NPASS Compound

Structure

NPC475588 OpenBabel07101719252D 38 44 0 0 1 0 0 0 0 0999 V2000 5.3697 3.8927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9567 -1.1724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2057 0.1871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4814 3.0728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8591 0.7256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3693 3.8290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2947 2.0436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9886 0.6747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8608 1.1426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1331 1.4707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3737 3.8030 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2037 -0.5145 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8608 2.9446 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2762 0.2913 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1041 1.5436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7926 2.0436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1041 2.5436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3171 1.3891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1530 1.2346 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3171 2.6981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8859 3.1671 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5323 0.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4524 2.4481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5652 2.0436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7158 4.5561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4149 -0.6945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8859 0.9201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6008 2.0799 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4524 1.6391 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1530 2.8526 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6261 3.6492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4348 2.0436 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9383 5.5310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0219 -1.6140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1806 -0.0354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4009 2.6797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7962 4.1631 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 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 1 1 1 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 2 1 1 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 7 1 6 0 0 0 13 21 1 0 0 0 0 14 8 1 6 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 15 27 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 19 24 1 0 0 0 0 19 29 1 6 0 0 0 20 23 1 0 0 0 0 20 31 1 1 0 0 0 21 17 1 1 0 0 0 21 37 1 0 0 0 0 22 18 1 1 0 0 0 22 38 1 0 0 0 0 23 29 1 1 0 0 0 23 30 1 0 0 0 0 24 30 1 0 0 0 0 24 32 2 0 0 0 0 25 33 2 0 0 0 0 25 37 1 0 0 0 0 26 34 2 0 0 0 0 26 38 1 0 0 0 0 27 3 1 1 0 0 0 27 35 1 0 0 0 0 28 4 1 1 0 0 0 28 36 1 0 0 0 0 29 5 1 1 0 0 0 30 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.26
Volume:	524.68
LogP:	1.879
LogD:	1.824
LogS:	-4.122
# Rotatable Bonds:	0
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	6.597
Fsp3:	0.767
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:	-5.334
MDCK Permeability:	9.015274554258212e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.224

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.158
Plasma Protein Binding (PPB):	54.26387405395508%
Volume Distribution (VD):	0.788
Pgp-substrate:	23.814468383789062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.756
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.665
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.878
CYP3A4-substrate:	0.709

ADMET: Excretion

Clearance (CL):	11.36
Half-life (T1/2):	0.011

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.598
Drug-inuced Liver Injury (DILI):	0.838
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.113
Carcinogencity:	0.238
Eye Corrosion:	0.006
Eye Irritation:	0.014
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC475588

Natural Product ID:	NPC475588
*Common Name:**	Absintholide
IUPAC Name:	n.a.
Synonyms:	Absintholide
Standard InCHIKey:	ANVQPXYQHSOZNE-BXSVONSTSA-N
Standard InCHI:	InChI=1S/C30H38O8/c1-11-13-7-9-27(3,35)15-17(21(13)37-25(11)33)30(6)23-20(31)16-18(29(23,5)19(15)24(30)32)22-14(8-10-28(16,4)36)12(2)26(34)38-22/h11-14,19-23,31,35-36H,7-10H2,1-6H3/t11-,12-,13-,14-,19-,20+,21-,22-,23+,27-,28-,29-,30-/m0/s1
SMILES:	CC1C2CCC(C3=C(C2OC1=O)C4(C(C3O)C5(C6=C(C4C5=O)C(CCC7C6OC(=O)C7C)(C)O)C)C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508743
PubChem CID:	44558931
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO32823	artemisia caruifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141102]

☑ 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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	Inhibition	=	22.0	%	PMID[529435]

☑ 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 NPC475588 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	296
0.1-0.2	2036
0.2-0.3	6716
0.3-0.4	15780
0.4-0.5	9023
0.5-0.6	6727
0.6-0.7	1987
0.7-0.8	115
0.8-0.85	15
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8762	High Similarity	NPC252234
0.8571	High Similarity	NPC161060
0.8482	Intermediate Similarity	NPC36754
0.8411	Intermediate Similarity	NPC475217
0.8378	Intermediate Similarity	NPC209058
0.8304	Intermediate Similarity	NPC471382
0.8304	Intermediate Similarity	NPC471380
0.8288	Intermediate Similarity	NPC23967
0.8273	Intermediate Similarity	NPC48305
0.8273	Intermediate Similarity	NPC474923
0.8108	Intermediate Similarity	NPC471884
0.8	Intermediate Similarity	NPC475238
0.7736	Intermediate Similarity	NPC37408
0.7727	Intermediate Similarity	NPC474775
0.7672	Intermediate Similarity	NPC123117
0.7586	Intermediate Similarity	NPC312017
0.7586	Intermediate Similarity	NPC9848
0.7565	Intermediate Similarity	NPC287311
0.7541	Intermediate Similarity	NPC144625
0.75	Intermediate Similarity	NPC172823
0.7459	Intermediate Similarity	NPC42747
0.7459	Intermediate Similarity	NPC1538
0.7459	Intermediate Similarity	NPC129992
0.7459	Intermediate Similarity	NPC186339
0.7434	Intermediate Similarity	NPC179891
0.7431	Intermediate Similarity	NPC161493
0.7429	Intermediate Similarity	NPC212664
0.7429	Intermediate Similarity	NPC32922
0.7411	Intermediate Similarity	NPC475321
0.7407	Intermediate Similarity	NPC213698
0.7407	Intermediate Similarity	NPC469873
0.7407	Intermediate Similarity	NPC67584
0.7407	Intermediate Similarity	NPC170120
0.7407	Intermediate Similarity	NPC52044
0.7395	Intermediate Similarity	NPC475323
0.7391	Intermediate Similarity	NPC273433
0.7377	Intermediate Similarity	NPC192309
0.7373	Intermediate Similarity	NPC474181
0.7368	Intermediate Similarity	NPC473037
0.735	Intermediate Similarity	NPC126691
0.7345	Intermediate Similarity	NPC100487
0.7339	Intermediate Similarity	NPC213078
0.7328	Intermediate Similarity	NPC475463
0.7321	Intermediate Similarity	NPC86077
0.7315	Intermediate Similarity	NPC90453
0.7315	Intermediate Similarity	NPC127019
0.7311	Intermediate Similarity	NPC49492
0.7311	Intermediate Similarity	NPC148458
0.7311	Intermediate Similarity	NPC277583
0.7311	Intermediate Similarity	NPC266728
0.7304	Intermediate Similarity	NPC308191
0.7302	Intermediate Similarity	NPC13071
0.7297	Intermediate Similarity	NPC477521
0.7297	Intermediate Similarity	NPC218383
0.7297	Intermediate Similarity	NPC280963
0.7281	Intermediate Similarity	NPC196528
0.7281	Intermediate Similarity	NPC223450
0.7281	Intermediate Similarity	NPC243998
0.728	Intermediate Similarity	NPC11732
0.7273	Intermediate Similarity	NPC213947
0.7273	Intermediate Similarity	NPC170143
0.7273	Intermediate Similarity	NPC108475
0.7273	Intermediate Similarity	NPC475894
0.7273	Intermediate Similarity	NPC230513
0.7265	Intermediate Similarity	NPC474750
0.7257	Intermediate Similarity	NPC36688
0.7257	Intermediate Similarity	NPC140723
0.725	Intermediate Similarity	NPC473656
0.7244	Intermediate Similarity	NPC469351
0.7232	Intermediate Similarity	NPC150923
0.7232	Intermediate Similarity	NPC475099
0.7232	Intermediate Similarity	NPC171759
0.7232	Intermediate Similarity	NPC477950
0.7227	Intermediate Similarity	NPC474872
0.7222	Intermediate Similarity	NPC473273
0.7222	Intermediate Similarity	NPC37816
0.7222	Intermediate Similarity	NPC470254
0.7222	Intermediate Similarity	NPC308656
0.7222	Intermediate Similarity	NPC60386
0.7222	Intermediate Similarity	NPC473234
0.7222	Intermediate Similarity	NPC135776
0.7222	Intermediate Similarity	NPC473263
0.7217	Intermediate Similarity	NPC469318
0.7217	Intermediate Similarity	NPC473173
0.7217	Intermediate Similarity	NPC112780
0.7213	Intermediate Similarity	NPC17938
0.7212	Intermediate Similarity	NPC245434
0.7207	Intermediate Similarity	NPC271387
0.7207	Intermediate Similarity	NPC221615
0.7207	Intermediate Similarity	NPC153792
0.7196	Intermediate Similarity	NPC301969
0.7196	Intermediate Similarity	NPC37607
0.719	Intermediate Similarity	NPC475372
0.7182	Intermediate Similarity	NPC91771
0.7182	Intermediate Similarity	NPC142529
0.7179	Intermediate Similarity	NPC473036
0.7179	Intermediate Similarity	NPC477103
0.7179	Intermediate Similarity	NPC272898
0.7179	Intermediate Similarity	NPC257240
0.7177	Intermediate Similarity	NPC471392
0.7177	Intermediate Similarity	NPC469352
0.7168	Intermediate Similarity	NPC66110
0.7167	Intermediate Similarity	NPC154363
0.7167	Intermediate Similarity	NPC234858
0.7167	Intermediate Similarity	NPC471127
0.7156	Intermediate Similarity	NPC262133
0.7156	Intermediate Similarity	NPC96541
0.7156	Intermediate Similarity	NPC198853
0.7156	Intermediate Similarity	NPC471720
0.7156	Intermediate Similarity	NPC470010
0.7156	Intermediate Similarity	NPC477131
0.7156	Intermediate Similarity	NPC323008
0.7156	Intermediate Similarity	NPC184870
0.7156	Intermediate Similarity	NPC470013
0.7143	Intermediate Similarity	NPC67493
0.7143	Intermediate Similarity	NPC71889
0.7143	Intermediate Similarity	NPC962
0.7143	Intermediate Similarity	NPC25909
0.7132	Intermediate Similarity	NPC224623
0.7131	Intermediate Similarity	NPC42673
0.7131	Intermediate Similarity	NPC469380
0.7131	Intermediate Similarity	NPC312536
0.713	Intermediate Similarity	NPC131209
0.713	Intermediate Similarity	NPC150383
0.713	Intermediate Similarity	NPC290651
0.713	Intermediate Similarity	NPC107690
0.713	Intermediate Similarity	NPC190867
0.713	Intermediate Similarity	NPC133698
0.7119	Intermediate Similarity	NPC475480
0.7119	Intermediate Similarity	NPC473921
0.7119	Intermediate Similarity	NPC475668
0.7117	Intermediate Similarity	NPC121339
0.7117	Intermediate Similarity	NPC477949
0.7107	Intermediate Similarity	NPC10721
0.7107	Intermediate Similarity	NPC55296
0.7107	Intermediate Similarity	NPC239273
0.7105	Intermediate Similarity	NPC110989
0.7097	Intermediate Similarity	NPC222688
0.7094	Intermediate Similarity	NPC286174
0.7094	Intermediate Similarity	NPC304495
0.7094	Intermediate Similarity	NPC77947
0.7094	Intermediate Similarity	NPC477102
0.7091	Intermediate Similarity	NPC163228
0.7091	Intermediate Similarity	NPC36954
0.7091	Intermediate Similarity	NPC304886
0.708	Intermediate Similarity	NPC62670
0.708	Intermediate Similarity	NPC474327
0.708	Intermediate Similarity	NPC116139
0.7073	Intermediate Similarity	NPC471126
0.7073	Intermediate Similarity	NPC471128
0.7073	Intermediate Similarity	NPC157252
0.7073	Intermediate Similarity	NPC19336
0.7073	Intermediate Similarity	NPC147635
0.7073	Intermediate Similarity	NPC163693
0.7073	Intermediate Similarity	NPC145182
0.7073	Intermediate Similarity	NPC109973
0.7073	Intermediate Similarity	NPC143755
0.7073	Intermediate Similarity	NPC185876
0.7069	Intermediate Similarity	NPC59530
0.7069	Intermediate Similarity	NPC204884
0.7064	Intermediate Similarity	NPC153590
0.7064	Intermediate Similarity	NPC200237
0.7059	Intermediate Similarity	NPC123855
0.7059	Intermediate Similarity	NPC475391
0.7059	Intermediate Similarity	NPC221144
0.7059	Intermediate Similarity	NPC100267
0.7059	Intermediate Similarity	NPC76550
0.7059	Intermediate Similarity	NPC475524
0.7054	Intermediate Similarity	NPC23364
0.7054	Intermediate Similarity	NPC470188
0.7054	Intermediate Similarity	NPC141191
0.7049	Intermediate Similarity	NPC475309
0.7048	Intermediate Similarity	NPC235792
0.7043	Intermediate Similarity	NPC473577
0.7043	Intermediate Similarity	NPC470104
0.7043	Intermediate Similarity	NPC203659
0.7043	Intermediate Similarity	NPC475585
0.7043	Intermediate Similarity	NPC471293
0.7043	Intermediate Similarity	NPC28656
0.7043	Intermediate Similarity	NPC294259
0.7043	Intermediate Similarity	NPC309190
0.7043	Intermediate Similarity	NPC258532
0.7043	Intermediate Similarity	NPC474550
0.704	Intermediate Similarity	NPC472768
0.704	Intermediate Similarity	NPC472399
0.7037	Intermediate Similarity	NPC289213
0.7037	Intermediate Similarity	NPC71533
0.7037	Intermediate Similarity	NPC129419
0.7037	Intermediate Similarity	NPC54065
0.7037	Intermediate Similarity	NPC106510
0.7037	Intermediate Similarity	NPC297474
0.7034	Intermediate Similarity	NPC475563
0.7034	Intermediate Similarity	NPC129689
0.7034	Intermediate Similarity	NPC206595
0.7034	Intermediate Similarity	NPC475134
0.7034	Intermediate Similarity	NPC179642
0.7031	Intermediate Similarity	NPC470851
0.7027	Intermediate Similarity	NPC18019
0.7027	Intermediate Similarity	NPC320231
0.7027	Intermediate Similarity	NPC476315

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 NPC475588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	2762
0.2-0.3	3867
0.3-0.4	1530
0.4-0.5	396
0.5-0.6	238
0.6-0.7	28
0.7-0.8	0
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
0.7179	Intermediate Similarity	NPD6371	Approved
0.7059	Intermediate Similarity	NPD6053	Discontinued
0.6786	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5362	Discontinued
0.6696	Remote Similarity	NPD7640	Approved
0.6696	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6609	Remote Similarity	NPD7638	Approved
0.6583	Remote Similarity	NPD7320	Approved
0.6581	Remote Similarity	NPD7632	Discontinued
0.6577	Remote Similarity	NPD5785	Approved
0.6557	Remote Similarity	NPD6649	Approved
0.6557	Remote Similarity	NPD6650	Approved
0.6555	Remote Similarity	NPD6008	Approved
0.6555	Remote Similarity	NPD5739	Approved
0.6555	Remote Similarity	NPD6675	Approved
0.6555	Remote Similarity	NPD7128	Approved
0.6555	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6084	Phase 2
0.6522	Remote Similarity	NPD6083	Phase 2
0.6515	Remote Similarity	NPD7319	Approved
0.6514	Remote Similarity	NPD5786	Approved
0.6486	Remote Similarity	NPD1695	Approved
0.646	Remote Similarity	NPD6399	Phase 3
0.6455	Remote Similarity	NPD4251	Approved
0.6455	Remote Similarity	NPD4250	Approved
0.6449	Remote Similarity	NPD6435	Approved
0.6446	Remote Similarity	NPD6899	Approved
0.6446	Remote Similarity	NPD6881	Approved
0.6429	Remote Similarity	NPD7115	Discovery
0.6422	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD8297	Approved
0.6371	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD7078	Approved
0.6364	Remote Similarity	NPD4249	Approved
0.6364	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD5701	Approved
0.6348	Remote Similarity	NPD5695	Phase 3
0.6341	Remote Similarity	NPD7290	Approved
0.6341	Remote Similarity	NPD7102	Approved
0.6341	Remote Similarity	NPD6883	Approved
0.6341	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD7492	Approved
0.6325	Remote Similarity	NPD5696	Approved
0.6316	Remote Similarity	NPD5778	Approved
0.6316	Remote Similarity	NPD5779	Approved
0.6311	Remote Similarity	NPD6686	Approved
0.6296	Remote Similarity	NPD4269	Approved
0.6296	Remote Similarity	NPD4270	Approved
0.629	Remote Similarity	NPD8130	Phase 1
0.629	Remote Similarity	NPD6847	Approved
0.629	Remote Similarity	NPD6869	Approved
0.629	Remote Similarity	NPD6617	Approved
0.6288	Remote Similarity	NPD6616	Approved
0.6279	Remote Similarity	NPD6059	Approved
0.6279	Remote Similarity	NPD6054	Approved
0.6279	Remote Similarity	NPD6319	Approved
0.6262	Remote Similarity	NPD5368	Approved
0.626	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6012	Approved
0.626	Remote Similarity	NPD6014	Approved
0.626	Remote Similarity	NPD6013	Approved
0.6241	Remote Similarity	NPD8293	Discontinued
0.6239	Remote Similarity	NPD7154	Phase 3
0.6228	Remote Similarity	NPD7637	Suspended
0.6228	Remote Similarity	NPD7983	Approved
0.6207	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4790	Discontinued
0.6204	Remote Similarity	NPD5369	Approved
0.6198	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD7736	Approved
0.619	Remote Similarity	NPD4632	Approved
0.6183	Remote Similarity	NPD6370	Approved
0.6179	Remote Similarity	NPD6011	Approved
0.6179	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD5211	Phase 2
0.616	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6698	Approved
0.614	Remote Similarity	NPD46	Approved
0.6131	Remote Similarity	NPD6845	Suspended
0.6126	Remote Similarity	NPD5363	Approved
0.6124	Remote Similarity	NPD7327	Approved
0.6124	Remote Similarity	NPD7328	Approved
0.6121	Remote Similarity	NPD5282	Discontinued
0.6111	Remote Similarity	NPD4820	Approved
0.6111	Remote Similarity	NPD4252	Approved
0.6111	Remote Similarity	NPD4819	Approved
0.6111	Remote Similarity	NPD4822	Approved
0.6111	Remote Similarity	NPD4821	Approved
0.6111	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD6015	Approved
0.6107	Remote Similarity	NPD6016	Approved
0.6106	Remote Similarity	NPD6903	Approved
0.6102	Remote Similarity	NPD4755	Approved
0.6098	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6412	Phase 2
0.6091	Remote Similarity	NPD5332	Approved
0.6091	Remote Similarity	NPD5331	Approved
0.6087	Remote Similarity	NPD5693	Phase 1
0.6083	Remote Similarity	NPD1700	Approved
0.6077	Remote Similarity	NPD7516	Approved
0.6071	Remote Similarity	NPD7521	Approved
0.6071	Remote Similarity	NPD6684	Approved
0.6071	Remote Similarity	NPD5330	Approved
0.6071	Remote Similarity	NPD6409	Approved
0.6071	Remote Similarity	NPD7146	Approved
0.6071	Remote Similarity	NPD7334	Approved
0.6066	Remote Similarity	NPD5141	Approved
0.6063	Remote Similarity	NPD8133	Approved
0.6061	Remote Similarity	NPD5988	Approved
0.6053	Remote Similarity	NPD6051	Approved
0.6053	Remote Similarity	NPD4753	Phase 2
0.6053	Remote Similarity	NPD5328	Approved
0.605	Remote Similarity	NPD4225	Approved
0.6047	Remote Similarity	NPD6009	Approved
0.6036	Remote Similarity	NPD4786	Approved
0.6032	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD8377	Approved
0.6031	Remote Similarity	NPD8294	Approved
0.6015	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD5207	Approved
0.5985	Remote Similarity	NPD8296	Approved
0.5985	Remote Similarity	NPD8380	Approved
0.5985	Remote Similarity	NPD8379	Approved
0.5985	Remote Similarity	NPD8378	Approved
0.5985	Remote Similarity	NPD8516	Approved
0.5985	Remote Similarity	NPD8033	Approved
0.5985	Remote Similarity	NPD8335	Approved
0.5985	Remote Similarity	NPD5983	Phase 2
0.5985	Remote Similarity	NPD8515	Approved
0.5985	Remote Similarity	NPD8517	Approved
0.5985	Remote Similarity	NPD8513	Phase 3
0.5985	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD1694	Approved
0.5982	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6274	Approved
0.5965	Remote Similarity	NPD5737	Approved
0.5965	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6672	Approved
0.5954	Remote Similarity	NPD7101	Approved
0.5954	Remote Similarity	NPD7100	Approved
0.5948	Remote Similarity	NPD6411	Approved
0.5948	Remote Similarity	NPD8034	Phase 2
0.5948	Remote Similarity	NPD8035	Phase 2
0.5948	Remote Similarity	NPD5284	Approved
0.5948	Remote Similarity	NPD5281	Approved
0.5948	Remote Similarity	NPD6079	Approved
0.5946	Remote Similarity	NPD6695	Phase 3
0.5942	Remote Similarity	NPD7260	Phase 2
0.5932	Remote Similarity	NPD4629	Approved
0.5932	Remote Similarity	NPD5210	Approved
0.5929	Remote Similarity	NPD6098	Approved
0.5926	Remote Similarity	NPD4271	Approved
0.5926	Remote Similarity	NPD4268	Approved
0.5926	Remote Similarity	NPD6336	Discontinued
0.5913	Remote Similarity	NPD6673	Approved
0.5913	Remote Similarity	NPD6080	Approved
0.5913	Remote Similarity	NPD6904	Approved
0.5902	Remote Similarity	NPD4633	Approved
0.5902	Remote Similarity	NPD5224	Approved
0.5902	Remote Similarity	NPD5226	Approved
0.5902	Remote Similarity	NPD5225	Approved
0.5893	Remote Similarity	NPD3666	Approved
0.5893	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD3133	Approved
0.5893	Remote Similarity	NPD3665	Phase 1
0.5887	Remote Similarity	NPD4767	Approved
0.5887	Remote Similarity	NPD4768	Approved
0.5882	Remote Similarity	NPD4697	Phase 3
0.5882	Remote Similarity	NPD7839	Suspended
0.5878	Remote Similarity	NPD6335	Approved
0.5865	Remote Similarity	NPD6908	Approved
0.5865	Remote Similarity	NPD6909	Approved
0.5865	Remote Similarity	NPD7503	Approved
0.5856	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD3667	Approved
0.5854	Remote Similarity	NPD5174	Approved
0.5854	Remote Similarity	NPD5175	Approved
0.5847	Remote Similarity	NPD6001	Approved
0.5841	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD6033	Approved
0.5827	Remote Similarity	NPD4634	Approved
0.582	Remote Similarity	NPD5223	Approved
0.5812	Remote Similarity	NPD6050	Approved
0.5806	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD4788	Approved
0.5802	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD6317	Approved
0.5794	Remote Similarity	NPD4730	Approved
0.5794	Remote Similarity	NPD3702	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