NPASS Compound

Structure

NPC163002 OpenBabel07101718192D 27 31 0 0 1 0 0 0 0 0999 V2000 4.0402 -2.7519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1427 1.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1301 3.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5988 -1.8546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6010 -1.7882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1301 1.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9962 0.1037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8331 0.3650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1814 -1.0988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4010 1.1037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0108 0.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3506 0.5104 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1301 0.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9962 2.1037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8622 0.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2988 -0.1843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1134 0.3434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2641 0.1037 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8622 1.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1596 -0.8909 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6814 -0.2327 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2666 0.0673 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9962 3.1037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8133 0.2947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6989 0.9323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8133 1.9127 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 4 2 0 0 0 0 2 12 1 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 6 13 2 0 0 0 0 6 14 1 0 0 0 0 7 13 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 8 17 2 0 0 0 0 9 20 1 0 0 0 0 10 24 1 0 0 0 0 10 26 1 0 0 0 0 11 25 1 0 0 0 0 11 27 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 6 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 20 1 0 0 0 0 16 22 2 0 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 20 1 6 0 0 0 19 26 1 0 0 0 0 20 5 1 1 0 0 0 21 9 1 6 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.14
Volume:	365.912
LogP:	2.933
LogD:	2.897
LogS:	-5.075
# Rotatable Bonds:	4
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	5.869
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.814
MDCK Permeability:	1.569603045936674e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	88.9706802368164%
Volume Distribution (VD):	0.96
Pgp-substrate:	2.9583678245544434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.24
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.499
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.47
CYP2C9-substrate:	0.539
CYP2D6-inhibitor:	0.785
CYP2D6-substrate:	0.208
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.865

ADMET: Excretion

Clearance (CL):	9.963
Half-life (T1/2):	0.529

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.597
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.565
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.825
Skin Sensitization:	0.928
Carcinogencity:	0.881
Eye Corrosion:	0.011
Eye Irritation:	0.279
Respiratory Toxicity:	0.569

Download Data

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

Natural Product: NPC163002

Natural Product ID:	NPC163002
*Common Name:**	VMBFNOIPGQFDTB-XFHMVGKKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VMBFNOIPGQFDTB-XFHMVGKKSA-N
Standard InCHI:	InChI=1S/C21H22O6/c1-4-5-20-9-21(17(8-16(20)22)25-11-27-21)12(2)18(20)13-6-14(23-3)19-15(7-13)24-10-26-19/h4,6-8,12,18H,1,5,9-11H2,2-3H3/t12-,18-,20+,21-/m1/s1
SMILES:	C=CC[C@]12C[C@]3([C@@H]([C@@H]2c2cc(OC)c4c(c2)OCO4)C)OCOC3=CC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577192
PubChem CID:	197600
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
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	=	4100.0	nM	PMID[538065]

☑ 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 NPC163002 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	469
0.1-0.2	1682
0.2-0.3	3427
0.3-0.4	9150
0.4-0.5	10176
0.5-0.6	5497
0.6-0.7	10927
0.7-0.8	1290
0.8-0.85	63
0.85-0.9	11
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.986	High Similarity	NPC472567
0.9533	High Similarity	NPC472565
0.9441	High Similarity	NPC472564
0.9205	High Similarity	NPC476363
0.8968	High Similarity	NPC476337
0.8874	High Similarity	NPC475170
0.8859	High Similarity	NPC476362
0.8733	High Similarity	NPC472560
0.8688	High Similarity	NPC476277
0.8675	High Similarity	NPC25496
0.8645	High Similarity	NPC476364
0.86	High Similarity	NPC177644
0.86	High Similarity	NPC15743
0.86	High Similarity	NPC191158
0.8591	High Similarity	NPC176586
0.8591	High Similarity	NPC210354
0.8544	High Similarity	NPC475095
0.8543	High Similarity	NPC474158
0.8533	High Similarity	NPC474288
0.8516	High Similarity	NPC476335
0.85	High Similarity	NPC476244
0.8487	Intermediate Similarity	NPC193779
0.8477	Intermediate Similarity	NPC475000
0.8477	Intermediate Similarity	NPC50696
0.8477	Intermediate Similarity	NPC92693
0.8477	Intermediate Similarity	NPC218841
0.8467	Intermediate Similarity	NPC40237
0.8467	Intermediate Similarity	NPC151423
0.8446	Intermediate Similarity	NPC166184
0.8431	Intermediate Similarity	NPC476336
0.8411	Intermediate Similarity	NPC474966
0.84	Intermediate Similarity	NPC51681
0.8366	Intermediate Similarity	NPC87295
0.8365	Intermediate Similarity	NPC474990
0.8354	Intermediate Similarity	NPC202249
0.8354	Intermediate Similarity	NPC188962
0.8354	Intermediate Similarity	NPC42871
0.8344	Intermediate Similarity	NPC46180
0.828	Intermediate Similarity	NPC220577
0.8264	Intermediate Similarity	NPC64948
0.8258	Intermediate Similarity	NPC262804
0.8258	Intermediate Similarity	NPC40654
0.825	Intermediate Similarity	NPC220462
0.825	Intermediate Similarity	NPC476340
0.8247	Intermediate Similarity	NPC296575
0.8247	Intermediate Similarity	NPC224687
0.8243	Intermediate Similarity	NPC145769
0.8217	Intermediate Similarity	NPC474975
0.8212	Intermediate Similarity	NPC278076
0.8205	Intermediate Similarity	NPC145569
0.8205	Intermediate Similarity	NPC262455
0.8205	Intermediate Similarity	NPC177476
0.8205	Intermediate Similarity	NPC216223
0.8194	Intermediate Similarity	NPC101755
0.8194	Intermediate Similarity	NPC304687
0.8194	Intermediate Similarity	NPC104024
0.8194	Intermediate Similarity	NPC476338
0.8194	Intermediate Similarity	NPC65574
0.8194	Intermediate Similarity	NPC476359
0.8194	Intermediate Similarity	NPC80230
0.8188	Intermediate Similarity	NPC211386
0.8182	Intermediate Similarity	NPC474948
0.8182	Intermediate Similarity	NPC42230
0.8165	Intermediate Similarity	NPC104353
0.8165	Intermediate Similarity	NPC28724
0.8163	Intermediate Similarity	NPC192255
0.8155	Intermediate Similarity	NPC107739
0.8153	Intermediate Similarity	NPC177830
0.8146	Intermediate Similarity	NPC470962
0.8125	Intermediate Similarity	NPC254163
0.8121	Intermediate Similarity	NPC37065
0.8113	Intermediate Similarity	NPC308555
0.8107	Intermediate Similarity	NPC263955
0.8107	Intermediate Similarity	NPC23593
0.8101	Intermediate Similarity	NPC164082
0.8101	Intermediate Similarity	NPC234152
0.8101	Intermediate Similarity	NPC32079
0.8101	Intermediate Similarity	NPC477700
0.8098	Intermediate Similarity	NPC209411
0.8098	Intermediate Similarity	NPC239890
0.8095	Intermediate Similarity	NPC474568
0.8095	Intermediate Similarity	NPC477705
0.8095	Intermediate Similarity	NPC477694
0.8089	Intermediate Similarity	NPC477695
0.8089	Intermediate Similarity	NPC293757
0.8089	Intermediate Similarity	NPC668
0.8089	Intermediate Similarity	NPC474965
0.8089	Intermediate Similarity	NPC477698
0.8089	Intermediate Similarity	NPC174512
0.8067	Intermediate Similarity	NPC44245
0.8067	Intermediate Similarity	NPC38101
0.8067	Intermediate Similarity	NPC189474
0.8067	Intermediate Similarity	NPC72796
0.8063	Intermediate Similarity	NPC178195
0.8063	Intermediate Similarity	NPC273578
0.8063	Intermediate Similarity	NPC348849
0.8063	Intermediate Similarity	NPC478213
0.8061	Intermediate Similarity	NPC475953
0.8061	Intermediate Similarity	NPC474647
0.8059	Intermediate Similarity	NPC29587
0.8054	Intermediate Similarity	NPC266848
0.8054	Intermediate Similarity	NPC136750
0.8054	Intermediate Similarity	NPC205915
0.805	Intermediate Similarity	NPC56184
0.8049	Intermediate Similarity	NPC61141
0.8049	Intermediate Similarity	NPC76687
0.8041	Intermediate Similarity	NPC477706
0.8038	Intermediate Similarity	NPC149505
0.8038	Intermediate Similarity	NPC12854
0.8025	Intermediate Similarity	NPC258644
0.8025	Intermediate Similarity	NPC310206
0.8013	Intermediate Similarity	NPC209229
0.8013	Intermediate Similarity	NPC230968
0.8013	Intermediate Similarity	NPC11453
0.8013	Intermediate Similarity	NPC102260
0.8012	Intermediate Similarity	NPC236089
0.8	Intermediate Similarity	NPC148497
0.8	Intermediate Similarity	NPC475865
0.8	Intermediate Similarity	NPC31530
0.8	Intermediate Similarity	NPC19890
0.8	Intermediate Similarity	NPC144162
0.8	Intermediate Similarity	NPC110958
0.8	Intermediate Similarity	NPC68882
0.8	Intermediate Similarity	NPC153008
0.7987	Intermediate Similarity	NPC72046
0.7987	Intermediate Similarity	NPC13985
0.7987	Intermediate Similarity	NPC210642
0.7987	Intermediate Similarity	NPC261812
0.7987	Intermediate Similarity	NPC65183
0.7987	Intermediate Similarity	NPC303519
0.7975	Intermediate Similarity	NPC325122
0.7975	Intermediate Similarity	NPC76211
0.7973	Intermediate Similarity	NPC233961
0.7973	Intermediate Similarity	NPC339621
0.7973	Intermediate Similarity	NPC280399
0.7963	Intermediate Similarity	NPC477380
0.7962	Intermediate Similarity	NPC153620
0.7962	Intermediate Similarity	NPC24257
0.7962	Intermediate Similarity	NPC30720
0.7961	Intermediate Similarity	NPC231719
0.7961	Intermediate Similarity	NPC14022
0.7961	Intermediate Similarity	NPC52968
0.795	Intermediate Similarity	NPC57211
0.7947	Intermediate Similarity	NPC148893
0.7947	Intermediate Similarity	NPC49235
0.7947	Intermediate Similarity	NPC25333
0.7937	Intermediate Similarity	NPC477699
0.7937	Intermediate Similarity	NPC279061
0.7935	Intermediate Similarity	NPC86455
0.7935	Intermediate Similarity	NPC125134
0.7935	Intermediate Similarity	NPC137920
0.7927	Intermediate Similarity	NPC474770
0.7922	Intermediate Similarity	NPC28398
0.7917	Intermediate Similarity	NPC256167
0.7914	Intermediate Similarity	NPC477885
0.7911	Intermediate Similarity	NPC304821
0.7908	Intermediate Similarity	NPC113550
0.7908	Intermediate Similarity	NPC46947
0.7901	Intermediate Similarity	NPC234730
0.7901	Intermediate Similarity	NPC117154
0.7901	Intermediate Similarity	NPC478238
0.7898	Intermediate Similarity	NPC3982
0.7898	Intermediate Similarity	NPC189054
0.7895	Intermediate Similarity	NPC143895
0.7895	Intermediate Similarity	NPC121651
0.7891	Intermediate Similarity	NPC286683
0.7888	Intermediate Similarity	NPC52623
0.7888	Intermediate Similarity	NPC292460
0.7885	Intermediate Similarity	NPC46880
0.7885	Intermediate Similarity	NPC18211
0.7875	Intermediate Similarity	NPC62354
0.7866	Intermediate Similarity	NPC179914
0.7866	Intermediate Similarity	NPC125713
0.7866	Intermediate Similarity	NPC113055
0.7853	Intermediate Similarity	NPC301897
0.7853	Intermediate Similarity	NPC473900
0.7853	Intermediate Similarity	NPC155063
0.7848	Intermediate Similarity	NPC88345
0.7844	Intermediate Similarity	NPC187923
0.7843	Intermediate Similarity	NPC185908
0.784	Intermediate Similarity	NPC244371
0.784	Intermediate Similarity	NPC30009
0.784	Intermediate Similarity	NPC136757
0.784	Intermediate Similarity	NPC103197
0.7834	Intermediate Similarity	NPC327052
0.7831	Intermediate Similarity	NPC478199
0.7831	Intermediate Similarity	NPC469512
0.7829	Intermediate Similarity	NPC150534
0.7826	Intermediate Similarity	NPC151425
0.7824	Intermediate Similarity	NPC470685
0.7821	Intermediate Similarity	NPC273657
0.7821	Intermediate Similarity	NPC106920
0.7818	Intermediate Similarity	NPC218471
0.7818	Intermediate Similarity	NPC474936
0.7818	Intermediate Similarity	NPC470637
0.7818	Intermediate Similarity	NPC239818
0.7818	Intermediate Similarity	NPC131557
0.7818	Intermediate Similarity	NPC96593
0.7815	Intermediate Similarity	NPC196937
0.7806	Intermediate Similarity	NPC323601

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 NPC163002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	931
0.2-0.3	1887
0.3-0.4	2826
0.4-0.5	1949
0.5-0.6	864
0.6-0.7	278
0.7-0.8	19
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7028	Phase 2
0.8258	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7199	Phase 2
0.7892	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4966	Approved
0.7744	Intermediate Similarity	NPD4967	Phase 2
0.7744	Intermediate Similarity	NPD4965	Approved
0.7669	Intermediate Similarity	NPD37	Approved
0.7651	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD5494	Approved
0.7442	Intermediate Similarity	NPD3818	Discontinued
0.7401	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7685	Pre-registration
0.7365	Intermediate Similarity	NPD3705	Approved
0.7341	Intermediate Similarity	NPD7228	Approved
0.7321	Intermediate Similarity	NPD3882	Suspended
0.7267	Intermediate Similarity	NPD3926	Phase 2
0.7202	Intermediate Similarity	NPD2801	Approved
0.7184	Intermediate Similarity	NPD7473	Discontinued
0.7175	Intermediate Similarity	NPD7240	Approved
0.716	Intermediate Similarity	NPD3817	Phase 2
0.7159	Intermediate Similarity	NPD7074	Phase 3
0.7143	Intermediate Similarity	NPD1934	Approved
0.7143	Intermediate Similarity	NPD5536	Phase 2
0.7135	Intermediate Similarity	NPD919	Approved
0.711	Intermediate Similarity	NPD6232	Discontinued
0.7103	Intermediate Similarity	NPD5283	Phase 1
0.7102	Intermediate Similarity	NPD7054	Approved
0.7099	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4110	Phase 3
0.7069	Intermediate Similarity	NPD5242	Approved
0.7063	Intermediate Similarity	NPD6100	Approved
0.7063	Intermediate Similarity	NPD6099	Approved
0.7062	Intermediate Similarity	NPD7472	Approved
0.7059	Intermediate Similarity	NPD5353	Approved
0.7056	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD1247	Approved
0.7024	Intermediate Similarity	NPD6599	Discontinued
0.7	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1876	Approved
0.6987	Remote Similarity	NPD3027	Phase 3
0.6975	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2981	Phase 2
0.6974	Remote Similarity	NPD3972	Approved
0.6959	Remote Similarity	NPD5977	Approved
0.6959	Remote Similarity	NPD5978	Approved
0.6957	Remote Similarity	NPD2796	Approved
0.6954	Remote Similarity	NPD8127	Discontinued
0.6944	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7808	Phase 3
0.6943	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1357	Approved
0.6933	Remote Similarity	NPD2800	Approved
0.6928	Remote Similarity	NPD2983	Phase 2
0.6928	Remote Similarity	NPD2982	Phase 2
0.6927	Remote Similarity	NPD6797	Phase 2
0.6919	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD230	Phase 1
0.6899	Remote Similarity	NPD8032	Phase 2
0.6894	Remote Similarity	NPD3748	Approved
0.689	Remote Similarity	NPD4628	Phase 3
0.6889	Remote Similarity	NPD7251	Discontinued
0.6887	Remote Similarity	NPD17	Approved
0.6879	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6799	Approved
0.6867	Remote Similarity	NPD1511	Approved
0.6867	Remote Similarity	NPD4357	Discontinued
0.6864	Remote Similarity	NPD7458	Discontinued
0.6859	Remote Similarity	NPD3018	Phase 2
0.6855	Remote Similarity	NPD1240	Approved
0.6836	Remote Similarity	NPD2403	Approved
0.6836	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6166	Phase 2
0.6836	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6111	Discontinued
0.6826	Remote Similarity	NPD2533	Approved
0.6826	Remote Similarity	NPD2534	Approved
0.6826	Remote Similarity	NPD2532	Approved
0.6818	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5844	Phase 1
0.6813	Remote Similarity	NPD3657	Discovery
0.6807	Remote Similarity	NPD7124	Phase 2
0.6802	Remote Similarity	NPD7819	Suspended
0.679	Remote Similarity	NPD1510	Phase 2
0.6788	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1512	Approved
0.6784	Remote Similarity	NPD6385	Approved
0.6784	Remote Similarity	NPD6386	Approved
0.677	Remote Similarity	NPD6651	Approved
0.677	Remote Similarity	NPD1607	Approved
0.676	Remote Similarity	NPD3751	Discontinued
0.6753	Remote Similarity	NPD1608	Approved
0.6752	Remote Similarity	NPD9494	Approved
0.675	Remote Similarity	NPD3620	Phase 2
0.675	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD920	Approved
0.6727	Remote Similarity	NPD2654	Approved
0.6727	Remote Similarity	NPD1243	Approved
0.6726	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3787	Discontinued
0.6711	Remote Similarity	NPD1651	Approved
0.6708	Remote Similarity	NPD1933	Approved
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD6005	Phase 3
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD1653	Approved
0.6705	Remote Similarity	NPD5761	Phase 2
0.6705	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5760	Phase 2
0.6705	Remote Similarity	NPD1465	Phase 2
0.6703	Remote Similarity	NPD6559	Discontinued
0.6688	Remote Similarity	NPD4624	Approved
0.6687	Remote Similarity	NPD3750	Approved
0.6686	Remote Similarity	NPD6273	Approved
0.6686	Remote Similarity	NPD6873	Phase 2
0.6684	Remote Similarity	NPD5005	Approved
0.6684	Remote Similarity	NPD5006	Approved
0.6667	Remote Similarity	NPD5297	Approved
0.6649	Remote Similarity	NPD7680	Approved
0.6647	Remote Similarity	NPD6190	Approved
0.6646	Remote Similarity	NPD943	Approved
0.6644	Remote Similarity	NPD1241	Discontinued
0.663	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7229	Phase 3
0.6628	Remote Similarity	NPD4380	Phase 2
0.6627	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3146	Approved
0.6625	Remote Similarity	NPD1296	Phase 2
0.6624	Remote Similarity	NPD3266	Approved
0.6624	Remote Similarity	NPD3267	Approved
0.6615	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6764	Approved
0.6612	Remote Similarity	NPD6765	Approved
0.6607	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6355	Discontinued
0.6603	Remote Similarity	NPD5327	Phase 3
0.6601	Remote Similarity	NPD3025	Approved
0.6601	Remote Similarity	NPD3024	Approved
0.6591	Remote Similarity	NPD7075	Discontinued
0.6591	Remote Similarity	NPD3749	Approved
0.6587	Remote Similarity	NPD8166	Discontinued
0.6582	Remote Similarity	NPD5647	Approved
0.6582	Remote Similarity	NPD2798	Approved
0.6582	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD1281	Approved
0.6575	Remote Similarity	NPD7799	Discontinued
0.6571	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1549	Phase 2
0.6564	Remote Similarity	NPD2492	Phase 1
0.6564	Remote Similarity	NPD6653	Approved
0.6562	Remote Similarity	NPD7095	Approved
0.6562	Remote Similarity	NPD4420	Approved
0.6561	Remote Similarity	NPD7296	Approved
0.6558	Remote Similarity	NPD2932	Approved
0.6557	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6801	Discontinued
0.6548	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2438	Suspended
0.6543	Remote Similarity	NPD4140	Approved
0.6536	Remote Similarity	NPD7315	Approved
0.6534	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD8434	Phase 2
0.6522	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3268	Approved
0.6516	Remote Similarity	NPD3026	Approved
0.6516	Remote Similarity	NPD3023	Approved
0.6512	Remote Similarity	NPD4210	Discontinued
0.6506	Remote Similarity	NPD1375	Discontinued
0.6506	Remote Similarity	NPD5763	Approved
0.6506	Remote Similarity	NPD5762	Approved
0.6503	Remote Similarity	NPD447	Suspended
0.6503	Remote Similarity	NPD5735	Approved
0.65	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4749	Approved
0.6494	Remote Similarity	NPD5089	Approved
0.6494	Remote Similarity	NPD5090	Approved
0.6494	Remote Similarity	NPD9268	Approved
0.6494	Remote Similarity	NPD7411	Suspended
0.6494	Remote Similarity	NPD5585	Approved
0.6481	Remote Similarity	NPD6663	Approved
0.6471	Remote Similarity	NPD6785	Approved
0.6471	Remote Similarity	NPD6784	Approved
0.6463	Remote Similarity	NPD6353	Approved
0.6456	Remote Similarity	NPD1283	Approved
0.6455	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3019	Approved
0.6446	Remote Similarity	NPD3539	Phase 1
0.6446	Remote Similarity	NPD2935	Discontinued

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