NPASS Compound

Structure

NPC295676 OpenBabel07101718312D 44 53 0 0 0 0 0 0 0 0999 V2000 -5.0918 -0.8980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4169 -2.0329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3178 0.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6848 -1.0329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4894 1.7358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8188 -0.5329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7913 5.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0867 3.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8604 4.8481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9528 3.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5040 4.9553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4783 1.9428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0162 1.2814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5508 0.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7330 3.6080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7705 -0.0231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5731 4.5900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0867 2.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5813 0.7571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5508 -0.5329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9243 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8188 0.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1877 2.0329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6848 0.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2858 4.3318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4207 1.1741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4241 3.6011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9528 1.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5508 2.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6848 1.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2059 2.9776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9528 0.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4932 3.2358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8188 2.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1368 3.3430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2162 0.7399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7114 3.8593 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8188 3.4671 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3587 -0.2179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4169 -1.0329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2723 4.4956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0305 0.7026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0312 2.8957 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 39 1 0 0 0 0 2 40 1 0 0 0 0 3 5 2 0 0 0 0 3 19 1 0 0 0 0 4 6 2 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 37 1 0 0 0 0 10 38 1 0 0 0 0 11 17 2 0 0 0 0 11 25 1 0 0 0 0 12 18 2 0 0 0 0 12 26 1 0 0 0 0 13 19 2 0 0 0 0 13 23 1 0 0 0 0 14 20 2 0 0 0 0 14 24 1 0 0 0 0 15 41 1 0 0 0 0 15 43 1 0 0 0 0 16 42 1 0 0 0 0 16 44 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 39 1 0 0 0 0 20 40 1 0 0 0 0 21 23 2 0 0 0 0 21 31 1 0 0 0 0 22 24 2 0 0 0 0 22 32 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 35 2 0 0 0 0 25 41 1 0 0 0 0 26 36 2 0 0 0 0 26 42 1 0 0 0 0 27 31 2 0 0 0 0 27 33 1 0 0 0 0 28 32 2 0 0 0 0 28 34 1 0 0 0 0 29 30 1 0 0 0 0 29 33 2 0 0 0 0 30 34 2 0 0 0 0 31 35 1 0 0 0 0 32 36 1 0 0 0 0 33 37 1 0 0 0 0 34 38 1 0 0 0 0 35 43 1 0 0 0 0 36 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.19
Volume:	583.472
LogP:	8.109
LogD:	4.273
LogS:	-10.395
# Rotatable Bonds:	3
TPSA:	79.44
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	10
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	3.533
Fsp3:	0.222
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.455
MDCK Permeability:	2.1572688638116233e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.906
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	94.07311248779297%
Volume Distribution (VD):	0.683
Pgp-substrate:	0.9490158557891846%

ADMET: Metabolism

CYP1A2-inhibitor:	0.858
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.987
CYP2C19-substrate:	0.161
CYP2C9-inhibitor:	0.628
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.888
CYP2D6-substrate:	0.962
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	8.408
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.119
Human Hepatotoxicity (H-HT):	0.937
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.335
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.873
Carcinogencity:	0.928
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.618

Download Data

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

Natural Product: NPC295676

Natural Product ID:	NPC295676
*Common Name:**	Bidebiline E
IUPAC Name:	n.a.
Synonyms:	Bidebiline E
Standard InCHIKey:	ORORFDPGSXPOAI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C36H28N2O6/c1-39-19-3-5-21-23(13-19)29(33-27-17(7-9-37-33)11-25-35(31(21)27)43-15-41-25)30-24-14-20(40-2)4-6-22(24)32-28-18(8-10-38-34(28)30)12-26-36(32)44-16-42-26/h3-6,11-14,37-38H,7-10,15-16H2,1-2H3
SMILES:	COc1ccc2c(c1)c(c1c3NCCc4c3c(c3c1cc(OC)cc3)c1c(c4)OCO1)c1c3c2c2OCOc2cc3CCN1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400245
PubChem CID:	23642920
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002348] Phenylquinolines [CHEMONTID:0002196] Naphthylquinolines

*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
NPO32512	polyalthia cerasoides	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[17845001]
NPO40530	Polyalthia cerasoides	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27490091]

☑ 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
MIC	1

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4.2	ug.mL-1	PMID[485713]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	6.25	ug.mL-1	PMID[485713]
NPT610	Others	Molecular identity unknown		IC50	=	20200.0	nM	PMID[485714]

☑ 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 NPC295676 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	509
0.1-0.2	2719
0.2-0.3	12286
0.3-0.4	5757
0.4-0.5	13274
0.5-0.6	6657
0.6-0.7	1038
0.7-0.8	414
0.8-0.85	28
0.85-0.9	11
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC212163
0.9834	High Similarity	NPC244606
0.9834	High Similarity	NPC156728
0.8944	High Similarity	NPC179704
0.8895	High Similarity	NPC249405
0.8883	High Similarity	NPC287588
0.8804	High Similarity	NPC474904
0.8804	High Similarity	NPC312531
0.8763	High Similarity	NPC302001
0.8571	High Similarity	NPC162653
0.8564	High Similarity	NPC285941
0.8492	Intermediate Similarity	NPC86144
0.8492	Intermediate Similarity	NPC304659
0.8424	Intermediate Similarity	NPC190461
0.8385	Intermediate Similarity	NPC23080
0.8385	Intermediate Similarity	NPC193906
0.838	Intermediate Similarity	NPC189470
0.8352	Intermediate Similarity	NPC6152
0.8245	Intermediate Similarity	NPC276674
0.8245	Intermediate Similarity	NPC33902
0.8167	Intermediate Similarity	NPC232924
0.8167	Intermediate Similarity	NPC306902
0.8167	Intermediate Similarity	NPC160298
0.8167	Intermediate Similarity	NPC266753
0.8167	Intermediate Similarity	NPC477559
0.8158	Intermediate Similarity	NPC320088
0.8152	Intermediate Similarity	NPC152212
0.8142	Intermediate Similarity	NPC210918
0.8138	Intermediate Similarity	NPC474506
0.8138	Intermediate Similarity	NPC32413
0.8128	Intermediate Similarity	NPC23219
0.8122	Intermediate Similarity	NPC24954
0.8101	Intermediate Similarity	NPC170503
0.8101	Intermediate Similarity	NPC203784
0.8101	Intermediate Similarity	NPC126519
0.8087	Intermediate Similarity	NPC476432
0.8087	Intermediate Similarity	NPC24264
0.8085	Intermediate Similarity	NPC267408
0.8085	Intermediate Similarity	NPC258695
0.8085	Intermediate Similarity	NPC470879
0.8075	Intermediate Similarity	NPC112575
0.8053	Intermediate Similarity	NPC135772
0.8043	Intermediate Similarity	NPC247389
0.8042	Intermediate Similarity	NPC476574
0.8042	Intermediate Similarity	NPC312918
0.8042	Intermediate Similarity	NPC477561
0.8042	Intermediate Similarity	NPC155442
0.8033	Intermediate Similarity	NPC16805
0.8033	Intermediate Similarity	NPC302527
0.8033	Intermediate Similarity	NPC225774
0.8033	Intermediate Similarity	NPC167546
0.8021	Intermediate Similarity	NPC477558
0.799	Intermediate Similarity	NPC78284
0.7989	Intermediate Similarity	NPC219341
0.7979	Intermediate Similarity	NPC281581
0.7946	Intermediate Similarity	NPC298979
0.7912	Intermediate Similarity	NPC477080
0.7906	Intermediate Similarity	NPC275132
0.7903	Intermediate Similarity	NPC241055
0.7901	Intermediate Similarity	NPC31311
0.7901	Intermediate Similarity	NPC234392
0.788	Intermediate Similarity	NPC475393
0.7876	Intermediate Similarity	NPC57036
0.7846	Intermediate Similarity	NPC475754
0.7845	Intermediate Similarity	NPC216459
0.7845	Intermediate Similarity	NPC41178
0.7845	Intermediate Similarity	NPC76079
0.7845	Intermediate Similarity	NPC138487
0.7838	Intermediate Similarity	NPC168409
0.7835	Intermediate Similarity	NPC476576
0.7835	Intermediate Similarity	NPC186546
0.7833	Intermediate Similarity	NPC210148
0.7833	Intermediate Similarity	NPC233029
0.7819	Intermediate Similarity	NPC19520
0.7819	Intermediate Similarity	NPC149090
0.7812	Intermediate Similarity	NPC476575
0.7802	Intermediate Similarity	NPC146288
0.7799	Intermediate Similarity	NPC46451
0.7796	Intermediate Similarity	NPC81247
0.7796	Intermediate Similarity	NPC476573
0.7796	Intermediate Similarity	NPC35627
0.7778	Intermediate Similarity	NPC55470
0.7778	Intermediate Similarity	NPC81733
0.7778	Intermediate Similarity	NPC235076
0.7778	Intermediate Similarity	NPC326316
0.7772	Intermediate Similarity	NPC302275
0.7756	Intermediate Similarity	NPC188420
0.7754	Intermediate Similarity	NPC204947
0.7751	Intermediate Similarity	NPC100079
0.7751	Intermediate Similarity	NPC23614
0.7749	Intermediate Similarity	NPC320223
0.7749	Intermediate Similarity	NPC114364
0.7739	Intermediate Similarity	NPC17677
0.7737	Intermediate Similarity	NPC128560
0.7737	Intermediate Similarity	NPC199465
0.7737	Intermediate Similarity	NPC229166
0.7729	Intermediate Similarity	NPC271215
0.7729	Intermediate Similarity	NPC149471
0.772	Intermediate Similarity	NPC73492
0.772	Intermediate Similarity	NPC299990
0.7716	Intermediate Similarity	NPC117717
0.7684	Intermediate Similarity	NPC477020
0.7684	Intermediate Similarity	NPC66341
0.7684	Intermediate Similarity	NPC192135
0.7672	Intermediate Similarity	NPC26240
0.7672	Intermediate Similarity	NPC69712
0.7672	Intermediate Similarity	NPC477562
0.7667	Intermediate Similarity	NPC92541
0.7665	Intermediate Similarity	NPC79213
0.7663	Intermediate Similarity	NPC476572
0.7656	Intermediate Similarity	NPC118633
0.7656	Intermediate Similarity	NPC148693
0.7656	Intermediate Similarity	NPC294790
0.7653	Intermediate Similarity	NPC296742
0.765	Intermediate Similarity	NPC93593
0.765	Intermediate Similarity	NPC99659
0.765	Intermediate Similarity	NPC325871
0.7632	Intermediate Similarity	NPC475215
0.7632	Intermediate Similarity	NPC108434
0.7629	Intermediate Similarity	NPC248642
0.7624	Intermediate Similarity	NPC471489
0.7617	Intermediate Similarity	NPC475479
0.7617	Intermediate Similarity	NPC126284
0.7617	Intermediate Similarity	NPC243454
0.7611	Intermediate Similarity	NPC475959
0.761	Intermediate Similarity	NPC222561
0.7609	Intermediate Similarity	NPC247639
0.7609	Intermediate Similarity	NPC25084
0.7602	Intermediate Similarity	NPC14507
0.7602	Intermediate Similarity	NPC477186
0.7602	Intermediate Similarity	NPC47077
0.7602	Intermediate Similarity	NPC224293
0.759	Intermediate Similarity	NPC156576
0.7577	Intermediate Similarity	NPC239584
0.7569	Intermediate Similarity	NPC219162
0.7563	Intermediate Similarity	NPC112676
0.7561	Intermediate Similarity	NPC261388
0.7556	Intermediate Similarity	NPC144863
0.7554	Intermediate Similarity	NPC80129
0.7554	Intermediate Similarity	NPC187022
0.7554	Intermediate Similarity	NPC244112
0.7553	Intermediate Similarity	NPC238530
0.7553	Intermediate Similarity	NPC232514
0.7553	Intermediate Similarity	NPC276944
0.7551	Intermediate Similarity	NPC69213
0.7542	Intermediate Similarity	NPC145304
0.7538	Intermediate Similarity	NPC478093
0.7538	Intermediate Similarity	NPC116284
0.7526	Intermediate Similarity	NPC474507
0.7523	Intermediate Similarity	NPC118121
0.7514	Intermediate Similarity	NPC130941
0.7512	Intermediate Similarity	NPC251160
0.75	Intermediate Similarity	NPC204446
0.75	Intermediate Similarity	NPC473589
0.75	Intermediate Similarity	NPC256124
0.75	Intermediate Similarity	NPC478092
0.75	Intermediate Similarity	NPC30182
0.75	Intermediate Similarity	NPC478091
0.7487	Intermediate Similarity	NPC473716
0.7487	Intermediate Similarity	NPC166014
0.7487	Intermediate Similarity	NPC27410
0.7487	Intermediate Similarity	NPC475597
0.7475	Intermediate Similarity	NPC237579
0.7473	Intermediate Similarity	NPC211296
0.7459	Intermediate Similarity	NPC90844
0.7459	Intermediate Similarity	NPC51957
0.7459	Intermediate Similarity	NPC95075
0.7459	Intermediate Similarity	NPC210437
0.7459	Intermediate Similarity	NPC476144
0.7459	Intermediate Similarity	NPC253883
0.7459	Intermediate Similarity	NPC16107
0.7459	Intermediate Similarity	NPC106295
0.745	Intermediate Similarity	NPC24260
0.744	Intermediate Similarity	NPC308943
0.7438	Intermediate Similarity	NPC5374
0.7436	Intermediate Similarity	NPC40496
0.7436	Intermediate Similarity	NPC119068
0.7433	Intermediate Similarity	NPC111485
0.7424	Intermediate Similarity	NPC214116
0.7423	Intermediate Similarity	NPC148709
0.7423	Intermediate Similarity	NPC476577
0.7423	Intermediate Similarity	NPC173416
0.7418	Intermediate Similarity	NPC7467
0.7413	Intermediate Similarity	NPC29472
0.7407	Intermediate Similarity	NPC324144
0.7402	Intermediate Similarity	NPC25897
0.7398	Intermediate Similarity	NPC257269
0.7398	Intermediate Similarity	NPC230276
0.7382	Intermediate Similarity	NPC205421
0.7382	Intermediate Similarity	NPC474931
0.7382	Intermediate Similarity	NPC81218
0.7382	Intermediate Similarity	NPC12053
0.7382	Intermediate Similarity	NPC145832
0.7382	Intermediate Similarity	NPC306555
0.7382	Intermediate Similarity	NPC158376
0.7382	Intermediate Similarity	NPC117188
0.7379	Intermediate Similarity	NPC159101
0.7368	Intermediate Similarity	NPC13504
0.7368	Intermediate Similarity	NPC96603
0.7368	Intermediate Similarity	NPC136508

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 NPC295676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	785
0.2-0.3	1080
0.3-0.4	1700
0.4-0.5	3082
0.5-0.6	1834
0.6-0.7	380
0.7-0.8	30
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
0.81	Intermediate Similarity	NPD4859	Phase 1
0.7799	Intermediate Similarity	NPD3763	Approved
0.7554	Intermediate Similarity	NPD7298	Approved
0.7552	Intermediate Similarity	NPD7479	Phase 2
0.7459	Intermediate Similarity	NPD4584	Approved
0.7436	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD5810	Discontinued
0.7377	Intermediate Similarity	NPD6030	Approved
0.7377	Intermediate Similarity	NPD6031	Approved
0.7363	Intermediate Similarity	NPD7262	Phase 1
0.7358	Intermediate Similarity	NPD8251	Approved
0.7358	Intermediate Similarity	NPD8099	Discontinued
0.7358	Intermediate Similarity	NPD8252	Approved
0.732	Intermediate Similarity	NPD8156	Discontinued
0.7316	Intermediate Similarity	NPD6037	Discontinued
0.7297	Intermediate Similarity	NPD6723	Discontinued
0.7293	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD3815	Phase 1
0.7264	Intermediate Similarity	NPD3816	Phase 1
0.7243	Intermediate Similarity	NPD8149	Discontinued
0.7222	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4083	Discontinued
0.7164	Intermediate Similarity	NPD3349	Phase 2
0.715	Intermediate Similarity	NPD6612	Phase 2
0.7143	Intermediate Similarity	NPD7922	Phase 1
0.7136	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD8053	Approved
0.71	Intermediate Similarity	NPD8054	Approved
0.7098	Intermediate Similarity	NPD4885	Approved
0.7097	Intermediate Similarity	NPD4727	Phase 1
0.7073	Intermediate Similarity	NPD6493	Phase 3
0.7068	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5071	Phase 2
0.7044	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5582	Discontinued
0.7027	Intermediate Similarity	NPD7598	Phase 2
0.7016	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7034	Discontinued
0.7	Intermediate Similarity	NPD3515	Approved
0.7	Intermediate Similarity	NPD3516	Approved
0.6973	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5641	Discontinued
0.6923	Remote Similarity	NPD6107	Approved
0.6916	Remote Similarity	NPD5658	Approved
0.6911	Remote Similarity	NPD1769	Discontinued
0.6904	Remote Similarity	NPD4481	Phase 3
0.6888	Remote Similarity	NPD4166	Phase 2
0.6888	Remote Similarity	NPD3051	Approved
0.6884	Remote Similarity	NPD5600	Discontinued
0.6882	Remote Similarity	NPD3845	Phase 1
0.6872	Remote Similarity	NPD554	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3920	Phase 2
0.6845	Remote Similarity	NPD2421	Approved
0.6845	Remote Similarity	NPD2420	Approved
0.6837	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD3983	Phase 3
0.6833	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3301	Approved
0.6818	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6340	Approved
0.6814	Remote Similarity	NPD6339	Approved
0.6814	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3922	Approved
0.6812	Remote Similarity	NPD3923	Approved
0.6812	Remote Similarity	NPD3921	Approved
0.6812	Remote Similarity	NPD3924	Approved
0.681	Remote Similarity	NPD6877	Discontinued
0.6793	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5938	Phase 3
0.6784	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6526	Approved
0.6772	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7833	Phase 2
0.6769	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7831	Phase 2
0.6768	Remote Similarity	NPD2969	Approved
0.6768	Remote Similarity	NPD2970	Approved
0.6763	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4017	Approved
0.6751	Remote Similarity	NPD7802	Discontinued
0.6737	Remote Similarity	NPD3639	Approved
0.6737	Remote Similarity	NPD3640	Phase 3
0.6737	Remote Similarity	NPD5976	Discontinued
0.6737	Remote Similarity	NPD3641	Approved
0.6734	Remote Similarity	NPD2489	Approved
0.6734	Remote Similarity	NPD27	Approved
0.6734	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6297	Approved
0.6718	Remote Similarity	NPD6788	Approved
0.6712	Remote Similarity	NPD7827	Phase 1
0.6702	Remote Similarity	NPD2883	Discontinued
0.6702	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD2977	Approved
0.6701	Remote Similarity	NPD2978	Approved
0.6699	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD8095	Phase 1
0.6696	Remote Similarity	NPD6625	Approved
0.6685	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6527	Approved
0.6667	Remote Similarity	NPD5530	Phase 1
0.6667	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8358	Approved
0.6667	Remote Similarity	NPD6357	Discontinued
0.6667	Remote Similarity	NPD7906	Approved
0.6667	Remote Similarity	NPD4597	Approved
0.6667	Remote Similarity	NPD4598	Approved
0.6653	Remote Similarity	NPD6230	Discontinued
0.6652	Remote Similarity	NPD5930	Phase 3
0.6652	Remote Similarity	NPD5903	Approved
0.6652	Remote Similarity	NPD5902	Approved
0.6652	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4420	Approved
0.665	Remote Similarity	NPD4796	Discontinued
0.6636	Remote Similarity	NPD7225	Discontinued
0.6635	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD2843	Phase 2
0.6635	Remote Similarity	NPD2845	Phase 2
0.6634	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD19	Approved
0.6633	Remote Similarity	NPD1742	Approved
0.6633	Remote Similarity	NPD1743	Approved
0.6632	Remote Similarity	NPD1424	Approved
0.6623	Remote Similarity	NPD6494	Phase 2
0.6618	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8244	Phase 2
0.6602	Remote Similarity	NPD6618	Phase 2
0.6602	Remote Similarity	NPD6853	Approved
0.6602	Remote Similarity	NPD6851	Approved
0.6598	Remote Similarity	NPD4773	Phase 2
0.6598	Remote Similarity	NPD4772	Phase 2
0.6587	Remote Similarity	NPD3398	Discontinued
0.6583	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD2898	Approved
0.6564	Remote Similarity	NPD7278	Phase 2
0.6564	Remote Similarity	NPD7279	Phase 2
0.6562	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5241	Discontinued
0.6558	Remote Similarity	NPD6238	Discontinued
0.6557	Remote Similarity	NPD3110	Approved
0.6557	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3109	Approved
0.6555	Remote Similarity	NPD5928	Phase 1
0.6553	Remote Similarity	NPD7311	Approved
0.6553	Remote Similarity	NPD7310	Approved
0.6553	Remote Similarity	NPD7281	Phase 3
0.6553	Remote Similarity	NPD2971	Approved
0.6553	Remote Similarity	NPD7313	Approved
0.6553	Remote Similarity	NPD7280	Phase 3
0.6553	Remote Similarity	NPD7312	Approved
0.6553	Remote Similarity	NPD2968	Approved
0.6552	Remote Similarity	NPD5560	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5183	Approved
0.655	Remote Similarity	NPD5186	Approved
0.6542	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5718	Phase 2
0.6538	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5005	Approved
0.6528	Remote Similarity	NPD5006	Approved
0.6522	Remote Similarity	NPD7309	Approved
0.6516	Remote Similarity	NPD8091	Phase 3
0.6516	Remote Similarity	NPD4502	Phase 2
0.6512	Remote Similarity	NPD5457	Discontinued
0.6508	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5754	Discontinued
0.6507	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD3124	Discontinued
0.649	Remote Similarity	NPD7956	Approved
0.649	Remote Similarity	NPD7955	Approved
0.6482	Remote Similarity	NPD7400	Phase 3
0.648	Remote Similarity	NPD5720	Discontinued
0.6476	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD4577	Approved
0.6473	Remote Similarity	NPD4578	Approved
0.6471	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6071	Discontinued
0.6465	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7708	Approved
0.6462	Remote Similarity	NPD5150	Phase 2
0.6459	Remote Similarity	NPD4663	Approved
0.6457	Remote Similarity	NPD4356	Discontinued

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