NPASS Compound

Structure

CID52557 OpenBabel06191715392D 26 30 0 0 1 0 0 0 0 0999 V2000 -3.9845 3.5583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6306 4.9201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0840 3.5583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4163 1.1789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4163 0.2783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6364 1.6291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6364 -0.1720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3663 2.2798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0819 1.0471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8591 1.9644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5498 3.1208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1834 1.9985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8565 1.1789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3161 1.7006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8565 0.2783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4250 0.8227 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2619 2.3740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5293 0.7286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9915 3.1908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9511 2.2911 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7913 1.6454 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -4.3087 2.6360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2326 3.6756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5902 4.0204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 26 1 0 0 0 0 3 12 2 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 16 2 0 0 0 0 8 14 1 0 0 0 0 8 18 1 0 0 0 0 9 15 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 19 2 0 0 0 0 15 21 1 6 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 23 1 1 0 0 0 18 21 1 6 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.18
Volume:	361.535
LogP:	2.408
LogD:	2.649
LogS:	-2.71
# Rotatable Bonds:	3
TPSA:	65.56
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	5.357
Fsp3:	0.476
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:	-4.928
MDCK Permeability:	2.8541122446767986e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.277
Human Intestinal Absorption (HIA):	0.606
20% Bioavailability (F20%):	0.553
30% Bioavailability (F30%):	0.64

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.95
Plasma Protein Binding (PPB):	82.54151153564453%
Volume Distribution (VD):	1.303
Pgp-substrate:	21.667556762695312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.693
CYP1A2-substrate:	0.219
CYP2C19-inhibitor:	0.375
CYP2C19-substrate:	0.596
CYP2C9-inhibitor:	0.146
CYP2C9-substrate:	0.507
CYP2D6-inhibitor:	0.151
CYP2D6-substrate:	0.821
CYP3A4-inhibitor:	0.78
CYP3A4-substrate:	0.801

ADMET: Excretion

Clearance (CL):	9.637
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.917
AMES Toxicity:	0.474
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.63
Carcinogencity:	0.949
Eye Corrosion:	0.013
Eye Irritation:	0.025
Respiratory Toxicity:	0.992

Download Data

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

Natural Product: NPC52557

Natural Product ID:	NPC52557
*Common Name:**	Polyneuridine
IUPAC Name:	n.a.
Synonyms:	Polyneuridine
Standard InCHIKey:	RCEFXZXHYFOPIE-QZQCDTMFSA-N
Standard InCHI:	InChI=1S/C21H24N2O3/c1-3-12-10-23-17-9-15(12)21(11-24,20(25)26-2)18(23)8-14-13-6-4-5-7-16(13)22-19(14)17/h3-7,15,17-18,22,24H,8-11H2,1-2H3/b12-3-/t15-,17-,18-,21+/m0/s1
SMILES:	C/C=C1/CN2[C@H]3C[C@@H]1[C@@]([C@@H]2Cc1c3[nH]c2c1cccc2)(CO)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454572
PubChem CID:	15558573
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003759] Macroline alkaloids

*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
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26359402]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	100.0	ug ml-1	PMID[568255]
NPT168	Cell Line	P388	Mus musculus	ED50	>	100.0	ug ml-1	PMID[568255]

☑ 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 NPC52557 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	257
0.1-0.2	1367
0.2-0.3	6351
0.3-0.4	24531
0.4-0.5	5159
0.5-0.6	2580
0.6-0.7	1771
0.7-0.8	556
0.8-0.85	87
0.85-0.9	21
0.9-0.95	16
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9543	High Similarity	NPC175474
0.9235	High Similarity	NPC313985
0.9235	High Similarity	NPC195461
0.9235	High Similarity	NPC249150
0.9235	High Similarity	NPC81654
0.9235	High Similarity	NPC79129
0.9235	High Similarity	NPC49196
0.9126	High Similarity	NPC50503
0.8857	High Similarity	NPC472123
0.8791	High Similarity	NPC102338
0.8791	High Similarity	NPC111602
0.8791	High Similarity	NPC63199
0.8791	High Similarity	NPC196251
0.8743	High Similarity	NPC472112
0.8722	High Similarity	NPC139291
0.8722	High Similarity	NPC472108
0.8649	High Similarity	NPC472113
0.8649	High Similarity	NPC55493
0.8634	High Similarity	NPC472323
0.8632	High Similarity	NPC162730
0.8611	High Similarity	NPC15840
0.861	High Similarity	NPC245916
0.8571	High Similarity	NPC241024
0.8556	High Similarity	NPC219336
0.8541	High Similarity	NPC469470
0.8541	High Similarity	NPC314333
0.8541	High Similarity	NPC329858
0.8541	High Similarity	NPC469501
0.8534	High Similarity	NPC474116
0.8526	High Similarity	NPC312870
0.8526	High Similarity	NPC128265
0.8526	High Similarity	NPC199851
0.8526	High Similarity	NPC294909
0.8526	High Similarity	NPC254240
0.8525	High Similarity	NPC79062
0.8525	High Similarity	NPC472107
0.8516	High Similarity	NPC143533
0.8508	High Similarity	NPC469896
0.85	High Similarity	NPC217372
0.85	High Similarity	NPC183662
0.85	High Similarity	NPC15573
0.847	Intermediate Similarity	NPC472119
0.8457	Intermediate Similarity	NPC57994
0.8457	Intermediate Similarity	NPC289299
0.8418	Intermediate Similarity	NPC234999
0.8415	Intermediate Similarity	NPC472110
0.8415	Intermediate Similarity	NPC472109
0.8371	Intermediate Similarity	NPC317430
0.836	Intermediate Similarity	NPC19692
0.836	Intermediate Similarity	NPC220151
0.8274	Intermediate Similarity	NPC469743
0.827	Intermediate Similarity	NPC258480
0.8267	Intermediate Similarity	NPC52254
0.8242	Intermediate Similarity	NPC24594
0.8242	Intermediate Similarity	NPC472122
0.8241	Intermediate Similarity	NPC475778
0.8238	Intermediate Similarity	NPC214428
0.8216	Intermediate Similarity	NPC472104
0.8211	Intermediate Similarity	NPC269886
0.8211	Intermediate Similarity	NPC472295
0.8211	Intermediate Similarity	NPC472210
0.8211	Intermediate Similarity	NPC81802
0.8211	Intermediate Similarity	NPC247735
0.8207	Intermediate Similarity	NPC472105
0.8207	Intermediate Similarity	NPC187827
0.8202	Intermediate Similarity	NPC271797
0.8202	Intermediate Similarity	NPC21174
0.8201	Intermediate Similarity	NPC472097
0.8182	Intermediate Similarity	NPC478077
0.8182	Intermediate Similarity	NPC66210
0.8152	Intermediate Similarity	NPC133261
0.8125	Intermediate Similarity	NPC472116
0.8122	Intermediate Similarity	NPC277350
0.809	Intermediate Similarity	NPC255229
0.809	Intermediate Similarity	NPC81229
0.8065	Intermediate Similarity	NPC113626
0.8039	Intermediate Similarity	NPC174788
0.8039	Intermediate Similarity	NPC82070
0.8038	Intermediate Similarity	NPC33949
0.803	Intermediate Similarity	NPC476114
0.8021	Intermediate Similarity	NPC19679
0.799	Intermediate Similarity	NPC477065
0.7989	Intermediate Similarity	NPC329688
0.7989	Intermediate Similarity	NPC189812
0.7989	Intermediate Similarity	NPC62749
0.798	Intermediate Similarity	NPC475847
0.798	Intermediate Similarity	NPC185742
0.7979	Intermediate Similarity	NPC474121
0.7959	Intermediate Similarity	NPC249040
0.7957	Intermediate Similarity	NPC213468
0.7946	Intermediate Similarity	NPC267885
0.7944	Intermediate Similarity	NPC194881
0.7941	Intermediate Similarity	NPC330009
0.7941	Intermediate Similarity	NPC469928
0.7935	Intermediate Similarity	NPC161861
0.7933	Intermediate Similarity	NPC475271
0.7931	Intermediate Similarity	NPC221100
0.7931	Intermediate Similarity	NPC234078
0.7921	Intermediate Similarity	NPC285469
0.7914	Intermediate Similarity	NPC91179
0.7903	Intermediate Similarity	NPC234987
0.7903	Intermediate Similarity	NPC326575
0.7895	Intermediate Similarity	NPC235684
0.7892	Intermediate Similarity	NPC149155
0.7892	Intermediate Similarity	NPC203468
0.7892	Intermediate Similarity	NPC110500
0.7887	Intermediate Similarity	NPC85066
0.7887	Intermediate Similarity	NPC181502
0.7884	Intermediate Similarity	NPC472294
0.7876	Intermediate Similarity	NPC472292
0.7869	Intermediate Similarity	NPC78020
0.7864	Intermediate Similarity	NPC281049
0.7861	Intermediate Similarity	NPC248041
0.7861	Intermediate Similarity	NPC126709
0.7854	Intermediate Similarity	NPC152768
0.7854	Intermediate Similarity	NPC148183
0.7807	Intermediate Similarity	NPC84827
0.7807	Intermediate Similarity	NPC14113
0.7807	Intermediate Similarity	NPC145885
0.7789	Intermediate Similarity	NPC476874
0.7783	Intermediate Similarity	NPC475422
0.7772	Intermediate Similarity	NPC87755
0.7766	Intermediate Similarity	NPC283219
0.776	Intermediate Similarity	NPC470508
0.7755	Intermediate Similarity	NPC472293
0.7754	Intermediate Similarity	NPC476441
0.7747	Intermediate Similarity	NPC16667
0.7734	Intermediate Similarity	NPC478158
0.7727	Intermediate Similarity	NPC472297
0.7727	Intermediate Similarity	NPC472296
0.7725	Intermediate Similarity	NPC21638
0.7721	Intermediate Similarity	NPC473105
0.772	Intermediate Similarity	NPC321708
0.7713	Intermediate Similarity	NPC111275
0.7708	Intermediate Similarity	NPC315555
0.7707	Intermediate Similarity	NPC75634
0.7703	Intermediate Similarity	NPC472099
0.7684	Intermediate Similarity	NPC71037
0.7672	Intermediate Similarity	NPC55772
0.767	Intermediate Similarity	NPC472291
0.7667	Intermediate Similarity	NPC207726
0.7662	Intermediate Similarity	NPC165599
0.7662	Intermediate Similarity	NPC476098
0.7644	Intermediate Similarity	NPC159125
0.7633	Intermediate Similarity	NPC478157
0.7626	Intermediate Similarity	NPC469736
0.7612	Intermediate Similarity	NPC137589
0.7611	Intermediate Similarity	NPC478076
0.7608	Intermediate Similarity	NPC473041
0.7608	Intermediate Similarity	NPC96321
0.7604	Intermediate Similarity	NPC228835
0.7594	Intermediate Similarity	NPC64216
0.7593	Intermediate Similarity	NPC475720
0.7593	Intermediate Similarity	NPC474192
0.759	Intermediate Similarity	NPC95783
0.7588	Intermediate Similarity	NPC473640
0.7586	Intermediate Similarity	NPC238457
0.7586	Intermediate Similarity	NPC18661
0.7585	Intermediate Similarity	NPC54744
0.7581	Intermediate Similarity	NPC477175
0.7581	Intermediate Similarity	NPC470730
0.7579	Intermediate Similarity	NPC248462
0.7569	Intermediate Similarity	NPC470507
0.7562	Intermediate Similarity	NPC475506
0.7551	Intermediate Similarity	NPC243716
0.755	Intermediate Similarity	NPC293917
0.7549	Intermediate Similarity	NPC54420
0.7548	Intermediate Similarity	NPC313640
0.7546	Intermediate Similarity	NPC475969
0.7546	Intermediate Similarity	NPC475859
0.7541	Intermediate Similarity	NPC67056
0.754	Intermediate Similarity	NPC280548
0.7538	Intermediate Similarity	NPC141454
0.7537	Intermediate Similarity	NPC473376
0.7535	Intermediate Similarity	NPC311906
0.7527	Intermediate Similarity	NPC54988
0.7527	Intermediate Similarity	NPC49954
0.7527	Intermediate Similarity	NPC474561
0.7525	Intermediate Similarity	NPC155143
0.7525	Intermediate Similarity	NPC193761
0.7512	Intermediate Similarity	NPC165743
0.75	Intermediate Similarity	NPC306376
0.75	Intermediate Similarity	NPC229348
0.75	Intermediate Similarity	NPC6982
0.7488	Intermediate Similarity	NPC469720
0.7488	Intermediate Similarity	NPC476115
0.7487	Intermediate Similarity	NPC201700
0.7487	Intermediate Similarity	NPC11445
0.7487	Intermediate Similarity	NPC17059
0.7486	Intermediate Similarity	NPC88097
0.7476	Intermediate Similarity	NPC162860
0.7476	Intermediate Similarity	NPC312645
0.7476	Intermediate Similarity	NPC477548
0.7476	Intermediate Similarity	NPC305984
0.7476	Intermediate Similarity	NPC271862
0.7475	Intermediate Similarity	NPC471944
0.7466	Intermediate Similarity	NPC475816
0.7465	Intermediate Similarity	NPC14288
0.7463	Intermediate Similarity	NPC474905
0.7463	Intermediate Similarity	NPC244741

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 NPC52557 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	459
0.2-0.3	618
0.3-0.4	1879
0.4-0.5	2684
0.5-0.6	2434
0.6-0.7	778
0.7-0.8	130
0.8-0.85	3
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9235	High Similarity	NPD4601	Approved
0.9235	High Similarity	NPD4600	Approved
0.8541	High Similarity	NPD4499	Approved
0.8526	High Similarity	NPD4500	Approved
0.8526	High Similarity	NPD4501	Approved
0.8457	Intermediate Similarity	NPD4602	Approved
0.801	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD4520	Approved
0.7897	Intermediate Similarity	NPD5003	Discontinued
0.7892	Intermediate Similarity	NPD482	Approved
0.7879	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD2094	Phase 2
0.7831	Intermediate Similarity	NPD2095	Phase 2
0.7831	Intermediate Similarity	NPD2092	Phase 2
0.7789	Intermediate Similarity	NPD2091	Phase 2
0.7789	Intermediate Similarity	NPD2096	Phase 2
0.7772	Intermediate Similarity	NPD2844	Phase 3
0.7742	Intermediate Similarity	NPD750	Phase 2
0.7727	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD3393	Approved
0.7596	Intermediate Similarity	NPD3394	Approved
0.7596	Intermediate Similarity	NPD3389	Approved
0.759	Intermediate Similarity	NPD2564	Approved
0.759	Intermediate Similarity	NPD2565	Phase 2
0.755	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7619	Phase 3
0.7525	Intermediate Similarity	NPD7618	Phase 3
0.7513	Intermediate Similarity	NPD6178	Phase 3
0.75	Intermediate Similarity	NPD7957	Phase 1
0.75	Intermediate Similarity	NPD4397	Phase 1
0.75	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD8072	Approved
0.7488	Intermediate Similarity	NPD7470	Discontinued
0.7475	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD6249	Phase 2
0.7463	Intermediate Similarity	NPD6248	Phase 2
0.7451	Intermediate Similarity	NPD5901	Discontinued
0.7451	Intermediate Similarity	NPD5426	Phase 3
0.7449	Intermediate Similarity	NPD4334	Discontinued
0.7448	Intermediate Similarity	NPD5898	Approved
0.7448	Intermediate Similarity	NPD5897	Approved
0.7448	Intermediate Similarity	NPD5899	Approved
0.7415	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7778	Approved
0.7413	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7777	Approved
0.7413	Intermediate Similarity	NPD53	Approved
0.7407	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD6176	Phase 1
0.7382	Intermediate Similarity	NPD5104	Approved
0.7379	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD8115	Approved
0.7366	Intermediate Similarity	NPD8114	Approved
0.736	Intermediate Similarity	NPD1534	Approved
0.7356	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7944	Discontinued
0.7339	Intermediate Similarity	NPD7824	Approved
0.733	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8272	Phase 2
0.7277	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8073	Approved
0.7268	Intermediate Similarity	NPD6595	Phase 3
0.7263	Intermediate Similarity	NPD1326	Approved
0.7263	Intermediate Similarity	NPD1325	Approved
0.726	Intermediate Similarity	NPD2509	Approved
0.726	Intermediate Similarity	NPD2510	Approved
0.726	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4315	Phase 2
0.7249	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7730	Approved
0.7248	Intermediate Similarity	NPD7731	Approved
0.724	Intermediate Similarity	NPD7951	Approved
0.724	Intermediate Similarity	NPD7953	Approved
0.724	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7952	Approved
0.724	Intermediate Similarity	NPD7790	Approved
0.724	Intermediate Similarity	NPD7789	Approved
0.724	Intermediate Similarity	NPD7950	Approved
0.724	Intermediate Similarity	NPD7791	Approved
0.7235	Intermediate Similarity	NPD7271	Approved
0.7233	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2920	Discontinued
0.7231	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4948	Discontinued
0.7216	Intermediate Similarity	NPD8386	Phase 2
0.7216	Intermediate Similarity	NPD4079	Approved
0.7216	Intermediate Similarity	NPD4076	Approved
0.7212	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7878	Phase 2
0.7193	Intermediate Similarity	NPD8358	Approved
0.7192	Intermediate Similarity	NPD6664	Approved
0.7188	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6182	Approved
0.7188	Intermediate Similarity	NPD43	Approved
0.7179	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5473	Discontinued
0.7177	Intermediate Similarity	NPD2916	Discontinued
0.7177	Intermediate Similarity	NPD7665	Phase 2
0.7177	Intermediate Similarity	NPD7666	Phase 3
0.7169	Intermediate Similarity	NPD6164	Phase 2
0.7169	Intermediate Similarity	NPD6165	Phase 2
0.7165	Intermediate Similarity	NPD3506	Approved
0.7165	Intermediate Similarity	NPD2144	Approved
0.7165	Intermediate Similarity	NPD3505	Approved
0.7165	Intermediate Similarity	NPD7865	Approved
0.7163	Intermediate Similarity	NPD6770	Approved
0.715	Intermediate Similarity	NPD5065	Approved
0.715	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5487	Phase 1
0.7143	Intermediate Similarity	NPD3038	Discontinued
0.7143	Intermediate Similarity	NPD4506	Discontinued
0.7136	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7455	Approved
0.7123	Intermediate Similarity	NPD7454	Approved
0.7121	Intermediate Similarity	NPD5075	Discontinued
0.7117	Intermediate Similarity	NPD4885	Approved
0.7114	Intermediate Similarity	NPD2336	Approved
0.7114	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6206	Phase 1
0.7107	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2915	Discontinued
0.71	Intermediate Similarity	NPD7234	Approved
0.71	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7233	Approved
0.7087	Intermediate Similarity	NPD484	Approved
0.7085	Intermediate Similarity	NPD5444	Phase 1
0.7079	Intermediate Similarity	NPD5505	Discontinued
0.7073	Intermediate Similarity	NPD6261	Phase 3
0.7072	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7482	Phase 2
0.7071	Intermediate Similarity	NPD7483	Phase 2
0.7064	Intermediate Similarity	NPD7956	Approved
0.7064	Intermediate Similarity	NPD7955	Approved
0.7056	Intermediate Similarity	NPD7970	Approved
0.7056	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5140	Approved
0.7053	Intermediate Similarity	NPD7727	Phase 2
0.7053	Intermediate Similarity	NPD5138	Approved
0.7053	Intermediate Similarity	NPD7817	Phase 1
0.705	Intermediate Similarity	NPD8431	Approved
0.7048	Intermediate Similarity	NPD8322	Phase 2
0.7039	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6999	Discontinued
0.7037	Intermediate Similarity	NPD2511	Approved
0.7033	Intermediate Similarity	NPD8282	Approved
0.7033	Intermediate Similarity	NPD8283	Approved
0.7033	Intermediate Similarity	NPD6987	Phase 1
0.7033	Intermediate Similarity	NPD56	Approved
0.7033	Intermediate Similarity	NPD8098	Approved
0.7027	Intermediate Similarity	NPD4463	Approved
0.7027	Intermediate Similarity	NPD4462	Approved
0.7026	Intermediate Similarity	NPD2381	Approved
0.7026	Intermediate Similarity	NPD2382	Approved
0.7026	Intermediate Similarity	NPD2380	Approved
0.7021	Intermediate Similarity	NPD4326	Phase 2
0.702	Intermediate Similarity	NPD5596	Phase 2
0.7014	Intermediate Similarity	NPD8423	Phase 2
0.7014	Intermediate Similarity	NPD4882	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8399	Phase 1
0.7005	Intermediate Similarity	NPD6479	Discontinued
0.7005	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD8325	Phase 3
0.6991	Remote Similarity	NPD8326	Phase 3
0.699	Remote Similarity	NPD6641	Approved
0.699	Remote Similarity	NPD6642	Approved
0.699	Remote Similarity	NPD7946	Pre-registration
0.6989	Remote Similarity	NPD2882	Phase 1
0.6977	Remote Similarity	NPD5293	Phase 2
0.6976	Remote Similarity	NPD2307	Discontinued
0.6962	Remote Similarity	NPD7708	Approved
0.6959	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7308	Discontinued
0.6952	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7103	Approved
0.695	Remote Similarity	NPD6227	Discontinued
0.6946	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5913	Phase 3
0.6944	Remote Similarity	NPD7218	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