7162	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD8016	Phase 3
0.7158	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5903	Approved
0.7143	Intermediate Similarity	NPD5902	Approved
0.7136	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7675	Phase 3
0.713	Intermediate Similarity	NPD7674	Phase 3
0.713	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD2177	Approved
0.7129	Intermediate Similarity	NPD4927	Discontinued
0.7129	Intermediate Similarity	NPD2175	Phase 3
0.7129	Intermediate Similarity	NPD2176	Approved
0.7123	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2334	Discontinued
0.712	Intermediate Similarity	NPD5100	Phase 3
0.7114	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD3396	Approved
0.71	Intermediate Similarity	NPD3395	Approved
0.71	Intermediate Similarity	NPD6251	Discontinued
0.7089	Intermediate Similarity	NPD6501	Approved
0.7089	Intermediate Similarity	NPD6500	Approved
0.7089	Intermediate Similarity	NPD3875	Discontinued
0.7089	Intermediate Similarity	NPD7194	Discontinued
0.7088	Intermediate Similarity	NPD2882	Phase 1
0.7081	Intermediate Similarity	NPD6220	Phase 3
0.707	Intermediate Similarity	NPD7219	Approved
0.707	Intermediate Similarity	NPD7221	Approved
0.707	Intermediate Similarity	NPD6736	Discontinued
0.7056	Intermediate Similarity	NPD5930	Phase 3
0.7053	Intermediate Similarity	NPD6290	Phase 2
0.7053	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1038	Approved
0.7044	Intermediate Similarity	NPD8395	Approved
0.7044	Intermediate Similarity	NPD8396	Approved
0.7041	Intermediate Similarity	NPD2762	Phase 2
0.7039	Intermediate Similarity	NPD4795	Phase 2
0.7037	Intermediate Similarity	NPD2781	Approved
0.7032	Intermediate Similarity	NPD7567	Approved
0.7028	Intermediate Similarity	NPD5612	Discontinued
0.7021	Intermediate Similarity	NPD2780	Approved
0.7021	Intermediate Similarity	NPD2782	Approved
0.7019	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5617	Suspended
0.701	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6246	Approved
0.7	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3963	Phase 1
0.7	Intermediate Similarity	NPD5416	Discontinued
0.6991	Remote Similarity	NPD1954	Phase 1
0.699	Remote Similarity	NPD4044	Discontinued
0.6987	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3525	Discontinued
0.6983	Remote Similarity	NPD8244	Phase 2
0.6981	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3477	Phase 2
0.6976	Remote Similarity	NPD4511	Phase 1
0.6976	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3037	Phase 1
0.6972	Remote Similarity	NPD7426	Phase 1
0.6963	Remote Similarity	NPD6568	Discontinued
0.6963	Remote Similarity	NPD6985	Discontinued
0.6961	Remote Similarity	NPD4052	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7948	Phase 1
0.6946	Remote Similarity	NPD2952	Discontinued
0.6935	Remote Similarity	NPD4021	Phase 2
0.6931	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD1740	Approved
0.6927	Remote Similarity	NPD1739	Approved
0.6915	Remote Similarity	NPD4372	Phase 1
0.6907	Remote Similarity	NPD6642	Approved
0.6907	Remote Similarity	NPD6641	Approved
0.6901	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3342	Phase 2
0.6898	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5938	Phase 3
0.6891	Remote Similarity	NPD6492	Phase 2
0.6886	Remote Similarity	NPD4349	Approved
0.6886	Remote Similarity	NPD4350	Approved
0.6884	Remote Similarity	NPD2749	Discontinued
0.6884	Remote Similarity	NPD2383	Phase 1
0.6881	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD1768	Approved
0.6872	Remote Similarity	NPD6473	Phase 1
0.6864	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1229	Phase 2
0.6861	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5945	Phase 1
0.6854	Remote Similarity	NPD5944	Phase 1
0.6851	Remote Similarity	NPD3301	Approved
0.6847	Remote Similarity	NPD6962	Phase 2
0.6845	Remote Similarity	NPD6219	Discontinued
0.6844	Remote Similarity	NPD5805	Approved
0.6842	Remote Similarity	NPD3842	Clinical (unspecified phase)

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