NPASS Compound

Structure

NPC473685 OpenBabel07101718232D 28 30 0 0 1 0 0 0 0 0999 V2000 2.8559 0.6796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7771 -1.3510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1016 1.8338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9984 0.1479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9984 0.1479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7629 -3.2096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1147 -0.2863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3644 -2.2181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9934 -2.4076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9593 -2.6664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3644 -1.2181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4984 -2.7181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6323 -1.2181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8861 -0.8970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8970 1.8861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4076 -0.9934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7346 -1.4417 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6664 -1.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 -0.7346 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1564 -0.9877 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9877 0.1564 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4984 -0.7181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6323 -2.2181 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8338 0.1016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3510 2.7771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0474 -1.4417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 1.0474 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 7 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 7 16 2 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 10 18 2 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 22 1 0 0 0 0 13 23 1 0 0 0 0 14 24 2 0 0 0 0 14 26 1 0 0 0 0 15 25 2 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 17 9 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 19 16 1 1 0 0 0 19 21 1 0 0 0 0 20 26 1 6 0 0 0 20 28 1 0 0 0 0 21 27 1 6 0 0 0 21 28 1 0 0 0 0 23 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.24
Volume:	414.1
LogP:	5.135
LogD:	4.045
LogS:	-5.065
# Rotatable Bonds:	5
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.641
Synthetic Accessibility Score:	4.762
Fsp3:	0.739
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.736
MDCK Permeability:	1.8290240404894575e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.809

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	91.37965393066406%
Volume Distribution (VD):	2.331
Pgp-substrate:	5.610080242156982%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.694
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.52
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.709
CYP3A4-substrate:	0.346

ADMET: Excretion

Clearance (CL):	1.572
Half-life (T1/2):	0.157

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.809
Drug-inuced Liver Injury (DILI):	0.432
AMES Toxicity:	0.875
Rat Oral Acute Toxicity:	0.312
Maximum Recommended Daily Dose:	0.334
Skin Sensitization:	0.376
Carcinogencity:	0.799
Eye Corrosion:	0.072
Eye Irritation:	0.039
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC473685

Natural Product ID:	NPC473685
*Common Name:**	Gracilin A
IUPAC Name:	[(1S,3R,3aR,4Z,7aR)-3-acetyloxy-4-ethylidene-5-[(1S)-1,3,3-trimethylcyclohexyl]-3,3a,7,7a-tetrahydro-1H-2-benzofuran-1-yl] acetate
Synonyms:
Standard InCHIKey:	APJJJQRQXHYHMQ-WQFOLUMZSA-N
Standard InCHI:	InChI=1S/C23H34O5/c1-7-16-18(23(6)12-8-11-22(4,5)13-23)10-9-17-19(16)21(27-15(3)25)28-20(17)26-14(2)24/h7,10,17,19-21H,8-9,11-13H2,1-6H3/b16-7+/t17-,19+,20-,21+,23+/m1/s1
SMILES:	C/C=C1/[C@@H]2[C@@H](OC(=O)C)O[C@H]([C@@H]2CC=C1[C@@]1(C)CCCC(C1)(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449214
PubChem CID:	21602349
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003408] Isobenzofurans

*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
NPO33023	aplysilla sp.	Species	Darwinellidae	Eukaryota	n.a.	La Jolla	n.a.	PMID[1294693]
NPO33347	spongionella sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19601607]

☑ 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	2
Others	1

Activity Type	# Activity
Cell Line	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	600.0	nM	PMID[549959]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	800.0	nM	PMID[549959]
NPT24397	SINGLE PROTEIN	Phospholipase A2	Apis mellifera	Activity	=	69.0	%	PMID[549958]

☑ 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 NPC473685 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	165
0.1-0.2	1062
0.2-0.3	6296
0.3-0.4	15784
0.4-0.5	8423
0.5-0.6	8028
0.6-0.7	2672
0.7-0.8	248
0.8-0.85	17
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.881	High Similarity	NPC469403
0.8554	High Similarity	NPC118266
0.8506	High Similarity	NPC88507
0.8471	Intermediate Similarity	NPC293044
0.8415	Intermediate Similarity	NPC472440
0.8315	Intermediate Similarity	NPC311166
0.8222	Intermediate Similarity	NPC98112
0.8214	Intermediate Similarity	NPC472442
0.8202	Intermediate Similarity	NPC471362
0.8202	Intermediate Similarity	NPC471372
0.8202	Intermediate Similarity	NPC472189
0.8118	Intermediate Similarity	NPC244174
0.8111	Intermediate Similarity	NPC171598
0.8095	Intermediate Similarity	NPC471367
0.8068	Intermediate Similarity	NPC65513
0.8043	Intermediate Similarity	NPC473204
0.8022	Intermediate Similarity	NPC472188
0.8	Intermediate Similarity	NPC230347
0.8	Intermediate Similarity	NPC286612
0.8	Intermediate Similarity	NPC275310
0.7935	Intermediate Similarity	NPC476800
0.7935	Intermediate Similarity	NPC318917
0.7935	Intermediate Similarity	NPC472186
0.7935	Intermediate Similarity	NPC471366
0.7927	Intermediate Similarity	NPC170561
0.7912	Intermediate Similarity	NPC94905
0.7912	Intermediate Similarity	NPC112654
0.7912	Intermediate Similarity	NPC8954
0.7907	Intermediate Similarity	NPC471368
0.7907	Intermediate Similarity	NPC471369
0.7865	Intermediate Similarity	NPC179517
0.7865	Intermediate Similarity	NPC165904
0.7857	Intermediate Similarity	NPC15910
0.7849	Intermediate Similarity	NPC473545
0.7849	Intermediate Similarity	NPC472187
0.7848	Intermediate Similarity	NPC12680
0.7831	Intermediate Similarity	NPC269791
0.7826	Intermediate Similarity	NPC257726
0.7826	Intermediate Similarity	NPC204054
0.7805	Intermediate Similarity	NPC4827
0.7789	Intermediate Similarity	NPC134270
0.7778	Intermediate Similarity	NPC267266
0.7778	Intermediate Similarity	NPC277721
0.7727	Intermediate Similarity	NPC263079
0.7711	Intermediate Similarity	NPC17550
0.7711	Intermediate Similarity	NPC44083
0.7711	Intermediate Similarity	NPC153987
0.7708	Intermediate Similarity	NPC201880
0.7708	Intermediate Similarity	NPC473207
0.7708	Intermediate Similarity	NPC81567
0.7708	Intermediate Similarity	NPC470321
0.7708	Intermediate Similarity	NPC264867
0.7701	Intermediate Similarity	NPC173917
0.7684	Intermediate Similarity	NPC471363
0.7684	Intermediate Similarity	NPC238397
0.7667	Intermediate Similarity	NPC474631
0.7629	Intermediate Similarity	NPC172867
0.7629	Intermediate Similarity	NPC252296
0.7604	Intermediate Similarity	NPC7644
0.7604	Intermediate Similarity	NPC7613
0.7604	Intermediate Similarity	NPC127933
0.7604	Intermediate Similarity	NPC475889
0.7604	Intermediate Similarity	NPC132395
0.7604	Intermediate Similarity	NPC471365
0.7604	Intermediate Similarity	NPC471364
0.7586	Intermediate Similarity	NPC300985
0.7586	Intermediate Similarity	NPC473251
0.7586	Intermediate Similarity	NPC42586
0.7582	Intermediate Similarity	NPC470656
0.7561	Intermediate Similarity	NPC899
0.7561	Intermediate Similarity	NPC41017
0.7558	Intermediate Similarity	NPC469
0.7556	Intermediate Similarity	NPC471370
0.7556	Intermediate Similarity	NPC159876
0.7556	Intermediate Similarity	NPC471371
0.7551	Intermediate Similarity	NPC184512
0.7551	Intermediate Similarity	NPC109376
0.7531	Intermediate Similarity	NPC306928
0.75	Intermediate Similarity	NPC104925
0.75	Intermediate Similarity	NPC298973
0.75	Intermediate Similarity	NPC286153
0.75	Intermediate Similarity	NPC128488
0.75	Intermediate Similarity	NPC304968
0.75	Intermediate Similarity	NPC327674
0.75	Intermediate Similarity	NPC134077
0.7475	Intermediate Similarity	NPC311223
0.7475	Intermediate Similarity	NPC224660
0.7475	Intermediate Similarity	NPC470024
0.7474	Intermediate Similarity	NPC219285
0.7474	Intermediate Similarity	NPC146188
0.7474	Intermediate Similarity	NPC477968
0.7474	Intermediate Similarity	NPC477971
0.7474	Intermediate Similarity	NPC161527
0.7474	Intermediate Similarity	NPC20113
0.7474	Intermediate Similarity	NPC228251
0.7474	Intermediate Similarity	NPC477972
0.7473	Intermediate Similarity	NPC477122
0.7471	Intermediate Similarity	NPC319238
0.7471	Intermediate Similarity	NPC100391
0.7471	Intermediate Similarity	NPC469569
0.7471	Intermediate Similarity	NPC71626
0.7444	Intermediate Similarity	NPC470819
0.7444	Intermediate Similarity	NPC284561
0.7444	Intermediate Similarity	NPC470734
0.7444	Intermediate Similarity	NPC473058
0.7442	Intermediate Similarity	NPC122945
0.7442	Intermediate Similarity	NPC109938
0.7442	Intermediate Similarity	NPC471218
0.7412	Intermediate Similarity	NPC195424
0.74	Intermediate Similarity	NPC316974
0.7396	Intermediate Similarity	NPC63249
0.7396	Intermediate Similarity	NPC21064
0.7396	Intermediate Similarity	NPC121072
0.7391	Intermediate Similarity	NPC166346
0.7391	Intermediate Similarity	NPC471571
0.7386	Intermediate Similarity	NPC329738
0.7381	Intermediate Similarity	NPC35574
0.7374	Intermediate Similarity	NPC88013
0.7374	Intermediate Similarity	NPC125423
0.7368	Intermediate Similarity	NPC473154
0.7363	Intermediate Similarity	NPC470817
0.7363	Intermediate Similarity	NPC469595
0.7363	Intermediate Similarity	NPC212679
0.7363	Intermediate Similarity	NPC220454
0.7356	Intermediate Similarity	NPC324243
0.7356	Intermediate Similarity	NPC52108
0.7356	Intermediate Similarity	NPC477124
0.7356	Intermediate Similarity	NPC474789
0.7356	Intermediate Similarity	NPC132386
0.7333	Intermediate Similarity	NPC144069
0.7333	Intermediate Similarity	NPC470612
0.7333	Intermediate Similarity	NPC477128
0.7333	Intermediate Similarity	NPC196407
0.7333	Intermediate Similarity	NPC97884
0.7333	Intermediate Similarity	NPC472220
0.7333	Intermediate Similarity	NPC473879
0.7333	Intermediate Similarity	NPC470613
0.7327	Intermediate Similarity	NPC316708
0.7327	Intermediate Similarity	NPC119550
0.7326	Intermediate Similarity	NPC149237
0.7326	Intermediate Similarity	NPC25554
0.7326	Intermediate Similarity	NPC327002
0.7326	Intermediate Similarity	NPC108476
0.7326	Intermediate Similarity	NPC474955
0.732	Intermediate Similarity	NPC154452
0.7312	Intermediate Similarity	NPC469697
0.7312	Intermediate Similarity	NPC477722
0.7312	Intermediate Similarity	NPC477129
0.7312	Intermediate Similarity	NPC477130
0.7312	Intermediate Similarity	NPC470255
0.7312	Intermediate Similarity	NPC211238
0.7303	Intermediate Similarity	NPC474970
0.73	Intermediate Similarity	NPC128795
0.73	Intermediate Similarity	NPC217921
0.73	Intermediate Similarity	NPC135015
0.73	Intermediate Similarity	NPC48548
0.7294	Intermediate Similarity	NPC242767
0.7294	Intermediate Similarity	NPC100906
0.7292	Intermediate Similarity	NPC477720
0.7273	Intermediate Similarity	NPC470800
0.7273	Intermediate Similarity	NPC139566
0.7273	Intermediate Similarity	NPC218158
0.7263	Intermediate Similarity	NPC155319
0.7263	Intermediate Similarity	NPC239547
0.7263	Intermediate Similarity	NPC309503
0.7263	Intermediate Similarity	NPC96597
0.7263	Intermediate Similarity	NPC125551
0.7263	Intermediate Similarity	NPC91197
0.7262	Intermediate Similarity	NPC283619
0.7255	Intermediate Similarity	NPC17791
0.7255	Intermediate Similarity	NPC470026
0.7245	Intermediate Similarity	NPC120009
0.7241	Intermediate Similarity	NPC256112
0.7241	Intermediate Similarity	NPC286786
0.7241	Intermediate Similarity	NPC296367
0.7234	Intermediate Similarity	NPC473369
0.7228	Intermediate Similarity	NPC40728
0.7222	Intermediate Similarity	NPC288952
0.7222	Intermediate Similarity	NPC478104
0.7222	Intermediate Similarity	NPC167877
0.7222	Intermediate Similarity	NPC265580
0.7209	Intermediate Similarity	NPC206062
0.7209	Intermediate Similarity	NPC233332
0.7204	Intermediate Similarity	NPC12297
0.72	Intermediate Similarity	NPC293512
0.7195	Intermediate Similarity	NPC476490
0.7195	Intermediate Similarity	NPC476489
0.7191	Intermediate Similarity	NPC470223
0.7191	Intermediate Similarity	NPC329630
0.7191	Intermediate Similarity	NPC119001
0.7191	Intermediate Similarity	NPC76333
0.7188	Intermediate Similarity	NPC474440
0.7188	Intermediate Similarity	NPC477928
0.7188	Intermediate Similarity	NPC241657
0.7184	Intermediate Similarity	NPC317460
0.7184	Intermediate Similarity	NPC470025
0.7184	Intermediate Similarity	NPC328074
0.7184	Intermediate Similarity	NPC321272
0.7176	Intermediate Similarity	NPC321514
0.7174	Intermediate Similarity	NPC469372

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 NPC473685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1308
0.2-0.3	4366
0.3-0.4	2359
0.4-0.5	578
0.5-0.6	297
0.6-0.7	90
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
0.7021	Intermediate Similarity	NPD6399	Phase 3
0.6957	Remote Similarity	NPD5737	Approved
0.6957	Remote Similarity	NPD6672	Approved
0.6923	Remote Similarity	NPD7146	Approved
0.6923	Remote Similarity	NPD5330	Approved
0.6923	Remote Similarity	NPD7521	Approved
0.6923	Remote Similarity	NPD6684	Approved
0.6923	Remote Similarity	NPD6409	Approved
0.6923	Remote Similarity	NPD7334	Approved
0.6882	Remote Similarity	NPD6051	Approved
0.6854	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6903	Approved
0.6737	Remote Similarity	NPD6050	Approved
0.6703	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5692	Phase 3
0.6632	Remote Similarity	NPD5207	Approved
0.6628	Remote Similarity	NPD8039	Approved
0.6625	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7900	Approved
0.6562	Remote Similarity	NPD6411	Approved
0.6562	Remote Similarity	NPD5694	Approved
0.6559	Remote Similarity	NPD6098	Approved
0.6538	Remote Similarity	NPD6412	Phase 2
0.6531	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6904	Approved
0.6526	Remote Similarity	NPD6673	Approved
0.6526	Remote Similarity	NPD6080	Approved
0.6522	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6926	Approved
0.6512	Remote Similarity	NPD6924	Approved
0.6476	Remote Similarity	NPD6686	Approved
0.6456	Remote Similarity	NPD1145	Discontinued
0.6452	Remote Similarity	NPD1694	Approved
0.6437	Remote Similarity	NPD7339	Approved
0.6437	Remote Similarity	NPD6942	Approved
0.6429	Remote Similarity	NPD7748	Approved
0.6413	Remote Similarity	NPD6695	Phase 3
0.64	Remote Similarity	NPD7902	Approved
0.64	Remote Similarity	NPD6083	Phase 2
0.64	Remote Similarity	NPD6084	Phase 2
0.6392	Remote Similarity	NPD7637	Suspended
0.6392	Remote Similarity	NPD5281	Approved
0.6392	Remote Similarity	NPD5284	Approved
0.6372	Remote Similarity	NPD7503	Approved
0.6364	Remote Similarity	NPD6933	Approved
0.6364	Remote Similarity	NPD5695	Phase 3
0.6364	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6101	Approved
0.6344	Remote Similarity	NPD4786	Approved
0.6344	Remote Similarity	NPD3668	Phase 3
0.6304	Remote Similarity	NPD3667	Approved
0.6286	Remote Similarity	NPD6008	Approved
0.6264	Remote Similarity	NPD7525	Registered
0.6264	Remote Similarity	NPD7509	Discontinued
0.625	Remote Similarity	NPD5208	Approved
0.6239	Remote Similarity	NPD6882	Approved
0.6235	Remote Similarity	NPD6923	Approved
0.6235	Remote Similarity	NPD6922	Approved
0.6224	Remote Similarity	NPD5693	Phase 1
0.6224	Remote Similarity	NPD7515	Phase 2
0.62	Remote Similarity	NPD5654	Approved
0.6176	Remote Similarity	NPD5696	Approved
0.6176	Remote Similarity	NPD4225	Approved
0.6176	Remote Similarity	NPD7638	Approved
0.6163	Remote Similarity	NPD7143	Approved
0.6163	Remote Similarity	NPD7144	Approved
0.6162	Remote Similarity	NPD5779	Approved
0.6162	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD7645	Phase 2
0.6154	Remote Similarity	NPD6929	Approved
0.6146	Remote Similarity	NPD7750	Discontinued
0.6146	Remote Similarity	NPD7524	Approved
0.6146	Remote Similarity	NPD3573	Approved
0.6136	Remote Similarity	NPD4785	Approved
0.6136	Remote Similarity	NPD4784	Approved
0.6132	Remote Similarity	NPD6675	Approved
0.6132	Remote Similarity	NPD6402	Approved
0.6132	Remote Similarity	NPD7128	Approved
0.6132	Remote Similarity	NPD5739	Approved
0.6117	Remote Similarity	NPD7639	Approved
0.6117	Remote Similarity	NPD7640	Approved
0.6111	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7327	Approved
0.6106	Remote Similarity	NPD7328	Approved
0.61	Remote Similarity	NPD6001	Approved
0.6092	Remote Similarity	NPD7151	Approved
0.6092	Remote Similarity	NPD4243	Approved
0.6092	Remote Similarity	NPD7152	Approved
0.6092	Remote Similarity	NPD7150	Approved
0.6087	Remote Similarity	NPD6931	Approved
0.6087	Remote Similarity	NPD6930	Phase 2
0.6087	Remote Similarity	NPD8033	Approved
0.6078	Remote Similarity	NPD5959	Approved
0.6067	Remote Similarity	NPD8264	Approved
0.6061	Remote Similarity	NPD8034	Phase 2
0.6061	Remote Similarity	NPD8035	Phase 2
0.6053	Remote Similarity	NPD7516	Approved
0.6042	Remote Similarity	NPD5279	Phase 3
0.6019	Remote Similarity	NPD7320	Approved
0.6019	Remote Similarity	NPD6899	Approved
0.6019	Remote Similarity	NPD6881	Approved
0.6019	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8294	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD8377	Approved
0.5983	Remote Similarity	NPD7122	Discontinued
0.5978	Remote Similarity	NPD4195	Approved
0.5966	Remote Similarity	NPD8293	Discontinued
0.5963	Remote Similarity	NPD6373	Approved
0.5963	Remote Similarity	NPD6372	Approved
0.5957	Remote Similarity	NPD5209	Approved
0.5955	Remote Similarity	NPD5733	Approved
0.5948	Remote Similarity	NPD8513	Phase 3
0.5948	Remote Similarity	NPD8296	Approved
0.5948	Remote Similarity	NPD8335	Approved
0.5948	Remote Similarity	NPD8516	Approved
0.5948	Remote Similarity	NPD8380	Approved
0.5948	Remote Similarity	NPD8379	Approved
0.5948	Remote Similarity	NPD8517	Approved
0.5948	Remote Similarity	NPD8515	Approved
0.5948	Remote Similarity	NPD8378	Approved
0.5943	Remote Similarity	NPD6052	Approved
0.5941	Remote Similarity	NPD5707	Approved
0.5934	Remote Similarity	NPD6932	Approved
0.5934	Remote Similarity	NPD5776	Phase 2
0.5934	Remote Similarity	NPD6925	Approved
0.5926	Remote Similarity	NPD5701	Approved
0.5926	Remote Similarity	NPD5697	Approved
0.5917	Remote Similarity	NPD7736	Approved
0.5914	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD4695	Discontinued
0.5909	Remote Similarity	NPD6883	Approved
0.5909	Remote Similarity	NPD7102	Approved
0.5909	Remote Similarity	NPD7290	Approved
0.59	Remote Similarity	NPD7087	Discontinued
0.5897	Remote Similarity	NPD6370	Approved
0.5877	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD4694	Approved
0.5876	Remote Similarity	NPD5280	Approved
0.5876	Remote Similarity	NPD3618	Phase 1
0.5872	Remote Similarity	NPD6011	Approved
0.587	Remote Similarity	NPD7145	Approved
0.587	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4753	Phase 2
0.5859	Remote Similarity	NPD5328	Approved
0.5856	Remote Similarity	NPD6649	Approved
0.5856	Remote Similarity	NPD8130	Phase 1
0.5856	Remote Similarity	NPD6650	Approved
0.5856	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6869	Approved
0.5856	Remote Similarity	NPD6617	Approved
0.5856	Remote Similarity	NPD6847	Approved
0.5847	Remote Similarity	NPD8328	Phase 3
0.5847	Remote Similarity	NPD6067	Discontinued
0.5825	Remote Similarity	NPD7732	Phase 3
0.5825	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6013	Approved
0.5818	Remote Similarity	NPD6012	Approved
0.5818	Remote Similarity	NPD6014	Approved
0.581	Remote Similarity	NPD6404	Discontinued
0.581	Remote Similarity	NPD6648	Approved
0.5806	Remote Similarity	NPD6683	Phase 2
0.5804	Remote Similarity	NPD8297	Approved
0.58	Remote Similarity	NPD7838	Discovery
0.5798	Remote Similarity	NPD7492	Approved
0.5789	Remote Similarity	NPD6435	Approved
0.5789	Remote Similarity	NPD4221	Approved
0.5789	Remote Similarity	NPD4223	Phase 3
0.5783	Remote Similarity	NPD4193	Approved
0.5783	Remote Similarity	NPD4194	Approved
0.5783	Remote Similarity	NPD4192	Approved
0.5783	Remote Similarity	NPD4191	Approved
0.5778	Remote Similarity	NPD4058	Approved
0.5778	Remote Similarity	NPD4687	Approved
0.5773	Remote Similarity	NPD6893	Approved
0.5773	Remote Similarity	NPD5329	Approved
0.5773	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6858	Approved
0.5752	Remote Similarity	NPD7094	Approved
0.5752	Remote Similarity	NPD8133	Approved
0.575	Remote Similarity	NPD6616	Approved
0.575	Remote Similarity	NPD7507	Approved
0.5745	Remote Similarity	NPD4821	Approved
0.5745	Remote Similarity	NPD4822	Approved
0.5745	Remote Similarity	NPD7332	Phase 2
0.5745	Remote Similarity	NPD4820	Approved
0.5745	Remote Similarity	NPD7514	Phase 3
0.5745	Remote Similarity	NPD4819	Approved
0.5743	Remote Similarity	NPD6079	Approved
0.5739	Remote Similarity	NPD6009	Approved
0.573	Remote Similarity	NPD5276	Approved
0.5729	Remote Similarity	NPD5362	Discontinued

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