NPASS Compound

Structure

NPC472560 OpenBabel07101718332D 27 29 0 0 1 0 0 0 0 0999 V2000 -1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 13 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 6 21 1 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 17 2 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 12 26 1 0 0 0 0 12 27 1 0 0 0 0 13 21 1 0 0 0 0 15 18 1 0 0 0 0 15 26 1 0 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 25 1 0 0 0 0 18 27 1 0 0 0 0 19 21 1 0 0 0 0 19 22 2 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	380.389
LogP:	2.974
LogD:	3.46
LogS:	-4.886
# Rotatable Bonds:	7
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	4.189
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.81
MDCK Permeability:	1.994917147385422e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	97.0484848022461%
Volume Distribution (VD):	0.94
Pgp-substrate:	3.7079918384552%

ADMET: Metabolism

CYP1A2-inhibitor:	0.901
CYP1A2-substrate:	0.891
CYP2C19-inhibitor:	0.936
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.963
CYP2D6-substrate:	0.856
CYP3A4-inhibitor:	0.961
CYP3A4-substrate:	0.754

ADMET: Excretion

Clearance (CL):	13.933
Half-life (T1/2):	0.764

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.624
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.801
Skin Sensitization:	0.936
Carcinogencity:	0.875
Eye Corrosion:	0.005
Eye Irritation:	0.282
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC472560

Natural Product ID:	NPC472560
*Common Name:**	NLYYQPRJAOMDPF-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NLYYQPRJAOMDPF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-5-6-21(11-18-15(10-19(21)22)26-12-27-18)13(2)7-14-8-16(24-3)20(23)17(9-14)25-4/h5,8-11,13,23H,1,6-7,12H2,2-4H3
SMILES:	COc1cc(CC(C2(CC=C)C=C3OCOC3=CC2=O)C)cc(c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577101
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO33212	ocotea cymosa	Species	Lauraceae	Eukaryota	stems or bark	Zahamena National Park, 1728'45?S, 04844'10?E, Madagascar	2000-JAN	PMID[25650896]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	42100.0	nM	PMID[530734]

☑ 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 NPC472560 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	343
0.1-0.2	1377
0.2-0.3	3008
0.3-0.4	7670
0.4-0.5	11417
0.5-0.6	3973
0.6-0.7	8266
0.7-0.8	6263
0.8-0.85	344
0.85-0.9	34
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.92	High Similarity	NPC472565
0.9048	High Similarity	NPC177830
0.898	High Similarity	NPC216223
0.898	High Similarity	NPC145569
0.8859	High Similarity	NPC32079
0.8859	High Similarity	NPC477700
0.8851	High Similarity	NPC472567
0.8851	High Similarity	NPC474965
0.8851	High Similarity	NPC174512
0.8851	High Similarity	NPC293757
0.8851	High Similarity	NPC477695
0.8851	High Similarity	NPC668
0.8828	High Similarity	NPC106920
0.8828	High Similarity	NPC273657
0.8792	High Similarity	NPC475170
0.8733	High Similarity	NPC163002
0.8733	High Similarity	NPC234152
0.8716	High Similarity	NPC30720
0.8716	High Similarity	NPC88345
0.8699	High Similarity	NPC477696
0.8699	High Similarity	NPC477697
0.8699	High Similarity	NPC470811
0.8675	High Similarity	NPC477699
0.8667	High Similarity	NPC12854
0.8658	High Similarity	NPC304821
0.8643	High Similarity	NPC477705
0.8643	High Similarity	NPC63574
0.8643	High Similarity	NPC477694
0.8639	High Similarity	NPC16353
0.8639	High Similarity	NPC46880
0.8636	High Similarity	NPC474990
0.8621	High Similarity	NPC144284
0.8621	High Similarity	NPC284464
0.8611	High Similarity	NPC474039
0.8592	High Similarity	NPC471391
0.8592	High Similarity	NPC471390
0.8591	High Similarity	NPC25496
0.8582	High Similarity	NPC477706
0.8581	High Similarity	NPC476843
0.8581	High Similarity	NPC476841
0.8571	High Similarity	NPC470633
0.8571	High Similarity	NPC228769
0.8571	High Similarity	NPC474966
0.8562	High Similarity	NPC28398
0.8562	High Similarity	NPC103197
0.8562	High Similarity	NPC136757
0.8562	High Similarity	NPC30009
0.8562	High Similarity	NPC19158
0.8553	High Similarity	NPC476434
0.8552	High Similarity	NPC6369
0.8552	High Similarity	NPC30951
0.8535	High Similarity	NPC469512
0.8535	High Similarity	NPC76687
0.8526	High Similarity	NPC476337
0.8521	High Similarity	NPC239302
0.8514	High Similarity	NPC50696
0.8503	High Similarity	NPC52664
0.8503	High Similarity	NPC210354
0.8503	High Similarity	NPC176586
0.8503	High Similarity	NPC46180
0.8493	Intermediate Similarity	NPC177868
0.8481	Intermediate Similarity	NPC469518
0.8481	Intermediate Similarity	NPC469475
0.8477	Intermediate Similarity	NPC474903
0.8462	Intermediate Similarity	NPC327410
0.8462	Intermediate Similarity	NPC196937
0.8456	Intermediate Similarity	NPC474158
0.8456	Intermediate Similarity	NPC207732
0.8456	Intermediate Similarity	NPC477702
0.8446	Intermediate Similarity	NPC298317
0.8446	Intermediate Similarity	NPC474288
0.8446	Intermediate Similarity	NPC255566
0.8442	Intermediate Similarity	NPC25127
0.8435	Intermediate Similarity	NPC282291
0.8435	Intermediate Similarity	NPC166137
0.8435	Intermediate Similarity	NPC51681
0.8431	Intermediate Similarity	NPC56184
0.8429	Intermediate Similarity	NPC127587
0.8429	Intermediate Similarity	NPC64948
0.8428	Intermediate Similarity	NPC475738
0.8414	Intermediate Similarity	NPC197166
0.8411	Intermediate Similarity	NPC40654
0.8411	Intermediate Similarity	NPC262804
0.8411	Intermediate Similarity	NPC77598
0.8403	Intermediate Similarity	NPC145769
0.84	Intermediate Similarity	NPC212890
0.84	Intermediate Similarity	NPC157133
0.8397	Intermediate Similarity	NPC163527
0.8397	Intermediate Similarity	NPC220462
0.8397	Intermediate Similarity	NPC181168
0.8397	Intermediate Similarity	NPC115281
0.8392	Intermediate Similarity	NPC471505
0.8389	Intermediate Similarity	NPC27159
0.8389	Intermediate Similarity	NPC475000
0.8389	Intermediate Similarity	NPC177644
0.8389	Intermediate Similarity	NPC191158
0.8389	Intermediate Similarity	NPC15743
0.8387	Intermediate Similarity	NPC238834
0.838	Intermediate Similarity	NPC172673
0.838	Intermediate Similarity	NPC184814
0.8378	Intermediate Similarity	NPC476840
0.8378	Intermediate Similarity	NPC476842
0.8378	Intermediate Similarity	NPC40237
0.8378	Intermediate Similarity	NPC133934
0.8378	Intermediate Similarity	NPC253722
0.8378	Intermediate Similarity	NPC151423
0.8378	Intermediate Similarity	NPC110419
0.8378	Intermediate Similarity	NPC472335
0.8378	Intermediate Similarity	NPC472332
0.8378	Intermediate Similarity	NPC184641
0.8378	Intermediate Similarity	NPC253481
0.8378	Intermediate Similarity	NPC184684
0.8378	Intermediate Similarity	NPC31751
0.8378	Intermediate Similarity	NPC191231
0.8377	Intermediate Similarity	NPC104728
0.8377	Intermediate Similarity	NPC35544
0.8367	Intermediate Similarity	NPC203351
0.8367	Intermediate Similarity	NPC322021
0.8357	Intermediate Similarity	NPC84076
0.8357	Intermediate Similarity	NPC76451
0.8357	Intermediate Similarity	NPC303680
0.8357	Intermediate Similarity	NPC90128
0.8357	Intermediate Similarity	NPC274356
0.8356	Intermediate Similarity	NPC166184
0.8355	Intermediate Similarity	NPC477698
0.8355	Intermediate Similarity	NPC125570
0.8354	Intermediate Similarity	NPC260640
0.8354	Intermediate Similarity	NPC295009
0.8345	Intermediate Similarity	NPC211386
0.8345	Intermediate Similarity	NPC208760
0.8344	Intermediate Similarity	NPC476336
0.8333	Intermediate Similarity	NPC158331
0.8323	Intermediate Similarity	NPC287504
0.8323	Intermediate Similarity	NPC311912
0.8322	Intermediate Similarity	NPC185071
0.8322	Intermediate Similarity	NPC312256
0.8322	Intermediate Similarity	NPC12728
0.8312	Intermediate Similarity	NPC151425
0.8311	Intermediate Similarity	NPC470991
0.8311	Intermediate Similarity	NPC100675
0.831	Intermediate Similarity	NPC304622
0.8302	Intermediate Similarity	NPC476244
0.8299	Intermediate Similarity	NPC9068
0.8298	Intermediate Similarity	NPC276466
0.8298	Intermediate Similarity	NPC5018
0.8298	Intermediate Similarity	NPC123722
0.8298	Intermediate Similarity	NPC123228
0.8298	Intermediate Similarity	NPC151167
0.8291	Intermediate Similarity	NPC268718
0.8291	Intermediate Similarity	NPC150943
0.8291	Intermediate Similarity	NPC91634
0.8291	Intermediate Similarity	NPC225624
0.8291	Intermediate Similarity	NPC285973
0.8288	Intermediate Similarity	NPC90431
0.8286	Intermediate Similarity	NPC251855
0.8286	Intermediate Similarity	NPC472093
0.8286	Intermediate Similarity	NPC208950
0.8286	Intermediate Similarity	NPC221077
0.8286	Intermediate Similarity	NPC233410
0.8286	Intermediate Similarity	NPC173608
0.8286	Intermediate Similarity	NPC117214
0.8286	Intermediate Similarity	NPC53305
0.8286	Intermediate Similarity	NPC203133
0.8286	Intermediate Similarity	NPC193544
0.8286	Intermediate Similarity	NPC475169
0.8286	Intermediate Similarity	NPC17943
0.8286	Intermediate Similarity	NPC57490
0.8286	Intermediate Similarity	NPC116907
0.8286	Intermediate Similarity	NPC298757
0.8286	Intermediate Similarity	NPC257589
0.8282	Intermediate Similarity	NPC469506
0.8278	Intermediate Similarity	NPC296575
0.8278	Intermediate Similarity	NPC474799
0.8278	Intermediate Similarity	NPC193779
0.8276	Intermediate Similarity	NPC4982
0.8276	Intermediate Similarity	NPC5310
0.8276	Intermediate Similarity	NPC37065
0.8276	Intermediate Similarity	NPC287745
0.8276	Intermediate Similarity	NPC300776
0.8276	Intermediate Similarity	NPC176814
0.8276	Intermediate Similarity	NPC68779
0.8273	Intermediate Similarity	NPC163083
0.8273	Intermediate Similarity	NPC257976
0.8273	Intermediate Similarity	NPC242372
0.8273	Intermediate Similarity	NPC164778
0.8273	Intermediate Similarity	NPC4181
0.8273	Intermediate Similarity	NPC238810
0.8272	Intermediate Similarity	NPC88557
0.8269	Intermediate Similarity	NPC18954
0.8269	Intermediate Similarity	NPC476065
0.8269	Intermediate Similarity	NPC476363
0.8267	Intermediate Similarity	NPC473046
0.8267	Intermediate Similarity	NPC472713
0.8267	Intermediate Similarity	NPC121661
0.8267	Intermediate Similarity	NPC472712
0.8267	Intermediate Similarity	NPC297342
0.8267	Intermediate Similarity	NPC187774
0.8267	Intermediate Similarity	NPC92693
0.8267	Intermediate Similarity	NPC73467
0.8267	Intermediate Similarity	NPC118385

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 NPC472560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	833
0.2-0.3	1706
0.3-0.4	2683
0.4-0.5	2009
0.5-0.6	1085
0.6-0.7	457
0.7-0.8	74
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8344	Intermediate Similarity	NPD6234	Discontinued
0.8289	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD37	Approved
0.8212	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7028	Phase 2
0.8101	Intermediate Similarity	NPD4966	Approved
0.8101	Intermediate Similarity	NPD4967	Phase 2
0.8101	Intermediate Similarity	NPD4965	Approved
0.8098	Intermediate Similarity	NPD3818	Discontinued
0.8056	Intermediate Similarity	NPD3027	Phase 3
0.8012	Intermediate Similarity	NPD7199	Phase 2
0.7988	Intermediate Similarity	NPD7228	Approved
0.7987	Intermediate Similarity	NPD3882	Suspended
0.7914	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1934	Approved
0.7892	Intermediate Similarity	NPD7074	Phase 3
0.7887	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2801	Approved
0.7831	Intermediate Similarity	NPD7054	Approved
0.7784	Intermediate Similarity	NPD7472	Approved
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1357	Approved
0.7658	Intermediate Similarity	NPD1653	Approved
0.7633	Intermediate Similarity	NPD6797	Phase 2
0.7628	Intermediate Similarity	NPD1511	Approved
0.7622	Intermediate Similarity	NPD3705	Approved
0.7616	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7473	Discontinued
0.76	Intermediate Similarity	NPD230	Phase 1
0.7588	Intermediate Similarity	NPD7251	Discontinued
0.7548	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD8166	Discontinued
0.7548	Intermediate Similarity	NPD4110	Phase 3
0.7546	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6166	Phase 2
0.7545	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7808	Phase 3
0.7544	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1512	Approved
0.753	Intermediate Similarity	NPD6232	Discontinued
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD3817	Phase 2
0.7485	Intermediate Similarity	NPD7240	Approved
0.7464	Intermediate Similarity	NPD228	Approved
0.7436	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4628	Phase 3
0.7436	Intermediate Similarity	NPD3750	Approved
0.7432	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD9494	Approved
0.7417	Intermediate Similarity	NPD1240	Approved
0.7417	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1613	Approved
0.741	Intermediate Similarity	NPD5494	Approved
0.7405	Intermediate Similarity	NPD4357	Discontinued
0.7394	Intermediate Similarity	NPD5536	Phase 2
0.7384	Intermediate Similarity	NPD7685	Pre-registration
0.7372	Intermediate Similarity	NPD2800	Approved
0.7357	Intermediate Similarity	NPD5283	Phase 1
0.7355	Intermediate Similarity	NPD7266	Discontinued
0.7346	Intermediate Similarity	NPD6599	Discontinued
0.7338	Intermediate Similarity	NPD1510	Phase 2
0.732	Intermediate Similarity	NPD1607	Approved
0.732	Intermediate Similarity	NPD6651	Approved
0.7317	Intermediate Similarity	NPD1465	Phase 2
0.7303	Intermediate Similarity	NPD3620	Phase 2
0.7303	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD943	Approved
0.7285	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7458	Discontinued
0.7279	Intermediate Similarity	NPD2983	Phase 2
0.7279	Intermediate Similarity	NPD2982	Phase 2
0.725	Intermediate Similarity	NPD2534	Approved
0.725	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2532	Approved
0.725	Intermediate Similarity	NPD2533	Approved
0.7248	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4380	Phase 2
0.7211	Intermediate Similarity	NPD2981	Phase 2
0.7209	Intermediate Similarity	NPD5844	Phase 1
0.7209	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3018	Phase 2
0.7188	Intermediate Similarity	NPD6799	Approved
0.7186	Intermediate Similarity	NPD7075	Discontinued
0.7179	Intermediate Similarity	NPD2935	Discontinued
0.7176	Intermediate Similarity	NPD3926	Phase 2
0.7171	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6190	Approved
0.7162	Intermediate Similarity	NPD4749	Approved
0.716	Intermediate Similarity	NPD8127	Discontinued
0.7158	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7134	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2932	Approved
0.7115	Intermediate Similarity	NPD3748	Approved
0.7108	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7819	Suspended
0.7105	Intermediate Similarity	NPD7095	Approved
0.7097	Intermediate Similarity	NPD7680	Approved
0.7095	Intermediate Similarity	NPD1608	Approved
0.7095	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD9269	Phase 2
0.7089	Intermediate Similarity	NPD1549	Phase 2
0.7071	Intermediate Similarity	NPD3022	Approved
0.7071	Intermediate Similarity	NPD3021	Approved
0.7067	Intermediate Similarity	NPD2797	Approved
0.7066	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3268	Approved
0.7059	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD3751	Discontinued
0.7051	Intermediate Similarity	NPD6111	Discontinued
0.7037	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD447	Suspended
0.7027	Intermediate Similarity	NPD1610	Phase 2
0.702	Intermediate Similarity	NPD2798	Approved
0.7019	Intermediate Similarity	NPD7124	Phase 2
0.7007	Intermediate Similarity	NPD3019	Approved
0.7006	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1283	Approved
0.698	Remote Similarity	NPD3972	Approved
0.6977	Remote Similarity	NPD5242	Approved
0.6968	Remote Similarity	NPD4060	Phase 1
0.6964	Remote Similarity	NPD5353	Approved
0.6962	Remote Similarity	NPD2796	Approved
0.6959	Remote Similarity	NPD1247	Approved
0.6948	Remote Similarity	NPD3764	Approved
0.6946	Remote Similarity	NPD6801	Discontinued
0.6939	Remote Similarity	NPD1651	Approved
0.6937	Remote Similarity	NPD6674	Discontinued
0.6933	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7768	Phase 2
0.6923	Remote Similarity	NPD1933	Approved
0.6919	Remote Similarity	NPD3787	Discontinued
0.6913	Remote Similarity	NPD1091	Approved
0.691	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2978	Approved
0.6905	Remote Similarity	NPD2977	Approved
0.6903	Remote Similarity	NPD8032	Phase 2
0.6897	Remote Similarity	NPD7157	Approved
0.6892	Remote Similarity	NPD4626	Approved
0.6892	Remote Similarity	NPD17	Approved
0.6887	Remote Similarity	NPD1876	Approved
0.6886	Remote Similarity	NPD7411	Suspended
0.6886	Remote Similarity	NPD5090	Approved
0.6886	Remote Similarity	NPD6873	Phase 2
0.6886	Remote Similarity	NPD5089	Approved
0.6882	Remote Similarity	NPD3749	Approved
0.6879	Remote Similarity	NPD6653	Approved
0.6875	Remote Similarity	NPD1241	Discontinued
0.6871	Remote Similarity	NPD5297	Approved
0.6864	Remote Similarity	NPD5402	Approved
0.6855	Remote Similarity	NPD1551	Phase 2
0.6852	Remote Similarity	NPD2219	Phase 1
0.6848	Remote Similarity	NPD5403	Approved
0.6839	Remote Similarity	NPD1296	Phase 2
0.6839	Remote Similarity	NPD6798	Discontinued
0.6832	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4750	Phase 3
0.6824	Remote Similarity	NPD9268	Approved
0.6821	Remote Similarity	NPD7229	Phase 3
0.6815	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5124	Phase 1
0.6813	Remote Similarity	NPD6002	Phase 3
0.6813	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1375	Discontinued
0.6813	Remote Similarity	NPD6004	Phase 3
0.6813	Remote Similarity	NPD6005	Phase 3
0.6805	Remote Similarity	NPD8455	Phase 2
0.6805	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1281	Approved
0.6797	Remote Similarity	NPD5647	Approved
0.6796	Remote Similarity	NPD8434	Phase 2
0.6795	Remote Similarity	NPD6233	Phase 2
0.6792	Remote Similarity	NPD2799	Discontinued
0.679	Remote Similarity	NPD7003	Approved
0.6788	Remote Similarity	NPD6273	Approved
0.6784	Remote Similarity	NPD6971	Discontinued
0.6784	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1778	Approved
0.6776	Remote Similarity	NPD8651	Approved
0.6774	Remote Similarity	NPD4625	Phase 3
0.6772	Remote Similarity	NPD2492	Phase 1
0.677	Remote Similarity	NPD2424	Discontinued
0.677	Remote Similarity	NPD4534	Discontinued
0.6763	Remote Similarity	NPD6959	Discontinued
0.6758	Remote Similarity	NPD6841	Approved
0.6758	Remote Similarity	NPD6843	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