NPASS Compound

Structure

NPC180722 OpenBabel07101719252D 41 41 0 0 1 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 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 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 18 1 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 19 1 0 0 0 0 13 25 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 17 28 1 0 0 0 0 19 3 1 1 0 0 0 19 29 1 0 0 0 0 20 4 1 6 0 0 0 20 31 1 0 0 0 0 21 5 1 6 0 0 0 21 29 1 0 0 0 0 22 6 1 6 0 0 0 22 30 1 0 0 0 0 23 7 1 1 0 0 0 23 26 1 0 0 0 0 23 27 1 0 0 0 0 24 8 1 6 0 0 0 24 30 1 0 0 0 0 24 31 1 0 0 0 0 25 34 1 1 0 0 0 26 35 1 1 0 0 0 27 16 1 6 0 0 0 27 40 1 0 0 0 0 28 36 2 0 0 0 0 28 40 1 0 0 0 0 29 37 1 6 0 0 0 30 38 1 6 0 0 0 31 41 1 1 0 0 0 32 33 2 0 0 0 0 32 39 1 0 0 0 0 32 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	579.38
Volume:	618.971
LogP:	3.399
LogD:	3.435
LogS:	-4.049
# Rotatable Bonds:	17
TPSA:	159.54
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	1
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.104
Synthetic Accessibility Score:	5.634
Fsp3:	0.688
Lipinski Rule-of-5:	Rejected
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:	-5.259
MDCK Permeability:	0.00010046176612377167
Pgp-inhibitor:	0.557
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.738
20% Bioavailability (F20%):	0.404
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.155
Plasma Protein Binding (PPB):	75.8990707397461%
Volume Distribution (VD):	0.737
Pgp-substrate:	9.885994911193848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.348
CYP3A4-substrate:	0.387

ADMET: Excretion

Clearance (CL):	13.272
Half-life (T1/2):	0.889

ADMET: Toxicity

hERG Blockers:	0.521
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.639
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.377
Carcinogencity:	0.506
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC180722

Natural Product ID:	NPC180722
*Common Name:**	2-Des-Methyldiscodermolide
IUPAC Name:	[(3Z,5S,6S,7S,8R,9S,11Z,13S,14S,15S,16Z,18S)-8,14,18-trihydroxy-19-[(2S,3R,4R)-4-hydroxy-3-methyl-6-oxooxan-2-yl]-5,7,9,11,13,15-hexamethylnonadeca-1,3,11,16-tetraen-6-yl] carbamate
Synonyms:	2-Des-Methyldiscodermolide
Standard InCHIKey:	HZBDUFFQZCAYAX-NMSLFDRSSA-N
Standard InCHI:	InChI=1S/C32H53NO8/c1-9-10-11-20(4)31(41-32(33)39)24(8)30(38)22(6)15-18(2)14-21(5)29(37)19(3)12-13-25(34)16-27-23(7)26(35)17-28(36)40-27/h9-14,19-27,29-31,34-35,37-38H,1,15-17H2,2-8H3,(H2,33,39)/b11-10-,13-12-,18-14-/t19-,20-,21-,22-,23+,24-,25+,26+,27-,29-,30+,31-/m0/s1
SMILES:	C=C/C=C[C@H](C)[C@@H]([C@@H](C)[C@@H]([C@@H](C)C/C(=C[C@H](C)[C@H]([C@@H](C)/C=C[C@H](C[C@H]1[C@H](C)[C@@H](CC(=O)O1)O)O)O)/C)O)OC(=N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451449
PubChem CID:	10120980
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO32706	Discodermia sp.	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11809067]
NPO32706	Discodermia sp.	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444691]
NPO32706	Discodermia sp.	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158168]

☑ 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

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	172.0	nM	PMID[569152]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	120.0	nM	PMID[569152]

☑ 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 NPC180722 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	98
0.1-0.2	698
0.2-0.3	3437
0.3-0.4	9233
0.4-0.5	16762
0.5-0.6	9311
0.6-0.7	2942
0.7-0.8	202
0.8-0.85	5
0.85-0.9	3
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC165332
1.0	High Similarity	NPC195645
0.9556	High Similarity	NPC5418
0.9101	High Similarity	NPC86005
0.8889	High Similarity	NPC477959
0.8646	High Similarity	NPC475438
0.8602	High Similarity	NPC313670
0.8043	Intermediate Similarity	NPC69469
0.802	Intermediate Similarity	NPC316250
0.7938	Intermediate Similarity	NPC472199
0.7917	Intermediate Similarity	NPC118193
0.7917	Intermediate Similarity	NPC256902
0.7857	Intermediate Similarity	NPC478036
0.7857	Intermediate Similarity	NPC478037
0.7788	Intermediate Similarity	NPC469869
0.7778	Intermediate Similarity	NPC472198
0.7755	Intermediate Similarity	NPC472197
0.7736	Intermediate Similarity	NPC193765
0.7736	Intermediate Similarity	NPC473807
0.7732	Intermediate Similarity	NPC97577
0.7714	Intermediate Similarity	NPC476740
0.7714	Intermediate Similarity	NPC476738
0.7692	Intermediate Similarity	NPC473816
0.7692	Intermediate Similarity	NPC309398
0.7692	Intermediate Similarity	NPC475367
0.7692	Intermediate Similarity	NPC474581
0.7692	Intermediate Similarity	NPC127526
0.7679	Intermediate Similarity	NPC477515
0.7679	Intermediate Similarity	NPC313802
0.7679	Intermediate Similarity	NPC67917
0.7679	Intermediate Similarity	NPC314268
0.7642	Intermediate Similarity	NPC315531
0.7604	Intermediate Similarity	NPC315395
0.7604	Intermediate Similarity	NPC316426
0.7604	Intermediate Similarity	NPC116575
0.7593	Intermediate Similarity	NPC477997
0.7576	Intermediate Similarity	NPC36491
0.7573	Intermediate Similarity	NPC469871
0.7573	Intermediate Similarity	NPC469870
0.7549	Intermediate Similarity	NPC40812
0.7525	Intermediate Similarity	NPC54905
0.7525	Intermediate Similarity	NPC314009
0.7523	Intermediate Similarity	NPC21713
0.7523	Intermediate Similarity	NPC475608
0.75	Intermediate Similarity	NPC315836
0.75	Intermediate Similarity	NPC121200
0.75	Intermediate Similarity	NPC313668
0.75	Intermediate Similarity	NPC476049
0.7476	Intermediate Similarity	NPC255592
0.7476	Intermediate Similarity	NPC261377
0.7476	Intermediate Similarity	NPC308567
0.7475	Intermediate Similarity	NPC477866
0.7475	Intermediate Similarity	NPC477865
0.7473	Intermediate Similarity	NPC239127
0.7449	Intermediate Similarity	NPC201046
0.7447	Intermediate Similarity	NPC315731
0.7429	Intermediate Similarity	NPC473596
0.7423	Intermediate Similarity	NPC475753
0.7419	Intermediate Similarity	NPC321728
0.7416	Intermediate Similarity	NPC320119
0.7414	Intermediate Similarity	NPC315783
0.7391	Intermediate Similarity	NPC281296
0.7383	Intermediate Similarity	NPC472749
0.7383	Intermediate Similarity	NPC472751
0.7374	Intermediate Similarity	NPC212598
0.7363	Intermediate Similarity	NPC255060
0.7353	Intermediate Similarity	NPC272050
0.7347	Intermediate Similarity	NPC316138
0.7347	Intermediate Similarity	NPC313658
0.7345	Intermediate Similarity	NPC475642
0.7333	Intermediate Similarity	NPC326024
0.7327	Intermediate Similarity	NPC320089
0.732	Intermediate Similarity	NPC474369
0.7308	Intermediate Similarity	NPC187761
0.7308	Intermediate Similarity	NPC203627
0.7308	Intermediate Similarity	NPC161855
0.7308	Intermediate Similarity	NPC83895
0.7292	Intermediate Similarity	NPC16488
0.729	Intermediate Similarity	NPC472748
0.729	Intermediate Similarity	NPC239162
0.7283	Intermediate Similarity	NPC474447
0.7283	Intermediate Similarity	NPC61863
0.7283	Intermediate Similarity	NPC12740
0.7283	Intermediate Similarity	NPC110461
0.7282	Intermediate Similarity	NPC473291
0.7264	Intermediate Similarity	NPC478156
0.7264	Intermediate Similarity	NPC313569
0.7263	Intermediate Similarity	NPC184208
0.7263	Intermediate Similarity	NPC8538
0.7255	Intermediate Similarity	NPC71589
0.7248	Intermediate Similarity	NPC475150
0.7245	Intermediate Similarity	NPC122502
0.7245	Intermediate Similarity	NPC476982
0.7245	Intermediate Similarity	NPC477994
0.7245	Intermediate Similarity	NPC477993
0.7245	Intermediate Similarity	NPC164393
0.7241	Intermediate Similarity	NPC183353
0.7241	Intermediate Similarity	NPC170880
0.7241	Intermediate Similarity	NPC469812
0.7238	Intermediate Similarity	NPC475053
0.7228	Intermediate Similarity	NPC470373
0.7228	Intermediate Similarity	NPC470379
0.7216	Intermediate Similarity	NPC70424
0.7216	Intermediate Similarity	NPC243618
0.7204	Intermediate Similarity	NPC107668
0.7203	Intermediate Similarity	NPC314451
0.7203	Intermediate Similarity	NPC314512
0.7203	Intermediate Similarity	NPC313333
0.7203	Intermediate Similarity	NPC313342
0.7196	Intermediate Similarity	NPC472747
0.7196	Intermediate Similarity	NPC472750
0.7184	Intermediate Similarity	NPC36954
0.7184	Intermediate Similarity	NPC300710
0.7182	Intermediate Similarity	NPC133625
0.7174	Intermediate Similarity	NPC199445
0.7174	Intermediate Similarity	NPC60718
0.7172	Intermediate Similarity	NPC199382
0.7172	Intermediate Similarity	NPC179659
0.7172	Intermediate Similarity	NPC471738
0.7158	Intermediate Similarity	NPC103634
0.7157	Intermediate Similarity	NPC472196
0.7157	Intermediate Similarity	NPC159092
0.7157	Intermediate Similarity	NPC238090
0.7157	Intermediate Similarity	NPC472195
0.7157	Intermediate Similarity	NPC109406
0.7155	Intermediate Similarity	NPC314482
0.7143	Intermediate Similarity	NPC469865
0.7143	Intermediate Similarity	NPC325627
0.7143	Intermediate Similarity	NPC471494
0.7143	Intermediate Similarity	NPC475653
0.7143	Intermediate Similarity	NPC242233
0.7143	Intermediate Similarity	NPC137033
0.713	Intermediate Similarity	NPC309190
0.7129	Intermediate Similarity	NPC476004
0.7129	Intermediate Similarity	NPC316228
0.7129	Intermediate Similarity	NPC474761
0.7115	Intermediate Similarity	NPC476315
0.7115	Intermediate Similarity	NPC288350
0.7115	Intermediate Similarity	NPC255410
0.7115	Intermediate Similarity	NPC173329
0.7103	Intermediate Similarity	NPC475091
0.7103	Intermediate Similarity	NPC66110
0.7103	Intermediate Similarity	NPC472754
0.71	Intermediate Similarity	NPC227379
0.71	Intermediate Similarity	NPC473151
0.71	Intermediate Similarity	NPC474471
0.71	Intermediate Similarity	NPC137368
0.7097	Intermediate Similarity	NPC469514
0.7097	Intermediate Similarity	NPC469880
0.7094	Intermediate Similarity	NPC475383
0.7094	Intermediate Similarity	NPC156379
0.7094	Intermediate Similarity	NPC473228
0.7094	Intermediate Similarity	NPC470829
0.7087	Intermediate Similarity	NPC159698
0.7083	Intermediate Similarity	NPC79277
0.7083	Intermediate Similarity	NPC475481
0.7075	Intermediate Similarity	NPC324667
0.7075	Intermediate Similarity	NPC474718
0.7071	Intermediate Similarity	NPC234038
0.7071	Intermediate Similarity	NPC198314
0.7071	Intermediate Similarity	NPC311163
0.7069	Intermediate Similarity	NPC241050
0.7065	Intermediate Similarity	NPC474551
0.7064	Intermediate Similarity	NPC478038
0.7059	Intermediate Similarity	NPC476075
0.7059	Intermediate Similarity	NPC476084
0.7059	Intermediate Similarity	NPC471324
0.7059	Intermediate Similarity	NPC206679
0.7059	Intermediate Similarity	NPC114172
0.7048	Intermediate Similarity	NPC472290
0.7048	Intermediate Similarity	NPC120299
0.7048	Intermediate Similarity	NPC471462
0.7043	Intermediate Similarity	NPC6531
0.7041	Intermediate Similarity	NPC196487
0.7041	Intermediate Similarity	NPC9868
0.7041	Intermediate Similarity	NPC474776
0.7041	Intermediate Similarity	NPC14575
0.7037	Intermediate Similarity	NPC472755
0.703	Intermediate Similarity	NPC106040
0.703	Intermediate Similarity	NPC115179
0.703	Intermediate Similarity	NPC295312
0.703	Intermediate Similarity	NPC474032
0.7021	Intermediate Similarity	NPC240170
0.7021	Intermediate Similarity	NPC120776
0.7019	Intermediate Similarity	NPC471142
0.701	Intermediate Similarity	NPC477385
0.701	Intermediate Similarity	NPC477390
0.701	Intermediate Similarity	NPC7414
0.7009	Intermediate Similarity	NPC62670
0.7009	Intermediate Similarity	NPC472753
0.7009	Intermediate Similarity	NPC116139
0.6991	Remote Similarity	NPC66108
0.6991	Remote Similarity	NPC174836
0.699	Remote Similarity	NPC476300
0.699	Remote Similarity	NPC475912
0.6983	Remote Similarity	NPC13710
0.6981	Remote Similarity	NPC244411
0.6975	Remote Similarity	NPC314629
0.6972	Remote Similarity	NPC231271
0.6972	Remote Similarity	NPC220964

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 NPC180722 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	102
0.1-0.2	863
0.2-0.3	3295
0.3-0.4	3024
0.4-0.5	1384
0.5-0.6	405
0.6-0.7	58
0.7-0.8	15
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7839	Suspended
0.8511	High Similarity	NPD7983	Approved
0.8229	Intermediate Similarity	NPD5778	Approved
0.8229	Intermediate Similarity	NPD5779	Approved
0.7732	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD6101	Approved
0.7576	Intermediate Similarity	NPD6411	Approved
0.7544	Intermediate Similarity	NPD8444	Approved
0.7414	Intermediate Similarity	NPD7829	Approved
0.7414	Intermediate Similarity	NPD7830	Approved
0.7373	Intermediate Similarity	NPD8074	Phase 3
0.7308	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD46	Approved
0.73	Intermediate Similarity	NPD6698	Approved
0.7292	Intermediate Similarity	NPD7154	Phase 3
0.7245	Intermediate Similarity	NPD5786	Approved
0.7241	Intermediate Similarity	NPD8517	Approved
0.7241	Intermediate Similarity	NPD8515	Approved
0.7241	Intermediate Similarity	NPD8516	Approved
0.7241	Intermediate Similarity	NPD8513	Phase 3
0.7228	Intermediate Similarity	NPD7637	Suspended
0.7203	Intermediate Similarity	NPD8299	Approved
0.7203	Intermediate Similarity	NPD8340	Approved
0.7203	Intermediate Similarity	NPD8341	Approved
0.7203	Intermediate Similarity	NPD8342	Approved
0.701	Intermediate Similarity	NPD4270	Approved
0.701	Intermediate Similarity	NPD4269	Approved
0.7	Intermediate Similarity	NPD8451	Approved
0.6966	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7838	Discovery
0.6942	Remote Similarity	NPD8448	Approved
0.6939	Remote Similarity	NPD5362	Discontinued
0.6903	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7500	Approved
0.6838	Remote Similarity	NPD7641	Discontinued
0.6837	Remote Similarity	NPD6435	Approved
0.6804	Remote Similarity	NPD4252	Approved
0.6804	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5363	Approved
0.6774	Remote Similarity	NPD8390	Approved
0.6774	Remote Similarity	NPD8392	Approved
0.6774	Remote Similarity	NPD8391	Approved
0.6754	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5369	Approved
0.6721	Remote Similarity	NPD8273	Phase 1
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD4251	Approved
0.6635	Remote Similarity	NPD5785	Approved
0.6633	Remote Similarity	NPD4822	Approved
0.6633	Remote Similarity	NPD4820	Approved
0.6633	Remote Similarity	NPD4819	Approved
0.6633	Remote Similarity	NPD4821	Approved
0.6633	Remote Similarity	NPD5368	Approved
0.6632	Remote Similarity	NPD8039	Approved
0.6598	Remote Similarity	NPD3732	Approved
0.6598	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4271	Approved
0.6598	Remote Similarity	NPD4268	Approved
0.6569	Remote Similarity	NPD4249	Approved
0.6557	Remote Similarity	NPD7642	Approved
0.6542	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6686	Approved
0.6471	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5048	Discontinued
0.6436	Remote Similarity	NPD5332	Approved
0.6436	Remote Similarity	NPD5331	Approved
0.6415	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6422	Discontinued
0.6404	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4790	Discontinued
0.6381	Remote Similarity	NPD5370	Suspended
0.6379	Remote Similarity	NPD6421	Discontinued
0.6308	Remote Similarity	NPD8415	Approved
0.6296	Remote Similarity	NPD5282	Discontinued
0.6292	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.626	Remote Similarity	NPD8267	Approved
0.626	Remote Similarity	NPD8269	Approved
0.626	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.626	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.626	Remote Similarity	NPD8268	Approved
0.626	Remote Similarity	NPD8266	Approved
0.6239	Remote Similarity	NPD6371	Approved
0.6214	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7623	Phase 3
0.621	Remote Similarity	NPD8080	Discontinued
0.6198	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD1719	Phase 1
0.6179	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4756	Discovery
0.616	Remote Similarity	NPD8328	Phase 3
0.6154	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7747	Phase 1
0.6142	Remote Similarity	NPD7746	Phase 1
0.6134	Remote Similarity	NPD6053	Discontinued
0.6129	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6914	Discontinued
0.6117	Remote Similarity	NPD6695	Phase 3
0.6071	Remote Similarity	NPD4225	Approved
0.6058	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7319	Approved
0.6038	Remote Similarity	NPD7750	Discontinued
0.6019	Remote Similarity	NPD5209	Approved
0.6018	Remote Similarity	NPD7639	Approved
0.6018	Remote Similarity	NPD6648	Approved
0.6018	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6882	Approved
0.5986	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7332	Phase 2
0.598	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7514	Phase 3
0.5966	Remote Similarity	NPD6420	Discontinued
0.5965	Remote Similarity	NPD5344	Discontinued
0.596	Remote Similarity	NPD8264	Approved
0.5957	Remote Similarity	NPD7331	Phase 2
0.5954	Remote Similarity	NPD7260	Phase 2
0.5941	Remote Similarity	NPD7145	Approved
0.5938	Remote Similarity	NPD7507	Approved
0.5935	Remote Similarity	NPD7115	Discovery
0.5935	Remote Similarity	NPD7505	Discontinued
0.5932	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7638	Approved
0.5922	Remote Similarity	NPD6902	Approved
0.5914	Remote Similarity	NPD3197	Phase 1
0.5912	Remote Similarity	NPD8384	Approved
0.5909	Remote Similarity	NPD6399	Phase 3
0.5897	Remote Similarity	NPD4211	Phase 1
0.5897	Remote Similarity	NPD7333	Discontinued
0.5888	Remote Similarity	NPD7524	Approved
0.5882	Remote Similarity	NPD6929	Approved
0.5882	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD8297	Approved
0.5865	Remote Similarity	NPD7345	Approved
0.5862	Remote Similarity	NPD6647	Phase 2
0.5859	Remote Similarity	NPD7492	Approved
0.5856	Remote Similarity	NPD7748	Approved
0.5847	Remote Similarity	NPD6685	Approved
0.5847	Remote Similarity	NPD6412	Phase 2
0.5846	Remote Similarity	NPD7736	Approved
0.5842	Remote Similarity	NPD5776	Phase 2
0.5842	Remote Similarity	NPD6925	Approved
0.5825	Remote Similarity	NPD6931	Approved
0.5825	Remote Similarity	NPD6930	Phase 2
0.5814	Remote Similarity	NPD6616	Approved
0.581	Remote Similarity	NPD6110	Phase 1
0.5798	Remote Similarity	NPD6899	Approved
0.5798	Remote Similarity	NPD6881	Approved
0.5794	Remote Similarity	NPD6319	Approved
0.5794	Remote Similarity	NPD6054	Approved
0.5785	Remote Similarity	NPD6649	Approved
0.5785	Remote Similarity	NPD6650	Approved
0.5785	Remote Similarity	NPD8130	Phase 1
0.5784	Remote Similarity	NPD4802	Phase 2
0.5784	Remote Similarity	NPD4238	Approved
0.5776	Remote Similarity	NPD8082	Approved
0.5776	Remote Similarity	NPD8139	Approved
0.5776	Remote Similarity	NPD8083	Approved
0.5776	Remote Similarity	NPD8084	Approved
0.5776	Remote Similarity	NPD8085	Approved
0.5776	Remote Similarity	NPD8086	Approved
0.5776	Remote Similarity	NPD8138	Approved
0.5772	Remote Similarity	NPD6010	Discontinued
0.5769	Remote Similarity	NPD8293	Discontinued
0.5769	Remote Similarity	NPD7078	Approved
0.5763	Remote Similarity	NPD7128	Approved
0.5763	Remote Similarity	NPD5739	Approved
0.5763	Remote Similarity	NPD6402	Approved
0.5763	Remote Similarity	NPD6675	Approved
0.5758	Remote Similarity	NPD4732	Discontinued
0.5752	Remote Similarity	NPD4228	Discovery
0.575	Remote Similarity	NPD6372	Approved
0.575	Remote Similarity	NPD6413	Approved
0.575	Remote Similarity	NPD6373	Approved
0.5748	Remote Similarity	NPD6921	Approved
0.5745	Remote Similarity	NPD7909	Approved
0.5738	Remote Similarity	NPD6912	Phase 3
0.5726	Remote Similarity	NPD8275	Approved
0.5726	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8276	Approved
0.5714	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5697	Approved
0.5703	Remote Similarity	NPD6370	Approved
0.5702	Remote Similarity	NPD7902	Approved
0.5702	Remote Similarity	NPD6084	Phase 2
0.5702	Remote Similarity	NPD7290	Approved
0.5702	Remote Similarity	NPD6083	Phase 2
0.5702	Remote Similarity	NPD8087	Discontinued
0.5702	Remote Similarity	NPD7102	Approved
0.5702	Remote Similarity	NPD6883	Approved
0.5691	Remote Similarity	NPD8133	Approved
0.5686	Remote Similarity	NPD6932	Approved
0.5684	Remote Similarity	NPD7341	Phase 2
0.5678	Remote Similarity	NPD8081	Approved
0.5676	Remote Similarity	NPD7087	Discontinued
0.5676	Remote Similarity	NPD7515	Phase 2
0.5672	Remote Similarity	NPD2613	Approved
0.5669	Remote Similarity	NPD6059	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