NPASS Compound

Structure

NPC475000 OpenBabel07101718232D 31 34 0 0 1 0 0 0 0 0999 V2000 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6369 3.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 5.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 5.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 4.5388 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 -3.0491 2.7298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0491 4.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 13 2 0 0 0 0 6 16 1 0 0 0 0 7 13 1 0 0 0 0 7 17 2 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 9 19 2 0 0 0 0 10 15 1 0 0 0 0 10 29 1 0 0 0 0 11 30 1 0 0 0 0 11 31 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 14 20 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 26 1 0 0 0 0 18 22 2 0 0 0 0 18 27 1 0 0 0 0 19 22 1 0 0 0 0 19 30 1 0 0 0 0 21 28 1 0 0 0 0 22 31 1 0 0 0 0 23 24 2 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.15
Volume:	421.368
LogP:	2.614
LogD:	3.174
LogS:	-4.603
# Rotatable Bonds:	7
TPSA:	81.68
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.491
Synthetic Accessibility Score:	3.618
Fsp3:	0.348
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.806
MDCK Permeability:	3.0467990654869936e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	94.80874633789062%
Volume Distribution (VD):	0.719
Pgp-substrate:	6.860735893249512%

ADMET: Metabolism

CYP1A2-inhibitor:	0.079
CYP1A2-substrate:	0.975
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.866
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.668
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.961
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	10.187
Half-life (T1/2):	0.151

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.501
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.239
Maximum Recommended Daily Dose:	0.774
Skin Sensitization:	0.139
Carcinogencity:	0.414
Eye Corrosion:	0.003
Eye Irritation:	0.117
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC475000

Natural Product ID:	NPC475000
*Common Name:**	4-[(7-Methoxy-1,3-Benzodioxol-5-Yl)-(3,4,5-Trimethoxyphenyl)Methyl]-3-Methylideneoxolan-2-One
IUPAC Name:	4-[(7-methoxy-1,3-benzodioxol-5-yl)-(3,4,5-trimethoxyphenyl)methyl]-3-methylideneoxolan-2-one
Synonyms:
Standard InCHIKey:	NXCYGTFQPAUJIS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H24O8/c1-12-15(10-29-23(12)24)20(13-6-16(25-2)21(28-5)17(7-13)26-3)14-8-18(27-4)22-19(9-14)30-11-31-22/h6-9,15,20H,1,10-11H2,2-5H3
SMILES:	COC1=CC(=CC2=C1OCO2)C(C3COC(=O)C3=C)C4=CC(=C(C(=C4)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491522
PubChem CID:	9867239
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499324]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13657	Peperomia pellucida	Species	Piperaceae	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	3
Others	3

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	1400.0	nM	PMID[488075]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3800.0	nM	PMID[488075]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	9100.0	nM	PMID[488075]
NPT116	Cell Line	HL-60	Homo sapiens	GI	=	92.0	%	PMID[488075]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	91.0	%	PMID[488075]
NPT165	Cell Line	HeLa	Homo sapiens	GI	=	96.0	%	PMID[488075]

☑ 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 NPC475000 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	360
0.1-0.2	1480
0.2-0.3	3302
0.3-0.4	8523
0.4-0.5	10602
0.5-0.6	4364
0.6-0.7	9549
0.7-0.8	4066
0.8-0.85	280
0.85-0.9	114
0.9-0.95	47
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9855	High Similarity	NPC193779
0.9853	High Similarity	NPC151423
0.9853	High Similarity	NPC40237
0.971	High Similarity	NPC218841
0.971	High Similarity	NPC92693
0.9708	High Similarity	NPC210354
0.9708	High Similarity	NPC176586
0.9568	High Similarity	NPC177644
0.9568	High Similarity	NPC191158
0.951	High Similarity	NPC477700
0.95	High Similarity	NPC474158
0.9496	High Similarity	NPC474288
0.9412	High Similarity	NPC72796
0.9412	High Similarity	NPC44245
0.9375	High Similarity	NPC32079
0.9371	High Similarity	NPC668
0.9371	High Similarity	NPC174512
0.9371	High Similarity	NPC477695
0.9371	High Similarity	NPC293757
0.9371	High Similarity	NPC477698
0.9371	High Similarity	NPC474965
0.9366	High Similarity	NPC304687
0.9366	High Similarity	NPC80230
0.9366	High Similarity	NPC101755
0.9366	High Similarity	NPC65574
0.9366	High Similarity	NPC104024
0.9343	High Similarity	NPC11453
0.9315	High Similarity	NPC178195
0.9315	High Similarity	NPC348849
0.9306	High Similarity	NPC149505
0.927	High Similarity	NPC211386
0.9241	High Similarity	NPC303519
0.9241	High Similarity	NPC164082
0.9241	High Similarity	NPC13985
0.9241	High Similarity	NPC210642
0.9236	High Similarity	NPC216223
0.9236	High Similarity	NPC145569
0.9236	High Similarity	NPC262455
0.9236	High Similarity	NPC177476
0.9178	High Similarity	NPC56184
0.9178	High Similarity	NPC477699
0.9167	High Similarity	NPC262804
0.9167	High Similarity	NPC40654
0.9124	High Similarity	NPC205915
0.9065	High Similarity	NPC143895
0.9054	High Similarity	NPC273578
0.9054	High Similarity	NPC136757
0.9014	High Similarity	NPC287124
0.8978	High Similarity	NPC192255
0.8973	High Similarity	NPC85141
0.8951	High Similarity	NPC477697
0.8951	High Similarity	NPC470811
0.8951	High Similarity	NPC477696
0.8947	High Similarity	NPC209411
0.8947	High Similarity	NPC239890
0.8933	High Similarity	NPC32373
0.8933	High Similarity	NPC237946
0.8929	High Similarity	NPC209229
0.8929	High Similarity	NPC230968
0.8929	High Similarity	NPC102260
0.8926	High Similarity	NPC103197
0.8926	High Similarity	NPC30009
0.8921	High Similarity	NPC110958
0.8921	High Similarity	NPC19890
0.8919	High Similarity	NPC104353
0.8913	High Similarity	NPC72046
0.8913	High Similarity	NPC65183
0.8913	High Similarity	NPC261812
0.8889	High Similarity	NPC141569
0.8889	High Similarity	NPC166884
0.8889	High Similarity	NPC477701
0.8889	High Similarity	NPC61141
0.8889	High Similarity	NPC76687
0.8874	High Similarity	NPC163527
0.8874	High Similarity	NPC207584
0.8874	High Similarity	NPC115281
0.8874	High Similarity	NPC19947
0.8874	High Similarity	NPC181168
0.8867	High Similarity	NPC234730
0.8859	High Similarity	NPC308555
0.8857	High Similarity	NPC148893
0.8857	High Similarity	NPC49235
0.8857	High Similarity	NPC25333
0.8851	High Similarity	NPC474975
0.8849	High Similarity	NPC266848
0.8849	High Similarity	NPC136750
0.8844	High Similarity	NPC125570
0.8828	High Similarity	NPC477702
0.8824	High Similarity	NPC258322
0.8824	High Similarity	NPC191352
0.8819	High Similarity	NPC106920
0.8819	High Similarity	NPC273657
0.8816	High Similarity	NPC325122
0.8816	High Similarity	NPC474043
0.8808	High Similarity	NPC477380
0.8794	High Similarity	NPC121651
0.8786	High Similarity	NPC31530
0.8784	High Similarity	NPC316989
0.8776	High Similarity	NPC252281
0.8776	High Similarity	NPC477375
0.8776	High Similarity	NPC327352
0.8776	High Similarity	NPC198129
0.8767	High Similarity	NPC321696
0.8767	High Similarity	NPC321958
0.8767	High Similarity	NPC212890
0.8767	High Similarity	NPC3982
0.8767	High Similarity	NPC87295
0.8759	High Similarity	NPC15743
0.8759	High Similarity	NPC143092
0.8759	High Similarity	NPC18211
0.8758	High Similarity	NPC96593
0.8758	High Similarity	NPC474770
0.8758	High Similarity	NPC150943
0.8758	High Similarity	NPC119910
0.8758	High Similarity	NPC268718
0.8758	High Similarity	NPC91634
0.875	High Similarity	NPC477885
0.8742	High Similarity	NPC254163
0.8733	High Similarity	NPC245948
0.8732	High Similarity	NPC283949
0.8723	High Similarity	NPC189474
0.8723	High Similarity	NPC150534
0.8716	High Similarity	NPC477376
0.8716	High Similarity	NPC477374
0.8716	High Similarity	NPC322426
0.8701	High Similarity	NPC288149
0.8701	High Similarity	NPC152424
0.8701	High Similarity	NPC100465
0.8701	High Similarity	NPC115624
0.8699	High Similarity	NPC327651
0.8699	High Similarity	NPC318286
0.8696	High Similarity	NPC476748
0.869	High Similarity	NPC76415
0.869	High Similarity	NPC218510
0.8686	High Similarity	NPC223807
0.8684	High Similarity	NPC473900
0.8681	High Similarity	NPC282291
0.8681	High Similarity	NPC166137
0.8675	High Similarity	NPC312763
0.8675	High Similarity	NPC198461
0.8671	High Similarity	NPC113550
0.8667	High Similarity	NPC476434
0.8658	High Similarity	NPC475170
0.8649	High Similarity	NPC304821
0.8639	High Similarity	NPC213482
0.8636	High Similarity	NPC470637
0.863	High Similarity	NPC326144
0.8623	High Similarity	NPC328682
0.8623	High Similarity	NPC281864
0.8623	High Similarity	NPC54321
0.8621	High Similarity	NPC46180
0.8611	High Similarity	NPC56091
0.8611	High Similarity	NPC226547
0.8611	High Similarity	NPC46591
0.8609	High Similarity	NPC473236
0.8609	High Similarity	NPC474514
0.8601	High Similarity	NPC166184
0.8601	High Similarity	NPC185908
0.8601	High Similarity	NPC14022
0.859	High Similarity	NPC14294
0.859	High Similarity	NPC116759
0.8582	High Similarity	NPC1474
0.8581	High Similarity	NPC24257
0.8581	High Similarity	NPC319749
0.8581	High Similarity	NPC153620
0.8552	High Similarity	NPC51681
0.8552	High Similarity	NPC218092
0.8552	High Similarity	NPC246474
0.8552	High Similarity	NPC312199
0.8552	High Similarity	NPC162851
0.8551	High Similarity	NPC473092
0.8551	High Similarity	NPC8050
0.8551	High Similarity	NPC473093
0.8544	High Similarity	NPC79322
0.8543	High Similarity	NPC220577
0.8535	High Similarity	NPC222531
0.8533	High Similarity	NPC158635
0.8533	High Similarity	NPC473989
0.8533	High Similarity	NPC229882
0.8526	High Similarity	NPC280778
0.8511	High Similarity	NPC7744
0.8506	High Similarity	NPC474990
0.8503	High Similarity	NPC27159
0.8503	High Similarity	NPC474036
0.8503	High Similarity	NPC50696
0.85	High Similarity	NPC178737
0.8497	Intermediate Similarity	NPC186316
0.8497	Intermediate Similarity	NPC238834
0.8497	Intermediate Similarity	NPC202249
0.8497	Intermediate Similarity	NPC188962
0.8497	Intermediate Similarity	NPC42871
0.8493	Intermediate Similarity	NPC52664
0.8489	Intermediate Similarity	NPC57119
0.8489	Intermediate Similarity	NPC158471
0.8489	Intermediate Similarity	NPC165128
0.8489	Intermediate Similarity	NPC222127
0.8489	Intermediate Similarity	NPC226862
0.8489	Intermediate Similarity	NPC82862
0.8487	Intermediate Similarity	NPC217708
0.8487	Intermediate Similarity	NPC77237

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 NPC475000 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	870
0.2-0.3	1684
0.3-0.4	2767
0.4-0.5	1941
0.5-0.6	1085
0.6-0.7	431
0.7-0.8	71
0.8-0.85	6
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8933	High Similarity	NPD4965	Approved
0.8933	High Similarity	NPD4967	Phase 2
0.8933	High Similarity	NPD4966	Approved
0.8816	High Similarity	NPD6234	Discontinued
0.8776	High Similarity	NPD6980	Clinical (unspecified phase)
0.8733	High Similarity	NPD37	Approved
0.8462	Intermediate Similarity	NPD7199	Phase 2
0.8428	Intermediate Similarity	NPD7228	Approved
0.8354	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7240	Approved
0.7986	Intermediate Similarity	NPD3705	Approved
0.7964	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD3818	Discontinued
0.7826	Intermediate Similarity	NPD5494	Approved
0.775	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3817	Phase 2
0.7683	Intermediate Similarity	NPD5242	Approved
0.764	Intermediate Similarity	NPD3882	Suspended
0.7619	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD5283	Phase 1
0.7578	Intermediate Similarity	NPD5353	Approved
0.7576	Intermediate Similarity	NPD3926	Phase 2
0.7552	Intermediate Similarity	NPD2981	Phase 2
0.7551	Intermediate Similarity	NPD3027	Phase 3
0.7546	Intermediate Similarity	NPD919	Approved
0.7532	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4110	Phase 3
0.7528	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD5536	Phase 2
0.75	Intermediate Similarity	NPD2982	Phase 2
0.75	Intermediate Similarity	NPD2438	Suspended
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.7471	Intermediate Similarity	NPD7685	Pre-registration
0.7467	Intermediate Similarity	NPD1933	Approved
0.7467	Intermediate Similarity	NPD230	Phase 1
0.7465	Intermediate Similarity	NPD17	Approved
0.7456	Intermediate Similarity	NPD7074	Phase 3
0.7438	Intermediate Similarity	NPD7028	Phase 2
0.7434	Intermediate Similarity	NPD3748	Approved
0.7427	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1653	Approved
0.7415	Intermediate Similarity	NPD3018	Phase 2
0.7407	Intermediate Similarity	NPD1465	Phase 2
0.7407	Intermediate Similarity	NPD7819	Suspended
0.7396	Intermediate Similarity	NPD5844	Phase 1
0.7396	Intermediate Similarity	NPD7054	Approved
0.7391	Intermediate Similarity	NPD6386	Approved
0.7391	Intermediate Similarity	NPD6385	Approved
0.7389	Intermediate Similarity	NPD6799	Approved
0.7368	Intermediate Similarity	NPD6559	Discontinued
0.7363	Intermediate Similarity	NPD7680	Approved
0.7353	Intermediate Similarity	NPD7472	Approved
0.7351	Intermediate Similarity	NPD6355	Discontinued
0.7346	Intermediate Similarity	NPD1934	Approved
0.7338	Intermediate Similarity	NPD7266	Discontinued
0.7329	Intermediate Similarity	NPD6599	Discontinued
0.731	Intermediate Similarity	NPD1608	Approved
0.7308	Intermediate Similarity	NPD5006	Approved
0.7308	Intermediate Similarity	NPD4628	Phase 3
0.7308	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5005	Approved
0.7301	Intermediate Similarity	NPD2801	Approved
0.729	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2979	Phase 3
0.7278	Intermediate Similarity	NPD4357	Discontinued
0.7273	Intermediate Similarity	NPD2796	Approved
0.7273	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6190	Approved
0.7246	Intermediate Similarity	NPD1247	Approved
0.7246	Intermediate Similarity	NPD8127	Discontinued
0.7241	Intermediate Similarity	NPD1281	Approved
0.7233	Intermediate Similarity	NPD2532	Approved
0.7233	Intermediate Similarity	NPD2534	Approved
0.7233	Intermediate Similarity	NPD2533	Approved
0.7225	Intermediate Similarity	NPD7808	Phase 3
0.7209	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6797	Phase 2
0.7202	Intermediate Similarity	NPD7229	Phase 3
0.7197	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3750	Approved
0.7195	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4420	Approved
0.7169	Intermediate Similarity	NPD7075	Discontinued
0.7168	Intermediate Similarity	NPD7251	Discontinued
0.7153	Intermediate Similarity	NPD5585	Approved
0.7152	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD920	Approved
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1243	Approved
0.7134	Intermediate Similarity	NPD6801	Discontinued
0.7133	Intermediate Similarity	NPD6832	Phase 2
0.7118	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6166	Phase 2
0.7095	Intermediate Similarity	NPD1283	Approved
0.7095	Intermediate Similarity	NPD7296	Approved
0.7091	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD8455	Phase 2
0.7081	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7411	Suspended
0.7073	Intermediate Similarity	NPD6873	Phase 2
0.7067	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1613	Approved
0.7059	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7458	Discontinued
0.7053	Intermediate Similarity	NPD7827	Phase 1
0.7051	Intermediate Similarity	NPD2935	Discontinued
0.7051	Intermediate Similarity	NPD2531	Phase 2
0.7047	Intermediate Similarity	NPD2797	Approved
0.7047	Intermediate Similarity	NPD3267	Approved
0.7047	Intermediate Similarity	NPD3266	Approved
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.7039	Intermediate Similarity	NPD1296	Phase 2
0.7039	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD5403	Approved
0.7034	Intermediate Similarity	NPD1357	Approved
0.7034	Intermediate Similarity	NPD1651	Approved
0.7029	Intermediate Similarity	NPD1358	Approved
0.702	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4908	Phase 1
0.7019	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5401	Approved
0.7019	Intermediate Similarity	NPD3146	Approved
0.7013	Intermediate Similarity	NPD447	Suspended
0.7012	Intermediate Similarity	NPD4380	Phase 2
0.7006	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7768	Phase 2
0.7	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7124	Phase 2
0.6993	Remote Similarity	NPD6233	Phase 2
0.6993	Remote Similarity	NPD8032	Phase 2
0.6987	Remote Similarity	NPD1510	Phase 2
0.6987	Remote Similarity	NPD2799	Discontinued
0.6983	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1876	Approved
0.6975	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7095	Approved
0.697	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6971	Discontinued
0.6957	Remote Similarity	NPD1511	Approved
0.6957	Remote Similarity	NPD3134	Approved
0.6948	Remote Similarity	NPD4060	Phase 1
0.6948	Remote Similarity	NPD1240	Approved
0.6943	Remote Similarity	NPD6099	Approved
0.6943	Remote Similarity	NPD6100	Approved
0.6943	Remote Similarity	NPD1551	Phase 2
0.6943	Remote Similarity	NPD3539	Phase 1
0.6937	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3268	Approved
0.6928	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7097	Phase 1
0.6923	Remote Similarity	NPD6111	Discontinued
0.6918	Remote Similarity	NPD6674	Discontinued
0.6918	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5691	Approved
0.6913	Remote Similarity	NPD4359	Approved
0.6903	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3787	Discontinued
0.6901	Remote Similarity	NPD5535	Approved
0.6899	Remote Similarity	NPD6004	Phase 3
0.6899	Remote Similarity	NPD3540	Phase 1
0.6899	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6005	Phase 3
0.6899	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6002	Phase 3
0.6897	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7281	Phase 3
0.6893	Remote Similarity	NPD7280	Phase 3
0.6892	Remote Similarity	NPD1610	Phase 2
0.6889	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2798	Approved
0.6883	Remote Similarity	NPD4062	Phase 3
0.6875	Remote Similarity	NPD8166	Discontinued
0.6871	Remote Similarity	NPD6273	Approved
0.6871	Remote Similarity	NPD1512	Approved
0.6864	Remote Similarity	NPD3749	Approved
0.6864	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1607	Approved
0.6855	Remote Similarity	NPD1549	Phase 2
0.6855	Remote Similarity	NPD5958	Discontinued
0.6853	Remote Similarity	NPD1241	Discontinued
0.6852	Remote Similarity	NPD5297	Approved
0.6849	Remote Similarity	NPD1894	Discontinued
0.6846	Remote Similarity	NPD3972	Approved
0.6845	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9494	Approved
0.6839	Remote Similarity	NPD3751	Discontinued
0.6836	Remote Similarity	NPD7549	Discontinued
0.6826	Remote Similarity	NPD3382	Approved
0.6826	Remote Similarity	NPD3383	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