NPASS Compound

Structure

NPC126882 OpenBabel07101719242D 24 26 0 0 1 0 0 0 0 0999 V2000 -0.9749 1.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 -4.0489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 -3.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -4.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1656 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 -3.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9478 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2157 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9478 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -1.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1656 -1.5245 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7317 -0.6235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2157 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 -4.9499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8138 -3.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -0.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5637 0.0000 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 -3.7289 -0.6982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 1 0 0 0 0 2 4 2 0 0 0 0 3 5 1 0 0 0 0 4 12 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 1 1 1 0 0 0 10 23 1 0 0 0 0 11 17 1 0 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 15 5 1 1 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 6 1 6 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.13
Volume:	331.137
LogP:	3.061
LogD:	1.56
LogS:	-2.306
# Rotatable Bonds:	0
TPSA:	96.36
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	4.469
Fsp3:	0.444
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:	-4.817
MDCK Permeability:	1.1616132724157069e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.143
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.242
Plasma Protein Binding (PPB):	86.11837005615234%
Volume Distribution (VD):	1.302
Pgp-substrate:	6.7229509353637695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.541
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.219
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.458
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.638
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.616
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	14.682
Half-life (T1/2):	0.9

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.404
Rat Oral Acute Toxicity:	0.37
Maximum Recommended Daily Dose:	0.783
Skin Sensitization:	0.814
Carcinogencity:	0.848
Eye Corrosion:	0.005
Eye Irritation:	0.412
Respiratory Toxicity:	0.327

Download Data

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

Natural Product: NPC126882

Natural Product ID:	NPC126882
*Common Name:**	Monocillin Iii
IUPAC Name:	n.a.
Synonyms:	Monocillin III
Standard InCHIKey:	XFALPAMSDFFXGY-XLFSOCHTSA-N
Standard InCHI:	InChI=1S/C18H20O6/c1-10-6-16-15(24-16)5-3-2-4-12(19)7-11-8-13(20)9-14(21)17(11)18(22)23-10/h2,4,8-10,15-16,20-21H,3,5-7H2,1H3/b4-2+/t10-,15-,16-/m1/s1
SMILES:	C[C@@H]1C[C@@H]2[C@@H](CC/C=C/C(=O)Cc3cc(cc(c3C(=O)O1)O)O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL404204
PubChem CID:	23305941
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid 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
NPO27821.1	Pochonia chlamydosporia	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12828470]
NPO11145	Chaetomium chiversii	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18052326]
NPO32692	paraphaeosphaeria quadriseptata	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18052326]
NPO11145	Chaetomium chiversii	Species	Chaetomiaceae	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	10
Others	2

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	400.0	nM	PMID[508882]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	300.0	nM	PMID[508882]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	500.0	nM	PMID[508882]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3400.0	nM	PMID[508885]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2100.0	nM	PMID[508885]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[508885]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	400.0	nM	PMID[508883]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Selectivity Index	=	7.5	n.a.	PMID[508883]
NPT2	Others	Unspecified		IC50	=	9430.0	nM	PMID[508884]
NPT27	Others	Unspecified		TC50	=	28.87	uM	PMID[508884]
NPT25805	ORGANISM	Phytophthora litchii	Phytophthora litchii	IC50	=	12000.0	nM	PMID[508885]
NPT2781	Organism	Fusarium moniliforme	Gibberella moniliformis	IC50	>	100000.0	nM	PMID[508885]

☑ 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 NPC126882 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	339
0.1-0.2	1487
0.2-0.3	3643
0.3-0.4	8388
0.4-0.5	10154
0.5-0.6	4302
0.6-0.7	6983
0.7-0.8	6517
0.8-0.85	709
0.85-0.9	139
0.9-0.95	31
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478203
1.0	High Similarity	NPC210966
0.9928	High Similarity	NPC257558
0.9781	High Similarity	NPC472035
0.9781	High Similarity	NPC478201
0.9638	High Similarity	NPC478217
0.9638	High Similarity	NPC313123
0.9562	High Similarity	NPC478200
0.9562	High Similarity	NPC177307
0.9562	High Similarity	NPC9121
0.9562	High Similarity	NPC33144
0.9507	High Similarity	NPC472036
0.9504	High Similarity	NPC472034
0.95	High Similarity	NPC478202
0.9437	High Similarity	NPC472033
0.942	High Similarity	NPC191835
0.942	High Similarity	NPC472403
0.9366	High Similarity	NPC83272
0.9362	High Similarity	NPC354984
0.9348	High Similarity	NPC65837
0.9348	High Similarity	NPC474771
0.9348	High Similarity	NPC149372
0.9348	High Similarity	NPC70380
0.9348	High Similarity	NPC474849
0.9348	High Similarity	NPC178467
0.931	High Similarity	NPC56204
0.9301	High Similarity	NPC107625
0.9286	High Similarity	NPC158472
0.9281	High Similarity	NPC212693
0.9281	High Similarity	NPC94248
0.9281	High Similarity	NPC475974
0.922	High Similarity	NPC244923
0.922	High Similarity	NPC158634
0.9214	High Similarity	NPC52358
0.9214	High Similarity	NPC92655
0.9209	High Similarity	NPC71256
0.9197	High Similarity	NPC153783
0.9197	High Similarity	NPC43627
0.9155	High Similarity	NPC474385
0.9143	High Similarity	NPC472602
0.9137	High Similarity	NPC235115
0.913	High Similarity	NPC474097
0.9091	High Similarity	NPC51106
0.9091	High Similarity	NPC472006
0.9085	High Similarity	NPC1704
0.9085	High Similarity	NPC475730
0.9085	High Similarity	NPC472603
0.9085	High Similarity	NPC67650
0.9085	High Similarity	NPC53649
0.9078	High Similarity	NPC268052
0.9078	High Similarity	NPC32360
0.9078	High Similarity	NPC474655
0.9078	High Similarity	NPC139634
0.9078	High Similarity	NPC105456
0.906	High Similarity	NPC99381
0.9051	High Similarity	NPC219892
0.9051	High Similarity	NPC189823
0.9048	High Similarity	NPC469619
0.9048	High Similarity	NPC469670
0.9041	High Similarity	NPC240622
0.9041	High Similarity	NPC471642
0.9041	High Similarity	NPC240253
0.9041	High Similarity	NPC471641
0.9041	High Similarity	NPC215711
0.9041	High Similarity	NPC73411
0.9028	High Similarity	NPC280404
0.9028	High Similarity	NPC210425
0.9028	High Similarity	NPC277426
0.9028	High Similarity	NPC151607
0.9028	High Similarity	NPC86373
0.9028	High Similarity	NPC42540
0.9014	High Similarity	NPC472600
0.9014	High Similarity	NPC472601
0.8973	High Similarity	NPC210320
0.8966	High Similarity	NPC312789
0.8958	High Similarity	NPC159721
0.8951	High Similarity	NPC472605
0.8951	High Similarity	NPC472604
0.8936	High Similarity	NPC194579
0.8936	High Similarity	NPC135837
0.8929	High Similarity	NPC27407
0.8912	High Similarity	NPC153417
0.8881	High Similarity	NPC155205
0.8873	High Similarity	NPC221104
0.8857	High Similarity	NPC175943
0.8851	High Similarity	NPC84142
0.8839	High Similarity	NPC173352
0.8839	High Similarity	NPC58653
0.8832	High Similarity	NPC41263
0.8828	High Similarity	NPC471731
0.8828	High Similarity	NPC472610
0.8828	High Similarity	NPC469542
0.8819	High Similarity	NPC90411
0.8819	High Similarity	NPC37530
0.8819	High Similarity	NPC470842
0.8811	High Similarity	NPC275356
0.8811	High Similarity	NPC88269
0.8808	High Similarity	NPC472890
0.88	High Similarity	NPC184284
0.88	High Similarity	NPC115249
0.88	High Similarity	NPC76041
0.8794	High Similarity	NPC180905
0.8794	High Similarity	NPC182496
0.8794	High Similarity	NPC142027
0.8792	High Similarity	NPC472891
0.8792	High Similarity	NPC164762
0.8782	High Similarity	NPC28669
0.8777	High Similarity	NPC470831
0.8777	High Similarity	NPC214702
0.8776	High Similarity	NPC473023
0.8759	High Similarity	NPC471733
0.8759	High Similarity	NPC471640
0.8759	High Similarity	NPC471644
0.8759	High Similarity	NPC250755
0.8759	High Similarity	NPC469579
0.875	High Similarity	NPC99441
0.8742	High Similarity	NPC137301
0.8733	High Similarity	NPC91809
0.8733	High Similarity	NPC200773
0.8733	High Similarity	NPC70016
0.8733	High Similarity	NPC215921
0.8733	High Similarity	NPC240768
0.8732	High Similarity	NPC291454
0.8732	High Similarity	NPC158481
0.8725	High Similarity	NPC476684
0.8716	High Similarity	NPC14098
0.8714	High Similarity	NPC476389
0.8707	High Similarity	NPC473692
0.8705	High Similarity	NPC247477
0.8705	High Similarity	NPC17840
0.8699	High Similarity	NPC471639
0.8699	High Similarity	NPC471643
0.8693	High Similarity	NPC478225
0.8693	High Similarity	NPC472889
0.8686	High Similarity	NPC95309
0.8684	High Similarity	NPC478230
0.8684	High Similarity	NPC170189
0.8684	High Similarity	NPC208173
0.8684	High Similarity	NPC69043
0.8684	High Similarity	NPC478221
0.8681	High Similarity	NPC471819
0.8681	High Similarity	NPC247409
0.8675	High Similarity	NPC478224
0.8671	High Similarity	NPC261292
0.8671	High Similarity	NPC301915
0.8667	High Similarity	NPC60413
0.8667	High Similarity	NPC295036
0.8658	High Similarity	NPC2569
0.8658	High Similarity	NPC221352
0.8658	High Similarity	NPC172329
0.8649	High Similarity	NPC202112
0.8649	High Similarity	NPC51513
0.8645	High Similarity	NPC298401
0.8639	High Similarity	NPC95123
0.8639	High Similarity	NPC184702
0.8639	High Similarity	NPC66404
0.863	High Similarity	NPC49108
0.863	High Similarity	NPC96692
0.8618	High Similarity	NPC478231
0.8613	High Similarity	NPC262671
0.8613	High Similarity	NPC201728
0.8611	High Similarity	NPC197666
0.8611	High Similarity	NPC126739
0.8601	High Similarity	NPC50455
0.86	High Similarity	NPC6923
0.86	High Similarity	NPC270160
0.86	High Similarity	NPC237440
0.8591	High Similarity	NPC471734
0.8591	High Similarity	NPC166583
0.8591	High Similarity	NPC81835
0.8591	High Similarity	NPC476463
0.8591	High Similarity	NPC53362
0.8591	High Similarity	NPC137296
0.859	High Similarity	NPC474096
0.859	High Similarity	NPC473696
0.8581	High Similarity	NPC134621
0.8571	High Similarity	NPC263483
0.8562	High Similarity	NPC16455
0.8562	High Similarity	NPC79998
0.8562	High Similarity	NPC307990
0.8562	High Similarity	NPC317585
0.8562	High Similarity	NPC130485
0.8552	High Similarity	NPC162939
0.8552	High Similarity	NPC57380
0.8543	High Similarity	NPC470107
0.8542	High Similarity	NPC473391
0.8542	High Similarity	NPC472364
0.8542	High Similarity	NPC476333
0.8542	High Similarity	NPC472367
0.8523	High Similarity	NPC470570
0.8523	High Similarity	NPC471735
0.8523	High Similarity	NPC225173
0.8523	High Similarity	NPC163846
0.8523	High Similarity	NPC237208
0.8521	High Similarity	NPC48036
0.8514	High Similarity	NPC470932
0.8511	High Similarity	NPC7012
0.8511	High Similarity	NPC198249
0.8506	High Similarity	NPC472050
0.8503	High Similarity	NPC82913

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 NPC126882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	954
0.2-0.3	1829
0.3-0.4	2643
0.4-0.5	1876
0.5-0.6	1103
0.6-0.7	330
0.7-0.8	116
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8681	High Similarity	NPD970	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD2534	Approved
0.8456	Intermediate Similarity	NPD2532	Approved
0.8456	Intermediate Similarity	NPD2533	Approved
0.8377	Intermediate Similarity	NPD7819	Suspended
0.8264	Intermediate Similarity	NPD230	Phase 1
0.8129	Intermediate Similarity	NPD7411	Suspended
0.8095	Intermediate Similarity	NPD1510	Phase 2
0.8069	Intermediate Similarity	NPD1240	Approved
0.8054	Intermediate Similarity	NPD1549	Phase 2
0.8029	Intermediate Similarity	NPD9545	Approved
0.8026	Intermediate Similarity	NPD6799	Approved
0.8025	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7075	Discontinued
0.7975	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1934	Approved
0.7959	Intermediate Similarity	NPD1607	Approved
0.7949	Intermediate Similarity	NPD4380	Phase 2
0.7947	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD3750	Approved
0.7919	Intermediate Similarity	NPD2796	Approved
0.7919	Intermediate Similarity	NPD2935	Discontinued
0.7914	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6232	Discontinued
0.7883	Intermediate Similarity	NPD9493	Approved
0.7866	Intermediate Similarity	NPD7473	Discontinued
0.7862	Intermediate Similarity	NPD3817	Phase 2
0.7852	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6959	Discontinued
0.7834	Intermediate Similarity	NPD6599	Discontinued
0.7812	Intermediate Similarity	NPD3882	Suspended
0.78	Intermediate Similarity	NPD1551	Phase 2
0.7799	Intermediate Similarity	NPD2801	Approved
0.7792	Intermediate Similarity	NPD1511	Approved
0.7771	Intermediate Similarity	NPD3226	Approved
0.7764	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3749	Approved
0.7763	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6801	Discontinued
0.7703	Intermediate Similarity	NPD943	Approved
0.7702	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7768	Phase 2
0.7692	Intermediate Similarity	NPD1512	Approved
0.7687	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD5711	Approved
0.7683	Intermediate Similarity	NPD5710	Approved
0.7677	Intermediate Similarity	NPD7390	Discontinued
0.7665	Intermediate Similarity	NPD5844	Phase 1
0.764	Intermediate Similarity	NPD5402	Approved
0.7628	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3748	Approved
0.7605	Intermediate Similarity	NPD3818	Discontinued
0.759	Intermediate Similarity	NPD6166	Phase 2
0.759	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3764	Approved
0.7566	Intermediate Similarity	NPD5404	Approved
0.7566	Intermediate Similarity	NPD5408	Approved
0.7566	Intermediate Similarity	NPD5405	Approved
0.7566	Intermediate Similarity	NPD5406	Approved
0.756	Intermediate Similarity	NPD7054	Approved
0.7532	Intermediate Similarity	NPD5403	Approved
0.7532	Intermediate Similarity	NPD920	Approved
0.7532	Intermediate Similarity	NPD2800	Approved
0.7515	Intermediate Similarity	NPD7472	Approved
0.7515	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD9269	Phase 2
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.7465	Intermediate Similarity	NPD9268	Approved
0.7455	Intermediate Similarity	NPD5494	Approved
0.7427	Intermediate Similarity	NPD7251	Discontinued
0.7427	Intermediate Similarity	NPD6559	Discontinued
0.7419	Intermediate Similarity	NPD1243	Approved
0.7417	Intermediate Similarity	NPD447	Suspended
0.7405	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5401	Approved
0.7403	Intermediate Similarity	NPD2346	Discontinued
0.7389	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2799	Discontinued
0.7384	Intermediate Similarity	NPD7808	Phase 3
0.7376	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6651	Approved
0.7368	Intermediate Similarity	NPD5953	Discontinued
0.7362	Intermediate Similarity	NPD1465	Phase 2
0.7353	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7286	Phase 2
0.7347	Intermediate Similarity	NPD1470	Approved
0.7347	Intermediate Similarity	NPD1203	Approved
0.7345	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD411	Approved
0.7325	Intermediate Similarity	NPD6190	Approved
0.7315	Intermediate Similarity	NPD6832	Phase 2
0.7314	Intermediate Similarity	NPD8150	Discontinued
0.731	Intermediate Similarity	NPD1201	Approved
0.7303	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD9266	Approved
0.7299	Intermediate Similarity	NPD74	Approved
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.7289	Intermediate Similarity	NPD919	Approved
0.7267	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1164	Approved
0.7226	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD9264	Approved
0.7226	Intermediate Similarity	NPD9263	Approved
0.7226	Intermediate Similarity	NPD6100	Approved
0.7226	Intermediate Similarity	NPD6099	Approved
0.7226	Intermediate Similarity	NPD9267	Approved
0.7219	Intermediate Similarity	NPD3268	Approved
0.7205	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1247	Approved
0.7197	Intermediate Similarity	NPD2654	Approved
0.7192	Intermediate Similarity	NPD422	Phase 1
0.7181	Intermediate Similarity	NPD1019	Discontinued
0.7179	Intermediate Similarity	NPD2344	Approved
0.716	Intermediate Similarity	NPD3787	Discontinued
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2313	Discontinued
0.7091	Intermediate Similarity	NPD37	Approved
0.7083	Intermediate Similarity	NPD6234	Discontinued
0.7081	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2798	Approved
0.7066	Intermediate Similarity	NPD4965	Approved
0.7066	Intermediate Similarity	NPD4966	Approved
0.7066	Intermediate Similarity	NPD4967	Phase 2
0.7059	Intermediate Similarity	NPD7229	Phase 3
0.7055	Intermediate Similarity	NPD4626	Approved
0.7051	Intermediate Similarity	NPD7033	Discontinued
0.705	Intermediate Similarity	NPD2182	Approved
0.7045	Intermediate Similarity	NPD8312	Approved
0.7045	Intermediate Similarity	NPD8313	Approved
0.7027	Intermediate Similarity	NPD1608	Approved
0.7018	Intermediate Similarity	NPD3926	Phase 2
0.7006	Intermediate Similarity	NPD5353	Approved
0.7006	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD7199	Phase 2
0.7	Intermediate Similarity	NPD2309	Approved
0.6993	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD9281	Approved
0.6989	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5691	Approved
0.6986	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6535	Approved
0.6978	Remote Similarity	NPD6534	Approved
0.6973	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7435	Discontinued
0.695	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD520	Approved
0.6947	Remote Similarity	NPD8151	Discontinued
0.6939	Remote Similarity	NPD1778	Approved
0.6937	Remote Similarity	NPD7003	Approved
0.6937	Remote Similarity	NPD8166	Discontinued
0.6934	Remote Similarity	NPD9261	Approved
0.6933	Remote Similarity	NPD6273	Approved
0.6932	Remote Similarity	NPD7685	Pre-registration
0.6931	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8434	Phase 2
0.6919	Remote Similarity	NPD5242	Approved
0.6919	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD8320	Phase 1
0.6915	Remote Similarity	NPD8319	Approved
0.6914	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7458	Discontinued
0.6908	Remote Similarity	NPD9494	Approved
0.6897	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3496	Discontinued
0.6887	Remote Similarity	NPD3266	Approved
0.6887	Remote Similarity	NPD2797	Approved
0.6887	Remote Similarity	NPD3267	Approved
0.6882	Remote Similarity	NPD6780	Approved
0.6882	Remote Similarity	NPD6782	Approved
0.6882	Remote Similarity	NPD6776	Approved
0.6882	Remote Similarity	NPD6781	Approved
0.6882	Remote Similarity	NPD6778	Approved
0.6882	Remote Similarity	NPD6777	Approved
0.6882	Remote Similarity	NPD6779	Approved
0.6872	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7700	Phase 2
0.6865	Remote Similarity	NPD7699	Phase 2
0.6863	Remote Similarity	NPD4908	Phase 1
0.686	Remote Similarity	NPD6808	Phase 2
0.6859	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5124	Phase 1
0.6855	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6005	Phase 3
0.6855	Remote Similarity	NPD7266	Discontinued
0.6855	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1471	Phase 3
0.6855	Remote Similarity	NPD6004	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