NPASS Compound

Structure

NPC250076 OpenBabel07101719402D 26 28 0 0 0 0 0 0 0 0999 V2000 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 0.8090 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 11 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 12 1 0 0 0 0 7 15 2 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 10 21 2 0 0 0 0 11 14 1 0 0 0 0 11 18 2 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 15 19 1 0 0 0 0 15 22 1 0 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 17 24 1 0 0 0 0 18 26 1 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	360.456
LogP:	3.751
LogD:	3.412
LogS:	-5.393
# Rotatable Bonds:	6
TPSA:	67.13
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.615
Synthetic Accessibility Score:	2.437
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.692
MDCK Permeability:	4.077670382685028e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	79.18849182128906%
Volume Distribution (VD):	1.046
Pgp-substrate:	15.181737899780273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.527
CYP1A2-substrate:	0.979
CYP2C19-inhibitor:	0.309
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.281
CYP2C9-substrate:	0.872
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.667
CYP3A4-substrate:	0.485

ADMET: Excretion

Clearance (CL):	8.727
Half-life (T1/2):	0.595

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.15
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.283
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.179
Skin Sensitization:	0.095
Carcinogencity:	0.041
Eye Corrosion:	0.006
Eye Irritation:	0.033
Respiratory Toxicity:	0.646

Download Data

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

Natural Product: NPC250076

Natural Product ID:	NPC250076
*Common Name:**	Ocophyllals B
IUPAC Name:	7-methoxy-3-methyl-2-(3,4,5-trimethoxyphenyl)-1-benzofuran-5-carbaldehyde
Synonyms:
Standard InCHIKey:	ABGNFLATGXMICB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-11-14-6-12(10-21)7-15(22-2)19(14)26-18(11)13-8-16(23-3)20(25-5)17(9-13)24-4/h6-10H,1-5H3
SMILES:	Cc1c2cc(cc(c2oc1c1cc(c(c(c1)OC)OC)OC)OC)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL571617
PubChem CID:	44470606
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19548690]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO27964	Nectandra amazonum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27964	Nectandra amazonum	Species	Lauraceae	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
Others	1

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	102000.0	nM	PMID[469197]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	12700.0	nM	PMID[469197]
NPT2	Others	Unspecified		IC50	=	8020.0	nM	PMID[469197]
NPT2	Others	Unspecified		Ratio IC50	=	412.0	n.a.	PMID[469197]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	847000.0	nM	PMID[469197]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	425000.0	nM	PMID[469197]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	98300.0	nM	PMID[469197]

☑ 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 NPC250076 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	503
0.1-0.2	2034
0.2-0.3	4791
0.3-0.4	11624
0.4-0.5	6248
0.5-0.6	4094
0.6-0.7	5919
0.7-0.8	5805
0.8-0.85	1449
0.85-0.9	220
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9241	High Similarity	NPC65846
0.9236	High Similarity	NPC264293
0.9114	High Similarity	NPC109238
0.908	High Similarity	NPC62640
0.9074	High Similarity	NPC190351
0.9032	High Similarity	NPC60211
0.9006	High Similarity	NPC210460
0.9006	High Similarity	NPC193881
0.9006	High Similarity	NPC155264
0.9006	High Similarity	NPC67450
0.8994	High Similarity	NPC216092
0.8974	High Similarity	NPC41719
0.8963	High Similarity	NPC277510
0.8931	High Similarity	NPC243509
0.891	High Similarity	NPC38361
0.891	High Similarity	NPC130015
0.8903	High Similarity	NPC472406
0.8896	High Similarity	NPC41853
0.8882	High Similarity	NPC179464
0.8874	High Similarity	NPC27220
0.8868	High Similarity	NPC33320
0.8862	High Similarity	NPC104682
0.8841	High Similarity	NPC131866
0.8834	High Similarity	NPC167479
0.8834	High Similarity	NPC241820
0.8831	High Similarity	NPC117463
0.8831	High Similarity	NPC198427
0.882	High Similarity	NPC193998
0.882	High Similarity	NPC78612
0.882	High Similarity	NPC272722
0.882	High Similarity	NPC234536
0.8797	High Similarity	NPC268008
0.8797	High Similarity	NPC233776
0.8797	High Similarity	NPC3273
0.8795	High Similarity	NPC66804
0.8788	High Similarity	NPC157522
0.8782	High Similarity	NPC148423
0.8782	High Similarity	NPC135303
0.8773	High Similarity	NPC472895
0.875	High Similarity	NPC15764
0.875	High Similarity	NPC28326
0.8735	High Similarity	NPC65885
0.8727	High Similarity	NPC144288
0.872	High Similarity	NPC247973
0.872	High Similarity	NPC186392
0.8712	High Similarity	NPC38914
0.8712	High Similarity	NPC187923
0.8712	High Similarity	NPC36320
0.8712	High Similarity	NPC173149
0.8712	High Similarity	NPC179015
0.8712	High Similarity	NPC45449
0.8696	High Similarity	NPC139876
0.8671	High Similarity	NPC263676
0.8671	High Similarity	NPC253872
0.8654	High Similarity	NPC306788
0.865	High Similarity	NPC132054
0.865	High Similarity	NPC263092
0.865	High Similarity	NPC59295
0.865	High Similarity	NPC1706
0.865	High Similarity	NPC1755
0.865	High Similarity	NPC39305
0.8645	High Similarity	NPC190572
0.8642	High Similarity	NPC296540
0.8642	High Similarity	NPC309335
0.8642	High Similarity	NPC99968
0.8634	High Similarity	NPC228501
0.8631	High Similarity	NPC8127
0.8631	High Similarity	NPC107244
0.8631	High Similarity	NPC49667
0.8625	High Similarity	NPC45131
0.8616	High Similarity	NPC473664
0.8614	High Similarity	NPC28042
0.8614	High Similarity	NPC51404
0.8614	High Similarity	NPC476641
0.8608	High Similarity	NPC474414
0.8608	High Similarity	NPC472407
0.8598	High Similarity	NPC291110
0.8598	High Similarity	NPC37183
0.859	High Similarity	NPC299923
0.8589	High Similarity	NPC19948
0.8589	High Similarity	NPC84515
0.8589	High Similarity	NPC219861
0.8589	High Similarity	NPC238995
0.8589	High Similarity	NPC475144
0.8589	High Similarity	NPC312056
0.858	High Similarity	NPC298093
0.8571	High Similarity	NPC19097
0.8571	High Similarity	NPC53917
0.8571	High Similarity	NPC287243
0.8571	High Similarity	NPC289244
0.8571	High Similarity	NPC224165
0.8563	High Similarity	NPC60848
0.8554	High Similarity	NPC247136
0.8545	High Similarity	NPC191012
0.8545	High Similarity	NPC277480
0.8545	High Similarity	NPC43065
0.8545	High Similarity	NPC298071
0.8538	High Similarity	NPC228209
0.8537	High Similarity	NPC133065
0.8537	High Similarity	NPC472581
0.8535	High Similarity	NPC476342
0.8528	High Similarity	NPC188486
0.8526	High Similarity	NPC310259
0.8519	High Similarity	NPC196879
0.8512	High Similarity	NPC233956
0.8512	High Similarity	NPC82217
0.8512	High Similarity	NPC72455
0.8512	High Similarity	NPC216842
0.8512	High Similarity	NPC476640
0.8512	High Similarity	NPC310794
0.8509	High Similarity	NPC160015
0.8509	High Similarity	NPC472461
0.8509	High Similarity	NPC247677
0.8509	High Similarity	NPC261484
0.85	High Similarity	NPC183874
0.8491	Intermediate Similarity	NPC170169
0.8491	Intermediate Similarity	NPC116604
0.8485	Intermediate Similarity	NPC39306
0.8485	Intermediate Similarity	NPC279768
0.8481	Intermediate Similarity	NPC181250
0.8481	Intermediate Similarity	NPC69752
0.8481	Intermediate Similarity	NPC178202
0.8476	Intermediate Similarity	NPC302741
0.8471	Intermediate Similarity	NPC246877
0.8471	Intermediate Similarity	NPC77179
0.8471	Intermediate Similarity	NPC470511
0.8471	Intermediate Similarity	NPC23553
0.8471	Intermediate Similarity	NPC294972
0.8466	Intermediate Similarity	NPC220582
0.8466	Intermediate Similarity	NPC304839
0.8462	Intermediate Similarity	NPC471590
0.8462	Intermediate Similarity	NPC136278
0.8462	Intermediate Similarity	NPC208584
0.8457	Intermediate Similarity	NPC76458
0.8457	Intermediate Similarity	NPC82733
0.8457	Intermediate Similarity	NPC260902
0.8457	Intermediate Similarity	NPC296957
0.8452	Intermediate Similarity	NPC476054
0.8452	Intermediate Similarity	NPC230619
0.8452	Intermediate Similarity	NPC475964
0.8452	Intermediate Similarity	NPC54098
0.8447	Intermediate Similarity	NPC284353
0.8447	Intermediate Similarity	NPC148938
0.8447	Intermediate Similarity	NPC198490
0.8447	Intermediate Similarity	NPC300757
0.8447	Intermediate Similarity	NPC180901
0.8443	Intermediate Similarity	NPC211309
0.8443	Intermediate Similarity	NPC152477
0.8438	Intermediate Similarity	NPC40033
0.8438	Intermediate Similarity	NPC131121
0.8438	Intermediate Similarity	NPC5871
0.843	Intermediate Similarity	NPC8927
0.8428	Intermediate Similarity	NPC259058
0.8428	Intermediate Similarity	NPC230713
0.8428	Intermediate Similarity	NPC189270
0.8428	Intermediate Similarity	NPC78335
0.8428	Intermediate Similarity	NPC191104
0.8428	Intermediate Similarity	NPC201547
0.8428	Intermediate Similarity	NPC5840
0.8424	Intermediate Similarity	NPC472582
0.8424	Intermediate Similarity	NPC18100
0.8424	Intermediate Similarity	NPC109180
0.8421	Intermediate Similarity	NPC476273
0.8418	Intermediate Similarity	NPC63256
0.8418	Intermediate Similarity	NPC10304
0.8415	Intermediate Similarity	NPC304387
0.8415	Intermediate Similarity	NPC30655
0.8415	Intermediate Similarity	NPC74854
0.8415	Intermediate Similarity	NPC45124
0.8405	Intermediate Similarity	NPC476349
0.8405	Intermediate Similarity	NPC195832
0.8405	Intermediate Similarity	NPC476350
0.8405	Intermediate Similarity	NPC16935
0.8397	Intermediate Similarity	NPC293201
0.8397	Intermediate Similarity	NPC113089
0.8395	Intermediate Similarity	NPC155063
0.8395	Intermediate Similarity	NPC180924
0.8395	Intermediate Similarity	NPC261090
0.8393	Intermediate Similarity	NPC135370
0.8393	Intermediate Similarity	NPC281835
0.8391	Intermediate Similarity	NPC240808
0.8387	Intermediate Similarity	NPC29536
0.8385	Intermediate Similarity	NPC1477
0.8385	Intermediate Similarity	NPC189130
0.8385	Intermediate Similarity	NPC235333
0.8385	Intermediate Similarity	NPC213608
0.8385	Intermediate Similarity	NPC279930
0.8385	Intermediate Similarity	NPC128961
0.8385	Intermediate Similarity	NPC472408
0.8383	Intermediate Similarity	NPC95715
0.8383	Intermediate Similarity	NPC50394
0.8383	Intermediate Similarity	NPC150131
0.8375	Intermediate Similarity	NPC58668
0.8375	Intermediate Similarity	NPC98028
0.8375	Intermediate Similarity	NPC220577
0.8375	Intermediate Similarity	NPC106372
0.8373	Intermediate Similarity	NPC472277
0.8366	Intermediate Similarity	NPC470962
0.8365	Intermediate Similarity	NPC88445
0.8365	Intermediate Similarity	NPC37226

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 NPC250076 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	430
0.1-0.2	1043
0.2-0.3	1851
0.3-0.4	2728
0.4-0.5	1739
0.5-0.6	884
0.6-0.7	345
0.7-0.8	107
0.8-0.85	18
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9236	High Similarity	NPD1247	Approved
0.8868	High Similarity	NPD919	Approved
0.865	High Similarity	NPD3926	Phase 2
0.858	High Similarity	NPD5494	Approved
0.8509	High Similarity	NPD3882	Suspended
0.8239	Intermediate Similarity	NPD920	Approved
0.8221	Intermediate Similarity	NPD3817	Phase 2
0.8113	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.7988	Intermediate Similarity	NPD1934	Approved
0.7987	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6166	Phase 2
0.7939	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD2801	Approved
0.7937	Intermediate Similarity	NPD6799	Approved
0.7911	Intermediate Similarity	NPD1243	Approved
0.7888	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD6559	Discontinued
0.7866	Intermediate Similarity	NPD6599	Discontinued
0.7849	Intermediate Similarity	NPD3818	Discontinued
0.7834	Intermediate Similarity	NPD2796	Approved
0.7824	Intermediate Similarity	NPD6232	Discontinued
0.7798	Intermediate Similarity	NPD7075	Discontinued
0.7791	Intermediate Similarity	NPD7473	Discontinued
0.7771	Intermediate Similarity	NPD6801	Discontinued
0.773	Intermediate Similarity	NPD1512	Approved
0.7725	Intermediate Similarity	NPD7819	Suspended
0.7714	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7411	Suspended
0.7688	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1471	Phase 3
0.763	Intermediate Similarity	NPD2403	Approved
0.7619	Intermediate Similarity	NPD1465	Phase 2
0.7607	Intermediate Similarity	NPD1511	Approved
0.7558	Intermediate Similarity	NPD6959	Discontinued
0.7545	Intermediate Similarity	NPD4380	Phase 2
0.7543	Intermediate Similarity	NPD2163	Approved
0.7529	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7808	Phase 3
0.7528	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6797	Phase 2
0.7485	Intermediate Similarity	NPD3749	Approved
0.7472	Intermediate Similarity	NPD7251	Discontinued
0.7471	Intermediate Similarity	NPD5242	Approved
0.7471	Intermediate Similarity	NPD5402	Approved
0.7469	Intermediate Similarity	NPD2800	Approved
0.7459	Intermediate Similarity	NPD8434	Phase 2
0.7458	Intermediate Similarity	NPD7074	Phase 3
0.7457	Intermediate Similarity	NPD7199	Phase 2
0.7455	Intermediate Similarity	NPD2533	Approved
0.7455	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2534	Approved
0.7455	Intermediate Similarity	NPD2532	Approved
0.7453	Intermediate Similarity	NPD2344	Approved
0.7443	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3748	Approved
0.7407	Intermediate Similarity	NPD1549	Phase 2
0.7401	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7054	Approved
0.736	Intermediate Similarity	NPD7472	Approved
0.7353	Intermediate Similarity	NPD37	Approved
0.7346	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1510	Phase 2
0.7326	Intermediate Similarity	NPD7768	Phase 2
0.7326	Intermediate Similarity	NPD4966	Approved
0.7326	Intermediate Similarity	NPD4965	Approved
0.7326	Intermediate Similarity	NPD4967	Phase 2
0.7314	Intermediate Similarity	NPD7229	Phase 3
0.7296	Intermediate Similarity	NPD1240	Approved
0.7289	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2309	Approved
0.7267	Intermediate Similarity	NPD5353	Approved
0.7262	Intermediate Similarity	NPD5403	Approved
0.725	Intermediate Similarity	NPD230	Phase 1
0.7246	Intermediate Similarity	NPD5401	Approved
0.7241	Intermediate Similarity	NPD6234	Discontinued
0.7216	Intermediate Similarity	NPD6808	Phase 2
0.7213	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3750	Approved
0.7212	Intermediate Similarity	NPD4628	Phase 3
0.7211	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1607	Approved
0.7193	Intermediate Similarity	NPD6386	Approved
0.7193	Intermediate Similarity	NPD6385	Approved
0.7176	Intermediate Similarity	NPD3226	Approved
0.7151	Intermediate Similarity	NPD6280	Approved
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.7151	Intermediate Similarity	NPD6279	Approved
0.7119	Intermediate Similarity	NPD3787	Discontinued
0.7117	Intermediate Similarity	NPD2799	Discontinued
0.7091	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD9494	Approved
0.7081	Intermediate Similarity	NPD943	Approved
0.7073	Intermediate Similarity	NPD1551	Phase 2
0.7073	Intermediate Similarity	NPD2935	Discontinued
0.7069	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD3887	Approved
0.7039	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5536	Phase 2
0.7037	Intermediate Similarity	NPD6355	Discontinued
0.7037	Intermediate Similarity	NPD447	Suspended
0.7037	Intermediate Similarity	NPD1933	Approved
0.7031	Intermediate Similarity	NPD4107	Approved
0.7029	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3027	Phase 3
0.6995	Remote Similarity	NPD6765	Approved
0.6995	Remote Similarity	NPD6764	Approved
0.6987	Remote Similarity	NPD3972	Approved
0.6981	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1613	Approved
0.697	Remote Similarity	NPD6100	Approved
0.697	Remote Similarity	NPD6099	Approved
0.6964	Remote Similarity	NPD6190	Approved
0.6962	Remote Similarity	NPD3266	Approved
0.6962	Remote Similarity	NPD3267	Approved
0.6961	Remote Similarity	NPD7228	Approved
0.6957	Remote Similarity	NPD6798	Discontinued
0.6957	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2654	Approved
0.6941	Remote Similarity	NPD3146	Approved
0.6941	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5953	Discontinued
0.6937	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6832	Phase 2
0.6933	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2346	Discontinued
0.6928	Remote Similarity	NPD2353	Approved
0.6927	Remote Similarity	NPD5711	Approved
0.6927	Remote Similarity	NPD5710	Approved
0.6923	Remote Similarity	NPD7286	Phase 2
0.6914	Remote Similarity	NPD5760	Phase 2
0.6914	Remote Similarity	NPD5761	Phase 2
0.6909	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4482	Phase 3
0.6905	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD17	Approved
0.6882	Remote Similarity	NPD7390	Discontinued
0.6879	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3018	Phase 2
0.6872	Remote Similarity	NPD3057	Approved
0.6871	Remote Similarity	NPD4060	Phase 1
0.6852	Remote Similarity	NPD2313	Discontinued
0.6852	Remote Similarity	NPD3268	Approved
0.6845	Remote Similarity	NPD6785	Approved
0.6845	Remote Similarity	NPD6784	Approved
0.6842	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1651	Approved
0.6832	Remote Similarity	NPD4908	Phase 1
0.6815	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3705	Approved
0.6811	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7240	Approved
0.681	Remote Similarity	NPD6233	Phase 2
0.6802	Remote Similarity	NPD5049	Phase 3
0.6802	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5090	Approved
0.68	Remote Similarity	NPD5089	Approved
0.6796	Remote Similarity	NPD7907	Approved
0.6792	Remote Similarity	NPD1876	Approved
0.6788	Remote Similarity	NPD2973	Approved
0.6788	Remote Similarity	NPD6651	Approved
0.6788	Remote Similarity	NPD2975	Approved
0.6788	Remote Similarity	NPD2974	Approved
0.6788	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2972	Approved
0.6786	Remote Similarity	NPD2424	Discontinued
0.6786	Remote Similarity	NPD3533	Approved
0.6784	Remote Similarity	NPD4357	Discontinued
0.6782	Remote Similarity	NPD7458	Discontinued
0.678	Remote Similarity	NPD5977	Approved
0.678	Remote Similarity	NPD5978	Approved
0.678	Remote Similarity	NPD2296	Approved
0.6778	Remote Similarity	NPD8127	Discontinued
0.6776	Remote Similarity	NPD1241	Discontinued
0.6776	Remote Similarity	NPD5283	Phase 1
0.6772	Remote Similarity	NPD1608	Approved
0.6772	Remote Similarity	NPD2981	Phase 2
0.6768	Remote Similarity	NPD2979	Phase 3
0.6766	Remote Similarity	NPD2438	Suspended
0.6765	Remote Similarity	NPD2354	Approved
0.6758	Remote Similarity	NPD7784	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