NPASS Compound

Structure

NPC261714 OpenBabel07101719522D 38 40 0 0 1 0 0 0 0 0999 V2000 2.3179 -4.1924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 -3.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8136 -5.5817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5043 -8.1561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6500 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9417 -7.1268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 -5.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 -3.5743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0885 -6.1998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9179 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5748 -4.8615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6237 -4.5525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1194 -5.2216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0519 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0396 -6.5088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9179 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7827 -5.8396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0519 -3.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7601 0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0705 -4.9126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0519 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2475 -7.4869 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7839 -3.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7338 -6.1487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0519 -4.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 28 1 0 0 0 0 5 31 1 0 0 0 0 6 32 1 0 0 0 0 7 33 1 0 0 0 0 8 34 1 0 0 0 0 9 35 1 0 0 0 0 10 36 1 0 0 0 0 11 13 3 0 0 0 0 11 19 1 0 0 0 0 12 14 3 0 0 0 0 12 20 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 17 19 2 0 0 0 0 17 25 1 0 0 0 0 18 20 2 0 0 0 0 18 26 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 23 25 2 0 0 0 0 23 33 1 0 0 0 0 24 26 2 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 30 2 0 0 0 0 27 37 1 0 0 0 0 27 38 1 0 0 0 0 28 29 1 1 0 0 0 28 37 1 0 0 0 0 29 4 1 6 0 0 0 29 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.2
Volume:	534.582
LogP:	4.266
LogD:	3.696
LogS:	-5.763
# Rotatable Bonds:	6
TPSA:	90.91
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.402
Synthetic Accessibility Score:	4.317
Fsp3:	0.414
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.891
MDCK Permeability:	2.7813877750304528e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.319

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	99.95368194580078%
Volume Distribution (VD):	1.13
Pgp-substrate:	2.0999691486358643%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.821
CYP2C19-substrate:	0.959
CYP2C9-inhibitor:	0.837
CYP2C9-substrate:	0.675
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.961
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	10.071
Half-life (T1/2):	0.243

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.626
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.681
Maximum Recommended Daily Dose:	0.878
Skin Sensitization:	0.31
Carcinogencity:	0.535
Eye Corrosion:	0.252
Eye Irritation:	0.796
Respiratory Toxicity:	0.322

Download Data

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

Natural Product: NPC261714

Natural Product ID:	NPC261714
*Common Name:**	Antrodioxolanone
IUPAC Name:	(4S,5R)-4,5-dimethyl-4,5-bis[2-(3,4,6-trimethoxy-2-methylphenyl)ethynyl]-1,3-dioxolan-2-one
Synonyms:	antrodioxolanone
Standard InCHIKey:	NJECTZSLZHQUFD-ISILISOKSA-N
Standard InCHI:	InChI=1S/C29H32O9/c1-17-19(21(31-5)15-23(33-7)25(17)35-9)11-13-28(3)29(4,38-27(30)37-28)14-12-20-18(2)26(36-10)24(34-8)16-22(20)32-6/h15-16H,1-10H3/t28-,29+
SMILES:	COc1cc(OC)c(c(c1C#C[C@]1(C)OC(=O)O[C@]1(C)C#Cc1c(OC)cc(c(c1C)OC)OC)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL229460
PubChem CID:	16737472
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738384]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[16643055]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387703]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[534835]

☑ 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 NPC261714 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	470
0.1-0.2	1780
0.2-0.3	5113
0.3-0.4	12863
0.4-0.5	5608
0.5-0.6	6181
0.6-0.7	8652
0.7-0.8	1851
0.8-0.85	156
0.85-0.9	22
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8864	High Similarity	NPC52593
0.8788	High Similarity	NPC64391
0.8759	High Similarity	NPC185680
0.8759	High Similarity	NPC145722
0.8759	High Similarity	NPC256776
0.8741	High Similarity	NPC258483
0.8732	High Similarity	NPC326144
0.8702	High Similarity	NPC264885
0.8671	High Similarity	NPC318286
0.8671	High Similarity	NPC327651
0.8662	High Similarity	NPC218510
0.8662	High Similarity	NPC76415
0.8643	High Similarity	NPC201404
0.8643	High Similarity	NPC290714
0.8643	High Similarity	NPC53722
0.8633	High Similarity	NPC197166
0.8633	High Similarity	NPC32189
0.8633	High Similarity	NPC143895
0.8611	High Similarity	NPC321958
0.8611	High Similarity	NPC321696
0.8603	High Similarity	NPC470624
0.8603	High Similarity	NPC237169
0.8571	High Similarity	NPC196420
0.8571	High Similarity	NPC191768
0.8571	High Similarity	NPC283170
0.8571	High Similarity	NPC92869
0.8561	High Similarity	NPC211231
0.8551	High Similarity	NPC1474
0.8519	High Similarity	NPC202904
0.8519	High Similarity	NPC189248
0.8511	High Similarity	NPC9068
0.8511	High Similarity	NPC30951
0.8511	High Similarity	NPC6369
0.85	High Similarity	NPC11453
0.8493	Intermediate Similarity	NPC327352
0.8493	Intermediate Similarity	NPC252281
0.8493	Intermediate Similarity	NPC477375
0.8493	Intermediate Similarity	NPC198129
0.8462	Intermediate Similarity	NPC174522
0.8456	Intermediate Similarity	NPC149008
0.8456	Intermediate Similarity	NPC283114
0.8456	Intermediate Similarity	NPC207702
0.8451	Intermediate Similarity	NPC216434
0.8451	Intermediate Similarity	NPC103448
0.8451	Intermediate Similarity	NPC284464
0.8446	Intermediate Similarity	NPC224472
0.844	Intermediate Similarity	NPC865
0.8435	Intermediate Similarity	NPC322426
0.8435	Intermediate Similarity	NPC477374
0.8435	Intermediate Similarity	NPC477376
0.8403	Intermediate Similarity	NPC324962
0.8378	Intermediate Similarity	NPC316989
0.8369	Intermediate Similarity	NPC121651
0.8367	Intermediate Similarity	NPC316676
0.8367	Intermediate Similarity	NPC325720
0.8357	Intermediate Similarity	NPC474600
0.8356	Intermediate Similarity	NPC87295
0.8356	Intermediate Similarity	NPC33832
0.8345	Intermediate Similarity	NPC65183
0.8345	Intermediate Similarity	NPC261812
0.8345	Intermediate Similarity	NPC72046
0.8345	Intermediate Similarity	NPC475856
0.8345	Intermediate Similarity	NPC102256
0.8333	Intermediate Similarity	NPC308739
0.8333	Intermediate Similarity	NPC16791
0.8333	Intermediate Similarity	NPC217708
0.8333	Intermediate Similarity	NPC184641
0.8333	Intermediate Similarity	NPC36531
0.8333	Intermediate Similarity	NPC53669
0.8333	Intermediate Similarity	NPC77237
0.8333	Intermediate Similarity	NPC472562
0.8333	Intermediate Similarity	NPC80326
0.8333	Intermediate Similarity	NPC230538
0.8333	Intermediate Similarity	NPC474295
0.8333	Intermediate Similarity	NPC297271
0.8333	Intermediate Similarity	NPC126405
0.8333	Intermediate Similarity	NPC229172
0.8333	Intermediate Similarity	NPC133934
0.8333	Intermediate Similarity	NPC103637
0.8333	Intermediate Similarity	NPC474514
0.8333	Intermediate Similarity	NPC184684
0.8311	Intermediate Similarity	NPC85141
0.8309	Intermediate Similarity	NPC186845
0.8309	Intermediate Similarity	NPC88297
0.8309	Intermediate Similarity	NPC9891
0.8299	Intermediate Similarity	NPC116019
0.8298	Intermediate Similarity	NPC150534
0.8298	Intermediate Similarity	NPC148893
0.8298	Intermediate Similarity	NPC73071
0.8298	Intermediate Similarity	NPC49235
0.8298	Intermediate Similarity	NPC25333
0.8298	Intermediate Similarity	NPC236522
0.8288	Intermediate Similarity	NPC475868
0.8286	Intermediate Similarity	NPC266848
0.8286	Intermediate Similarity	NPC196937
0.8286	Intermediate Similarity	NPC471391
0.8286	Intermediate Similarity	NPC471390
0.8286	Intermediate Similarity	NPC136750
0.8276	Intermediate Similarity	NPC474808
0.8273	Intermediate Similarity	NPC192255
0.8273	Intermediate Similarity	NPC184928
0.8273	Intermediate Similarity	NPC141493
0.8267	Intermediate Similarity	NPC477378
0.8267	Intermediate Similarity	NPC471154
0.8267	Intermediate Similarity	NPC475229
0.8264	Intermediate Similarity	NPC312199
0.8264	Intermediate Similarity	NPC58137
0.8264	Intermediate Similarity	NPC300798
0.8258	Intermediate Similarity	NPC308217
0.8255	Intermediate Similarity	NPC473989
0.8255	Intermediate Similarity	NPC24425
0.8252	Intermediate Similarity	NPC113550
0.8248	Intermediate Similarity	NPC471986
0.8243	Intermediate Similarity	NPC304821
0.8227	Intermediate Similarity	NPC474478
0.8227	Intermediate Similarity	NPC31530
0.8219	Intermediate Similarity	NPC121661
0.8219	Intermediate Similarity	NPC239254
0.8219	Intermediate Similarity	NPC73467
0.8219	Intermediate Similarity	NPC172171
0.8214	Intermediate Similarity	NPC7744
0.8212	Intermediate Similarity	NPC24562
0.8212	Intermediate Similarity	NPC474606
0.8212	Intermediate Similarity	NPC477377
0.8209	Intermediate Similarity	NPC477886
0.8207	Intermediate Similarity	NPC287124
0.8207	Intermediate Similarity	NPC191231
0.8201	Intermediate Similarity	NPC224157
0.8201	Intermediate Similarity	NPC63574
0.8201	Intermediate Similarity	NPC79184
0.8201	Intermediate Similarity	NPC307042
0.8201	Intermediate Similarity	NPC476399
0.8201	Intermediate Similarity	NPC192687
0.8201	Intermediate Similarity	NPC184814
0.82	Intermediate Similarity	NPC475756
0.82	Intermediate Similarity	NPC303519
0.8188	Intermediate Similarity	NPC328682
0.8188	Intermediate Similarity	NPC281864
0.8188	Intermediate Similarity	NPC474623
0.8188	Intermediate Similarity	NPC54321
0.8188	Intermediate Similarity	NPC474651
0.8182	Intermediate Similarity	NPC283949
0.8182	Intermediate Similarity	NPC474612
0.8175	Intermediate Similarity	NPC112571
0.8175	Intermediate Similarity	NPC50683
0.8175	Intermediate Similarity	NPC285725
0.817	Intermediate Similarity	NPC29727
0.8169	Intermediate Similarity	NPC240915
0.8169	Intermediate Similarity	NPC189474
0.8169	Intermediate Similarity	NPC474139
0.8163	Intermediate Similarity	NPC110763
0.8163	Intermediate Similarity	NPC197352
0.8163	Intermediate Similarity	NPC205316
0.8163	Intermediate Similarity	NPC189239
0.8163	Intermediate Similarity	NPC307466
0.8163	Intermediate Similarity	NPC166506
0.8158	Intermediate Similarity	NPC473425
0.8158	Intermediate Similarity	NPC198461
0.8156	Intermediate Similarity	NPC58585
0.8151	Intermediate Similarity	NPC474288
0.8146	Intermediate Similarity	NPC104353
0.8133	Intermediate Similarity	NPC149505
0.8129	Intermediate Similarity	NPC10225
0.8129	Intermediate Similarity	NPC190144
0.8129	Intermediate Similarity	NPC58164
0.812	Intermediate Similarity	NPC254625
0.812	Intermediate Similarity	NPC119949
0.812	Intermediate Similarity	NPC475961
0.8117	Intermediate Similarity	NPC475592
0.8116	Intermediate Similarity	NPC474670
0.8116	Intermediate Similarity	NPC473093
0.8116	Intermediate Similarity	NPC473092
0.8116	Intermediate Similarity	NPC8050
0.8112	Intermediate Similarity	NPC471182
0.8112	Intermediate Similarity	NPC286843
0.8112	Intermediate Similarity	NPC205442
0.8108	Intermediate Similarity	NPC162193
0.8108	Intermediate Similarity	NPC154971
0.8108	Intermediate Similarity	NPC252286
0.8106	Intermediate Similarity	NPC304208
0.8106	Intermediate Similarity	NPC52464
0.8105	Intermediate Similarity	NPC476065
0.8105	Intermediate Similarity	NPC238834
0.8095	Intermediate Similarity	NPC477701
0.8095	Intermediate Similarity	NPC141569
0.8095	Intermediate Similarity	NPC143092
0.8095	Intermediate Similarity	NPC166884
0.8085	Intermediate Similarity	NPC319969
0.8085	Intermediate Similarity	NPC6451
0.8082	Intermediate Similarity	NPC40237
0.8082	Intermediate Similarity	NPC41782
0.8082	Intermediate Similarity	NPC151423
0.8079	Intermediate Similarity	NPC210642
0.8079	Intermediate Similarity	NPC13985
0.8071	Intermediate Similarity	NPC126836
0.8071	Intermediate Similarity	NPC299221
0.8071	Intermediate Similarity	NPC51840
0.8071	Intermediate Similarity	NPC474617
0.8071	Intermediate Similarity	NPC234488
0.8071	Intermediate Similarity	NPC311680

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 NPC261714 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	992
0.2-0.3	2121
0.3-0.4	2948
0.4-0.5	1502
0.5-0.6	875
0.6-0.7	324
0.7-0.8	24
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8209	Intermediate Similarity	NPD3705	Approved
0.7974	Intermediate Similarity	NPD37	Approved
0.7857	Intermediate Similarity	NPD3018	Phase 2
0.7821	Intermediate Similarity	NPD4966	Approved
0.7821	Intermediate Similarity	NPD4967	Phase 2
0.7821	Intermediate Similarity	NPD4965	Approved
0.7754	Intermediate Similarity	NPD2981	Phase 2
0.7722	Intermediate Similarity	NPD6234	Discontinued
0.7698	Intermediate Similarity	NPD2983	Phase 2
0.7698	Intermediate Similarity	NPD2982	Phase 2
0.7697	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7199	Phase 2
0.7622	Intermediate Similarity	NPD3027	Phase 3
0.7537	Intermediate Similarity	NPD5283	Phase 1
0.7531	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7228	Approved
0.7372	Intermediate Similarity	NPD1653	Approved
0.7361	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3539	Phase 1
0.7321	Intermediate Similarity	NPD7240	Approved
0.731	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3540	Phase 1
0.723	Intermediate Similarity	NPD1613	Approved
0.723	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6674	Discontinued
0.7152	Intermediate Similarity	NPD6232	Discontinued
0.7134	Intermediate Similarity	NPD5494	Approved
0.7126	Intermediate Similarity	NPD7473	Discontinued
0.7115	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3817	Phase 2
0.7097	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5536	Phase 2
0.7051	Intermediate Similarity	NPD7124	Phase 2
0.7041	Intermediate Similarity	NPD5844	Phase 1
0.7037	Intermediate Similarity	NPD2801	Approved
0.7034	Intermediate Similarity	NPD6696	Suspended
0.7027	Intermediate Similarity	NPD4625	Phase 3
0.6987	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD3818	Discontinued
0.6974	Remote Similarity	NPD6111	Discontinued
0.6972	Remote Similarity	NPD1357	Approved
0.6959	Remote Similarity	NPD4908	Phase 1
0.6957	Remote Similarity	NPD7028	Phase 2
0.6954	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7266	Discontinued
0.6944	Remote Similarity	NPD1611	Approved
0.6941	Remote Similarity	NPD7054	Approved
0.6939	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1465	Phase 2
0.6918	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4055	Discovery
0.6901	Remote Similarity	NPD7074	Phase 3
0.6901	Remote Similarity	NPD7472	Approved
0.6897	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4005	Discontinued
0.6892	Remote Similarity	NPD2861	Phase 2
0.689	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4060	Phase 1
0.6879	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5109	Approved
0.6867	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5110	Phase 2
0.6867	Remote Similarity	NPD5111	Phase 2
0.6853	Remote Similarity	NPD5691	Approved
0.6849	Remote Similarity	NPD4749	Approved
0.6848	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3882	Suspended
0.6845	Remote Similarity	NPD3787	Discontinued
0.6839	Remote Similarity	NPD1375	Discontinued
0.6829	Remote Similarity	NPD7819	Suspended
0.6828	Remote Similarity	NPD1610	Phase 2
0.6818	Remote Similarity	NPD3748	Approved
0.681	Remote Similarity	NPD5090	Approved
0.681	Remote Similarity	NPD5089	Approved
0.6809	Remote Similarity	NPD709	Approved
0.6806	Remote Similarity	NPD4626	Approved
0.6805	Remote Similarity	NPD3926	Phase 2
0.6795	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4357	Discontinued
0.6783	Remote Similarity	NPD1548	Phase 1
0.6782	Remote Similarity	NPD7549	Discontinued
0.6782	Remote Similarity	NPD7808	Phase 3
0.6768	Remote Similarity	NPD3384	Approved
0.6768	Remote Similarity	NPD3383	Approved
0.6768	Remote Similarity	NPD1934	Approved
0.6768	Remote Similarity	NPD3382	Approved
0.6763	Remote Similarity	NPD228	Approved
0.6755	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7229	Phase 3
0.6735	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3657	Discovery
0.6732	Remote Similarity	NPD1933	Approved
0.6731	Remote Similarity	NPD5763	Approved
0.6731	Remote Similarity	NPD5762	Approved
0.6727	Remote Similarity	NPD4585	Approved
0.6724	Remote Similarity	NPD7251	Discontinued
0.6721	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7644	Approved
0.6712	Remote Similarity	NPD1091	Approved
0.6712	Remote Similarity	NPD422	Phase 1
0.6711	Remote Similarity	NPD4624	Approved
0.6709	Remote Similarity	NPD7466	Approved
0.669	Remote Similarity	NPD6671	Approved
0.6689	Remote Similarity	NPD7095	Approved
0.6689	Remote Similarity	NPD2922	Phase 1
0.6687	Remote Similarity	NPD5297	Approved
0.6686	Remote Similarity	NPD1247	Approved
0.6685	Remote Similarity	NPD6843	Phase 3
0.6685	Remote Similarity	NPD6842	Approved
0.6685	Remote Similarity	NPD6841	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD2438	Suspended
0.6667	Remote Similarity	NPD919	Approved
0.6667	Remote Similarity	NPD6797	Phase 2
0.6667	Remote Similarity	NPD3620	Phase 2
0.6667	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2219	Phase 1
0.6667	Remote Similarity	NPD6100	Approved
0.6648	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2534	Approved
0.6646	Remote Similarity	NPD2532	Approved
0.6646	Remote Similarity	NPD2533	Approved
0.6644	Remote Similarity	NPD3496	Discontinued
0.6629	Remote Similarity	NPD6559	Discontinued
0.6627	Remote Similarity	NPD5677	Discontinued
0.6627	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD5058	Phase 3
0.6623	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6355	Discontinued
0.6621	Remote Similarity	NPD1651	Approved
0.6608	Remote Similarity	NPD5242	Approved
0.6604	Remote Similarity	NPD3750	Approved
0.6604	Remote Similarity	NPD3892	Phase 2
0.6604	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1281	Approved
0.6596	Remote Similarity	NPD5535	Approved
0.659	Remote Similarity	NPD8252	Approved
0.659	Remote Similarity	NPD8099	Discontinued
0.659	Remote Similarity	NPD8251	Approved
0.659	Remote Similarity	NPD3751	Discontinued
0.6587	Remote Similarity	NPD5402	Approved
0.6587	Remote Similarity	NPD5353	Approved
0.6585	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1511	Approved
0.6584	Remote Similarity	NPD6799	Approved
0.6579	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7680	Approved
0.6573	Remote Similarity	NPD7157	Approved
0.6573	Remote Similarity	NPD6387	Discontinued
0.657	Remote Similarity	NPD6166	Phase 2
0.657	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD2979	Phase 3
0.6552	Remote Similarity	NPD8156	Discontinued
0.6545	Remote Similarity	NPD4675	Approved
0.6545	Remote Similarity	NPD4678	Approved
0.6541	Remote Similarity	NPD4237	Approved
0.6541	Remote Similarity	NPD4236	Phase 3
0.6541	Remote Similarity	NPD1652	Phase 2
0.6538	Remote Similarity	NPD6896	Approved
0.6538	Remote Similarity	NPD7097	Phase 1
0.6538	Remote Similarity	NPD6895	Approved
0.6536	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD5718	Phase 2
0.6536	Remote Similarity	NPD7985	Registered
0.6534	Remote Similarity	NPD7685	Pre-registration
0.6527	Remote Similarity	NPD8455	Phase 2
0.6527	Remote Similarity	NPD2977	Approved
0.6527	Remote Similarity	NPD2978	Approved
0.6524	Remote Similarity	NPD5005	Approved
0.6524	Remote Similarity	NPD5006	Approved
0.6524	Remote Similarity	NPD4210	Discontinued
0.6513	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5327	Phase 3
0.6509	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5585	Approved
0.6506	Remote Similarity	NPD6386	Approved
0.6506	Remote Similarity	NPD6385	Approved
0.6503	Remote Similarity	NPD1512	Approved
0.6503	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4110	Phase 3
0.6497	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4108	Discontinued
0.6494	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6233	Phase 2
0.6491	Remote Similarity	NPD8127	Discontinued
0.6484	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD7843	Approved
0.6478	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD1358	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