NPASS Compound

Structure

CID210320 OpenBabel06191716002D 26 27 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 -4.6798 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7317 -0.6235 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 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 3.1656 -1.5245 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 -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 1 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 -2.9478 -2.5245 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 -4.0489 0.0000 C 0 0 1 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 -1.2157 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7317 -3.4254 0.0000 C 0 0 2 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 4.1405 -2.7470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3837 -4.9499 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 3.5135 -4.0489 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 -3.8138 -3.0245 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 2 25 1 0 0 0 0 3 5 1 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 1 1 1 0 0 0 11 26 1 0 0 0 0 12 17 1 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 14 20 2 0 0 0 0 15 18 1 0 0 0 0 15 21 1 1 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 18 23 1 1 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.15
Volume:	365.78
LogP:	3.007
LogD:	2.423
LogS:	-4.063
# Rotatable Bonds:	1
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	3.843
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.776
MDCK Permeability:	6.248837598832324e-05
Pgp-inhibitor:	0.096
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.671

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.43
Plasma Protein Binding (PPB):	91.3563461303711%
Volume Distribution (VD):	0.173
Pgp-substrate:	4.263378143310547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.766
CYP1A2-substrate:	0.612
CYP2C19-inhibitor:	0.22
CYP2C19-substrate:	0.226
CYP2C9-inhibitor:	0.244
CYP2C9-substrate:	0.86
CYP2D6-inhibitor:	0.734
CYP2D6-substrate:	0.497
CYP3A4-inhibitor:	0.501
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	9.886
Half-life (T1/2):	0.611

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.192
Drug-inuced Liver Injury (DILI):	0.468
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.476
Carcinogencity:	0.03
Eye Corrosion:	0.006
Eye Irritation:	0.149
Respiratory Toxicity:	0.388

Download Data

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

Natural Product: NPC210320

Natural Product ID:	NPC210320
*Common Name:**	(2E,5S,6S,11S)-5,6,15-Trihydroxy-17-Methoxy-11-Methyl-12-Oxabicyclo[12.4.0]Octadeca-1(14),2,15,17-Tetraene-7,13-Dione
IUPAC Name:	(2E,5S,6S,11S)-5,6,15-trihydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,15,17-tetraene-7,13-dione
Synonyms:
Standard InCHIKey:	WFIUAGOQGGAREU-XZUJVHTDSA-N
Standard InCHI:	InChI=1S/C19H24O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h4,6,9-11,15,18,21-23H,3,5,7-8H2,1-2H3/b6-4+/t11-,15-,18+/m0/s1
SMILES:	C[C@H]1CCCC(=O)[C@H]([C@H](C/C=C/c2cc(cc(c2C(=O)O1)O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801951
PubChem CID:	9863860
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues [CHEMONTID:0001788] Zearalenones

*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
NPO30448	Cochliobolus lunatus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348465]

☑ 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	7
MIC	4
Potency	6

Activity Type	# Activity
Cell Line	5
Individual Protein	8
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[567748]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	25000.0	nM	PMID[567748]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	50000.0	nM	PMID[567748]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	50000.0	nM	PMID[567748]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	50000.0	nM	PMID[567748]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	1995.3	nM	PMID[567749]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[567749]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	7307.8	nM	PMID[567749]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	8199.5	nM	PMID[567749]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[567749]
NPT3442	Individual Protein	Mitogen-activated protein kinase kinase kinase 7	Homo sapiens	IC50	=	2600.0	nM	PMID[567750]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	50000.0	nM	PMID[567748]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	500.0	ug.mL-1	PMID[567748]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	500.0	ug.mL-1	PMID[567748]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	500.0	ug.mL-1	PMID[567748]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	500.0	ug.mL-1	PMID[567748]

☑ 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 NPC210320 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	331
0.1-0.2	1376
0.2-0.3	3790
0.3-0.4	8079
0.4-0.5	10183
0.5-0.6	3729
0.6-0.7	5681
0.7-0.8	7043
0.8-0.85	2067
0.85-0.9	338
0.9-0.95	72
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC215711
0.9929	High Similarity	NPC73411
0.9786	High Similarity	NPC280404
0.9786	High Similarity	NPC277426
0.9786	High Similarity	NPC86373
0.9786	High Similarity	NPC210425
0.9643	High Similarity	NPC474385
0.9524	High Similarity	NPC99381
0.95	High Similarity	NPC158472
0.9444	High Similarity	NPC472036
0.9441	High Similarity	NPC472034
0.9437	High Similarity	NPC51106
0.9437	High Similarity	NPC472006
0.9433	High Similarity	NPC475730
0.9433	High Similarity	NPC1704
0.9433	High Similarity	NPC67650
0.9384	High Similarity	NPC469619
0.9384	High Similarity	NPC469670
0.9375	High Similarity	NPC472033
0.9357	High Similarity	NPC478200
0.9357	High Similarity	NPC33144
0.932	High Similarity	NPC200773
0.932	High Similarity	NPC70016
0.932	High Similarity	NPC240768
0.932	High Similarity	NPC215921
0.9301	High Similarity	NPC469542
0.9296	High Similarity	NPC244923
0.9296	High Similarity	NPC158634
0.9286	High Similarity	NPC135837
0.9267	High Similarity	NPC246466
0.9257	High Similarity	NPC478224
0.9252	High Similarity	NPC56204
0.9252	High Similarity	NPC472891
0.9247	High Similarity	NPC471641
0.9247	High Similarity	NPC240253
0.9247	High Similarity	NPC471642
0.9247	High Similarity	NPC240622
0.9241	High Similarity	NPC107625
0.9231	High Similarity	NPC469579
0.922	High Similarity	NPC191835
0.922	High Similarity	NPC212693
0.922	High Similarity	NPC94248
0.9184	High Similarity	NPC4423
0.9184	High Similarity	NPC77325
0.9184	High Similarity	NPC270160
0.9184	High Similarity	NPC237440
0.9184	High Similarity	NPC476684
0.9178	High Similarity	NPC14098
0.9172	High Similarity	NPC83272
0.9161	High Similarity	NPC478217
0.9161	High Similarity	NPC313123
0.9161	High Similarity	NPC472035
0.9161	High Similarity	NPC478201
0.9155	High Similarity	NPC268052
0.9155	High Similarity	NPC32360
0.9155	High Similarity	NPC52358
0.9149	High Similarity	NPC70380
0.9143	High Similarity	NPC182496
0.9143	High Similarity	NPC180905
0.9133	High Similarity	NPC170189
0.9133	High Similarity	NPC478230
0.9133	High Similarity	NPC69043
0.9133	High Similarity	NPC208173
0.9128	High Similarity	NPC184284
0.9128	High Similarity	NPC76041
0.9128	High Similarity	NPC115249
0.9097	High Similarity	NPC250755
0.9067	High Similarity	NPC137301
0.9041	High Similarity	NPC257558
0.9041	High Similarity	NPC312789
0.9034	High Similarity	NPC478202
0.9028	High Similarity	NPC90411
0.9021	High Similarity	NPC139634
0.9021	High Similarity	NPC105456
0.9021	High Similarity	NPC247409
0.9014	High Similarity	NPC71256
0.9013	High Similarity	NPC472889
0.9013	High Similarity	NPC473395
0.9007	High Similarity	NPC79998
0.9007	High Similarity	NPC16082
0.9007	High Similarity	NPC82592
0.9007	High Similarity	NPC472890
0.9	High Similarity	NPC167903
0.9	High Similarity	NPC153783
0.8993	High Similarity	NPC179178
0.898	High Similarity	NPC473023
0.8973	High Similarity	NPC210966
0.8973	High Similarity	NPC95123
0.8973	High Similarity	NPC126882
0.8973	High Similarity	NPC478203
0.8973	High Similarity	NPC66404
0.8966	High Similarity	NPC96692
0.8961	High Similarity	NPC117985
0.8954	High Similarity	NPC470339
0.8951	High Similarity	NPC472602
0.8951	High Similarity	NPC177307
0.8951	High Similarity	NPC9121
0.8951	High Similarity	NPC475974
0.8947	High Similarity	NPC472050
0.8944	High Similarity	NPC235115
0.894	High Similarity	NPC478231
0.894	High Similarity	NPC281477
0.8933	High Similarity	NPC91809
0.8926	High Similarity	NPC84142
0.8917	High Similarity	NPC283041
0.8912	High Similarity	NPC134621
0.891	High Similarity	NPC191930
0.8897	High Similarity	NPC472603
0.8897	High Similarity	NPC472604
0.8897	High Similarity	NPC472605
0.8897	High Similarity	NPC53649
0.8896	High Similarity	NPC472055
0.8889	High Similarity	NPC84935
0.8889	High Similarity	NPC77679
0.8889	High Similarity	NPC478225
0.8889	High Similarity	NPC190020
0.8882	High Similarity	NPC317585
0.8882	High Similarity	NPC478221
0.8881	High Similarity	NPC474849
0.8881	High Similarity	NPC65837
0.8881	High Similarity	NPC474771
0.8881	High Similarity	NPC240147
0.8881	High Similarity	NPC178467
0.8881	High Similarity	NPC149372
0.8881	High Similarity	NPC121243
0.8867	High Similarity	NPC164762
0.8867	High Similarity	NPC96501
0.8859	High Similarity	NPC153417
0.8857	High Similarity	NPC219892
0.8857	High Similarity	NPC189823
0.8854	High Similarity	NPC20237
0.8851	High Similarity	NPC163846
0.8851	High Similarity	NPC237208
0.8851	High Similarity	NPC225173
0.8846	High Similarity	NPC249181
0.8844	High Similarity	NPC151607
0.8844	High Similarity	NPC42540
0.8836	High Similarity	NPC471640
0.8836	High Similarity	NPC82913
0.8836	High Similarity	NPC105648
0.8836	High Similarity	NPC49108
0.8836	High Similarity	NPC471644
0.8828	High Similarity	NPC472601
0.8828	High Similarity	NPC472600
0.8828	High Similarity	NPC165172
0.8824	High Similarity	NPC150227
0.8824	High Similarity	NPC227062
0.8819	High Similarity	NPC472403
0.8808	High Similarity	NPC46882
0.8808	High Similarity	NPC132990
0.8803	High Similarity	NPC175943
0.8792	High Similarity	NPC125801
0.8792	High Similarity	NPC8817
0.8792	High Similarity	NPC259632
0.8784	High Similarity	NPC29577
0.8784	High Similarity	NPC473692
0.8776	High Similarity	NPC159721
0.8776	High Similarity	NPC354984
0.8776	High Similarity	NPC471731
0.8776	High Similarity	NPC471643
0.8776	High Similarity	NPC471639
0.8767	High Similarity	NPC220106
0.8766	High Similarity	NPC478226
0.8759	High Similarity	NPC92655
0.8759	High Similarity	NPC474655
0.8758	High Similarity	NPC80534
0.8758	High Similarity	NPC473241
0.8758	High Similarity	NPC56786
0.8758	High Similarity	NPC199926
0.8758	High Similarity	NPC67396
0.875	High Similarity	NPC473391
0.875	High Similarity	NPC470397
0.875	High Similarity	NPC470338
0.875	High Similarity	NPC474843
0.875	High Similarity	NPC470340
0.875	High Similarity	NPC194579
0.875	High Similarity	NPC268992
0.875	High Similarity	NPC113608
0.875	High Similarity	NPC51824
0.875	High Similarity	NPC472367
0.875	High Similarity	NPC273483
0.875	High Similarity	NPC470337
0.875	High Similarity	NPC476333
0.875	High Similarity	NPC472364
0.8742	High Similarity	NPC295036
0.8742	High Similarity	NPC60413
0.8742	High Similarity	NPC158866
0.8742	High Similarity	NPC85131
0.8742	High Similarity	NPC475460
0.8741	High Similarity	NPC27407
0.8741	High Similarity	NPC142027
0.8733	High Similarity	NPC37139
0.8733	High Similarity	NPC172329
0.8733	High Similarity	NPC218569
0.8733	High Similarity	NPC2569
0.8732	High Similarity	NPC203817
0.8725	High Similarity	NPC138978
0.8725	High Similarity	NPC260946
0.8725	High Similarity	NPC470357
0.8718	High Similarity	NPC317544

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 NPC210320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	905
0.2-0.3	1867
0.3-0.4	2519
0.4-0.5	1840
0.5-0.6	1088
0.6-0.7	449
0.7-0.8	166
0.8-0.85	27
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9021	High Similarity	NPD970	Clinical (unspecified phase)
0.8716	High Similarity	NPD6799	Approved
0.8658	High Similarity	NPD2532	Approved
0.8658	High Similarity	NPD2533	Approved
0.8658	High Similarity	NPD2534	Approved
0.8645	High Similarity	NPD7075	Discontinued
0.8571	High Similarity	NPD7096	Clinical (unspecified phase)
0.8571	High Similarity	NPD7819	Suspended
0.8516	High Similarity	NPD3817	Phase 2
0.8506	High Similarity	NPD6801	Discontinued
0.8497	Intermediate Similarity	NPD6599	Discontinued
0.8462	Intermediate Similarity	NPD3882	Suspended
0.8452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1934	Approved
0.8377	Intermediate Similarity	NPD4380	Phase 2
0.8355	Intermediate Similarity	NPD1512	Approved
0.8323	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD5403	Approved
0.8299	Intermediate Similarity	NPD1510	Phase 2
0.828	Intermediate Similarity	NPD5402	Approved
0.8276	Intermediate Similarity	NPD1240	Approved
0.8267	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1549	Phase 2
0.8224	Intermediate Similarity	NPD1511	Approved
0.8217	Intermediate Similarity	NPD2801	Approved
0.8199	Intermediate Similarity	NPD6232	Discontinued
0.8193	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6797	Phase 2
0.8176	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD5401	Approved
0.8163	Intermediate Similarity	NPD1607	Approved
0.816	Intermediate Similarity	NPD7473	Discontinued
0.8146	Intermediate Similarity	NPD3750	Approved
0.8133	Intermediate Similarity	NPD7251	Discontinued
0.8121	Intermediate Similarity	NPD2796	Approved
0.8095	Intermediate Similarity	NPD230	Phase 1
0.8089	Intermediate Similarity	NPD7411	Suspended
0.8084	Intermediate Similarity	NPD7808	Phase 3
0.8061	Intermediate Similarity	NPD7054	Approved
0.8061	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD4628	Phase 3
0.8025	Intermediate Similarity	NPD6959	Discontinued
0.8014	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7472	Approved
0.8012	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.795	Intermediate Similarity	NPD3749	Approved
0.7919	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7768	Phase 2
0.7879	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD5711	Approved
0.7866	Intermediate Similarity	NPD5710	Approved
0.7857	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD3748	Approved
0.7811	Intermediate Similarity	NPD6559	Discontinued
0.7791	Intermediate Similarity	NPD919	Approved
0.773	Intermediate Similarity	NPD9545	Approved
0.7727	Intermediate Similarity	NPD2800	Approved
0.7727	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD9717	Approved
0.7682	Intermediate Similarity	NPD6651	Approved
0.7679	Intermediate Similarity	NPD3751	Discontinued
0.7667	Intermediate Similarity	NPD943	Approved
0.7654	Intermediate Similarity	NPD1465	Phase 2
0.7651	Intermediate Similarity	NPD3787	Discontinued
0.7636	Intermediate Similarity	NPD5494	Approved
0.7625	Intermediate Similarity	NPD3226	Approved
0.7616	Intermediate Similarity	NPD447	Suspended
0.7613	Intermediate Similarity	NPD1243	Approved
0.761	Intermediate Similarity	NPD920	Approved
0.7605	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7199	Phase 2
0.7589	Intermediate Similarity	NPD9493	Approved
0.7582	Intermediate Similarity	NPD2799	Discontinued
0.7582	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1203	Approved
0.755	Intermediate Similarity	NPD4060	Phase 1
0.7544	Intermediate Similarity	NPD5953	Discontinued
0.7533	Intermediate Similarity	NPD411	Approved
0.7532	Intermediate Similarity	NPD6100	Approved
0.7532	Intermediate Similarity	NPD6099	Approved
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7517	Intermediate Similarity	NPD6832	Phase 2
0.7516	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD2654	Approved
0.75	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7486	Intermediate Similarity	NPD7435	Discontinued
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD37	Approved
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.747	Intermediate Similarity	NPD6234	Discontinued
0.7468	Intermediate Similarity	NPD7033	Discontinued
0.7455	Intermediate Similarity	NPD4965	Approved
0.7455	Intermediate Similarity	NPD4966	Approved
0.7455	Intermediate Similarity	NPD4967	Phase 2
0.7444	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7286	Phase 2
0.7421	Intermediate Similarity	NPD7390	Discontinued
0.7418	Intermediate Similarity	NPD6782	Approved
0.7418	Intermediate Similarity	NPD6778	Approved
0.7418	Intermediate Similarity	NPD6776	Approved
0.7418	Intermediate Similarity	NPD6777	Approved
0.7418	Intermediate Similarity	NPD6780	Approved
0.7418	Intermediate Similarity	NPD6779	Approved
0.7418	Intermediate Similarity	NPD6781	Approved
0.7417	Intermediate Similarity	NPD6798	Discontinued
0.7414	Intermediate Similarity	NPD8313	Approved
0.7414	Intermediate Similarity	NPD8312	Approved
0.7407	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8434	Phase 2
0.7381	Intermediate Similarity	NPD1247	Approved
0.7379	Intermediate Similarity	NPD4626	Approved
0.7372	Intermediate Similarity	NPD2344	Approved
0.7356	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3027	Phase 3
0.7347	Intermediate Similarity	NPD9269	Phase 2
0.7347	Intermediate Similarity	NPD1608	Approved
0.7333	Intermediate Similarity	NPD9494	Approved
0.733	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5691	Approved
0.7308	Intermediate Similarity	NPD5405	Approved
0.7308	Intermediate Similarity	NPD5404	Approved
0.7308	Intermediate Similarity	NPD5406	Approved
0.7308	Intermediate Similarity	NPD5408	Approved
0.7303	Intermediate Similarity	NPD3764	Approved
0.7303	Intermediate Similarity	NPD3268	Approved
0.7287	Intermediate Similarity	NPD8151	Discontinued
0.7278	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2798	Approved
0.7267	Intermediate Similarity	NPD5647	Approved
0.7267	Intermediate Similarity	NPD7228	Approved
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7261	Intermediate Similarity	NPD5762	Approved
0.7261	Intermediate Similarity	NPD5763	Approved
0.726	Intermediate Similarity	NPD1778	Approved
0.7255	Intermediate Similarity	NPD6233	Phase 2
0.7249	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7874	Approved
0.7239	Intermediate Similarity	NPD1653	Approved
0.7235	Intermediate Similarity	NPD7229	Phase 3
0.7222	Intermediate Similarity	NPD6273	Approved
0.7208	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1613	Approved
0.7204	Intermediate Similarity	NPD7697	Approved
0.7204	Intermediate Similarity	NPD7696	Phase 3
0.7204	Intermediate Similarity	NPD7698	Approved
0.72	Intermediate Similarity	NPD2797	Approved
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.7192	Intermediate Similarity	NPD9268	Approved
0.719	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2313	Discontinued
0.7188	Intermediate Similarity	NPD2309	Approved
0.7186	Intermediate Similarity	NPD5353	Approved
0.7186	Intermediate Similarity	NPD4288	Approved
0.7171	Intermediate Similarity	NPD4908	Phase 1
0.7166	Intermediate Similarity	NPD7871	Phase 2
0.7166	Intermediate Similarity	NPD7870	Phase 2
0.7162	Intermediate Similarity	NPD1201	Approved
0.7152	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6002	Phase 3
0.7152	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6005	Phase 3
0.7152	Intermediate Similarity	NPD6004	Phase 3
0.7151	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD6535	Approved
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD4062	Phase 3
0.7143	Intermediate Similarity	NPD7701	Phase 2
0.7133	Intermediate Similarity	NPD1283	Approved
0.7125	Intermediate Similarity	NPD7003	Approved
0.7115	Intermediate Similarity	NPD6653	Approved
0.7103	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7685	Pre-registration
0.7095	Intermediate Similarity	NPD3496	Discontinued
0.7093	Intermediate Similarity	NPD5242	Approved
0.7089	Intermediate Similarity	NPD2438	Suspended

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