NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	562.33
Volume:	614.623
LogP:	7.635
LogD:	5.706
LogS:	-4.803
# Rotatable Bonds:	11
TPSA:	97.74
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.169
Synthetic Accessibility Score:	4.759
Fsp3:	0.543
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.32
MDCK Permeability:	2.8957972972420976e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.319
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.118
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	98.93850708007812%
Volume Distribution (VD):	0.469
Pgp-substrate:	1.9747340679168701%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.12
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.737
CYP2C9-substrate:	0.991
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.502
CYP3A4-substrate:	0.708

ADMET: Excretion

Clearance (CL):	15.502
Half-life (T1/2):	0.055

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.488
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.928
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.033
Carcinogencity:	0.307
Eye Corrosion:	0.882
Eye Irritation:	0.256
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC477475

Natural Product ID:	NPC477475
*Common Name:**	mahureone A
IUPAC Name:	3-[4-hydroxy-7,7-dimethyl-3-(3-methylbutanoyl)-4a,6-bis(3-methylbut-2-enyl)-2-oxo-5,6-dihydrochromen-8-yl]-3-phenylpropanoic acid
Synonyms:
Standard InCHIKey:	CNEAMBBQTZXVRE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C35H46O6/c1-21(2)14-15-25-20-35(17-16-22(3)4)31(39)29(27(36)18-23(5)6)33(40)41-32(35)30(34(25,7)8)26(19-28(37)38)24-12-10-9-11-13-24/h9-14,16,23,25-26,39H,15,17-20H2,1-8H3,(H,37,38)
SMILES:	CC(C)CC(=O)C1=C(C2(CC(C(C(=C2OC1=O)C(CC(=O)O)C3=CC=CC=C3)(C)C)CC=C(C)C)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	54687893
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO26156	Mahurea palustris	Species	Calophyllaceae	Eukaryota	leaves	French Guiana	1996-OCT	PMID[16038535]
NPO26156	Mahurea palustris	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	IC50	=	28000	nM	PMID[16038535]
NPT2	Others	Unspecified		FC	=	2	n.a.	PMID[16038535]

☑ 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 NPC477475 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	217
0.1-0.2	974
0.2-0.3	2213
0.3-0.4	7324
0.4-0.5	14426
0.5-0.6	15334
0.6-0.7	2004
0.7-0.8	184
0.8-0.85	16
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477476
0.9	High Similarity	NPC294458
0.8649	High Similarity	NPC218855
0.8496	Intermediate Similarity	NPC130591
0.8496	Intermediate Similarity	NPC234637
0.8462	Intermediate Similarity	NPC475827
0.8462	Intermediate Similarity	NPC474223
0.8407	Intermediate Similarity	NPC471481
0.8403	Intermediate Similarity	NPC474254
0.8403	Intermediate Similarity	NPC474159
0.8318	Intermediate Similarity	NPC54647
0.8305	Intermediate Similarity	NPC474222
0.8305	Intermediate Similarity	NPC475804
0.8198	Intermediate Similarity	NPC85560
0.8198	Intermediate Similarity	NPC244933
0.819	Intermediate Similarity	NPC260886
0.808	Intermediate Similarity	NPC471832
0.8073	Intermediate Similarity	NPC264728
0.8051	Intermediate Similarity	NPC268930
0.8051	Intermediate Similarity	NPC61651
0.7909	Intermediate Similarity	NPC225079
0.7909	Intermediate Similarity	NPC136810
0.7909	Intermediate Similarity	NPC133809
0.7909	Intermediate Similarity	NPC128248
0.7903	Intermediate Similarity	NPC294050
0.7903	Intermediate Similarity	NPC328997
0.789	Intermediate Similarity	NPC271475
0.789	Intermediate Similarity	NPC120393
0.7886	Intermediate Similarity	NPC325740
0.7886	Intermediate Similarity	NPC328107
0.7857	Intermediate Similarity	NPC329282
0.7851	Intermediate Similarity	NPC476225
0.784	Intermediate Similarity	NPC146239
0.7798	Intermediate Similarity	NPC477767
0.7798	Intermediate Similarity	NPC469891
0.7798	Intermediate Similarity	NPC469890
0.7798	Intermediate Similarity	NPC469892
0.7778	Intermediate Similarity	NPC268607
0.7778	Intermediate Similarity	NPC316553
0.7778	Intermediate Similarity	NPC93287
0.7769	Intermediate Similarity	NPC202015
0.7739	Intermediate Similarity	NPC475006
0.7727	Intermediate Similarity	NPC476120
0.7714	Intermediate Similarity	NPC477693
0.7714	Intermediate Similarity	NPC477704
0.7706	Intermediate Similarity	NPC469893
0.7692	Intermediate Similarity	NPC477478
0.7692	Intermediate Similarity	NPC477479
0.7679	Intermediate Similarity	NPC474820
0.7679	Intermediate Similarity	NPC475978
0.7658	Intermediate Similarity	NPC221825
0.7658	Intermediate Similarity	NPC476042
0.7652	Intermediate Similarity	NPC470007
0.7636	Intermediate Similarity	NPC226041
0.7636	Intermediate Similarity	NPC278228
0.7627	Intermediate Similarity	NPC469547
0.76	Intermediate Similarity	NPC318067
0.7597	Intermediate Similarity	NPC472692
0.7597	Intermediate Similarity	NPC472682
0.7589	Intermediate Similarity	NPC94487
0.7583	Intermediate Similarity	NPC471616
0.7568	Intermediate Similarity	NPC145052
0.7565	Intermediate Similarity	NPC94751
0.7565	Intermediate Similarity	NPC142326
0.7563	Intermediate Similarity	NPC471721
0.7542	Intermediate Similarity	NPC474689
0.7542	Intermediate Similarity	NPC280789
0.7541	Intermediate Similarity	NPC472698
0.7541	Intermediate Similarity	NPC472697
0.754	Intermediate Similarity	NPC478108
0.75	Intermediate Similarity	NPC21929
0.75	Intermediate Similarity	NPC86987
0.75	Intermediate Similarity	NPC215419
0.7481	Intermediate Similarity	NPC144257
0.748	Intermediate Similarity	NPC478107
0.748	Intermediate Similarity	NPC470649
0.748	Intermediate Similarity	NPC204784
0.7479	Intermediate Similarity	NPC143768
0.7478	Intermediate Similarity	NPC471186
0.7477	Intermediate Similarity	NPC240042
0.7459	Intermediate Similarity	NPC94425
0.7458	Intermediate Similarity	NPC475002
0.7458	Intermediate Similarity	NPC265513
0.7458	Intermediate Similarity	NPC95126
0.7456	Intermediate Similarity	NPC329556
0.7456	Intermediate Similarity	NPC247976
0.7438	Intermediate Similarity	NPC9274
0.7436	Intermediate Similarity	NPC475282
0.7414	Intermediate Similarity	NPC100767
0.7414	Intermediate Similarity	NPC477251
0.7411	Intermediate Similarity	NPC179411
0.7405	Intermediate Similarity	NPC209851
0.7404	Intermediate Similarity	NPC44830
0.7395	Intermediate Similarity	NPC292834
0.7385	Intermediate Similarity	NPC25736
0.7368	Intermediate Similarity	NPC474112
0.736	Intermediate Similarity	NPC476234
0.7355	Intermediate Similarity	NPC221275
0.7348	Intermediate Similarity	NPC15850
0.7345	Intermediate Similarity	NPC7435
0.7344	Intermediate Similarity	NPC470816
0.7333	Intermediate Similarity	NPC470253
0.7333	Intermediate Similarity	NPC118366
0.7323	Intermediate Similarity	NPC85511
0.7323	Intermediate Similarity	NPC140118
0.7323	Intermediate Similarity	NPC12881
0.7317	Intermediate Similarity	NPC45794
0.7317	Intermediate Similarity	NPC323440
0.7317	Intermediate Similarity	NPC152812
0.7317	Intermediate Similarity	NPC80605
0.7317	Intermediate Similarity	NPC471553
0.7317	Intermediate Similarity	NPC222968
0.7308	Intermediate Similarity	NPC225103
0.7302	Intermediate Similarity	NPC269923
0.7302	Intermediate Similarity	NPC167323
0.729	Intermediate Similarity	NPC322387
0.7288	Intermediate Similarity	NPC469511
0.7288	Intermediate Similarity	NPC40178
0.7287	Intermediate Similarity	NPC48992
0.7287	Intermediate Similarity	NPC470648
0.7287	Intermediate Similarity	NPC171007
0.7287	Intermediate Similarity	NPC190849
0.728	Intermediate Similarity	NPC472680
0.728	Intermediate Similarity	NPC472679
0.7273	Intermediate Similarity	NPC326664
0.7266	Intermediate Similarity	NPC295664
0.7265	Intermediate Similarity	NPC475905
0.7265	Intermediate Similarity	NPC193640
0.7265	Intermediate Similarity	NPC25385
0.7258	Intermediate Similarity	NPC64340
0.7252	Intermediate Similarity	NPC473443
0.7252	Intermediate Similarity	NPC472388
0.7248	Intermediate Similarity	NPC274455
0.7248	Intermediate Similarity	NPC70940
0.7248	Intermediate Similarity	NPC84288
0.7248	Intermediate Similarity	NPC86670
0.7241	Intermediate Similarity	NPC19136
0.7236	Intermediate Similarity	NPC212891
0.7236	Intermediate Similarity	NPC469843
0.7236	Intermediate Similarity	NPC190298
0.7231	Intermediate Similarity	NPC115797
0.7231	Intermediate Similarity	NPC472678
0.7231	Intermediate Similarity	NPC51448
0.7222	Intermediate Similarity	NPC329064
0.7213	Intermediate Similarity	NPC217111
0.7209	Intermediate Similarity	NPC470818
0.7209	Intermediate Similarity	NPC137416
0.7207	Intermediate Similarity	NPC34243
0.7203	Intermediate Similarity	NPC47536
0.7203	Intermediate Similarity	NPC20485
0.7197	Intermediate Similarity	NPC471334
0.719	Intermediate Similarity	NPC287055
0.719	Intermediate Similarity	NPC242957
0.719	Intermediate Similarity	NPC206414
0.719	Intermediate Similarity	NPC306977
0.7188	Intermediate Similarity	NPC469742
0.7188	Intermediate Similarity	NPC472681
0.7182	Intermediate Similarity	NPC187725
0.7182	Intermediate Similarity	NPC141607
0.7168	Intermediate Similarity	NPC103048
0.7167	Intermediate Similarity	NPC137315
0.7156	Intermediate Similarity	NPC231591
0.7155	Intermediate Similarity	NPC472691
0.7155	Intermediate Similarity	NPC274443
0.7155	Intermediate Similarity	NPC474866
0.7155	Intermediate Similarity	NPC475939
0.7155	Intermediate Similarity	NPC471829
0.7143	Intermediate Similarity	NPC172925
0.7132	Intermediate Similarity	NPC472694
0.7132	Intermediate Similarity	NPC472693
0.712	Intermediate Similarity	NPC318173
0.7119	Intermediate Similarity	NPC37914
0.7119	Intermediate Similarity	NPC474111
0.7119	Intermediate Similarity	NPC329705
0.7115	Intermediate Similarity	NPC127343
0.7109	Intermediate Similarity	NPC65627
0.7107	Intermediate Similarity	NPC471188
0.7107	Intermediate Similarity	NPC471189
0.7105	Intermediate Similarity	NPC329387
0.7105	Intermediate Similarity	NPC317280
0.7103	Intermediate Similarity	NPC95965
0.7097	Intermediate Similarity	NPC105141
0.7097	Intermediate Similarity	NPC242764
0.709	Intermediate Similarity	NPC159811
0.7077	Intermediate Similarity	NPC100402
0.7077	Intermediate Similarity	NPC470765
0.7077	Intermediate Similarity	NPC9180
0.7077	Intermediate Similarity	NPC275576
0.7069	Intermediate Similarity	NPC222390
0.7069	Intermediate Similarity	NPC244427
0.7068	Intermediate Similarity	NPC305162
0.7063	Intermediate Similarity	NPC42657
0.7059	Intermediate Similarity	NPC472804
0.7037	Intermediate Similarity	NPC475346
0.7037	Intermediate Similarity	NPC18982
0.7037	Intermediate Similarity	NPC203486
0.7037	Intermediate Similarity	NPC475627
0.7037	Intermediate Similarity	NPC475457
0.7034	Intermediate Similarity	NPC134120
0.7034	Intermediate Similarity	NPC172483

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 NPC477475 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	783
0.2-0.3	1399
0.3-0.4	2986
0.4-0.5	2479
0.5-0.6	1085
0.6-0.7	192
0.7-0.8	24
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.819	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD5909	Discontinued
0.7627	Intermediate Similarity	NPD7094	Approved
0.7627	Intermediate Similarity	NPD6858	Approved
0.75	Intermediate Similarity	NPD2066	Phase 3
0.7477	Intermediate Similarity	NPD5346	Phase 2
0.7477	Intermediate Similarity	NPD5347	Phase 2
0.7456	Intermediate Similarity	NPD1930	Approved
0.7456	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1929	Approved
0.7436	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1088	Approved
0.7297	Intermediate Similarity	NPD1693	Approved
0.729	Intermediate Similarity	NPD4793	Discontinued
0.7273	Intermediate Similarity	NPD6010	Discontinued
0.7248	Intermediate Similarity	NPD1089	Approved
0.7248	Intermediate Similarity	NPD1086	Approved
0.7248	Intermediate Similarity	NPD1090	Approved
0.7212	Intermediate Similarity	NPD226	Approved
0.7167	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD800	Approved
0.7155	Intermediate Similarity	NPD6647	Phase 2
0.7143	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3672	Approved
0.7091	Intermediate Similarity	NPD3673	Approved
0.7073	Intermediate Similarity	NPD5951	Approved
0.7069	Intermediate Similarity	NPD1932	Approved
0.7043	Intermediate Similarity	NPD7798	Approved
0.704	Intermediate Similarity	NPD7610	Discontinued
0.7034	Intermediate Similarity	NPD5048	Discontinued
0.7018	Intermediate Similarity	NPD3495	Discontinued
0.7015	Intermediate Similarity	NPD7961	Discontinued
0.7	Intermediate Similarity	NPD2329	Discontinued
0.6984	Remote Similarity	NPD7009	Phase 2
0.6975	Remote Similarity	NPD6685	Approved
0.6972	Remote Similarity	NPD1087	Approved
0.6964	Remote Similarity	NPD7631	Approved
0.6935	Remote Similarity	NPD2629	Approved
0.6923	Remote Similarity	NPD225	Approved
0.6923	Remote Similarity	NPD227	Approved
0.6916	Remote Similarity	NPD9491	Approved
0.6894	Remote Similarity	NPD2798	Approved
0.6875	Remote Similarity	NPD1239	Approved
0.6875	Remote Similarity	NPD2932	Approved
0.6875	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7609	Phase 3
0.6875	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1566	Phase 3
0.687	Remote Similarity	NPD1565	Approved
0.687	Remote Similarity	NPD1564	Approved
0.6866	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5765	Approved
0.6838	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1317	Discontinued
0.6789	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1989	Approved
0.6761	Remote Similarity	NPD8166	Discontinued
0.6744	Remote Similarity	NPD3019	Approved
0.6744	Remote Similarity	NPD4199	Phase 3
0.672	Remote Similarity	NPD2650	Approved
0.672	Remote Similarity	NPD2652	Approved
0.6696	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6049	Phase 2
0.6694	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3268	Approved
0.6642	Remote Similarity	NPD6085	Phase 2
0.6642	Remote Similarity	NPD8032	Phase 2
0.6642	Remote Similarity	NPD6663	Approved
0.6642	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD3317	Approved
0.6613	Remote Similarity	NPD3644	Approved
0.6613	Remote Similarity	NPD3643	Approved
0.6613	Remote Similarity	NPD3642	Approved
0.6612	Remote Similarity	NPD1018	Approved
0.6609	Remote Similarity	NPD1563	Approved
0.6593	Remote Similarity	NPD5736	Approved
0.6593	Remote Similarity	NPD7084	Phase 3
0.6591	Remote Similarity	NPD6637	Approved
0.6589	Remote Similarity	NPD4479	Discontinued
0.6583	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2313	Discontinued
0.6567	Remote Similarity	NPD2797	Approved
0.6565	Remote Similarity	NPD3023	Approved
0.6565	Remote Similarity	NPD4879	Approved
0.6565	Remote Similarity	NPD3026	Approved
0.656	Remote Similarity	NPD6912	Phase 3
0.6552	Remote Similarity	NPD7236	Approved
0.6542	Remote Similarity	NPD9490	Approved
0.6538	Remote Similarity	NPD3025	Approved
0.6538	Remote Similarity	NPD3024	Approved
0.6535	Remote Similarity	NPD4766	Approved
0.6535	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD2067	Discontinued
0.6525	Remote Similarity	NPD7305	Phase 1
0.6525	Remote Similarity	NPD2799	Discontinued
0.6525	Remote Similarity	NPD253	Approved
0.6518	Remote Similarity	NPD650	Approved
0.6515	Remote Similarity	NPD5618	Discontinued
0.6512	Remote Similarity	NPD6065	Approved
0.651	Remote Similarity	NPD7458	Discontinued
0.6496	Remote Similarity	NPD7008	Discontinued
0.6489	Remote Similarity	NPD2345	Approved
0.6484	Remote Similarity	NPD4198	Discontinued
0.6471	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD3971	Phase 1
0.6449	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3267	Approved
0.6444	Remote Similarity	NPD3266	Approved
0.6435	Remote Similarity	NPD6411	Approved
0.6434	Remote Similarity	NPD2346	Discontinued
0.6414	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD7714	Approved
0.6403	Remote Similarity	NPD7715	Approved
0.64	Remote Similarity	NPD5278	Discontinued
0.64	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD4218	Approved
0.6391	Remote Similarity	NPD3131	Approved
0.6391	Remote Similarity	NPD4215	Approved
0.6391	Remote Similarity	NPD2610	Approved
0.6391	Remote Similarity	NPD2609	Approved
0.6391	Remote Similarity	NPD3132	Approved
0.6391	Remote Similarity	NPD4216	Approved
0.6391	Remote Similarity	NPD2608	Approved
0.6391	Remote Similarity	NPD4217	Approved
0.6391	Remote Similarity	NPD2612	Approved
0.6391	Remote Similarity	NPD2611	Approved
0.6378	Remote Similarity	NPD2607	Approved
0.637	Remote Similarity	NPD1283	Approved
0.6349	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD4878	Approved
0.6343	Remote Similarity	NPD1608	Approved
0.6333	Remote Similarity	NPD7239	Suspended
0.6328	Remote Similarity	NPD3598	Phase 3
0.632	Remote Similarity	NPD2182	Approved
0.6304	Remote Similarity	NPD7055	Discontinued
0.6301	Remote Similarity	NPD7003	Approved
0.6293	Remote Similarity	NPD5284	Approved
0.6293	Remote Similarity	NPD5281	Approved
0.629	Remote Similarity	NPD467	Phase 1
0.6288	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD5981	Approved
0.627	Remote Similarity	NPD1752	Approved
0.627	Remote Similarity	NPD4233	Approved
0.627	Remote Similarity	NPD1756	Approved
0.627	Remote Similarity	NPD4234	Approved
0.6269	Remote Similarity	NPD6287	Discontinued
0.6269	Remote Similarity	NPD3603	Phase 3
0.6269	Remote Similarity	NPD1201	Approved
0.6269	Remote Similarity	NPD4806	Approved
0.6269	Remote Similarity	NPD4807	Approved
0.6261	Remote Similarity	NPD6101	Approved
0.6261	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.626	Remote Similarity	NPD164	Approved
0.6259	Remote Similarity	NPD7095	Approved
0.625	Remote Similarity	NPD7028	Phase 2
0.625	Remote Similarity	NPD9495	Approved
0.6241	Remote Similarity	NPD5306	Approved
0.6241	Remote Similarity	NPD5305	Approved
0.6239	Remote Similarity	NPD1508	Approved
0.6234	Remote Similarity	NPD7819	Suspended
0.6222	Remote Similarity	NPD3972	Approved
0.6212	Remote Similarity	NPD7741	Discontinued
0.6212	Remote Similarity	NPD3798	Phase 3
0.6211	Remote Similarity	NPD7799	Discontinued
0.6207	Remote Similarity	NPD9258	Approved
0.6207	Remote Similarity	NPD9256	Approved
0.6207	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD1470	Approved
0.6197	Remote Similarity	NPD6355	Discontinued
0.6194	Remote Similarity	NPD3881	Discontinued
0.6187	Remote Similarity	NPD2613	Approved
0.6186	Remote Similarity	NPD1066	Discontinued
0.6186	Remote Similarity	NPD1202	Approved
0.6186	Remote Similarity	NPD7748	Approved
0.6183	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD3797	Approved
0.6183	Remote Similarity	NPD4574	Approved
0.6183	Remote Similarity	NPD4576	Approved
0.6182	Remote Similarity	NPD4695	Discontinued
0.6182	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD531	Approved
0.6167	Remote Similarity	NPD9566	Approved
0.6165	Remote Similarity	NPD6993	Approved
0.6165	Remote Similarity	NPD4102	Approved
0.6165	Remote Similarity	NPD4105	Approved
0.6165	Remote Similarity	NPD6994	Approved
0.6154	Remote Similarity	NPD1246	Approved
0.6148	Remote Similarity	NPD1281	Approved
0.6148	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD6100	Approved
0.6138	Remote Similarity	NPD5408	Approved
0.6138	Remote Similarity	NPD6099	Approved
0.6138	Remote Similarity	NPD5405	Approved
0.6138	Remote Similarity	NPD5406	Approved
0.6138	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