NPASS Compound

Structure

NPC44378 OpenBabel07101718242D 26 28 0 0 1 0 0 0 0 0999 V2000 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 12 1 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 13 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 7 1 6 0 0 0 9 26 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 18 1 1 0 0 0 12 26 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 22 2 0 0 0 0 16 18 1 0 0 0 0 16 23 2 0 0 0 0 17 18 1 6 0 0 0 17 24 1 0 0 0 0 18 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.12
Volume:	348.718
LogP:	1.869
LogD:	0.609
LogS:	-2.51
# Rotatable Bonds:	4
TPSA:	141.36
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	4.304
Fsp3:	0.5
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:	-5.821
MDCK Permeability:	1.04605869637453e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.581
Human Intestinal Absorption (HIA):	0.727
20% Bioavailability (F20%):	0.929
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	85.31501007080078%
Volume Distribution (VD):	0.364
Pgp-substrate:	15.80972671508789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.596
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	2.727
Half-life (T1/2):	0.56

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.881
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.548
Carcinogencity:	0.293
Eye Corrosion:	0.003
Eye Irritation:	0.124
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC44378

Natural Product ID:	NPC44378
*Common Name:**	Frenolicin D
IUPAC Name:	2-[(1R,3S,4aS,10aR)-4a,9,10a-trihydroxy-5,10-dioxo-1-propyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid
Synonyms:
Standard InCHIKey:	XDYYASNFOIEXFT-KSVPUCKHSA-N
Standard InCHI:	InChI=1S/C18H20O8/c1-2-4-12-18(25)16(23)14-10(5-3-6-11(14)19)15(22)17(18,24)8-9(26-12)7-13(20)21/h3,5-6,9,12,19,24-25H,2,4,7-8H2,1H3,(H,20,21)/t9-,12-,17-,18+/m1/s1
SMILES:	CCC[C@@H]1[C@@]2(C(=O)c3c(cccc3O)C(=O)[C@@]2(C[C@@H](CC(=O)O)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409145
PubChem CID:	72191965
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones [CHEMONTID:0001646] Naphthopyranone glycosides

*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
NPO33097	Streptomyces sp. RM-4-15	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23944931]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	80000.0	nM	PMID[570793]

☑ 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 NPC44378 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	329
0.1-0.2	1265
0.2-0.3	2709
0.3-0.4	6208
0.4-0.5	10419
0.5-0.6	6899
0.6-0.7	6323
0.7-0.8	7925
0.8-0.85	535
0.85-0.9	79
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC280753
0.979	High Similarity	NPC94781
0.9586	High Similarity	NPC120171
0.9456	High Similarity	NPC205918
0.8993	High Similarity	NPC470479
0.8986	High Similarity	NPC285122
0.898	High Similarity	NPC103910
0.8947	High Similarity	NPC312482
0.8924	High Similarity	NPC471295
0.8917	High Similarity	NPC329647
0.8917	High Similarity	NPC470735
0.8897	High Similarity	NPC114620
0.8897	High Similarity	NPC103337
0.8889	High Similarity	NPC314257
0.8889	High Similarity	NPC3449
0.8859	High Similarity	NPC136878
0.8851	High Similarity	NPC29932
0.8839	High Similarity	NPC314795
0.8831	High Similarity	NPC478027
0.8824	High Similarity	NPC137301
0.8808	High Similarity	NPC474310
0.8792	High Similarity	NPC170055
0.8784	High Similarity	NPC21873
0.8776	High Similarity	NPC257003
0.8774	High Similarity	NPC206641
0.8774	High Similarity	NPC29552
0.8774	High Similarity	NPC472889
0.8774	High Similarity	NPC208651
0.8767	High Similarity	NPC295339
0.8766	High Similarity	NPC472890
0.8758	High Similarity	NPC115249
0.8725	High Similarity	NPC48130
0.8725	High Similarity	NPC300684
0.8725	High Similarity	NPC218866
0.8725	High Similarity	NPC84568
0.8716	High Similarity	NPC474300
0.8701	High Similarity	NPC209393
0.8701	High Similarity	NPC478231
0.8701	High Similarity	NPC474622
0.8701	High Similarity	NPC474621
0.8701	High Similarity	NPC470408
0.8701	High Similarity	NPC205172
0.8701	High Similarity	NPC182921
0.8701	High Similarity	NPC474824
0.8701	High Similarity	NPC218870
0.8699	High Similarity	NPC61590
0.8662	High Similarity	NPC472055
0.8658	High Similarity	NPC476473
0.8654	High Similarity	NPC478225
0.8645	High Similarity	NPC192219
0.8645	High Similarity	NPC82190
0.8645	High Similarity	NPC478221
0.8645	High Similarity	NPC69043
0.8645	High Similarity	NPC174599
0.8645	High Similarity	NPC478230
0.8645	High Similarity	NPC317585
0.8642	High Similarity	NPC294501
0.8639	High Similarity	NPC306835
0.8639	High Similarity	NPC476477
0.8639	High Similarity	NPC299405
0.8639	High Similarity	NPC111422
0.8639	High Similarity	NPC256463
0.8639	High Similarity	NPC216312
0.8639	High Similarity	NPC29771
0.8639	High Similarity	NPC471602
0.8636	High Similarity	NPC478224
0.8636	High Similarity	NPC76041
0.8636	High Similarity	NPC184284
0.8627	High Similarity	NPC475407
0.8627	High Similarity	NPC315520
0.8627	High Similarity	NPC56204
0.8627	High Similarity	NPC472891
0.8618	High Similarity	NPC112816
0.8609	High Similarity	NPC229264
0.8609	High Similarity	NPC120536
0.8599	High Similarity	NPC470339
0.859	High Similarity	NPC148323
0.859	High Similarity	NPC472050
0.859	High Similarity	NPC474861
0.859	High Similarity	NPC283480
0.8581	High Similarity	NPC42262
0.8581	High Similarity	NPC315578
0.8581	High Similarity	NPC220496
0.8581	High Similarity	NPC241349
0.8581	High Similarity	NPC37992
0.8581	High Similarity	NPC147542
0.8581	High Similarity	NPC32749
0.8581	High Similarity	NPC327916
0.858	High Similarity	NPC478021
0.8571	High Similarity	NPC473094
0.8571	High Similarity	NPC126739
0.8571	High Similarity	NPC173980
0.8571	High Similarity	NPC197666
0.8562	High Similarity	NPC478020
0.8562	High Similarity	NPC478022
0.8562	High Similarity	NPC472049
0.8562	High Similarity	NPC191930
0.8543	High Similarity	NPC474630
0.8542	High Similarity	NPC17843
0.8533	High Similarity	NPC143898
0.8528	High Similarity	NPC183441
0.8528	High Similarity	NPC270027
0.8528	High Similarity	NPC473113
0.8526	High Similarity	NPC266469
0.8526	High Similarity	NPC471456
0.8526	High Similarity	NPC170189
0.8526	High Similarity	NPC208173
0.8523	High Similarity	NPC471444
0.8519	High Similarity	NPC473096
0.8519	High Similarity	NPC473095
0.8516	High Similarity	NPC474534
0.8516	High Similarity	NPC474533
0.8514	High Similarity	NPC26924
0.85	High Similarity	NPC249181
0.8493	Intermediate Similarity	NPC27407
0.8491	Intermediate Similarity	NPC477627
0.8487	Intermediate Similarity	NPC63918
0.8477	Intermediate Similarity	NPC79627
0.8466	Intermediate Similarity	NPC470580
0.8462	Intermediate Similarity	NPC281703
0.8462	Intermediate Similarity	NPC125487
0.8457	Intermediate Similarity	NPC283041
0.8452	Intermediate Similarity	NPC215921
0.8452	Intermediate Similarity	NPC70016
0.8447	Intermediate Similarity	NPC478026
0.8443	Intermediate Similarity	NPC208069
0.8442	Intermediate Similarity	NPC478219
0.8438	Intermediate Similarity	NPC97637
0.8438	Intermediate Similarity	NPC187934
0.8435	Intermediate Similarity	NPC315275
0.8431	Intermediate Similarity	NPC476821
0.8431	Intermediate Similarity	NPC119767
0.8431	Intermediate Similarity	NPC81835
0.8424	Intermediate Similarity	NPC470583
0.8424	Intermediate Similarity	NPC19056
0.8421	Intermediate Similarity	NPC474309
0.8418	Intermediate Similarity	NPC246466
0.8418	Intermediate Similarity	NPC478226
0.8411	Intermediate Similarity	NPC127857
0.8411	Intermediate Similarity	NPC474692
0.8408	Intermediate Similarity	NPC478133
0.8408	Intermediate Similarity	NPC99381
0.8405	Intermediate Similarity	NPC175477
0.84	Intermediate Similarity	NPC130485
0.8397	Intermediate Similarity	NPC295646
0.8395	Intermediate Similarity	NPC20237
0.8392	Intermediate Similarity	NPC247250
0.8392	Intermediate Similarity	NPC767
0.8387	Intermediate Similarity	NPC164762
0.8378	Intermediate Similarity	NPC261292
0.8378	Intermediate Similarity	NPC301915
0.8375	Intermediate Similarity	NPC117985
0.8375	Intermediate Similarity	NPC317544
0.8375	Intermediate Similarity	NPC316457
0.8373	Intermediate Similarity	NPC176246
0.8367	Intermediate Similarity	NPC142027
0.8366	Intermediate Similarity	NPC147250
0.8366	Intermediate Similarity	NPC51513
0.8366	Intermediate Similarity	NPC473023
0.8366	Intermediate Similarity	NPC202112
0.8364	Intermediate Similarity	NPC65118
0.8356	Intermediate Similarity	NPC171968
0.8355	Intermediate Similarity	NPC274085
0.8355	Intermediate Similarity	NPC89664
0.8355	Intermediate Similarity	NPC42540
0.8355	Intermediate Similarity	NPC244691
0.8355	Intermediate Similarity	NPC471906
0.8355	Intermediate Similarity	NPC151607
0.8354	Intermediate Similarity	NPC478223
0.8344	Intermediate Similarity	NPC155686
0.8344	Intermediate Similarity	NPC308572
0.8344	Intermediate Similarity	NPC471695
0.8344	Intermediate Similarity	NPC107009
0.8343	Intermediate Similarity	NPC209865
0.8333	Intermediate Similarity	NPC262819
0.8333	Intermediate Similarity	NPC3218
0.8333	Intermediate Similarity	NPC178281
0.8333	Intermediate Similarity	NPC91809
0.8333	Intermediate Similarity	NPC227485
0.8323	Intermediate Similarity	NPC470581
0.8323	Intermediate Similarity	NPC83331
0.8323	Intermediate Similarity	NPC470582
0.8323	Intermediate Similarity	NPC84142
0.8323	Intermediate Similarity	NPC115447
0.8323	Intermediate Similarity	NPC266513
0.8322	Intermediate Similarity	NPC221104
0.8322	Intermediate Similarity	NPC9121
0.8322	Intermediate Similarity	NPC177307
0.8313	Intermediate Similarity	NPC294149
0.8313	Intermediate Similarity	NPC284495
0.8312	Intermediate Similarity	NPC112216
0.8312	Intermediate Similarity	NPC161239
0.8312	Intermediate Similarity	NPC165260
0.8312	Intermediate Similarity	NPC198455
0.8312	Intermediate Similarity	NPC476463
0.8312	Intermediate Similarity	NPC5568
0.8311	Intermediate Similarity	NPC291454
0.8303	Intermediate Similarity	NPC472620
0.8301	Intermediate Similarity	NPC83272
0.8301	Intermediate Similarity	NPC475923

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 NPC44378 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	811
0.2-0.3	1576
0.3-0.4	2650
0.4-0.5	2129
0.5-0.6	1131
0.6-0.7	429
0.7-0.8	148
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD8150	Discontinued
0.8246	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7075	Discontinued
0.8098	Intermediate Similarity	NPD6232	Discontinued
0.8061	Intermediate Similarity	NPD7473	Discontinued
0.8056	Intermediate Similarity	NPD1470	Approved
0.8	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7819	Suspended
0.7987	Intermediate Similarity	NPD6190	Approved
0.7975	Intermediate Similarity	NPD3226	Approved
0.7947	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD4380	Phase 2
0.7888	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6534	Approved
0.7841	Intermediate Similarity	NPD6535	Approved
0.784	Intermediate Similarity	NPD3817	Phase 2
0.7829	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6801	Discontinued
0.7826	Intermediate Similarity	NPD1934	Approved
0.7821	Intermediate Similarity	NPD3300	Phase 2
0.7803	Intermediate Similarity	NPD8434	Phase 2
0.7791	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD7435	Discontinued
0.7784	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6166	Phase 2
0.7778	Intermediate Similarity	NPD5408	Approved
0.7778	Intermediate Similarity	NPD1201	Approved
0.7778	Intermediate Similarity	NPD5404	Approved
0.7778	Intermediate Similarity	NPD5406	Approved
0.7778	Intermediate Similarity	NPD5405	Approved
0.7747	Intermediate Similarity	NPD8320	Phase 1
0.7747	Intermediate Similarity	NPD8319	Approved
0.7746	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD8312	Approved
0.7733	Intermediate Similarity	NPD8313	Approved
0.773	Intermediate Similarity	NPD5402	Approved
0.7727	Intermediate Similarity	NPD2346	Discontinued
0.7722	Intermediate Similarity	NPD2534	Approved
0.7722	Intermediate Similarity	NPD6781	Approved
0.7722	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6780	Approved
0.7722	Intermediate Similarity	NPD2532	Approved
0.7722	Intermediate Similarity	NPD6779	Approved
0.7722	Intermediate Similarity	NPD6782	Approved
0.7722	Intermediate Similarity	NPD2533	Approved
0.7722	Intermediate Similarity	NPD6778	Approved
0.7722	Intermediate Similarity	NPD6776	Approved
0.7722	Intermediate Similarity	NPD6777	Approved
0.7714	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7700	Phase 2
0.7709	Intermediate Similarity	NPD7699	Phase 2
0.7702	Intermediate Similarity	NPD6599	Discontinued
0.7683	Intermediate Similarity	NPD3882	Suspended
0.7682	Intermediate Similarity	NPD943	Approved
0.7674	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6799	Approved
0.7658	Intermediate Similarity	NPD7390	Discontinued
0.7647	Intermediate Similarity	NPD5844	Phase 1
0.7636	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6959	Discontinued
0.7588	Intermediate Similarity	NPD3751	Discontinued
0.7588	Intermediate Similarity	NPD3818	Discontinued
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7564	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2801	Approved
0.7558	Intermediate Similarity	NPD6797	Phase 2
0.7558	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3764	Approved
0.7548	Intermediate Similarity	NPD2935	Discontinued
0.7546	Intermediate Similarity	NPD7411	Suspended
0.7544	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD7874	Approved
0.7516	Intermediate Similarity	NPD5403	Approved
0.7516	Intermediate Similarity	NPD230	Phase 1
0.7514	Intermediate Similarity	NPD7251	Discontinued
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD7697	Approved
0.75	Intermediate Similarity	NPD7698	Approved
0.75	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD7696	Phase 3
0.7483	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7808	Phase 3
0.7459	Intermediate Similarity	NPD7870	Phase 2
0.7459	Intermediate Similarity	NPD7871	Phase 2
0.7455	Intermediate Similarity	NPD1465	Phase 2
0.7453	Intermediate Similarity	NPD1512	Approved
0.7452	Intermediate Similarity	NPD1549	Phase 2
0.7442	Intermediate Similarity	NPD7054	Approved
0.744	Intermediate Similarity	NPD5494	Approved
0.7433	Intermediate Similarity	NPD7701	Phase 2
0.7425	Intermediate Similarity	NPD3749	Approved
0.741	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7472	Approved
0.7391	Intermediate Similarity	NPD5401	Approved
0.7389	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6212	Phase 3
0.7389	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6213	Phase 3
0.7389	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1510	Phase 2
0.7371	Intermediate Similarity	NPD4954	Approved
0.7371	Intermediate Similarity	NPD4955	Approved
0.7371	Intermediate Similarity	NPD5026	Approved
0.7371	Intermediate Similarity	NPD5034	Approved
0.7371	Intermediate Similarity	NPD5028	Approved
0.7371	Intermediate Similarity	NPD36	Approved
0.7368	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8166	Discontinued
0.7353	Intermediate Similarity	NPD3787	Discontinued
0.7329	Intermediate Similarity	NPD1511	Approved
0.7326	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7801	Approved
0.7314	Intermediate Similarity	NPD5030	Phase 2
0.7303	Intermediate Similarity	NPD5037	Approved
0.7303	Intermediate Similarity	NPD5038	Approved
0.7302	Intermediate Similarity	NPD8151	Discontinued
0.7284	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7266	Discontinued
0.7278	Intermediate Similarity	NPD6234	Discontinued
0.7261	Intermediate Similarity	NPD2799	Discontinued
0.726	Intermediate Similarity	NPD9545	Approved
0.7251	Intermediate Similarity	NPD5711	Approved
0.7251	Intermediate Similarity	NPD5710	Approved
0.725	Intermediate Similarity	NPD3750	Approved
0.725	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD5036	Approved
0.7244	Intermediate Similarity	NPD1607	Approved
0.7226	Intermediate Similarity	NPD1240	Approved
0.7226	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1164	Approved
0.7216	Intermediate Similarity	NPD8368	Discontinued
0.7216	Intermediate Similarity	NPD7685	Pre-registration
0.7215	Intermediate Similarity	NPD2796	Approved
0.7212	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2313	Discontinued
0.7186	Intermediate Similarity	NPD37	Approved
0.7179	Intermediate Similarity	NPD447	Suspended
0.7176	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD6823	Phase 2
0.7161	Intermediate Similarity	NPD6663	Approved
0.716	Intermediate Similarity	NPD7768	Phase 2
0.716	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD7236	Approved
0.716	Intermediate Similarity	NPD4967	Phase 2
0.716	Intermediate Similarity	NPD4965	Approved
0.7157	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5035	Approved
0.7133	Intermediate Similarity	NPD9269	Phase 2
0.7124	Intermediate Similarity	NPD5736	Approved
0.7123	Intermediate Similarity	NPD9493	Approved
0.7119	Intermediate Similarity	NPD5029	Approved
0.7119	Intermediate Similarity	NPD5031	Approved
0.7119	Intermediate Similarity	NPD5027	Approved
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.711	Intermediate Similarity	NPD3926	Phase 2
0.7108	Intermediate Similarity	NPD7458	Discontinued
0.7107	Intermediate Similarity	NPD1551	Phase 2
0.7095	Intermediate Similarity	NPD8407	Phase 2
0.7086	Intermediate Similarity	NPD7228	Approved
0.7086	Intermediate Similarity	NPD7799	Discontinued
0.7076	Intermediate Similarity	NPD919	Approved
0.7073	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1471	Phase 3
0.7063	Intermediate Similarity	NPD2344	Approved
0.7062	Intermediate Similarity	NPD5953	Discontinued
0.7048	Intermediate Similarity	NPD7239	Suspended
0.7047	Intermediate Similarity	NPD7783	Phase 2
0.7047	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7033	Discontinued
0.7033	Intermediate Similarity	NPD8360	Approved
0.7033	Intermediate Similarity	NPD8361	Approved
0.7012	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8285	Discontinued
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD6100	Approved
0.6988	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6798	Discontinued
0.6986	Remote Similarity	NPD2629	Approved
0.698	Remote Similarity	NPD9268	Approved
0.6968	Remote Similarity	NPD6832	Phase 2
0.6962	Remote Similarity	NPD6355	Discontinued
0.6957	Remote Similarity	NPD5763	Approved
0.6957	Remote Similarity	NPD5762	Approved
0.6948	Remote Similarity	NPD2798	Approved
0.6948	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.694	Remote Similarity	NPD8435	Approved
0.6937	Remote Similarity	NPD3748	Approved
0.6933	Remote Similarity	NPD2932	Approved
0.6933	Remote Similarity	NPD3019	Approved
0.6933	Remote Similarity	NPD7003	Approved
0.6928	Remote Similarity	NPD6273	Approved
0.6923	Remote Similarity	NPD9266	Approved
0.6923	Remote Similarity	NPD74	Approved

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