NPASS Compound

Structure

CID79332 OpenBabel06191715412D 22 24 0 0 0 0 0 0 0 0999 V2000 -1.7330 2.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1977 3.8745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6840 2.5362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1488 4.1835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0388 2.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9898 2.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8920 3.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8430 3.8234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 4.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 -0.4612 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 1 3 1 0 0 0 0 1 10 2 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 13 2 0 0 0 0 4 13 1 0 0 0 0 5 10 1 0 0 0 0 5 12 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 15 2 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 9 22 1 0 0 0 0 11 16 1 0 0 0 0 12 16 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	299.778
LogP:	2.909
LogD:	2.949
LogS:	-2.957
# Rotatable Bonds:	3
TPSA:	94.06
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.595
Synthetic Accessibility Score:	2.683
Fsp3:	0.059
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:	-5.219
MDCK Permeability:	7.5254347393638454e-06
Pgp-inhibitor:	0.039
Pgp-substrate:	0.17
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.091

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	98.43170166015625%
Volume Distribution (VD):	0.687
Pgp-substrate:	1.3889050483703613%

ADMET: Metabolism

CYP1A2-inhibitor:	0.834
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.244
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.73
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.858
CYP2D6-substrate:	0.759
CYP3A4-inhibitor:	0.824
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	13.566
Half-life (T1/2):	0.917

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.666
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.39
Maximum Recommended Daily Dose:	0.116
Skin Sensitization:	0.826
Carcinogencity:	0.185
Eye Corrosion:	0.003
Eye Irritation:	0.426
Respiratory Toxicity:	0.179

Download Data

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

Natural Product: NPC79332

Natural Product ID:	NPC79332
*Common Name:**	Eutypoid D
IUPAC Name:	4-(3,5-dihydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2H-furan-5-one
Synonyms:	Eutypoid D
Standard InCHIKey:	QHJKSEDOBYAWIB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O5/c18-13-3-1-10(2-4-13)5-12-9-22-17(21)16(12)11-6-14(19)8-15(20)7-11/h1-4,6-8,18-20H,5,9H2
SMILES:	Oc1ccc(cc1)CC1=C(C(=O)OC1)c1cc(O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669587
PubChem CID:	50993751
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT591	Individual Protein	Glycogen synthase kinase-3 beta	Homo sapiens	IC50	=	4080.0	nM	PMID[533168]

☑ 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 NPC79332 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	299
0.1-0.2	1346
0.2-0.3	3360
0.3-0.4	8159
0.4-0.5	10579
0.5-0.6	4178
0.6-0.7	7941
0.7-0.8	6500
0.8-0.85	318
0.85-0.9	15
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9528	High Similarity	NPC248150
0.8926	High Similarity	NPC128249
0.874	High Similarity	NPC288945
0.8676	High Similarity	NPC155205
0.8636	High Similarity	NPC476389
0.8594	High Similarity	NPC85565
0.8571	High Similarity	NPC248363
0.8571	High Similarity	NPC153783
0.8529	High Similarity	NPC33144
0.8529	High Similarity	NPC478200
0.8529	High Similarity	NPC472602
0.8519	High Similarity	NPC235115
0.8519	High Similarity	NPC156892
0.848	Intermediate Similarity	NPC311091
0.848	Intermediate Similarity	NPC471033
0.8478	Intermediate Similarity	NPC158634
0.8473	Intermediate Similarity	NPC2596
0.8456	Intermediate Similarity	NPC70380
0.8456	Intermediate Similarity	NPC261292
0.8456	Intermediate Similarity	NPC71256
0.8456	Intermediate Similarity	NPC301915
0.8444	Intermediate Similarity	NPC18646
0.8433	Intermediate Similarity	NPC1321
0.8433	Intermediate Similarity	NPC156124
0.8433	Intermediate Similarity	NPC304929
0.8421	Intermediate Similarity	NPC318799
0.8421	Intermediate Similarity	NPC219892
0.8421	Intermediate Similarity	NPC189823
0.8417	Intermediate Similarity	NPC250755
0.8409	Intermediate Similarity	NPC214246
0.8406	Intermediate Similarity	NPC158472
0.8394	Intermediate Similarity	NPC212693
0.8394	Intermediate Similarity	NPC191835
0.8394	Intermediate Similarity	NPC94248
0.8382	Intermediate Similarity	NPC223616
0.837	Intermediate Similarity	NPC175943
0.8369	Intermediate Similarity	NPC287275
0.8359	Intermediate Similarity	NPC472271
0.8357	Intermediate Similarity	NPC121573
0.8357	Intermediate Similarity	NPC478202
0.8357	Intermediate Similarity	NPC22176
0.8357	Intermediate Similarity	NPC226738
0.8357	Intermediate Similarity	NPC190587
0.8346	Intermediate Similarity	NPC247779
0.8345	Intermediate Similarity	NPC53649
0.8345	Intermediate Similarity	NPC472035
0.8345	Intermediate Similarity	NPC478217
0.8345	Intermediate Similarity	NPC478201
0.8345	Intermediate Similarity	NPC313123
0.8333	Intermediate Similarity	NPC19622
0.8333	Intermediate Similarity	NPC27633
0.8333	Intermediate Similarity	NPC52358
0.8333	Intermediate Similarity	NPC112789
0.8333	Intermediate Similarity	NPC268052
0.8333	Intermediate Similarity	NPC247409
0.8333	Intermediate Similarity	NPC32360
0.8333	Intermediate Similarity	NPC94298
0.8321	Intermediate Similarity	NPC95309
0.8321	Intermediate Similarity	NPC472364
0.8321	Intermediate Similarity	NPC473391
0.8321	Intermediate Similarity	NPC135837
0.831	Intermediate Similarity	NPC202112
0.831	Intermediate Similarity	NPC51513
0.8308	Intermediate Similarity	NPC13238
0.8298	Intermediate Similarity	NPC151607
0.8298	Intermediate Similarity	NPC42540
0.8298	Intermediate Similarity	NPC66404
0.8298	Intermediate Similarity	NPC95123
0.8293	Intermediate Similarity	NPC17693
0.8286	Intermediate Similarity	NPC105648
0.8286	Intermediate Similarity	NPC474385
0.8284	Intermediate Similarity	NPC198388
0.8284	Intermediate Similarity	NPC264145
0.8273	Intermediate Similarity	NPC472600
0.8273	Intermediate Similarity	NPC275903
0.8273	Intermediate Similarity	NPC472601
0.8271	Intermediate Similarity	NPC94810
0.8268	Intermediate Similarity	NPC158222
0.8264	Intermediate Similarity	NPC476684
0.8261	Intermediate Similarity	NPC212767
0.8261	Intermediate Similarity	NPC177307
0.8261	Intermediate Similarity	NPC239943
0.8261	Intermediate Similarity	NPC9121
0.8258	Intermediate Similarity	NPC156539
0.8252	Intermediate Similarity	NPC476463
0.8252	Intermediate Similarity	NPC81835
0.8239	Intermediate Similarity	NPC134621
0.8235	Intermediate Similarity	NPC106406
0.8235	Intermediate Similarity	NPC68517
0.8227	Intermediate Similarity	NPC159721
0.8222	Intermediate Similarity	NPC307289
0.8222	Intermediate Similarity	NPC5419
0.8222	Intermediate Similarity	NPC112192
0.8222	Intermediate Similarity	NPC164236
0.8222	Intermediate Similarity	NPC309717
0.8222	Intermediate Similarity	NPC18074
0.8222	Intermediate Similarity	NPC66384
0.8222	Intermediate Similarity	NPC61
0.8222	Intermediate Similarity	NPC189106
0.8222	Intermediate Similarity	NPC128348
0.8222	Intermediate Similarity	NPC25581
0.8217	Intermediate Similarity	NPC147654
0.8214	Intermediate Similarity	NPC1704
0.8214	Intermediate Similarity	NPC472605
0.8214	Intermediate Similarity	NPC472603
0.8214	Intermediate Similarity	NPC220106
0.8214	Intermediate Similarity	NPC90411
0.8214	Intermediate Similarity	NPC472604
0.8214	Intermediate Similarity	NPC475730
0.8214	Intermediate Similarity	NPC67650
0.8209	Intermediate Similarity	NPC12694
0.8209	Intermediate Similarity	NPC469929
0.8207	Intermediate Similarity	NPC140151
0.8203	Intermediate Similarity	NPC159525
0.8201	Intermediate Similarity	NPC92655
0.8201	Intermediate Similarity	NPC105525
0.8201	Intermediate Similarity	NPC12218
0.8201	Intermediate Similarity	NPC139634
0.8201	Intermediate Similarity	NPC75763
0.8201	Intermediate Similarity	NPC105456
0.8201	Intermediate Similarity	NPC275356
0.8201	Intermediate Similarity	NPC225036
0.8201	Intermediate Similarity	NPC88269
0.8197	Intermediate Similarity	NPC79543
0.8195	Intermediate Similarity	NPC219923
0.8194	Intermediate Similarity	NPC107636
0.8194	Intermediate Similarity	NPC75945
0.8194	Intermediate Similarity	NPC42464
0.8194	Intermediate Similarity	NPC221352
0.8188	Intermediate Similarity	NPC474771
0.8188	Intermediate Similarity	NPC193792
0.8188	Intermediate Similarity	NPC474849
0.8188	Intermediate Similarity	NPC149372
0.8188	Intermediate Similarity	NPC194579
0.8188	Intermediate Similarity	NPC65837
0.8188	Intermediate Similarity	NPC178467
0.8182	Intermediate Similarity	NPC204579
0.8182	Intermediate Similarity	NPC237208
0.8182	Intermediate Similarity	NPC110211
0.8182	Intermediate Similarity	NPC163846
0.8182	Intermediate Similarity	NPC225173
0.8182	Intermediate Similarity	NPC8745
0.8175	Intermediate Similarity	NPC131192
0.8175	Intermediate Similarity	NPC70680
0.8175	Intermediate Similarity	NPC182496
0.8175	Intermediate Similarity	NPC123559
0.8175	Intermediate Similarity	NPC182217
0.8175	Intermediate Similarity	NPC180905
0.8175	Intermediate Similarity	NPC233350
0.8169	Intermediate Similarity	NPC126882
0.8169	Intermediate Similarity	NPC210425
0.8169	Intermediate Similarity	NPC210966
0.8169	Intermediate Similarity	NPC277426
0.8169	Intermediate Similarity	NPC257025
0.8169	Intermediate Similarity	NPC86373
0.8169	Intermediate Similarity	NPC478203
0.8169	Intermediate Similarity	NPC280404
0.8162	Intermediate Similarity	NPC212631
0.8162	Intermediate Similarity	NPC205468
0.8162	Intermediate Similarity	NPC257756
0.8162	Intermediate Similarity	NPC168799
0.8162	Intermediate Similarity	NPC185777
0.8162	Intermediate Similarity	NPC155209
0.8162	Intermediate Similarity	NPC87231
0.8162	Intermediate Similarity	NPC129132
0.8156	Intermediate Similarity	NPC273657
0.8156	Intermediate Similarity	NPC106920
0.8156	Intermediate Similarity	NPC471733
0.8151	Intermediate Similarity	NPC75695
0.8148	Intermediate Similarity	NPC470831
0.8148	Intermediate Similarity	NPC214702
0.8143	Intermediate Similarity	NPC470986
0.8143	Intermediate Similarity	NPC9218
0.8138	Intermediate Similarity	NPC473091
0.8138	Intermediate Similarity	NPC306343
0.8134	Intermediate Similarity	NPC226855
0.813	Intermediate Similarity	NPC183700
0.8129	Intermediate Similarity	NPC290291
0.8129	Intermediate Similarity	NPC188879
0.8129	Intermediate Similarity	NPC472403
0.8129	Intermediate Similarity	NPC303644
0.8129	Intermediate Similarity	NPC7013
0.8129	Intermediate Similarity	NPC275055
0.8129	Intermediate Similarity	NPC219428
0.8129	Intermediate Similarity	NPC142703
0.8129	Intermediate Similarity	NPC162680
0.8129	Intermediate Similarity	NPC302857
0.8129	Intermediate Similarity	NPC209560
0.8129	Intermediate Similarity	NPC181124
0.8129	Intermediate Similarity	NPC152942
0.8129	Intermediate Similarity	NPC294409
0.8129	Intermediate Similarity	NPC116632
0.8129	Intermediate Similarity	NPC24295
0.8129	Intermediate Similarity	NPC283560
0.8129	Intermediate Similarity	NPC37250
0.8129	Intermediate Similarity	NPC475974
0.8129	Intermediate Similarity	NPC278068
0.8125	Intermediate Similarity	NPC125801
0.8125	Intermediate Similarity	NPC43123
0.8125	Intermediate Similarity	NPC120621

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 NPC79332 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	848
0.2-0.3	1494
0.3-0.4	2618
0.4-0.5	2051
0.5-0.6	1278
0.6-0.7	479
0.7-0.8	126
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8433	Intermediate Similarity	NPD230	Phase 1
0.8346	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD9545	Approved
0.8201	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD1510	Phase 2
0.8074	Intermediate Similarity	NPD3764	Approved
0.8028	Intermediate Similarity	NPD6190	Approved
0.8	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD3750	Approved
0.7956	Intermediate Similarity	NPD1240	Approved
0.7943	Intermediate Similarity	NPD1549	Phase 2
0.7929	Intermediate Similarity	NPD1551	Phase 2
0.7917	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1608	Approved
0.7879	Intermediate Similarity	NPD9269	Phase 2
0.7846	Intermediate Similarity	NPD9268	Approved
0.7842	Intermediate Similarity	NPD1607	Approved
0.7826	Intermediate Similarity	NPD943	Approved
0.7815	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD7819	Suspended
0.7793	Intermediate Similarity	NPD6799	Approved
0.7793	Intermediate Similarity	NPD1511	Approved
0.7742	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD2534	Approved
0.774	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD2532	Approved
0.774	Intermediate Similarity	NPD2533	Approved
0.7733	Intermediate Similarity	NPD1934	Approved
0.7708	Intermediate Similarity	NPD4628	Phase 3
0.7697	Intermediate Similarity	NPD3882	Suspended
0.7687	Intermediate Similarity	NPD1512	Approved
0.7686	Intermediate Similarity	NPD1242	Phase 1
0.7682	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD2935	Discontinued
0.7669	Intermediate Similarity	NPD422	Phase 1
0.7667	Intermediate Similarity	NPD7411	Suspended
0.7652	Intermediate Similarity	NPD17	Approved
0.7647	Intermediate Similarity	NPD7075	Discontinued
0.7639	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3817	Phase 2
0.7619	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3748	Approved
0.76	Intermediate Similarity	NPD4380	Phase 2
0.7586	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD2801	Approved
0.7552	Intermediate Similarity	NPD2796	Approved
0.7532	Intermediate Similarity	NPD6971	Discontinued
0.7532	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD3225	Approved
0.75	Intermediate Similarity	NPD1894	Discontinued
0.7483	Intermediate Similarity	NPD6599	Discontinued
0.7483	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD9493	Approved
0.7481	Intermediate Similarity	NPD1481	Phase 2
0.7468	Intermediate Similarity	NPD7768	Phase 2
0.7466	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6232	Discontinued
0.7445	Intermediate Similarity	NPD1203	Approved
0.7419	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1610	Phase 2
0.7407	Intermediate Similarity	NPD1535	Discovery
0.7403	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6801	Discontinued
0.7383	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7266	Discontinued
0.7375	Intermediate Similarity	NPD3818	Discontinued
0.7372	Intermediate Similarity	NPD1283	Approved
0.7365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD7033	Discontinued
0.7358	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD3027	Phase 3
0.7338	Intermediate Similarity	NPD1465	Phase 2
0.7329	Intermediate Similarity	NPD5844	Phase 1
0.7319	Intermediate Similarity	NPD2797	Approved
0.7319	Intermediate Similarity	NPD1164	Approved
0.7312	Intermediate Similarity	NPD7473	Discontinued
0.731	Intermediate Similarity	NPD5408	Approved
0.731	Intermediate Similarity	NPD5404	Approved
0.731	Intermediate Similarity	NPD5405	Approved
0.731	Intermediate Similarity	NPD6099	Approved
0.731	Intermediate Similarity	NPD5406	Approved
0.731	Intermediate Similarity	NPD6100	Approved
0.7305	Intermediate Similarity	NPD3268	Approved
0.7305	Intermediate Similarity	NPD1296	Phase 2
0.729	Intermediate Similarity	NPD5402	Approved
0.7286	Intermediate Similarity	NPD4908	Phase 1
0.7285	Intermediate Similarity	NPD5403	Approved
0.7285	Intermediate Similarity	NPD920	Approved
0.7279	Intermediate Similarity	NPD1243	Approved
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD37	Approved
0.7267	Intermediate Similarity	NPD5401	Approved
0.7267	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6234	Discontinued
0.7256	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6663	Approved
0.725	Intermediate Similarity	NPD6166	Phase 2
0.725	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4967	Phase 2
0.7244	Intermediate Similarity	NPD4966	Approved
0.7244	Intermediate Similarity	NPD4965	Approved
0.7241	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7229	Phase 3
0.723	Intermediate Similarity	NPD8166	Discontinued
0.7222	Intermediate Similarity	NPD7054	Approved
0.7214	Intermediate Similarity	NPD5736	Approved
0.7203	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1613	Approved
0.72	Intermediate Similarity	NPD7390	Discontinued
0.7188	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7472	Approved
0.7178	Intermediate Similarity	NPD7074	Phase 3
0.717	Intermediate Similarity	NPD6959	Discontinued
0.7163	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6832	Phase 2
0.7162	Intermediate Similarity	NPD2800	Approved
0.7153	Intermediate Similarity	NPD1281	Approved
0.7153	Intermediate Similarity	NPD6355	Discontinued
0.7153	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1201	Approved
0.7152	Intermediate Similarity	NPD919	Approved
0.7134	Intermediate Similarity	NPD6797	Phase 2
0.7134	Intermediate Similarity	NPD5953	Discontinued
0.7133	Intermediate Similarity	NPD6233	Phase 2
0.7132	Intermediate Similarity	NPD9266	Approved
0.7132	Intermediate Similarity	NPD74	Approved
0.7132	Intermediate Similarity	NPD1778	Approved
0.7125	Intermediate Similarity	NPD5710	Approved
0.7125	Intermediate Similarity	NPD5711	Approved
0.7123	Intermediate Similarity	NPD4308	Phase 3
0.7121	Intermediate Similarity	NPD1241	Discontinued
0.7101	Intermediate Similarity	NPD9717	Approved
0.7097	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD9494	Approved
0.7091	Intermediate Similarity	NPD7251	Discontinued
0.7091	Intermediate Similarity	NPD6559	Discontinued
0.7086	Intermediate Similarity	NPD4357	Discontinued
0.7083	Intermediate Similarity	NPD2979	Phase 3
0.7081	Intermediate Similarity	NPD5242	Approved
0.708	Intermediate Similarity	NPD3847	Discontinued
0.7078	Intermediate Similarity	NPD3455	Phase 2
0.7071	Intermediate Similarity	NPD3266	Approved
0.7071	Intermediate Similarity	NPD3267	Approved
0.7071	Intermediate Similarity	NPD1470	Approved
0.707	Intermediate Similarity	NPD4288	Approved
0.7063	Intermediate Similarity	NPD940	Approved
0.7063	Intermediate Similarity	NPD846	Approved
0.7063	Intermediate Similarity	NPD6798	Discontinued
0.7055	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD9267	Approved
0.7054	Intermediate Similarity	NPD9264	Approved
0.7054	Intermediate Similarity	NPD9263	Approved
0.705	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7808	Phase 3
0.704	Intermediate Similarity	NPD1238	Approved
0.7034	Intermediate Similarity	NPD5124	Phase 1
0.7034	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5048	Discontinued
0.7027	Intermediate Similarity	NPD2344	Approved
0.7021	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4062	Phase 3
0.7012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7286	Phase 2
0.7007	Intermediate Similarity	NPD2799	Discontinued
0.7007	Intermediate Similarity	NPD3019	Approved
0.7007	Intermediate Similarity	NPD2932	Approved
0.7	Intermediate Similarity	NPD5494	Approved
0.6993	Remote Similarity	NPD6273	Approved
0.6992	Remote Similarity	NPD2934	Approved
0.6992	Remote Similarity	NPD2933	Approved
0.6987	Remote Similarity	NPD6385	Approved
0.6987	Remote Similarity	NPD6386	Approved
0.6986	Remote Similarity	NPD6651	Approved
0.6978	Remote Similarity	NPD3972	Approved
0.6972	Remote Similarity	NPD2861	Phase 2
0.6968	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3226	Approved
0.6966	Remote Similarity	NPD4060	Phase 1
0.6962	Remote Similarity	NPD5353	Approved
0.6959	Remote Similarity	NPD2438	Suspended
0.6957	Remote Similarity	NPD3496	Discontinued
0.6951	Remote Similarity	NPD7228	Approved
0.6947	Remote Similarity	NPD4750	Phase 3
0.6944	Remote Similarity	NPD411	Approved
0.6944	Remote Similarity	NPD2313	Discontinued
0.6935	Remote Similarity	NPD2860	Approved
0.6935	Remote Similarity	NPD2859	Approved
0.6934	Remote Similarity	NPD5585	Approved
0.6923	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2614	Approved
0.6923	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD447	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