NPASS Compound

Structure

CID225774 OpenBabel06191716022D 23 27 0 0 1 0 0 0 0 0999 V2000 -2.5858 -4.1318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0045 -0.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6195 0.4942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8084 0.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4184 0.0189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1973 -3.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9926 -4.1251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6056 -2.2761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5990 -2.2801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9139 0.0961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1925 -2.7392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7961 -0.8894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5950 -1.3648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7984 -2.7423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4061 -0.9107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6048 -1.3583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9883 -2.2797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9955 -1.3516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1911 -0.8989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7885 -3.6657 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1992 -1.3827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2877 -0.7434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 12 1 0 0 0 0 5 15 2 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 20 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 10 22 1 0 0 0 0 10 23 1 0 0 0 0 11 17 1 0 0 0 0 12 13 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 14 9 1 6 0 0 0 14 17 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	309.14
Volume:	315.947
LogP:	3.87
LogD:	2.849
LogS:	-3.748
# Rotatable Bonds:	1
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.809
Synthetic Accessibility Score:	3.135
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.861
MDCK Permeability:	2.8961660063941963e-05
Pgp-inhibitor:	0.424
Pgp-substrate:	0.918
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.984
Plasma Protein Binding (PPB):	94.44194793701172%
Volume Distribution (VD):	2.631
Pgp-substrate:	2.529019594192505%

ADMET: Metabolism

CYP1A2-inhibitor:	0.89
CYP1A2-substrate:	0.855
CYP2C19-inhibitor:	0.573
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.808
CYP2D6-inhibitor:	0.917
CYP2D6-substrate:	0.938
CYP3A4-inhibitor:	0.795
CYP3A4-substrate:	0.896

ADMET: Excretion

Clearance (CL):	13.795
Half-life (T1/2):	0.231

ADMET: Toxicity

hERG Blockers:	0.717
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.285
AMES Toxicity:	0.863
Rat Oral Acute Toxicity:	0.798
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.126
Carcinogencity:	0.836
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC225774

Natural Product ID:	NPC225774
*Common Name:**	Stephanine
IUPAC Name:	n.a.
Synonyms:	Stephanine
Standard InCHIKey:	UEAPAHNNFSZHMW-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C19H19NO3/c1-20-7-6-11-8-16-19(23-10-22-16)18-12-4-3-5-15(21-2)13(12)9-14(20)17(11)18/h3-5,8,14H,6-7,9-10H2,1-2H3/p+1/t14-/m1/s1
SMILES:	C[NH+]1CCc2cc3c(c4-c5cccc(c5C[C@@H]1c24)OC)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL601020
PubChem CID:	160501
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20426456]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392886]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9266	Stephania delavayi	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9266	Stephania delavayi	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9266	Stephania delavayi	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5902	Stephania bancroftii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11351	Stephania japonica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9266	Stephania delavayi	Species	Menispermaceae	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	1

Activity Type	# Activity
Individual Protein	1

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	>	50000.0	nM	PMID[533130]

☑ 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 NPC225774 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	407
0.1-0.2	1949
0.2-0.3	9032
0.3-0.4	8941
0.4-0.5	6729
0.5-0.6	11861
0.6-0.7	2903
0.7-0.8	548
0.8-0.85	175
0.85-0.9	93
0.9-0.95	45
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC476432
0.9935	High Similarity	NPC219341
0.9935	High Similarity	NPC24264
0.987	High Similarity	NPC247389
0.9869	High Similarity	NPC167546
0.9869	High Similarity	NPC302527
0.9869	High Similarity	NPC16805
0.9803	High Similarity	NPC306902
0.9803	High Similarity	NPC160298
0.9803	High Similarity	NPC232924
0.9803	High Similarity	NPC477559
0.9803	High Similarity	NPC266753
0.9742	High Similarity	NPC210918
0.9557	High Similarity	NPC19520
0.9557	High Similarity	NPC149090
0.9494	High Similarity	NPC6152
0.949	High Similarity	NPC298979
0.9441	High Similarity	NPC114364
0.9441	High Similarity	NPC320223
0.9437	High Similarity	NPC199465
0.9437	High Similarity	NPC229166
0.9437	High Similarity	NPC128560
0.943	High Similarity	NPC241055
0.9427	High Similarity	NPC304659
0.9427	High Similarity	NPC86144
0.9416	High Similarity	NPC476572
0.9412	High Similarity	NPC325871
0.9412	High Similarity	NPC99659
0.9383	High Similarity	NPC126284
0.9363	High Similarity	NPC168409
0.9342	High Similarity	NPC81733
0.9342	High Similarity	NPC326316
0.9299	High Similarity	NPC189470
0.9268	High Similarity	NPC248642
0.9264	High Similarity	NPC267408
0.9259	High Similarity	NPC112575
0.9212	High Similarity	NPC156576
0.9207	High Similarity	NPC474506
0.9207	High Similarity	NPC32413
0.9202	High Similarity	NPC23219
0.9198	High Similarity	NPC477558
0.9152	High Similarity	NPC116284
0.9146	High Similarity	NPC470879
0.9146	High Similarity	NPC258695
0.9096	High Similarity	NPC135772
0.9091	High Similarity	NPC476574
0.9091	High Similarity	NPC155442
0.9091	High Similarity	NPC312918
0.9091	High Similarity	NPC477561
0.9085	High Similarity	NPC118633
0.9085	High Similarity	NPC294790
0.9085	High Similarity	NPC148693
0.9048	High Similarity	NPC237579
0.9038	High Similarity	NPC216459
0.9038	High Similarity	NPC41178
0.9038	High Similarity	NPC138487
0.9038	High Similarity	NPC244112
0.902	High Similarity	NPC475959
0.9012	High Similarity	NPC152212
0.9006	High Similarity	NPC145832
0.9006	High Similarity	NPC474931
0.9006	High Similarity	NPC81218
0.9006	High Similarity	NPC12053
0.9006	High Similarity	NPC158376
0.9006	High Similarity	NPC306555
0.9006	High Similarity	NPC117188
0.9006	High Similarity	NPC205421
0.9	High Similarity	NPC253043
0.9	High Similarity	NPC477563
0.9	High Similarity	NPC212794
0.9	High Similarity	NPC306843
0.9	High Similarity	NPC136508
0.9	High Similarity	NPC13504
0.9	High Similarity	NPC96603
0.9	High Similarity	NPC196447
0.9	High Similarity	NPC78222
0.8988	High Similarity	NPC214116
0.8981	High Similarity	NPC170503
0.8981	High Similarity	NPC146288
0.8981	High Similarity	NPC126519
0.8981	High Similarity	NPC203784
0.8938	High Similarity	NPC324144
0.8938	High Similarity	NPC1229
0.8931	High Similarity	NPC27410
0.8931	High Similarity	NPC166014
0.8922	High Similarity	NPC476575
0.8917	High Similarity	NPC76079
0.8882	High Similarity	NPC82763
0.8876	High Similarity	NPC57036
0.8868	High Similarity	NPC477080
0.8861	High Similarity	NPC234392
0.8861	High Similarity	NPC31311
0.8839	High Similarity	NPC219162
0.8839	High Similarity	NPC211296
0.8824	High Similarity	NPC312531
0.8824	High Similarity	NPC476576
0.8824	High Similarity	NPC186546
0.879	High Similarity	NPC210148
0.879	High Similarity	NPC233029
0.878	High Similarity	NPC168753
0.878	High Similarity	NPC118274
0.8773	High Similarity	NPC204947
0.875	High Similarity	NPC179704
0.8727	High Similarity	NPC239775
0.871	High Similarity	NPC253883
0.871	High Similarity	NPC95075
0.871	High Similarity	NPC90844
0.8701	High Similarity	NPC145304
0.8698	High Similarity	NPC275132
0.8698	High Similarity	NPC249405
0.869	High Similarity	NPC220961
0.8684	High Similarity	NPC470925
0.8683	High Similarity	NPC287588
0.8679	High Similarity	NPC93593
0.8675	High Similarity	NPC477020
0.8675	High Similarity	NPC2314
0.8675	High Similarity	NPC66341
0.8675	High Similarity	NPC192135
0.8671	High Similarity	NPC117717
0.8667	High Similarity	NPC477562
0.8667	High Similarity	NPC69712
0.8667	High Similarity	NPC26240
0.8654	High Similarity	NPC130941
0.865	High Similarity	NPC232514
0.865	High Similarity	NPC276944
0.865	High Similarity	NPC238530
0.8625	High Similarity	NPC180756
0.8625	High Similarity	NPC323443
0.8618	High Similarity	NPC314682
0.8613	High Similarity	NPC475754
0.8605	High Similarity	NPC474904
0.8599	High Similarity	NPC92541
0.8598	High Similarity	NPC35627
0.8598	High Similarity	NPC476573
0.8598	High Similarity	NPC81247
0.859	High Similarity	NPC16107
0.859	High Similarity	NPC210437
0.859	High Similarity	NPC476144
0.859	High Similarity	NPC106295
0.859	High Similarity	NPC51957
0.8562	High Similarity	NPC188163
0.8562	High Similarity	NPC328750
0.8562	High Similarity	NPC474915
0.8562	High Similarity	NPC213206
0.8553	High Similarity	NPC470924
0.8545	High Similarity	NPC150879
0.8535	High Similarity	NPC7467
0.8528	High Similarity	NPC60186
0.8519	High Similarity	NPC111485
0.848	Intermediate Similarity	NPC73492
0.848	Intermediate Similarity	NPC233718
0.848	Intermediate Similarity	NPC299990
0.8476	Intermediate Similarity	NPC320104
0.8471	Intermediate Similarity	NPC144863
0.8471	Intermediate Similarity	NPC474507
0.8462	Intermediate Similarity	NPC148709
0.8462	Intermediate Similarity	NPC476577
0.8462	Intermediate Similarity	NPC173416
0.8452	Intermediate Similarity	NPC128019
0.8452	Intermediate Similarity	NPC476567
0.8452	Intermediate Similarity	NPC136860
0.8447	Intermediate Similarity	NPC78733
0.8443	Intermediate Similarity	NPC75958
0.8438	Intermediate Similarity	NPC148898
0.8438	Intermediate Similarity	NPC26601
0.8434	Intermediate Similarity	NPC474324
0.8434	Intermediate Similarity	NPC57812
0.843	Intermediate Similarity	NPC302275
0.8421	Intermediate Similarity	NPC7018
0.8418	Intermediate Similarity	NPC37144
0.8418	Intermediate Similarity	NPC59907
0.8412	Intermediate Similarity	NPC190461
0.8393	Intermediate Similarity	NPC65403
0.8383	Intermediate Similarity	NPC475845
0.8364	Intermediate Similarity	NPC233650
0.8354	Intermediate Similarity	NPC476151
0.8352	Intermediate Similarity	NPC302001
0.8344	Intermediate Similarity	NPC185838
0.8343	Intermediate Similarity	NPC285941
0.8333	Intermediate Similarity	NPC474708
0.8333	Intermediate Similarity	NPC123323
0.8333	Intermediate Similarity	NPC311991
0.8323	Intermediate Similarity	NPC190332
0.8323	Intermediate Similarity	NPC181653
0.8313	Intermediate Similarity	NPC247972
0.8313	Intermediate Similarity	NPC134858
0.8304	Intermediate Similarity	NPC477560
0.8303	Intermediate Similarity	NPC24954
0.8294	Intermediate Similarity	NPC187678
0.8282	Intermediate Similarity	NPC186063
0.8274	Intermediate Similarity	NPC266176
0.8274	Intermediate Similarity	NPC290759
0.8274	Intermediate Similarity	NPC82533
0.8274	Intermediate Similarity	NPC158148
0.8268	Intermediate Similarity	NPC193906
0.8268	Intermediate Similarity	NPC23080
0.8263	Intermediate Similarity	NPC124657
0.825	Intermediate Similarity	NPC103379
0.825	Intermediate Similarity	NPC477565
0.8246	Intermediate Similarity	NPC241704

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 NPC225774 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	858
0.2-0.3	1038
0.3-0.4	2073
0.4-0.5	2684
0.5-0.6	1625
0.6-0.7	501
0.7-0.8	122
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.859	High Similarity	NPD4584	Approved
0.8562	High Similarity	NPD4664	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD3051	Approved
0.8397	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD4481	Phase 3
0.8323	Intermediate Similarity	NPD2970	Approved
0.8323	Intermediate Similarity	NPD2969	Approved
0.8176	Intermediate Similarity	NPD2421	Approved
0.8176	Intermediate Similarity	NPD2420	Approved
0.8166	Intermediate Similarity	NPD2489	Approved
0.8166	Intermediate Similarity	NPD27	Approved
0.8113	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6788	Approved
0.807	Intermediate Similarity	NPD8252	Approved
0.807	Intermediate Similarity	NPD8251	Approved
0.807	Intermediate Similarity	NPD8099	Discontinued
0.8037	Intermediate Similarity	NPD4017	Approved
0.8023	Intermediate Similarity	NPD8156	Discontinued
0.8	Intermediate Similarity	NPD2968	Approved
0.8	Intermediate Similarity	NPD2971	Approved
0.7929	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD7906	Approved
0.7898	Intermediate Similarity	NPD4578	Approved
0.7898	Intermediate Similarity	NPD4577	Approved
0.7892	Intermediate Similarity	NPD7298	Approved
0.7871	Intermediate Similarity	NPD3109	Approved
0.7871	Intermediate Similarity	NPD3110	Approved
0.7844	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5241	Discontinued
0.7805	Intermediate Similarity	NPD3640	Phase 3
0.7805	Intermediate Similarity	NPD3639	Approved
0.7805	Intermediate Similarity	NPD3641	Approved
0.7797	Intermediate Similarity	NPD7310	Approved
0.7797	Intermediate Similarity	NPD7311	Approved
0.7797	Intermediate Similarity	NPD7313	Approved
0.7797	Intermediate Similarity	NPD7312	Approved
0.7785	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD4420	Approved
0.7765	Intermediate Similarity	NPD4663	Approved
0.7753	Intermediate Similarity	NPD7309	Approved
0.7753	Intermediate Similarity	NPD8053	Approved
0.7753	Intermediate Similarity	NPD8054	Approved
0.7746	Intermediate Similarity	NPD2898	Approved
0.7733	Intermediate Similarity	NPD6071	Discontinued
0.7706	Intermediate Similarity	NPD7831	Phase 2
0.7706	Intermediate Similarity	NPD7833	Phase 2
0.7706	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4727	Phase 1
0.7697	Intermediate Similarity	NPD6030	Approved
0.7697	Intermediate Similarity	NPD6031	Approved
0.7692	Intermediate Similarity	NPD2563	Approved
0.7692	Intermediate Similarity	NPD2560	Approved
0.7677	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5754	Discontinued
0.7637	Intermediate Similarity	NPD2490	Approved
0.7637	Intermediate Similarity	NPD2488	Approved
0.7628	Intermediate Similarity	NPD5718	Phase 2
0.7619	Intermediate Similarity	NPD4772	Phase 2
0.7619	Intermediate Similarity	NPD4773	Phase 2
0.7606	Intermediate Similarity	NPD5005	Approved
0.7606	Intermediate Similarity	NPD5006	Approved
0.7605	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD2973	Approved
0.7527	Intermediate Similarity	NPD2974	Approved
0.7527	Intermediate Similarity	NPD2975	Approved
0.75	Intermediate Similarity	NPD5604	Discontinued
0.7485	Intermediate Similarity	NPD5976	Discontinued
0.7473	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7802	Discontinued
0.747	Intermediate Similarity	NPD1424	Approved
0.7468	Intermediate Similarity	NPD4475	Approved
0.7468	Intermediate Similarity	NPD4474	Approved
0.7457	Intermediate Similarity	NPD7400	Phase 3
0.7455	Intermediate Similarity	NPD3845	Phase 1
0.7455	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4166	Phase 2
0.7429	Intermediate Similarity	NPD4010	Discontinued
0.7427	Intermediate Similarity	NPD2978	Approved
0.7427	Intermediate Similarity	NPD2977	Approved
0.741	Intermediate Similarity	NPD3124	Discontinued
0.7407	Intermediate Similarity	NPD4580	Approved
0.7401	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4055	Discovery
0.7394	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6107	Approved
0.7368	Intermediate Similarity	NPD3450	Approved
0.7368	Intermediate Similarity	NPD2493	Approved
0.7368	Intermediate Similarity	NPD2494	Approved
0.7368	Intermediate Similarity	NPD3452	Approved
0.7341	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2492	Phase 1
0.7322	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4859	Phase 1
0.7316	Intermediate Similarity	NPD4107	Approved
0.7308	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7281	Phase 3
0.7308	Intermediate Similarity	NPD7280	Phase 3
0.7305	Intermediate Similarity	NPD7598	Phase 2
0.73	Intermediate Similarity	NPD3763	Approved
0.7284	Intermediate Similarity	NPD6896	Approved
0.7284	Intermediate Similarity	NPD6895	Approved
0.7283	Intermediate Similarity	NPD5978	Approved
0.7283	Intermediate Similarity	NPD5977	Approved
0.7263	Intermediate Similarity	NPD8095	Phase 1
0.7262	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4583	Approved
0.7254	Intermediate Similarity	NPD4582	Approved
0.7253	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7124	Phase 2
0.7238	Intermediate Similarity	NPD6297	Approved
0.7238	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6748	Discontinued
0.7216	Intermediate Similarity	NPD6037	Discontinued
0.7202	Intermediate Similarity	NPD4002	Approved
0.7202	Intermediate Similarity	NPD4004	Approved
0.7188	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4482	Phase 3
0.7174	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4236	Phase 3
0.7169	Intermediate Similarity	NPD4237	Approved
0.7169	Intermediate Similarity	NPD5177	Phase 3
0.7151	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3349	Phase 2
0.715	Intermediate Similarity	NPD3057	Approved
0.7134	Intermediate Similarity	NPD4108	Discontinued
0.7127	Intermediate Similarity	NPD5313	Approved
0.7127	Intermediate Similarity	NPD5312	Approved
0.7125	Intermediate Similarity	NPD5156	Approved
0.7125	Intermediate Similarity	NPD5155	Approved
0.7119	Intermediate Similarity	NPD5677	Discontinued
0.7117	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5582	Discontinued
0.7095	Intermediate Similarity	NPD6687	Approved
0.7095	Intermediate Similarity	NPD6688	Approved
0.7093	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD3816	Phase 1
0.7085	Intermediate Similarity	NPD3815	Phase 1
0.7085	Intermediate Similarity	NPD7827	Phase 1
0.7081	Intermediate Similarity	NPD6851	Approved
0.7081	Intermediate Similarity	NPD6853	Approved
0.7077	Intermediate Similarity	NPD4040	Phase 1
0.7076	Intermediate Similarity	NPD1914	Approved
0.7069	Intermediate Similarity	NPD3384	Approved
0.7069	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3383	Approved
0.7069	Intermediate Similarity	NPD3382	Approved
0.7065	Intermediate Similarity	NPD7047	Phase 3
0.7063	Intermediate Similarity	NPD2606	Approved
0.7063	Intermediate Similarity	NPD3595	Approved
0.7063	Intermediate Similarity	NPD3594	Approved
0.7063	Intermediate Similarity	NPD2605	Approved
0.7062	Intermediate Similarity	NPD3533	Approved
0.7062	Intermediate Similarity	NPD2972	Approved
0.7059	Intermediate Similarity	NPD7291	Discontinued
0.7051	Intermediate Similarity	NPD3705	Approved
0.7048	Intermediate Similarity	NPD4725	Approved
0.7048	Intermediate Similarity	NPD4721	Approved
0.7048	Intermediate Similarity	NPD4726	Approved
0.7044	Intermediate Similarity	NPD7247	Discontinued
0.7041	Intermediate Similarity	NPD6666	Approved
0.7041	Intermediate Similarity	NPD6667	Approved
0.7035	Intermediate Similarity	NPD4210	Discontinued
0.703	Intermediate Similarity	NPD1753	Discontinued
0.7025	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6997	Phase 2
0.7021	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7110	Phase 1
0.7011	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3635	Approved
0.7	Intermediate Similarity	NPD3636	Approved
0.7	Intermediate Similarity	NPD3637	Approved
0.6995	Remote Similarity	NPD3885	Approved
0.6994	Remote Similarity	NPD4005	Discontinued
0.6982	Remote Similarity	NPD5160	Discontinued
0.6974	Remote Similarity	NPD2491	Approved
0.6974	Remote Similarity	NPD3448	Approved
0.6964	Remote Similarity	NPD3060	Approved
0.6962	Remote Similarity	NPD1669	Approved
0.6959	Remote Similarity	NPD5457	Discontinued
0.6946	Remote Similarity	NPD1375	Discontinued
0.6944	Remote Similarity	NPD6747	Phase 1
0.694	Remote Similarity	NPD42	Phase 2
0.694	Remote Similarity	NPD6042	Phase 2
0.6932	Remote Similarity	NPD5773	Approved
0.6932	Remote Similarity	NPD4585	Approved
0.6932	Remote Similarity	NPD5772	Approved
0.6923	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7466	Approved
0.6923	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6331	Phase 2
0.6919	Remote Similarity	NPD6090	Discontinued
0.6919	Remote Similarity	NPD5261	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