NPASS Compound

Structure

NPC472786 OpenBabel07101719512D 25 29 0 0 1 0 0 0 0 0999 V2000 0.0776 -3.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7553 -4.2599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5632 -2.1030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1509 -2.6649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3721 -3.8142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8471 -2.4883 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6066 -3.5399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7981 -3.3976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0817 -2.2140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4614 -2.7398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0574 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9923 -3.2884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9345 -1.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1562 -4.1865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2720 -4.2782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9449 -0.9406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 1 0 0 0 0 3 10 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 19 1 0 0 0 0 7 12 1 0 0 0 0 7 20 1 0 0 0 0 8 9 2 0 0 0 0 8 25 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 20 1 1 0 0 0 11 21 2 0 0 0 0 12 16 1 0 0 0 0 12 22 1 1 0 0 0 13 20 1 0 0 0 0 13 23 2 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 24 2 0 0 0 0 18 25 1 0 0 0 0 19 1 1 1 0 0 0 20 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.13
Volume:	339.826
LogP:	1.377
LogD:	1.427
LogS:	-4.088
# Rotatable Bonds:	0
TPSA:	81.42
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.725
Synthetic Accessibility Score:	4.625
Fsp3:	0.6
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:	-4.941
MDCK Permeability:	2.6662475647754036e-05
Pgp-inhibitor:	0.528
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.222

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.531
Plasma Protein Binding (PPB):	79.2089614868164%
Volume Distribution (VD):	0.661
Pgp-substrate:	19.0964412689209%

ADMET: Metabolism

CYP1A2-inhibitor:	0.167
CYP1A2-substrate:	0.797
CYP2C19-inhibitor:	0.366
CYP2C19-substrate:	0.58
CYP2C9-inhibitor:	0.293
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.264
CYP3A4-inhibitor:	0.695
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	8.259
Half-life (T1/2):	0.493

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.809
Skin Sensitization:	0.072
Carcinogencity:	0.929
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.363

Download Data

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

Natural Product: NPC472786

Natural Product ID:	NPC472786
*Common Name:**	ZLLLRXUQFGPJIK-PBYSILGBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZLLLRXUQFGPJIK-PBYSILGBSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-19-6-5-11(21)9-8-25-18(15(9)19)17(24)14-10-3-4-13(23)20(10,2)7-12(22)16(14)19/h8,10,12,22H,3-7H2,1-2H3/t10-,12-,19-,20-/m0/s1
SMILES:	CC12CCC(=O)C3=COC(=C31)C(=O)C4=C2C(CC5(C4CCC5=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582132
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives

*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
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12270179]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542359]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17363259]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25978520]

☑ 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	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Inhibition	=	98.8	%	PMID[506225]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	IC50	=	1200.0	nM	PMID[506225]

☑ 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 NPC472786 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	359
0.1-0.2	1475
0.2-0.3	3198
0.3-0.4	8213
0.4-0.5	12441
0.5-0.6	7366
0.6-0.7	8329
0.7-0.8	1286
0.8-0.85	24
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9467	High Similarity	NPC472785
0.9267	High Similarity	NPC472787
0.8974	High Similarity	NPC333139
0.882	High Similarity	NPC44602
0.8784	High Similarity	NPC18904
0.8718	High Similarity	NPC75310
0.871	High Similarity	NPC475777
0.8696	High Similarity	NPC472784
0.8671	High Similarity	NPC140952
0.8608	High Similarity	NPC81405
0.8599	High Similarity	NPC88958
0.8523	High Similarity	NPC177262
0.8509	High Similarity	NPC472780
0.8509	High Similarity	NPC472783
0.8487	Intermediate Similarity	NPC64568
0.8487	Intermediate Similarity	NPC103134
0.8457	Intermediate Similarity	NPC472664
0.8447	Intermediate Similarity	NPC472782
0.8447	Intermediate Similarity	NPC472781
0.8411	Intermediate Similarity	NPC61157
0.8411	Intermediate Similarity	NPC473681
0.8411	Intermediate Similarity	NPC218204
0.8405	Intermediate Similarity	NPC475779
0.84	Intermediate Similarity	NPC471996
0.8387	Intermediate Similarity	NPC224418
0.8365	Intermediate Similarity	NPC179170
0.8354	Intermediate Similarity	NPC471613
0.8354	Intermediate Similarity	NPC246164
0.8344	Intermediate Similarity	NPC56358
0.8333	Intermediate Similarity	NPC472665
0.8323	Intermediate Similarity	NPC116639
0.8323	Intermediate Similarity	NPC233763
0.8323	Intermediate Similarity	NPC97904
0.8323	Intermediate Similarity	NPC472823
0.8302	Intermediate Similarity	NPC114880
0.8301	Intermediate Similarity	NPC473152
0.8291	Intermediate Similarity	NPC272590
0.8282	Intermediate Similarity	NPC663
0.8282	Intermediate Similarity	NPC224394
0.828	Intermediate Similarity	NPC211625
0.828	Intermediate Similarity	NPC192069
0.8272	Intermediate Similarity	NPC287559
0.8261	Intermediate Similarity	NPC304692
0.8258	Intermediate Similarity	NPC185456
0.8242	Intermediate Similarity	NPC270312
0.8239	Intermediate Similarity	NPC145830
0.8232	Intermediate Similarity	NPC261184
0.8221	Intermediate Similarity	NPC18986
0.821	Intermediate Similarity	NPC473282
0.821	Intermediate Similarity	NPC104380
0.821	Intermediate Similarity	NPC217602
0.8205	Intermediate Similarity	NPC62799
0.8199	Intermediate Similarity	NPC104736
0.8182	Intermediate Similarity	NPC263337
0.8182	Intermediate Similarity	NPC121995
0.8166	Intermediate Similarity	NPC167340
0.8148	Intermediate Similarity	NPC221992
0.8129	Intermediate Similarity	NPC243577
0.8125	Intermediate Similarity	NPC470996
0.8121	Intermediate Similarity	NPC471995
0.8113	Intermediate Similarity	NPC226578
0.811	Intermediate Similarity	NPC197596
0.8098	Intermediate Similarity	NPC477403
0.8098	Intermediate Similarity	NPC476404
0.8098	Intermediate Similarity	NPC317900
0.8098	Intermediate Similarity	NPC294300
0.8098	Intermediate Similarity	NPC299094
0.8098	Intermediate Similarity	NPC474611
0.8098	Intermediate Similarity	NPC10051
0.8095	Intermediate Similarity	NPC20734
0.8086	Intermediate Similarity	NPC41880
0.8075	Intermediate Similarity	NPC178932
0.807	Intermediate Similarity	NPC295914
0.8065	Intermediate Similarity	NPC20578
0.8065	Intermediate Similarity	NPC62103
0.8061	Intermediate Similarity	NPC283209
0.8059	Intermediate Similarity	NPC475080
0.8052	Intermediate Similarity	NPC148374
0.8052	Intermediate Similarity	NPC90296
0.805	Intermediate Similarity	NPC280025
0.8049	Intermediate Similarity	NPC477402
0.8038	Intermediate Similarity	NPC302987
0.8038	Intermediate Similarity	NPC471174
0.8025	Intermediate Similarity	NPC469336
0.8025	Intermediate Similarity	NPC245522
0.8025	Intermediate Similarity	NPC92979
0.8025	Intermediate Similarity	NPC114513
0.8024	Intermediate Similarity	NPC316262
0.8024	Intermediate Similarity	NPC473766
0.8024	Intermediate Similarity	NPC478179
0.8024	Intermediate Similarity	NPC314653
0.8024	Intermediate Similarity	NPC473753
0.8013	Intermediate Similarity	NPC205071
0.8012	Intermediate Similarity	NPC294511
0.8012	Intermediate Similarity	NPC121615
0.8	Intermediate Similarity	NPC313368
0.8	Intermediate Similarity	NPC91650
0.8	Intermediate Similarity	NPC169018
0.8	Intermediate Similarity	NPC212257
0.8	Intermediate Similarity	NPC69028
0.7988	Intermediate Similarity	NPC473368
0.7988	Intermediate Similarity	NPC84349
0.7987	Intermediate Similarity	NPC19747
0.7976	Intermediate Similarity	NPC85047
0.7976	Intermediate Similarity	NPC191012
0.7976	Intermediate Similarity	NPC120857
0.7976	Intermediate Similarity	NPC17274
0.7974	Intermediate Similarity	NPC4764
0.7973	Intermediate Similarity	NPC329707
0.7965	Intermediate Similarity	NPC98943
0.7964	Intermediate Similarity	NPC478178
0.7962	Intermediate Similarity	NPC84479
0.7961	Intermediate Similarity	NPC158525
0.7952	Intermediate Similarity	NPC285567
0.7952	Intermediate Similarity	NPC288602
0.7952	Intermediate Similarity	NPC88841
0.7949	Intermediate Similarity	NPC52412
0.7941	Intermediate Similarity	NPC313717
0.7941	Intermediate Similarity	NPC315306
0.7937	Intermediate Similarity	NPC472654
0.7929	Intermediate Similarity	NPC193222
0.7927	Intermediate Similarity	NPC261597
0.7925	Intermediate Similarity	NPC250228
0.7925	Intermediate Similarity	NPC216755
0.7925	Intermediate Similarity	NPC281398
0.7917	Intermediate Similarity	NPC476850
0.7917	Intermediate Similarity	NPC136641
0.7917	Intermediate Similarity	NPC476861
0.7914	Intermediate Similarity	NPC35000
0.7914	Intermediate Similarity	NPC44675
0.7914	Intermediate Similarity	NPC469966
0.7914	Intermediate Similarity	NPC25351
0.7914	Intermediate Similarity	NPC214541
0.7911	Intermediate Similarity	NPC41182
0.7908	Intermediate Similarity	NPC46896
0.7907	Intermediate Similarity	NPC478177
0.7907	Intermediate Similarity	NPC475398
0.7904	Intermediate Similarity	NPC470940
0.7904	Intermediate Similarity	NPC276551
0.7904	Intermediate Similarity	NPC476858
0.7904	Intermediate Similarity	NPC476856
0.7904	Intermediate Similarity	NPC123088
0.7904	Intermediate Similarity	NPC476857
0.7901	Intermediate Similarity	NPC75906
0.7892	Intermediate Similarity	NPC193798
0.7892	Intermediate Similarity	NPC188649
0.7892	Intermediate Similarity	NPC329938
0.7892	Intermediate Similarity	NPC475107
0.7892	Intermediate Similarity	NPC43490
0.7892	Intermediate Similarity	NPC5079
0.7892	Intermediate Similarity	NPC68848
0.7888	Intermediate Similarity	NPC228842
0.7888	Intermediate Similarity	NPC196846
0.7882	Intermediate Similarity	NPC54903
0.7882	Intermediate Similarity	NPC286074
0.7875	Intermediate Similarity	NPC252208
0.7875	Intermediate Similarity	NPC93666
0.7871	Intermediate Similarity	NPC265181
0.787	Intermediate Similarity	NPC476056
0.787	Intermediate Similarity	NPC475109
0.787	Intermediate Similarity	NPC476255
0.7866	Intermediate Similarity	NPC469485
0.7857	Intermediate Similarity	NPC476931
0.7857	Intermediate Similarity	NPC100849
0.7857	Intermediate Similarity	NPC149945
0.7857	Intermediate Similarity	NPC470875
0.7857	Intermediate Similarity	NPC23387
0.7853	Intermediate Similarity	NPC57998
0.7853	Intermediate Similarity	NPC30222
0.7853	Intermediate Similarity	NPC282793
0.7848	Intermediate Similarity	NPC117674
0.7848	Intermediate Similarity	NPC238843
0.7848	Intermediate Similarity	NPC199044
0.7844	Intermediate Similarity	NPC477405
0.7844	Intermediate Similarity	NPC292389
0.7844	Intermediate Similarity	NPC234660
0.7844	Intermediate Similarity	NPC469338
0.7844	Intermediate Similarity	NPC51568
0.784	Intermediate Similarity	NPC144010
0.7836	Intermediate Similarity	NPC193698
0.7831	Intermediate Similarity	NPC472299
0.7831	Intermediate Similarity	NPC25255
0.7829	Intermediate Similarity	NPC293253
0.7826	Intermediate Similarity	NPC470998
0.7826	Intermediate Similarity	NPC195325
0.7824	Intermediate Similarity	NPC223413
0.7821	Intermediate Similarity	NPC67003
0.7818	Intermediate Similarity	NPC472283
0.7818	Intermediate Similarity	NPC36655
0.7818	Intermediate Similarity	NPC472772
0.7818	Intermediate Similarity	NPC197137
0.7818	Intermediate Similarity	NPC249021
0.7818	Intermediate Similarity	NPC194499
0.7818	Intermediate Similarity	NPC173544
0.7816	Intermediate Similarity	NPC233978
0.7816	Intermediate Similarity	NPC5671
0.7812	Intermediate Similarity	NPC71821
0.7811	Intermediate Similarity	NPC476853
0.7806	Intermediate Similarity	NPC236532
0.7805	Intermediate Similarity	NPC42458

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 NPC472786 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	1030
0.2-0.3	2045
0.3-0.4	2760
0.4-0.5	2073
0.5-0.6	711
0.6-0.7	205
0.7-0.8	14
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8974	High Similarity	NPD5537	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD5761	Phase 2
0.8025	Intermediate Similarity	NPD5760	Phase 2
0.7931	Intermediate Similarity	NPD8434	Phase 2
0.7871	Intermediate Similarity	NPD1471	Phase 3
0.7849	Intermediate Similarity	NPD6764	Approved
0.7849	Intermediate Similarity	NPD6765	Approved
0.767	Intermediate Similarity	NPD6785	Approved
0.767	Intermediate Similarity	NPD6784	Approved
0.7547	Intermediate Similarity	NPD2800	Approved
0.7312	Intermediate Similarity	NPD2344	Approved
0.7246	Intermediate Similarity	NPD3226	Approved
0.7178	Intermediate Similarity	NPD4628	Phase 3
0.717	Intermediate Similarity	NPD6651	Approved
0.7135	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2309	Approved
0.7126	Intermediate Similarity	NPD1247	Approved
0.7118	Intermediate Similarity	NPD6801	Discontinued
0.7117	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2533	Approved
0.7108	Intermediate Similarity	NPD2532	Approved
0.7108	Intermediate Similarity	NPD2534	Approved
0.7101	Intermediate Similarity	NPD6599	Discontinued
0.7099	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3882	Suspended
0.7076	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6273	Approved
0.7052	Intermediate Similarity	NPD7075	Discontinued
0.7024	Intermediate Similarity	NPD920	Approved
0.7022	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7236	Approved
0.6977	Remote Similarity	NPD7819	Suspended
0.6961	Remote Similarity	NPD6559	Discontinued
0.6959	Remote Similarity	NPD7411	Suspended
0.6951	Remote Similarity	NPD1549	Phase 2
0.6933	Remote Similarity	NPD2796	Approved
0.6932	Remote Similarity	NPD6959	Discontinued
0.6914	Remote Similarity	NPD919	Approved
0.6905	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2346	Discontinued
0.6879	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5494	Approved
0.6871	Remote Similarity	NPD2799	Discontinued
0.6857	Remote Similarity	NPD3749	Approved
0.6854	Remote Similarity	NPD3926	Phase 2
0.6845	Remote Similarity	NPD6799	Approved
0.6839	Remote Similarity	NPD3057	Approved
0.6833	Remote Similarity	NPD7799	Discontinued
0.6816	Remote Similarity	NPD8404	Phase 2
0.6805	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4380	Phase 2
0.6788	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6002	Phase 3
0.6788	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6005	Phase 3
0.6788	Remote Similarity	NPD6004	Phase 3
0.6786	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7239	Suspended
0.6768	Remote Similarity	NPD1510	Phase 2
0.6766	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD3533	Approved
0.6753	Remote Similarity	NPD2972	Approved
0.6747	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD5402	Approved
0.674	Remote Similarity	NPD3818	Discontinued
0.6727	Remote Similarity	NPD6100	Approved
0.6727	Remote Similarity	NPD6099	Approved
0.6725	Remote Similarity	NPD5403	Approved
0.6724	Remote Similarity	NPD1934	Approved
0.6722	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6166	Phase 2
0.6722	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD2403	Approved
0.6722	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD2313	Discontinued
0.6708	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1243	Approved
0.6704	Remote Similarity	NPD6808	Phase 2
0.6703	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7033	Discontinued
0.6648	Remote Similarity	NPD3817	Phase 2
0.6648	Remote Similarity	NPD8127	Discontinued
0.6648	Remote Similarity	NPD3751	Discontinued
0.6648	Remote Similarity	NPD2296	Approved
0.6646	Remote Similarity	NPD1876	Approved
0.6646	Remote Similarity	NPD1607	Approved
0.6645	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6280	Approved
0.6629	Remote Similarity	NPD6279	Approved
0.6627	Remote Similarity	NPD1551	Phase 2
0.6626	Remote Similarity	NPD1240	Approved
0.6624	Remote Similarity	NPD3972	Approved
0.6611	Remote Similarity	NPD5711	Approved
0.6611	Remote Similarity	NPD5710	Approved
0.6608	Remote Similarity	NPD5401	Approved
0.6593	Remote Similarity	NPD7473	Discontinued
0.6591	Remote Similarity	NPD2801	Approved
0.6587	Remote Similarity	NPD5762	Approved
0.6587	Remote Similarity	NPD5763	Approved
0.6585	Remote Similarity	NPD6355	Discontinued
0.6582	Remote Similarity	NPD2491	Approved
0.657	Remote Similarity	NPD1512	Approved
0.6568	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3750	Approved
0.6567	Remote Similarity	NPD5676	Approved
0.6564	Remote Similarity	NPD4107	Approved
0.6562	Remote Similarity	NPD2798	Approved
0.6561	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD9092	Discovery
0.6557	Remote Similarity	NPD2163	Approved
0.6552	Remote Similarity	NPD7458	Discontinued
0.6552	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6797	Phase 2
0.6538	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD8313	Approved
0.6524	Remote Similarity	NPD8312	Approved
0.6524	Remote Similarity	NPD4140	Approved
0.6522	Remote Similarity	NPD5844	Phase 1
0.6519	Remote Similarity	NPD6232	Discontinued
0.6517	Remote Similarity	NPD7768	Phase 2
0.6517	Remote Similarity	NPD7058	Phase 2
0.6517	Remote Similarity	NPD7057	Phase 3
0.6514	Remote Similarity	NPD7028	Phase 2
0.6508	Remote Similarity	NPD8150	Discontinued
0.6505	Remote Similarity	NPD7251	Discontinued
0.6505	Remote Similarity	NPD4665	Approved
0.6505	Remote Similarity	NPD4111	Phase 1
0.6503	Remote Similarity	NPD3268	Approved
0.65	Remote Similarity	NPD1470	Approved
0.6497	Remote Similarity	NPD3448	Approved
0.6485	Remote Similarity	NPD5735	Approved
0.6484	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7003	Approved
0.6471	Remote Similarity	NPD7808	Phase 3
0.6471	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD8032	Phase 2
0.6461	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5647	Approved
0.6459	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD1511	Approved
0.6447	Remote Similarity	NPD4482	Phase 3
0.6442	Remote Similarity	NPD7907	Approved
0.644	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2935	Discontinued
0.6425	Remote Similarity	NPD4967	Phase 2
0.6425	Remote Similarity	NPD4965	Approved
0.6425	Remote Similarity	NPD4966	Approved
0.6425	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1608	Approved
0.6402	Remote Similarity	NPD8407	Phase 2
0.6402	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD3764	Approved
0.6398	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD7074	Phase 3
0.6396	Remote Similarity	NPD6779	Approved
0.6396	Remote Similarity	NPD6777	Approved
0.6396	Remote Similarity	NPD6780	Approved
0.6396	Remote Similarity	NPD6781	Approved
0.6396	Remote Similarity	NPD6778	Approved
0.6396	Remote Similarity	NPD6782	Approved
0.6396	Remote Similarity	NPD6776	Approved
0.6382	Remote Similarity	NPD7435	Discontinued
0.6374	Remote Similarity	NPD7199	Phase 2
0.6369	Remote Similarity	NPD3748	Approved
0.6364	Remote Similarity	NPD5953	Discontinued
0.6364	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD37	Approved
0.6348	Remote Similarity	NPD6844	Discontinued
0.6344	Remote Similarity	NPD7054	Approved
0.6339	Remote Similarity	NPD3787	Discontinued
0.633	Remote Similarity	NPD8368	Discontinued
0.6329	Remote Similarity	NPD2932	Approved
0.6322	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8491	Approved
0.6319	Remote Similarity	NPD2861	Phase 2
0.6312	Remote Similarity	NPD9717	Approved
0.631	Remote Similarity	NPD7472	Approved
0.6303	Remote Similarity	NPD6798	Discontinued
0.63	Remote Similarity	NPD7698	Approved
0.63	Remote Similarity	NPD7697	Approved
0.63	Remote Similarity	NPD7696	Phase 3
0.6299	Remote Similarity	NPD1241	Discontinued
0.629	Remote Similarity	NPD7177	Discontinued
0.6289	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD8366	Approved
0.628	Remote Similarity	NPD6832	Phase 2
0.6279	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4110	Phase 3
0.6273	Remote Similarity	NPD5327	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