NPASS Compound

Structure

CID49547 OpenBabel06191715382D 24 27 0 0 0 0 0 0 0 0999 V2000 1.1509 4.4979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1948 3.7072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7370 3.5722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4032 1.3969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6102 0.9343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5961 -0.0011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7983 -0.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4015 1.3939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6021 2.7705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6009 0.9293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3992 2.3150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8130 1.3898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 2.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4006 2.3145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8026 1.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7954 2.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0100 0.9262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6024 2.7754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0076 2.7848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6074 3.6971 0.0000 N 0 0 0 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 -0.0137 3.7084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1989 2.7814 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1977 2.7751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 21 1 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 15 1 0 0 0 0 11 23 1 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 14 24 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 21 2 0 0 0 0 18 20 1 0 0 0 0 19 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.12
Volume:	327.59
LogP:	3.878
LogD:	3.025
LogS:	-6.518
# Rotatable Bonds:	3
TPSA:	60.45
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	2.569
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.81
MDCK Permeability:	1.5200439520413056e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.444

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	93.96581268310547%
Volume Distribution (VD):	0.725
Pgp-substrate:	4.358916282653809%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.76
CYP2C19-substrate:	0.307
CYP2C9-inhibitor:	0.738
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.596
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.768
CYP3A4-substrate:	0.136

ADMET: Excretion

Clearance (CL):	7.749
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.411
Human Hepatotoxicity (H-HT):	0.615
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.875
Rat Oral Acute Toxicity:	0.287
Maximum Recommended Daily Dose:	0.475
Skin Sensitization:	0.067
Carcinogencity:	0.873
Eye Corrosion:	0.003
Eye Irritation:	0.159
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC49547

Natural Product ID:	NPC49547
*Common Name:**	Daurioxoisoaporphine C
IUPAC Name:	n.a.
Synonyms:	Daurioxoisoaporphine C
Standard InCHIKey:	YRFCNSUMOFQEFS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16N2O3/c1-20-18-14(24-3)8-10-6-7-21-17-12-5-4-11(23-2)9-13(12)19(22)16(18)15(10)17/h4-9,20H,1-3H3
SMILES:	CNc1c(cc2ccnc3-c4ccc(cc4C(=O)c1c23)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651051
PubChem CID:	640928
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003018] Isoaporphines [CHEMONTID:0004118] Oxoisoaporphines

*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
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473438]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8281582]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20526	Menispermum dauricum	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	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	2090.0	nM	PMID[496632]
NPT1506	Cell Line	SK-MES-1	Homo sapiens	IC50	>	2090.0	nM	PMID[496632]
NPT1505	Cell Line	J82	Homo sapiens	IC50	>	2090.0	nM	PMID[496632]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	2090.0	nM	PMID[496632]

☑ 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 NPC49547 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	569
0.1-0.2	3611
0.2-0.3	13118
0.3-0.4	4770
0.4-0.5	14910
0.5-0.6	3374
0.6-0.7	1865
0.7-0.8	449
0.8-0.85	22
0.85-0.9	3
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC74575
0.9565	High Similarity	NPC470018
0.9535	High Similarity	NPC208522
0.9256	High Similarity	NPC470022
0.914	High Similarity	NPC270515
0.9073	High Similarity	NPC470020
0.9032	High Similarity	NPC470017
0.8913	High Similarity	NPC132385
0.8458	Intermediate Similarity	NPC142385
0.8402	Intermediate Similarity	NPC322482
0.8356	Intermediate Similarity	NPC210434
0.8296	Intermediate Similarity	NPC24019
0.8273	Intermediate Similarity	NPC216612
0.8273	Intermediate Similarity	NPC144452
0.8265	Intermediate Similarity	NPC225279
0.8253	Intermediate Similarity	NPC72905
0.824	Intermediate Similarity	NPC137353
0.8186	Intermediate Similarity	NPC329631
0.8178	Intermediate Similarity	NPC474688
0.8158	Intermediate Similarity	NPC472061
0.8119	Intermediate Similarity	NPC146976
0.8106	Intermediate Similarity	NPC22481
0.8089	Intermediate Similarity	NPC274640
0.8073	Intermediate Similarity	NPC236668
0.807	Intermediate Similarity	NPC39370
0.807	Intermediate Similarity	NPC90875
0.8053	Intermediate Similarity	NPC278525
0.8043	Intermediate Similarity	NPC101350
0.8	Intermediate Similarity	NPC182907
0.8	Intermediate Similarity	NPC235685
0.8	Intermediate Similarity	NPC189903
0.7982	Intermediate Similarity	NPC208284
0.7982	Intermediate Similarity	NPC473186
0.7982	Intermediate Similarity	NPC233334
0.7957	Intermediate Similarity	NPC108342
0.7931	Intermediate Similarity	NPC41501
0.7911	Intermediate Similarity	NPC122436
0.7909	Intermediate Similarity	NPC39500
0.79	Intermediate Similarity	NPC187501
0.7897	Intermediate Similarity	NPC475844
0.7892	Intermediate Similarity	NPC208084
0.7875	Intermediate Similarity	NPC53534
0.786	Intermediate Similarity	NPC477112
0.786	Intermediate Similarity	NPC260434
0.7832	Intermediate Similarity	NPC51388
0.783	Intermediate Similarity	NPC15406
0.7828	Intermediate Similarity	NPC162530
0.7821	Intermediate Similarity	NPC148889
0.7811	Intermediate Similarity	NPC166722
0.7797	Intermediate Similarity	NPC124313
0.7787	Intermediate Similarity	NPC207283
0.7787	Intermediate Similarity	NPC84164
0.7773	Intermediate Similarity	NPC199667
0.7768	Intermediate Similarity	NPC184408
0.7759	Intermediate Similarity	NPC253675
0.7745	Intermediate Similarity	NPC210296
0.7729	Intermediate Similarity	NPC257851
0.7727	Intermediate Similarity	NPC473181
0.7706	Intermediate Similarity	NPC474701
0.7683	Intermediate Similarity	NPC152620
0.7668	Intermediate Similarity	NPC324361
0.7665	Intermediate Similarity	NPC280799
0.7655	Intermediate Similarity	NPC17565
0.7652	Intermediate Similarity	NPC478078
0.7644	Intermediate Similarity	NPC293151
0.7642	Intermediate Similarity	NPC179287
0.7636	Intermediate Similarity	NPC193238
0.7635	Intermediate Similarity	NPC183537
0.7623	Intermediate Similarity	NPC251160
0.7623	Intermediate Similarity	NPC474428
0.7623	Intermediate Similarity	NPC94157
0.7623	Intermediate Similarity	NPC473180
0.7613	Intermediate Similarity	NPC188420
0.7613	Intermediate Similarity	NPC471304
0.7606	Intermediate Similarity	NPC195268
0.7606	Intermediate Similarity	NPC133140
0.7598	Intermediate Similarity	NPC65277
0.7591	Intermediate Similarity	NPC300156
0.7591	Intermediate Similarity	NPC45190
0.7589	Intermediate Similarity	NPC149471
0.7589	Intermediate Similarity	NPC271215
0.7582	Intermediate Similarity	NPC478083
0.758	Intermediate Similarity	NPC476138
0.758	Intermediate Similarity	NPC245816
0.7576	Intermediate Similarity	NPC157931
0.7562	Intermediate Similarity	NPC77878
0.7558	Intermediate Similarity	NPC476578
0.7558	Intermediate Similarity	NPC476582
0.7558	Intermediate Similarity	NPC4071
0.7557	Intermediate Similarity	NPC4687
0.7557	Intermediate Similarity	NPC249583
0.7552	Intermediate Similarity	NPC91868
0.7552	Intermediate Similarity	NPC63971
0.7545	Intermediate Similarity	NPC285558
0.7544	Intermediate Similarity	NPC323969
0.7543	Intermediate Similarity	NPC246381
0.7543	Intermediate Similarity	NPC471762
0.7521	Intermediate Similarity	NPC196718
0.75	Intermediate Similarity	NPC475774
0.75	Intermediate Similarity	NPC220337
0.7478	Intermediate Similarity	NPC118228
0.7478	Intermediate Similarity	NPC235076
0.7477	Intermediate Similarity	NPC103361
0.7466	Intermediate Similarity	NPC36229
0.7466	Intermediate Similarity	NPC327592
0.7466	Intermediate Similarity	NPC16452
0.7466	Intermediate Similarity	NPC476581
0.7465	Intermediate Similarity	NPC470021
0.7456	Intermediate Similarity	NPC23614
0.7456	Intermediate Similarity	NPC100079
0.7455	Intermediate Similarity	NPC309845
0.7447	Intermediate Similarity	NPC102593
0.7443	Intermediate Similarity	NPC234197
0.7434	Intermediate Similarity	NPC476287
0.7432	Intermediate Similarity	NPC317373
0.7424	Intermediate Similarity	NPC74360
0.7424	Intermediate Similarity	NPC288987
0.7422	Intermediate Similarity	NPC87413
0.7401	Intermediate Similarity	NPC237740
0.7393	Intermediate Similarity	NPC66777
0.7391	Intermediate Similarity	NPC132642
0.7391	Intermediate Similarity	NPC472099
0.7391	Intermediate Similarity	NPC276657
0.7389	Intermediate Similarity	NPC26679
0.7389	Intermediate Similarity	NPC219087
0.7389	Intermediate Similarity	NPC310211
0.7389	Intermediate Similarity	NPC308137
0.7385	Intermediate Similarity	NPC90229
0.7383	Intermediate Similarity	NPC242928
0.738	Intermediate Similarity	NPC473041
0.738	Intermediate Similarity	NPC204446
0.738	Intermediate Similarity	NPC46561
0.738	Intermediate Similarity	NPC96321
0.7373	Intermediate Similarity	NPC135950
0.7373	Intermediate Similarity	NPC207686
0.7366	Intermediate Similarity	NPC477111
0.7366	Intermediate Similarity	NPC82548
0.7364	Intermediate Similarity	NPC315957
0.7359	Intermediate Similarity	NPC60621
0.7359	Intermediate Similarity	NPC198503
0.7353	Intermediate Similarity	NPC473187
0.735	Intermediate Similarity	NPC473185
0.7349	Intermediate Similarity	NPC76748
0.7348	Intermediate Similarity	NPC46451
0.7347	Intermediate Similarity	NPC473188
0.7347	Intermediate Similarity	NPC67401
0.7336	Intermediate Similarity	NPC169402
0.7336	Intermediate Similarity	NPC27041
0.7336	Intermediate Similarity	NPC473513
0.7336	Intermediate Similarity	NPC469727
0.7333	Intermediate Similarity	NPC174758
0.7333	Intermediate Similarity	NPC185782
0.733	Intermediate Similarity	NPC31930
0.7328	Intermediate Similarity	NPC122463
0.7327	Intermediate Similarity	NPC307963
0.7325	Intermediate Similarity	NPC116238
0.7322	Intermediate Similarity	NPC6786
0.7322	Intermediate Similarity	NPC15801
0.7321	Intermediate Similarity	NPC183777
0.7321	Intermediate Similarity	NPC313189
0.7318	Intermediate Similarity	NPC287437
0.7316	Intermediate Similarity	NPC150239
0.7315	Intermediate Similarity	NPC92111
0.7313	Intermediate Similarity	NPC38237
0.7306	Intermediate Similarity	NPC26543
0.7304	Intermediate Similarity	NPC173080
0.7303	Intermediate Similarity	NPC119134
0.7302	Intermediate Similarity	NPC296527
0.7301	Intermediate Similarity	NPC290689
0.7301	Intermediate Similarity	NPC167860
0.7301	Intermediate Similarity	NPC123976
0.73	Intermediate Similarity	NPC469554
0.7295	Intermediate Similarity	NPC161801
0.7293	Intermediate Similarity	NPC477110
0.7289	Intermediate Similarity	NPC171787
0.7285	Intermediate Similarity	NPC477019
0.7285	Intermediate Similarity	NPC176538
0.7277	Intermediate Similarity	NPC477113
0.7273	Intermediate Similarity	NPC473179
0.7269	Intermediate Similarity	NPC9894
0.7269	Intermediate Similarity	NPC258048
0.726	Intermediate Similarity	NPC470023
0.7258	Intermediate Similarity	NPC478045
0.7257	Intermediate Similarity	NPC475253
0.7253	Intermediate Similarity	NPC118121
0.7252	Intermediate Similarity	NPC232727
0.7244	Intermediate Similarity	NPC283117
0.724	Intermediate Similarity	NPC128823
0.7238	Intermediate Similarity	NPC84347
0.7237	Intermediate Similarity	NPC296482
0.7237	Intermediate Similarity	NPC112206
0.7237	Intermediate Similarity	NPC264176
0.7237	Intermediate Similarity	NPC318299
0.7237	Intermediate Similarity	NPC53069
0.7237	Intermediate Similarity	NPC202605
0.7237	Intermediate Similarity	NPC202768
0.7235	Intermediate Similarity	NPC138370
0.7232	Intermediate Similarity	NPC470930
0.7229	Intermediate Similarity	NPC247803
0.7227	Intermediate Similarity	NPC101543

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 NPC49547 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	679
0.2-0.3	948
0.3-0.4	1358
0.4-0.5	2515
0.5-0.6	2160
0.6-0.7	1021
0.7-0.8	150
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8598	High Similarity	NPD4429	Discontinued
0.8214	Intermediate Similarity	NPD5022	Discontinued
0.8186	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.81	Intermediate Similarity	NPD6242	Discontinued
0.7992	Intermediate Similarity	NPD8091	Phase 3
0.7974	Intermediate Similarity	NPD6790	Phase 1
0.7974	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD7395	Discontinued
0.7879	Intermediate Similarity	NPD3006	Discontinued
0.7867	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7925	Phase 2
0.7805	Intermediate Similarity	NPD7924	Phase 2
0.7788	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD7010	Phase 3
0.7719	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD5429	Discontinued
0.7716	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7467	Discontinued
0.7652	Intermediate Similarity	NPD7994	Phase 2
0.7647	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD7069	Discontinued
0.7606	Intermediate Similarity	NPD3924	Approved
0.7606	Intermediate Similarity	NPD3923	Approved
0.7606	Intermediate Similarity	NPD3922	Approved
0.7606	Intermediate Similarity	NPD3921	Approved
0.7578	Intermediate Similarity	NPD4502	Phase 2
0.7578	Intermediate Similarity	NPD5416	Discontinued
0.7574	Intermediate Similarity	NPD5891	Approved
0.7572	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD6716	Phase 1
0.7542	Intermediate Similarity	NPD5488	Discontinued
0.7521	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5475	Discontinued
0.75	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4795	Phase 2
0.7429	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7853	Phase 2
0.7425	Intermediate Similarity	NPD3259	Approved
0.7424	Intermediate Similarity	NPD7404	Approved
0.7415	Intermediate Similarity	NPD6494	Phase 2
0.7406	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD6568	Discontinued
0.7377	Intermediate Similarity	NPD5482	Discontinued
0.7364	Intermediate Similarity	NPD1739	Approved
0.7364	Intermediate Similarity	NPD1740	Approved
0.7362	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5479	Discontinued
0.7361	Intermediate Similarity	NPD6569	Phase 2
0.7357	Intermediate Similarity	NPD3945	Discontinued
0.7349	Intermediate Similarity	NPD6531	Approved
0.7349	Intermediate Similarity	NPD6530	Approved
0.7348	Intermediate Similarity	NPD3763	Approved
0.7327	Intermediate Similarity	NPD1038	Approved
0.7327	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7222	Phase 2
0.7319	Intermediate Similarity	NPD5559	Phase 2
0.7318	Intermediate Similarity	NPD4548	Discontinued
0.7311	Intermediate Similarity	NPD2951	Discontinued
0.7309	Intermediate Similarity	NPD3947	Discontinued
0.7308	Intermediate Similarity	NPD7426	Phase 1
0.7304	Intermediate Similarity	NPD5632	Approved
0.7293	Intermediate Similarity	NPD3394	Approved
0.7293	Intermediate Similarity	NPD3389	Approved
0.7293	Intermediate Similarity	NPD3393	Approved
0.7289	Intermediate Similarity	NPD2509	Approved
0.7289	Intermediate Similarity	NPD2510	Approved
0.7277	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5530	Phase 1
0.7277	Intermediate Similarity	NPD4845	Discontinued
0.7269	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD5939	Approved
0.7269	Intermediate Similarity	NPD5936	Approved
0.7265	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5512	Phase 3
0.7257	Intermediate Similarity	NPD7688	Phase 1
0.7253	Intermediate Similarity	NPD6995	Phase 1
0.7253	Intermediate Similarity	NPD1856	Discontinued
0.7249	Intermediate Similarity	NPD5293	Phase 2
0.7243	Intermediate Similarity	NPD4889	Approved
0.724	Intermediate Similarity	NPD5999	Phase 2
0.7238	Intermediate Similarity	NPD6963	Approved
0.7238	Intermediate Similarity	NPD6964	Approved
0.7237	Intermediate Similarity	NPD3816	Phase 1
0.7237	Intermediate Similarity	NPD3815	Phase 1
0.7232	Intermediate Similarity	NPD5901	Discontinued
0.7231	Intermediate Similarity	NPD7417	Discontinued
0.7225	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4952	Phase 3
0.7205	Intermediate Similarity	NPD3794	Approved
0.7205	Intermediate Similarity	NPD3795	Approved
0.7195	Intermediate Similarity	NPD4558	Phase 2
0.719	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD8016	Phase 3
0.7189	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8100	Phase 3
0.7182	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD3477	Phase 2
0.7181	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3920	Phase 2
0.7166	Intermediate Similarity	NPD3809	Discontinued
0.7162	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2176	Approved
0.7162	Intermediate Similarity	NPD2175	Phase 3
0.7162	Intermediate Similarity	NPD2177	Approved
0.7156	Intermediate Similarity	NPD4122	Approved
0.7156	Intermediate Similarity	NPD6987	Phase 1
0.7156	Intermediate Similarity	NPD4037	Approved
0.7156	Intermediate Similarity	NPD4038	Approved
0.7156	Intermediate Similarity	NPD4039	Approved
0.7156	Intermediate Similarity	NPD4033	Approved
0.7156	Intermediate Similarity	NPD31	Approved
0.7156	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD4034	Approved
0.7156	Intermediate Similarity	NPD32	Approved
0.7156	Intermediate Similarity	NPD4036	Approved
0.7156	Intermediate Similarity	NPD4035	Approved
0.7155	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5867	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5612	Discontinued
0.7136	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2481	Approved
0.7136	Intermediate Similarity	NPD2479	Phase 3
0.7136	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4373	Phase 2
0.7125	Intermediate Similarity	NPD4850	Phase 1
0.7119	Intermediate Similarity	NPD7886	Phase 2
0.7119	Intermediate Similarity	NPD7885	Phase 2
0.7112	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5513	Phase 2
0.7104	Intermediate Similarity	NPD6550	Discontinued
0.7097	Intermediate Similarity	NPD8101	Phase 3
0.7094	Intermediate Similarity	NPD5850	Phase 3
0.7093	Intermediate Similarity	NPD7453	Approved
0.7093	Intermediate Similarity	NPD7452	Approved
0.7093	Intermediate Similarity	NPD6290	Phase 2
0.7092	Intermediate Similarity	NPD6961	Discontinued
0.7089	Intermediate Similarity	NPD3263	Phase 3
0.7085	Intermediate Similarity	NPD3825	Phase 3
0.7082	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD3354	Phase 2
0.7075	Intermediate Similarity	NPD7708	Approved
0.7071	Intermediate Similarity	NPD6968	Phase 2
0.7071	Intermediate Similarity	NPD6969	Phase 2
0.7061	Intermediate Similarity	NPD5658	Approved
0.7059	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4418	Discontinued
0.7059	Intermediate Similarity	NPD4894	Discontinued
0.7056	Intermediate Similarity	NPD6293	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6479	Discontinued
0.7054	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7558	Phase 2
0.7051	Intermediate Similarity	NPD3402	Phase 1
0.7049	Intermediate Similarity	NPD4561	Discontinued
0.7048	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD3925	Approved
0.7042	Intermediate Similarity	NPD6962	Phase 2
0.704	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6281	Approved
0.7031	Intermediate Similarity	NPD5450	Discontinued
0.7028	Intermediate Similarity	NPD3986	Discontinued
0.7021	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7603	Discontinued
0.7016	Intermediate Similarity	NPD8358	Approved
0.7013	Intermediate Similarity	NPD7225	Discontinued
0.7012	Intermediate Similarity	NPD3746	Discontinued
0.7012	Intermediate Similarity	NPD4885	Approved
0.7009	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6228	Discontinued
0.7005	Intermediate Similarity	NPD112	Approved
0.7005	Intermediate Similarity	NPD9705	Discontinued
0.7004	Intermediate Similarity	NPD6230	Discontinued
0.7	Intermediate Similarity	NPD4051	Discontinued
0.7	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5469	Phase 3
0.6996	Remote Similarity	NPD7948	Phase 1
0.6996	Remote Similarity	NPD8149	Discontinued
0.6996	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5601	Phase 2
0.6972	Remote Similarity	NPD7859	Phase 2
0.6972	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4921	Phase 3
0.6972	Remote Similarity	NPD4919	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data