NPASS Compound

Structure

NPC211592 OpenBabel07101719142D 30 33 0 0 1 0 0 0 0 0999 V2000 1.1554 2.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0685 -3.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8284 2.8284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0532 1.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4752 -1.6691 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 -1.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1213 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7944 2.5696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3461 0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3801 1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0739 -2.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5015 3.2767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6049 -0.0694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4048 -3.2213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9319 -0.5176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2588 0.9659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 21 1 0 0 0 0 9 16 1 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 24 2 0 0 0 0 11 17 1 0 0 0 0 12 6 1 1 0 0 0 12 18 1 0 0 0 0 13 23 1 0 0 0 0 14 25 1 0 0 0 0 15 17 2 0 0 0 0 15 26 1 0 0 0 0 16 23 1 6 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 1 0 0 0 19 21 1 0 0 0 0 19 27 1 1 0 0 0 20 28 2 0 0 0 0 20 30 1 0 0 0 0 22 23 1 1 0 0 0 23 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.18
Volume:	417.851
LogP:	3.469
LogD:	2.495
LogS:	-3.617
# Rotatable Bonds:	4
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	4.975
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.431
MDCK Permeability:	5.704279374185717e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.066
30% Bioavailability (F30%):	0.127

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.468
Plasma Protein Binding (PPB):	88.76565551757812%
Volume Distribution (VD):	0.792
Pgp-substrate:	10.386144638061523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.626
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.425
CYP2C19-substrate:	0.176
CYP2C9-inhibitor:	0.699
CYP2C9-substrate:	0.803
CYP2D6-inhibitor:	0.585
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.791
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	9.131
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.233
Human Hepatotoxicity (H-HT):	0.192
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.113
Rat Oral Acute Toxicity:	0.342
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.791
Carcinogencity:	0.841
Eye Corrosion:	0.007
Eye Irritation:	0.094
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC211592

Natural Product ID:	NPC211592
*Common Name:**	10Alpha-Hydroxymelleolide
IUPAC Name:	[(2R,2aS,4aS,7R,7aS,7bR)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1,2,4a,5,7,7a-hexahydrocyclobuta[e]inden-2-yl] 2,4-dihydroxy-6-methylbenzoate
Synonyms:	10Alpha-Hydroxymelleolide
Standard InCHIKey:	VNRLQDGXGABKPC-METLCYJQSA-N
Standard InCHI:	InChI=1S/C23H28O7/c1-11-5-14(25)7-15(26)17(11)20(28)30-16-9-22(4)18-12(8-21(2,3)19(18)27)6-13(10-24)23(16,22)29/h5-7,10,12,16,18-19,25-27,29H,8-9H2,1-4H3/t12-,16-,18-,19-,22-,23+/m1/s1
SMILES:	Cc1cc(cc(c1C(=O)O[C@@H]1C[C@]2(C)[C@@H]3[C@H](C=C(C=O)[C@]12O)CC(C)(C)[C@@H]3O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077563
PubChem CID:	14707329
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001777] Illudanes and illudins [CHEMONTID:0001776] Melleolides and analogues

*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
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19795841]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4040154]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28689	Armillaria mellea	Species	Physalacriaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	100000.0	nM	PMID[543429]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[543429]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	86170.0	nM	PMID[543429]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	63230.0	nM	PMID[543429]

☑ 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 NPC211592 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	362
0.1-0.2	1378
0.2-0.3	2975
0.3-0.4	6378
0.4-0.5	10962
0.5-0.6	6942
0.6-0.7	8297
0.7-0.8	5272
0.8-0.85	124
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC165460
0.9419	High Similarity	NPC470102
0.8728	High Similarity	NPC470103
0.8671	High Similarity	NPC166583
0.8671	High Similarity	NPC53362
0.865	High Similarity	NPC478225
0.8611	High Similarity	NPC108744
0.8608	High Similarity	NPC473023
0.8598	High Similarity	NPC470339
0.8589	High Similarity	NPC472050
0.858	High Similarity	NPC478231
0.8571	High Similarity	NPC221249
0.8545	High Similarity	NPC472055
0.8544	High Similarity	NPC83272
0.8539	High Similarity	NPC247104
0.8537	High Similarity	NPC472889
0.8528	High Similarity	NPC208173
0.8528	High Similarity	NPC472890
0.8528	High Similarity	NPC478221
0.8528	High Similarity	NPC69043
0.8528	High Similarity	NPC170189
0.8528	High Similarity	NPC478230
0.8519	High Similarity	NPC115249
0.8519	High Similarity	NPC76041
0.8519	High Similarity	NPC470340
0.8519	High Similarity	NPC184284
0.8509	High Similarity	NPC179178
0.8494	Intermediate Similarity	NPC117985
0.8483	Intermediate Similarity	NPC221185
0.8466	Intermediate Similarity	NPC137301
0.8462	Intermediate Similarity	NPC158472
0.8457	Intermediate Similarity	NPC240768
0.8457	Intermediate Similarity	NPC200773
0.8457	Intermediate Similarity	NPC215921
0.8457	Intermediate Similarity	NPC70016
0.8452	Intermediate Similarity	NPC212693
0.8452	Intermediate Similarity	NPC94248
0.8447	Intermediate Similarity	NPC270160
0.8447	Intermediate Similarity	NPC237440
0.8438	Intermediate Similarity	NPC81835
0.8424	Intermediate Similarity	NPC246466
0.8424	Intermediate Similarity	NPC473395
0.8421	Intermediate Similarity	NPC472620
0.8418	Intermediate Similarity	NPC471731
0.8418	Intermediate Similarity	NPC159721
0.8408	Intermediate Similarity	NPC472605
0.8408	Intermediate Similarity	NPC472604
0.8405	Intermediate Similarity	NPC478224
0.8395	Intermediate Similarity	NPC472891
0.8395	Intermediate Similarity	NPC56204
0.8393	Intermediate Similarity	NPC100849
0.8393	Intermediate Similarity	NPC161151
0.8389	Intermediate Similarity	NPC48822
0.8387	Intermediate Similarity	NPC70380
0.8371	Intermediate Similarity	NPC470100
0.8365	Intermediate Similarity	NPC42540
0.8365	Intermediate Similarity	NPC151607
0.8354	Intermediate Similarity	NPC322112
0.8354	Intermediate Similarity	NPC155686
0.8354	Intermediate Similarity	NPC82913
0.8354	Intermediate Similarity	NPC471733
0.8344	Intermediate Similarity	NPC472601
0.8344	Intermediate Similarity	NPC132990
0.8344	Intermediate Similarity	NPC46882
0.8344	Intermediate Similarity	NPC472600
0.8333	Intermediate Similarity	NPC472602
0.8333	Intermediate Similarity	NPC191835
0.8324	Intermediate Similarity	NPC294149
0.8313	Intermediate Similarity	NPC77679
0.8313	Intermediate Similarity	NPC84935
0.8313	Intermediate Similarity	NPC478226
0.8313	Intermediate Similarity	NPC190020
0.8304	Intermediate Similarity	NPC472619
0.8303	Intermediate Similarity	NPC317585
0.8303	Intermediate Similarity	NPC82592
0.8303	Intermediate Similarity	NPC16082
0.8303	Intermediate Similarity	NPC471456
0.8302	Intermediate Similarity	NPC51106
0.8294	Intermediate Similarity	NPC125465
0.8293	Intermediate Similarity	NPC113608
0.8293	Intermediate Similarity	NPC167903
0.8293	Intermediate Similarity	NPC470338
0.8293	Intermediate Similarity	NPC470337
0.8293	Intermediate Similarity	NPC268992
0.8293	Intermediate Similarity	NPC180944
0.8293	Intermediate Similarity	NPC51824
0.8291	Intermediate Similarity	NPC158634
0.8291	Intermediate Similarity	NPC472603
0.8291	Intermediate Similarity	NPC37530
0.8291	Intermediate Similarity	NPC53649
0.8282	Intermediate Similarity	NPC469670
0.8282	Intermediate Similarity	NPC469619
0.828	Intermediate Similarity	NPC139634
0.828	Intermediate Similarity	NPC247409
0.828	Intermediate Similarity	NPC88269
0.828	Intermediate Similarity	NPC275356
0.828	Intermediate Similarity	NPC32360
0.828	Intermediate Similarity	NPC105456
0.8274	Intermediate Similarity	NPC477627
0.8274	Intermediate Similarity	NPC96031
0.8261	Intermediate Similarity	NPC260946
0.8256	Intermediate Similarity	NPC313717
0.8256	Intermediate Similarity	NPC315306
0.8253	Intermediate Similarity	NPC150227
0.8253	Intermediate Similarity	NPC478027
0.825	Intermediate Similarity	NPC103910
0.825	Intermediate Similarity	NPC210425
0.825	Intermediate Similarity	NPC277426
0.825	Intermediate Similarity	NPC280404
0.825	Intermediate Similarity	NPC86373
0.8242	Intermediate Similarity	NPC303950
0.8242	Intermediate Similarity	NPC281477
0.8229	Intermediate Similarity	NPC469418
0.8228	Intermediate Similarity	NPC99441
0.8228	Intermediate Similarity	NPC64664
0.8217	Intermediate Similarity	NPC478200
0.8217	Intermediate Similarity	NPC197666
0.8217	Intermediate Similarity	NPC33144
0.8217	Intermediate Similarity	NPC126739
0.821	Intermediate Similarity	NPC471734
0.821	Intermediate Similarity	NPC8817
0.8205	Intermediate Similarity	NPC235115
0.8199	Intermediate Similarity	NPC257558
0.8193	Intermediate Similarity	NPC79998
0.8193	Intermediate Similarity	NPC199926
0.8193	Intermediate Similarity	NPC99381
0.8193	Intermediate Similarity	NPC68727
0.8187	Intermediate Similarity	NPC472621
0.8187	Intermediate Similarity	NPC20237
0.8187	Intermediate Similarity	NPC472610
0.8187	Intermediate Similarity	NPC478202
0.8187	Intermediate Similarity	NPC472006
0.8187	Intermediate Similarity	NPC469542
0.8176	Intermediate Similarity	NPC476822
0.8176	Intermediate Similarity	NPC313123
0.8176	Intermediate Similarity	NPC478217
0.8176	Intermediate Similarity	NPC470842
0.8176	Intermediate Similarity	NPC1704
0.8176	Intermediate Similarity	NPC67650
0.8176	Intermediate Similarity	NPC472035
0.8176	Intermediate Similarity	NPC244923
0.8176	Intermediate Similarity	NPC478201
0.8176	Intermediate Similarity	NPC249181
0.8176	Intermediate Similarity	NPC130485
0.8171	Intermediate Similarity	NPC478050
0.8171	Intermediate Similarity	NPC225854
0.8167	Intermediate Similarity	NPC470099
0.8166	Intermediate Similarity	NPC317544
0.8166	Intermediate Similarity	NPC266365
0.8165	Intermediate Similarity	NPC268052
0.816	Intermediate Similarity	NPC161955
0.816	Intermediate Similarity	NPC94781
0.816	Intermediate Similarity	NPC73411
0.816	Intermediate Similarity	NPC470359
0.816	Intermediate Similarity	NPC215711
0.8153	Intermediate Similarity	NPC71256
0.8153	Intermediate Similarity	NPC194579
0.8148	Intermediate Similarity	NPC470357
0.8148	Intermediate Similarity	NPC63918
0.8148	Intermediate Similarity	NPC107625
0.8148	Intermediate Similarity	NPC471735
0.8146	Intermediate Similarity	NPC99937
0.8144	Intermediate Similarity	NPC164427
0.8144	Intermediate Similarity	NPC4547
0.814	Intermediate Similarity	NPC472622
0.814	Intermediate Similarity	NPC473094
0.814	Intermediate Similarity	NPC283041
0.8137	Intermediate Similarity	NPC478203
0.8137	Intermediate Similarity	NPC126882
0.8137	Intermediate Similarity	NPC210966
0.8133	Intermediate Similarity	NPC192189
0.8133	Intermediate Similarity	NPC471695
0.8133	Intermediate Similarity	NPC472799
0.8129	Intermediate Similarity	NPC153783
0.8129	Intermediate Similarity	NPC191930
0.8125	Intermediate Similarity	NPC474385
0.8125	Intermediate Similarity	NPC469579
0.8121	Intermediate Similarity	NPC477276
0.8121	Intermediate Similarity	NPC91809
0.8118	Intermediate Similarity	NPC473022
0.8118	Intermediate Similarity	NPC315772
0.811	Intermediate Similarity	NPC77325
0.811	Intermediate Similarity	NPC84142
0.811	Intermediate Similarity	NPC4423
0.811	Intermediate Similarity	NPC142654
0.8107	Intermediate Similarity	NPC470810
0.8107	Intermediate Similarity	NPC313368
0.8107	Intermediate Similarity	NPC470358
0.8101	Intermediate Similarity	NPC472403
0.8101	Intermediate Similarity	NPC475974
0.8098	Intermediate Similarity	NPC137296
0.8098	Intermediate Similarity	NPC210320
0.8098	Intermediate Similarity	NPC472036
0.8092	Intermediate Similarity	NPC473095
0.8092	Intermediate Similarity	NPC473096
0.8089	Intermediate Similarity	NPC158481
0.8086	Intermediate Similarity	NPC75694
0.8081	Intermediate Similarity	NPC469419
0.8075	Intermediate Similarity	NPC21873
0.8072	Intermediate Similarity	NPC273483

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 NPC211592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	866
0.2-0.3	2055
0.3-0.4	2647
0.4-0.5	1971
0.5-0.6	922
0.6-0.7	317
0.7-0.8	56
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
0.8086	Intermediate Similarity	NPD2532	Approved
0.8086	Intermediate Similarity	NPD2533	Approved
0.8086	Intermediate Similarity	NPD2534	Approved
0.7937	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6232	Discontinued
0.7673	Intermediate Similarity	NPD230	Phase 1
0.767	Intermediate Similarity	NPD7473	Discontinued
0.7637	Intermediate Similarity	NPD8434	Phase 2
0.7633	Intermediate Similarity	NPD4380	Phase 2
0.7633	Intermediate Similarity	NPD6599	Discontinued
0.7602	Intermediate Similarity	NPD7819	Suspended
0.7602	Intermediate Similarity	NPD5761	Phase 2
0.7602	Intermediate Similarity	NPD5760	Phase 2
0.7572	Intermediate Similarity	NPD7075	Discontinued
0.7556	Intermediate Similarity	NPD6559	Discontinued
0.7541	Intermediate Similarity	NPD8150	Discontinued
0.7515	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD5711	Approved
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5844	Phase 1
0.7455	Intermediate Similarity	NPD2800	Approved
0.7442	Intermediate Similarity	NPD1934	Approved
0.7442	Intermediate Similarity	NPD6801	Discontinued
0.743	Intermediate Similarity	NPD3818	Discontinued
0.7425	Intermediate Similarity	NPD7236	Approved
0.7423	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3882	Suspended
0.7396	Intermediate Similarity	NPD6273	Approved
0.7381	Intermediate Similarity	NPD6799	Approved
0.738	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6959	Discontinued
0.7341	Intermediate Similarity	NPD37	Approved
0.733	Intermediate Similarity	NPD6234	Discontinued
0.7314	Intermediate Similarity	NPD4966	Approved
0.7314	Intermediate Similarity	NPD4965	Approved
0.7314	Intermediate Similarity	NPD4967	Phase 2
0.7299	Intermediate Similarity	NPD2801	Approved
0.7288	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD2935	Discontinued
0.7273	Intermediate Similarity	NPD3749	Approved
0.7268	Intermediate Similarity	NPD7685	Pre-registration
0.7268	Intermediate Similarity	NPD6765	Approved
0.7268	Intermediate Similarity	NPD6764	Approved
0.7257	Intermediate Similarity	NPD5402	Approved
0.7257	Intermediate Similarity	NPD3817	Phase 2
0.7251	Intermediate Similarity	NPD920	Approved
0.7247	Intermediate Similarity	NPD7199	Phase 2
0.7238	Intermediate Similarity	NPD7799	Discontinued
0.7235	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6166	Phase 2
0.7222	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6663	Approved
0.7212	Intermediate Similarity	NPD1510	Phase 2
0.7212	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7239	Suspended
0.7204	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3750	Approved
0.72	Intermediate Similarity	NPD1465	Phase 2
0.7195	Intermediate Similarity	NPD6651	Approved
0.7195	Intermediate Similarity	NPD1607	Approved
0.7188	Intermediate Similarity	NPD5736	Approved
0.7186	Intermediate Similarity	NPD1549	Phase 2
0.7184	Intermediate Similarity	NPD7411	Suspended
0.7178	Intermediate Similarity	NPD943	Approved
0.7178	Intermediate Similarity	NPD1240	Approved
0.7176	Intermediate Similarity	NPD7390	Discontinued
0.716	Intermediate Similarity	NPD3764	Approved
0.716	Intermediate Similarity	NPD6190	Approved
0.7159	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7074	Phase 3
0.7143	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD919	Approved
0.7135	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5763	Approved
0.7126	Intermediate Similarity	NPD5762	Approved
0.7126	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7768	Phase 2
0.7112	Intermediate Similarity	NPD6784	Approved
0.7112	Intermediate Similarity	NPD6785	Approved
0.7104	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7054	Approved
0.7097	Intermediate Similarity	NPD8312	Approved
0.7097	Intermediate Similarity	NPD8313	Approved
0.709	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1511	Approved
0.7072	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3226	Approved
0.7066	Intermediate Similarity	NPD5406	Approved
0.7066	Intermediate Similarity	NPD6100	Approved
0.7066	Intermediate Similarity	NPD5404	Approved
0.7066	Intermediate Similarity	NPD5405	Approved
0.7066	Intermediate Similarity	NPD5408	Approved
0.7066	Intermediate Similarity	NPD6099	Approved
0.7066	Intermediate Similarity	NPD2796	Approved
0.7065	Intermediate Similarity	NPD7472	Approved
0.7056	Intermediate Similarity	NPD8320	Phase 1
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7056	Intermediate Similarity	NPD8319	Approved
0.7052	Intermediate Similarity	NPD5403	Approved
0.7035	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6534	Approved
0.7031	Intermediate Similarity	NPD6535	Approved
0.7027	Intermediate Similarity	NPD6797	Phase 2
0.7019	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD8166	Discontinued
0.7	Intermediate Similarity	NPD8151	Discontinued
0.6994	Remote Similarity	NPD1512	Approved
0.6989	Remote Similarity	NPD7251	Discontinued
0.6987	Remote Similarity	NPD9545	Approved
0.6981	Remote Similarity	NPD9269	Phase 2
0.6961	Remote Similarity	NPD1247	Approved
0.6957	Remote Similarity	NPD3094	Phase 2
0.6957	Remote Similarity	NPD3751	Discontinued
0.6952	Remote Similarity	NPD7808	Phase 3
0.6941	Remote Similarity	NPD1243	Approved
0.6939	Remote Similarity	NPD6776	Approved
0.6939	Remote Similarity	NPD6782	Approved
0.6939	Remote Similarity	NPD6780	Approved
0.6939	Remote Similarity	NPD6778	Approved
0.6939	Remote Similarity	NPD6781	Approved
0.6939	Remote Similarity	NPD6777	Approved
0.6939	Remote Similarity	NPD6779	Approved
0.6936	Remote Similarity	NPD5401	Approved
0.6927	Remote Similarity	NPD7057	Phase 3
0.6927	Remote Similarity	NPD7058	Phase 2
0.6923	Remote Similarity	NPD6005	Phase 3
0.6923	Remote Similarity	NPD6002	Phase 3
0.6923	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7699	Phase 2
0.6923	Remote Similarity	NPD2346	Discontinued
0.6923	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7700	Phase 2
0.6923	Remote Similarity	NPD6004	Phase 3
0.6919	Remote Similarity	NPD7497	Discontinued
0.6914	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2799	Discontinued
0.6905	Remote Similarity	NPD3748	Approved
0.6898	Remote Similarity	NPD8368	Discontinued
0.6878	Remote Similarity	NPD8407	Phase 2
0.6875	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7458	Discontinued
0.6867	Remote Similarity	NPD4140	Approved
0.686	Remote Similarity	NPD4665	Approved
0.6859	Remote Similarity	NPD9493	Approved
0.6852	Remote Similarity	NPD1470	Approved
0.6848	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5953	Discontinued
0.6842	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD9268	Approved
0.6831	Remote Similarity	NPD7229	Phase 3
0.6828	Remote Similarity	NPD7286	Phase 2
0.6826	Remote Similarity	NPD447	Suspended
0.6813	Remote Similarity	NPD3092	Approved
0.681	Remote Similarity	NPD5647	Approved
0.6809	Remote Similarity	NPD7240	Approved
0.6805	Remote Similarity	NPD7033	Discontinued
0.6802	Remote Similarity	NPD7003	Approved
0.6798	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7874	Approved
0.6792	Remote Similarity	NPD2932	Approved
0.6786	Remote Similarity	NPD6653	Approved
0.6778	Remote Similarity	NPD5353	Approved
0.6766	Remote Similarity	NPD3620	Phase 2
0.6766	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7783	Phase 2
0.6765	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7697	Approved
0.675	Remote Similarity	NPD7696	Phase 3
0.675	Remote Similarity	NPD7698	Approved
0.6748	Remote Similarity	NPD7930	Approved
0.6742	Remote Similarity	NPD7028	Phase 2
0.6739	Remote Similarity	NPD3787	Discontinued
0.6736	Remote Similarity	NPD8360	Approved
0.6736	Remote Similarity	NPD8361	Approved
0.6726	Remote Similarity	NPD6355	Discontinued
0.6724	Remote Similarity	NPD3300	Phase 2
0.6718	Remote Similarity	NPD6212	Phase 3
0.6718	Remote Similarity	NPD6213	Phase 3
0.6718	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7871	Phase 2
0.6716	Remote Similarity	NPD7870	Phase 2

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