NPASS Compound

Structure

NPC30890 OpenBabel07101718222D 29 31 0 0 1 0 0 0 0 0999 V2000 5.0941 4.5214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5173 5.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8739 1.7807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2807 2.6943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2916 2.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8794 1.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6929 3.5033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6984 3.3988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4727 0.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2738 3.0485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0605 -0.0464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0996 4.4168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1106 4.2078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.9945 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 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 29 1 0 0 0 0 13 21 1 0 0 0 0 15 11 1 1 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 21 1 1 0 0 0 17 19 2 0 0 0 0 17 25 1 0 0 0 0 18 20 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 24 2 0 0 0 0 22 14 1 6 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.17
Volume:	406.475
LogP:	2.113
LogD:	2.272
LogS:	-4.478
# Rotatable Bonds:	8
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	3.298
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.75
MDCK Permeability:	5.2822197176283225e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.46
Plasma Protein Binding (PPB):	70.18402862548828%
Volume Distribution (VD):	0.596
Pgp-substrate:	13.879307746887207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.899
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.553
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.762
CYP3A4-substrate:	0.872

ADMET: Excretion

Clearance (CL):	9.218
Half-life (T1/2):	0.721

ADMET: Toxicity

hERG Blockers:	0.318
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.762
AMES Toxicity:	0.235
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.285
Carcinogencity:	0.252
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC30890

Natural Product ID:	NPC30890
*Common Name:**	Magnone A
IUPAC Name:	(3,4-dimethoxyphenyl)-[(3R,4R,5S)-5-(3,4-dimethoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methanone
Synonyms:
Standard InCHIKey:	PYUASVNLYYZKLA-PONJGIIJSA-N
Standard InCHI:	InChI=1S/C22H26O7/c1-25-17-7-5-13(9-19(17)27-3)21(24)16-12-29-22(15(16)11-23)14-6-8-18(26-2)20(10-14)28-4/h5-10,15-16,22-23H,11-12H2,1-4H3/t15-,16-,22+/m0/s1
SMILES:	COc1ccc(cc1OC)C(=O)[C@H]1CO[C@H](c2ccc(c(c2)OC)OC)[C@H]1CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476710
PubChem CID:	9822388
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003422] 7,9'-epoxylignans

*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
NPO17167	Magnolia fargesii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19110419]
NPO17167	Magnolia fargesii	Species	Magnoliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[9644071]
NPO17167	Magnolia fargesii	Species	Magnoliaceae	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
Others	4

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Activity	=	75.2	%	PMID[570937]
NPT2	Others	Unspecified	Activity	=	56.7	%	PMID[570937]
NPT2	Others	Unspecified	Activity	=	41.6	%	PMID[570937]
NPT2	Others	Unspecified	Activity	=	19.4	%	PMID[570937]
NPT2	Others	Unspecified	IC50	=	38000.0	nM	PMID[570937]

☑ 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 NPC30890 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	340
0.1-0.2	1202
0.2-0.3	2754
0.3-0.4	6687
0.4-0.5	11020
0.5-0.6	5029
0.6-0.7	5561
0.7-0.8	8954
0.8-0.85	1074
0.85-0.9	66
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.965	High Similarity	NPC62354
0.9583	High Similarity	NPC151425
0.9452	High Similarity	NPC25127
0.932	High Similarity	NPC287504
0.9296	High Similarity	NPC46161
0.9296	High Similarity	NPC239608
0.9139	High Similarity	NPC472962
0.9139	High Similarity	NPC472961
0.911	High Similarity	NPC474903
0.9103	High Similarity	NPC24257
0.9103	High Similarity	NPC153620
0.9013	High Similarity	NPC239818
0.9013	High Similarity	NPC218471
0.9	High Similarity	NPC180901
0.9	High Similarity	NPC300757
0.8993	High Similarity	NPC308555
0.8926	High Similarity	NPC267091
0.8904	High Similarity	NPC9370
0.8904	High Similarity	NPC213482
0.8904	High Similarity	NPC287495
0.8897	High Similarity	NPC473090
0.8881	High Similarity	NPC474784
0.8874	High Similarity	NPC254163
0.8874	High Similarity	NPC31018
0.8874	High Similarity	NPC255807
0.8867	High Similarity	NPC131121
0.8859	High Similarity	NPC243891
0.8846	High Similarity	NPC128293
0.8836	High Similarity	NPC327052
0.8819	High Similarity	NPC51681
0.8784	High Similarity	NPC472969
0.8782	High Similarity	NPC475738
0.8758	High Similarity	NPC299520
0.8758	High Similarity	NPC129684
0.8758	High Similarity	NPC181960
0.8742	High Similarity	NPC60211
0.8726	High Similarity	NPC173292
0.8725	High Similarity	NPC98809
0.8725	High Similarity	NPC476394
0.8718	High Similarity	NPC124038
0.8716	High Similarity	NPC476338
0.8716	High Similarity	NPC476359
0.8707	High Similarity	NPC223185
0.8693	High Similarity	NPC478223
0.869	High Similarity	NPC28398
0.869	High Similarity	NPC100675
0.8681	High Similarity	NPC470962
0.8681	High Similarity	NPC325625
0.8675	High Similarity	NPC262623
0.8667	High Similarity	NPC473091
0.8662	High Similarity	NPC472277
0.8658	High Similarity	NPC294972
0.8658	High Similarity	NPC93034
0.8658	High Similarity	NPC119660
0.8658	High Similarity	NPC470511
0.8645	High Similarity	NPC298093
0.8643	High Similarity	NPC339621
0.8643	High Similarity	NPC280399
0.8643	High Similarity	NPC233961
0.8639	High Similarity	NPC119663
0.8639	High Similarity	NPC46880
0.8639	High Similarity	NPC15743
0.8639	High Similarity	NPC50954
0.8627	High Similarity	NPC472909
0.8627	High Similarity	NPC37392
0.8623	High Similarity	NPC206882
0.8618	High Similarity	NPC137813
0.8618	High Similarity	NPC327225
0.8609	High Similarity	NPC156953
0.8609	High Similarity	NPC472279
0.8609	High Similarity	NPC338131
0.8609	High Similarity	NPC239363
0.8608	High Similarity	NPC235610
0.8608	High Similarity	NPC119589
0.8599	High Similarity	NPC18100
0.8599	High Similarity	NPC205265
0.8599	High Similarity	NPC100425
0.8599	High Similarity	NPC273959
0.8599	High Similarity	NPC472281
0.8591	High Similarity	NPC195919
0.8591	High Similarity	NPC12377
0.8591	High Similarity	NPC216314
0.8591	High Similarity	NPC120924
0.8581	High Similarity	NPC207732
0.8581	High Similarity	NPC469683
0.8571	High Similarity	NPC185607
0.8571	High Similarity	NPC28326
0.8562	High Similarity	NPC472915
0.8562	High Similarity	NPC124714
0.8562	High Similarity	NPC280937
0.8562	High Similarity	NPC469550
0.8562	High Similarity	NPC18727
0.8553	High Similarity	NPC75695
0.8553	High Similarity	NPC476335
0.8553	High Similarity	NPC247973
0.8552	High Similarity	NPC44573
0.8544	High Similarity	NPC300053
0.8544	High Similarity	NPC108433
0.8543	High Similarity	NPC333691
0.8543	High Similarity	NPC40290
0.8543	High Similarity	NPC69430
0.8543	High Similarity	NPC139293
0.8543	High Similarity	NPC142876
0.8543	High Similarity	NPC238366
0.8543	High Similarity	NPC200060
0.8543	High Similarity	NPC264550
0.8543	High Similarity	NPC12854
0.8543	High Similarity	NPC92722
0.8543	High Similarity	NPC195763
0.8543	High Similarity	NPC102003
0.8543	High Similarity	NPC264289
0.8535	High Similarity	NPC472635
0.8535	High Similarity	NPC312056
0.8535	High Similarity	NPC125991
0.8535	High Similarity	NPC84515
0.8535	High Similarity	NPC81679
0.8535	High Similarity	NPC472964
0.8535	High Similarity	NPC76687
0.8533	High Similarity	NPC117463
0.8526	High Similarity	NPC328102
0.8526	High Similarity	NPC472624
0.8526	High Similarity	NPC472902
0.8523	High Similarity	NPC471590
0.8523	High Similarity	NPC136278
0.8521	High Similarity	NPC50763
0.8516	High Similarity	NPC52530
0.8516	High Similarity	NPC474990
0.8516	High Similarity	NPC84935
0.8516	High Similarity	NPC162869
0.8516	High Similarity	NPC474208
0.8516	High Similarity	NPC472914
0.8516	High Similarity	NPC99597
0.8516	High Similarity	NPC226759
0.8516	High Similarity	NPC190020
0.8516	High Similarity	NPC19097
0.8516	High Similarity	NPC245758
0.8516	High Similarity	NPC474055
0.8516	High Similarity	NPC48208
0.8516	High Similarity	NPC78071
0.8516	High Similarity	NPC291508
0.8516	High Similarity	NPC108456
0.8516	High Similarity	NPC210084
0.8516	High Similarity	NPC474836
0.8516	High Similarity	NPC472911
0.8516	High Similarity	NPC77679
0.8516	High Similarity	NPC96167
0.8516	High Similarity	NPC475267
0.8516	High Similarity	NPC222814
0.8516	High Similarity	NPC472598
0.8516	High Similarity	NPC469584
0.8516	High Similarity	NPC472910
0.8516	High Similarity	NPC470402
0.8516	High Similarity	NPC156057
0.8516	High Similarity	NPC472913
0.8514	High Similarity	NPC469615
0.8509	High Similarity	NPC121333
0.8506	High Similarity	NPC226025
0.8506	High Similarity	NPC79998
0.8506	High Similarity	NPC10205
0.8503	High Similarity	NPC58229
0.85	High Similarity	NPC470084
0.85	High Similarity	NPC288813
0.85	High Similarity	NPC152477
0.8497	Intermediate Similarity	NPC219582
0.8497	Intermediate Similarity	NPC121522
0.8497	Intermediate Similarity	NPC39732
0.8497	Intermediate Similarity	NPC100971
0.8497	Intermediate Similarity	NPC323626
0.8497	Intermediate Similarity	NPC35763
0.8497	Intermediate Similarity	NPC181209
0.8497	Intermediate Similarity	NPC60972
0.8497	Intermediate Similarity	NPC295646
0.8497	Intermediate Similarity	NPC100263
0.8497	Intermediate Similarity	NPC269451
0.8497	Intermediate Similarity	NPC291802
0.8497	Intermediate Similarity	NPC245382
0.8497	Intermediate Similarity	NPC209487
0.8497	Intermediate Similarity	NPC477231
0.8497	Intermediate Similarity	NPC302950
0.8497	Intermediate Similarity	NPC216769
0.8497	Intermediate Similarity	NPC260979
0.8497	Intermediate Similarity	NPC131266
0.8497	Intermediate Similarity	NPC474993
0.8497	Intermediate Similarity	NPC472912
0.8497	Intermediate Similarity	NPC257648
0.8497	Intermediate Similarity	NPC236637
0.8497	Intermediate Similarity	NPC324233
0.8493	Intermediate Similarity	NPC322021
0.8493	Intermediate Similarity	NPC4796
0.8491	Intermediate Similarity	NPC43065
0.8487	Intermediate Similarity	NPC234152
0.8481	Intermediate Similarity	NPC272750
0.8481	Intermediate Similarity	NPC475865
0.8481	Intermediate Similarity	NPC89131
0.8481	Intermediate Similarity	NPC134047
0.8481	Intermediate Similarity	NPC223006
0.8481	Intermediate Similarity	NPC173729
0.8481	Intermediate Similarity	NPC475985
0.8477	Intermediate Similarity	NPC203747
0.8477	Intermediate Similarity	NPC80710

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 NPC30890 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	764
0.2-0.3	1528
0.3-0.4	2452
0.4-0.5	2167
0.5-0.6	1178
0.6-0.7	583
0.7-0.8	171
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8645	High Similarity	NPD5494	Approved
0.8571	High Similarity	NPD3882	Suspended
0.8497	Intermediate Similarity	NPD1934	Approved
0.8438	Intermediate Similarity	NPD3818	Discontinued
0.8323	Intermediate Similarity	NPD2801	Approved
0.8323	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD4628	Phase 3
0.8212	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6166	Phase 2
0.8199	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD3817	Phase 2
0.8129	Intermediate Similarity	NPD4380	Phase 2
0.8037	Intermediate Similarity	NPD7473	Discontinued
0.8025	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD7074	Phase 3
0.7987	Intermediate Similarity	NPD2796	Approved
0.7987	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1511	Approved
0.7963	Intermediate Similarity	NPD6232	Discontinued
0.7939	Intermediate Similarity	NPD5844	Phase 1
0.7939	Intermediate Similarity	NPD7054	Approved
0.7919	Intermediate Similarity	NPD1510	Phase 2
0.7917	Intermediate Similarity	NPD9494	Approved
0.7911	Intermediate Similarity	NPD37	Approved
0.7904	Intermediate Similarity	NPD7685	Pre-registration
0.7901	Intermediate Similarity	NPD1247	Approved
0.7892	Intermediate Similarity	NPD7472	Approved
0.7891	Intermediate Similarity	NPD1240	Approved
0.7881	Intermediate Similarity	NPD1549	Phase 2
0.7875	Intermediate Similarity	NPD4967	Phase 2
0.7875	Intermediate Similarity	NPD4966	Approved
0.7875	Intermediate Similarity	NPD4965	Approved
0.7871	Intermediate Similarity	NPD1512	Approved
0.7862	Intermediate Similarity	NPD7819	Suspended
0.7862	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6799	Approved
0.7848	Intermediate Similarity	NPD6385	Approved
0.7848	Intermediate Similarity	NPD6386	Approved
0.7826	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2344	Approved
0.7808	Intermediate Similarity	NPD3027	Phase 3
0.7806	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2799	Discontinued
0.7785	Intermediate Similarity	NPD6599	Discontinued
0.7785	Intermediate Similarity	NPD1607	Approved
0.7778	Intermediate Similarity	NPD919	Approved
0.777	Intermediate Similarity	NPD5536	Phase 2
0.7762	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.7751	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD2935	Discontinued
0.7738	Intermediate Similarity	NPD6797	Phase 2
0.7727	Intermediate Similarity	NPD6190	Approved
0.7718	Intermediate Similarity	NPD230	Phase 1
0.7718	Intermediate Similarity	NPD447	Suspended
0.7716	Intermediate Similarity	NPD7075	Discontinued
0.7712	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5242	Approved
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD2534	Approved
0.7692	Intermediate Similarity	NPD1608	Approved
0.7692	Intermediate Similarity	NPD7251	Discontinued
0.7692	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD3972	Approved
0.7688	Intermediate Similarity	NPD6801	Discontinued
0.7683	Intermediate Similarity	NPD7199	Phase 2
0.7674	Intermediate Similarity	NPD8434	Phase 2
0.7669	Intermediate Similarity	NPD6234	Discontinued
0.7662	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4110	Phase 3
0.7651	Intermediate Similarity	NPD943	Approved
0.7647	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2309	Approved
0.7609	Intermediate Similarity	NPD5283	Phase 1
0.7603	Intermediate Similarity	NPD2798	Approved
0.7593	Intermediate Similarity	NPD5402	Approved
0.7593	Intermediate Similarity	NPD5353	Approved
0.7588	Intermediate Similarity	NPD6559	Discontinued
0.7586	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1876	Approved
0.7576	Intermediate Similarity	NPD8127	Discontinued
0.7532	Intermediate Similarity	NPD6273	Approved
0.7531	Intermediate Similarity	NPD1465	Phase 2
0.7517	Intermediate Similarity	NPD3764	Approved
0.7516	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD3226	Approved
0.7485	Intermediate Similarity	NPD5977	Approved
0.7485	Intermediate Similarity	NPD5978	Approved
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2800	Approved
0.7484	Intermediate Similarity	NPD920	Approved
0.7483	Intermediate Similarity	NPD17	Approved
0.7483	Intermediate Similarity	NPD6355	Discontinued
0.747	Intermediate Similarity	NPD6959	Discontinued
0.7468	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7468	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7228	Approved
0.7451	Intermediate Similarity	NPD7033	Discontinued
0.7423	Intermediate Similarity	NPD5760	Phase 2
0.7423	Intermediate Similarity	NPD5761	Phase 2
0.7412	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2313	Discontinued
0.7394	Intermediate Similarity	NPD3749	Approved
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7379	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD3705	Approved
0.7375	Intermediate Similarity	NPD5403	Approved
0.7368	Intermediate Similarity	NPD1933	Approved
0.7358	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5401	Approved
0.7355	Intermediate Similarity	NPD1471	Phase 3
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7353	Intermediate Similarity	NPD2163	Approved
0.7346	Intermediate Similarity	NPD7028	Phase 2
0.7343	Intermediate Similarity	NPD9545	Approved
0.7325	Intermediate Similarity	NPD3750	Approved
0.7325	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3787	Discontinued
0.7303	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1613	Approved
0.7299	Intermediate Similarity	NPD8312	Approved
0.7299	Intermediate Similarity	NPD8313	Approved
0.7296	Intermediate Similarity	NPD4357	Discontinued
0.729	Intermediate Similarity	NPD2438	Suspended
0.7283	Intermediate Similarity	NPD7240	Approved
0.7283	Intermediate Similarity	NPD7039	Approved
0.7283	Intermediate Similarity	NPD7038	Approved
0.7278	Intermediate Similarity	NPD3887	Approved
0.7267	Intermediate Similarity	NPD6832	Phase 2
0.7261	Intermediate Similarity	NPD1243	Approved
0.7256	Intermediate Similarity	NPD6844	Discontinued
0.7255	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5647	Approved
0.7244	Intermediate Similarity	NPD7266	Discontinued
0.7241	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6233	Phase 2
0.7235	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1241	Discontinued
0.7233	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1283	Approved
0.7229	Intermediate Similarity	NPD7768	Phase 2
0.7226	Intermediate Similarity	NPD3748	Approved
0.7226	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2861	Phase 2
0.7197	Intermediate Similarity	NPD2424	Discontinued
0.7195	Intermediate Similarity	NPD6873	Phase 2
0.719	Intermediate Similarity	NPD2979	Phase 3
0.7179	Intermediate Similarity	NPD1551	Phase 2
0.7178	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8150	Discontinued
0.7172	Intermediate Similarity	NPD1651	Approved
0.7171	Intermediate Similarity	NPD6798	Discontinued
0.7171	Intermediate Similarity	NPD3268	Approved
0.717	Intermediate Similarity	NPD2354	Approved
0.7152	Intermediate Similarity	NPD4236	Phase 3
0.7152	Intermediate Similarity	NPD6280	Approved
0.7152	Intermediate Similarity	NPD6279	Approved
0.7152	Intermediate Similarity	NPD4237	Approved
0.7151	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4661	Approved
0.7143	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4662	Approved
0.7135	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2403	Approved
0.7134	Intermediate Similarity	NPD6002	Phase 3
0.7134	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6005	Phase 3
0.7134	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6004	Phase 3
0.7133	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5710	Approved
0.7118	Intermediate Similarity	NPD6808	Phase 2
0.7118	Intermediate Similarity	NPD5711	Approved
0.7118	Intermediate Similarity	NPD7229	Phase 3
0.7115	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8166	Discontinued
0.7097	Intermediate Similarity	NPD6653	Approved
0.7097	Intermediate Similarity	NPD6651	Approved
0.7078	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3620	Phase 2
0.7073	Intermediate Similarity	NPD3455	Phase 2
0.7073	Intermediate Similarity	NPD2649	Approved
0.7073	Intermediate Similarity	NPD2651	Approved
0.707	Intermediate Similarity	NPD6100	Approved
0.707	Intermediate Similarity	NPD6099	Approved
0.7067	Intermediate Similarity	NPD2797	Approved
0.7067	Intermediate Similarity	NPD1470	Approved

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