NPASS Compound

Structure

CID275539 OpenBabel06191716082D 29 33 0 0 1 0 0 0 0 0999 V2000 7.2350 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7350 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8690 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0029 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2350 3.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 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 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 6 15 2 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 29 1 0 0 0 0 14 22 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 25 1 6 0 0 0 17 22 1 6 0 0 0 17 23 1 0 0 0 0 18 24 1 6 0 0 0 18 25 1 0 0 0 0 19 23 1 6 0 0 0 19 24 1 0 0 0 0 20 25 1 6 0 0 0 20 27 1 0 0 0 0 21 28 2 0 0 0 0 21 29 1 0 0 0 0 22 1 1 6 0 0 0 23 2 1 6 0 0 0 24 3 1 6 0 0 0 25 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.28
Volume:	428.062
LogP:	3.616
LogD:	3.488
LogS:	-4.16
# Rotatable Bonds:	1
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.515
Synthetic Accessibility Score:	5.165
Fsp3:	0.88
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:	-4.957
MDCK Permeability:	6.295915954979137e-05
Pgp-inhibitor:	0.061
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.668
30% Bioavailability (F30%):	0.229

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.781
Plasma Protein Binding (PPB):	86.64643859863281%
Volume Distribution (VD):	0.956
Pgp-substrate:	13.763374328613281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.311
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.704
CYP2C9-inhibitor:	0.118
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.398
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	5.996
Half-life (T1/2):	0.407

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.401
Maximum Recommended Daily Dose:	0.354
Skin Sensitization:	0.207
Carcinogencity:	0.027
Eye Corrosion:	0.12
Eye Irritation:	0.42
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC275539

Natural Product ID:	NPC275539
*Common Name:**	12-O-Deacetyl-12-Epi-19-Deoxy-21-Hydroxyscalarin
IUPAC Name:	(5aS,5bR,7aR,8R,11aR,11bR,13R,13aS,13bR)-13-hydroxy-8-(hydroxymethyl)-5b,8,11a,13a-tetramethyl-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e][2]benzofuran-3-one
Synonyms:
Standard InCHIKey:	LXWMXTKOJPFGPW-NFXGRNOLSA-N
Standard InCHI:	InChI=1S/C25H38O4/c1-22(14-26)9-5-10-23(2)17(22)8-11-24(3)18-7-6-15-16(13-29-21(15)28)25(18,4)20(27)12-19(23)24/h6,16-20,26-27H,5,7-14H2,1-4H3/t16-,17-,18-,19+,20+,22-,23-,24-,25+/m0/s1
SMILES:	C[C@]1(CCC[C@@]2(C)[C@H]1CC[C@@]1(C)[C@@H]3CC=C4[C@H](COC4=O)[C@@]3(C)[C@@H](C[C@H]21)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251695
PubChem CID:	24178658
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane 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
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tongoa, Vanuatu Islands	1996	PMID[10757711]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662110]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497946]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tong-Yong City in the South Sea, Korea	n.a.	PMID[16905319]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17567172]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988093]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18407692]
NPO33664	Hyatella sp.	Species	n.a.	n.a.	n.a.	the coast of Soheuksan-do, Korea	n.a.	PMID[21341710]
NPO31085	Hyattella	Genus	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21341710]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[24992702]

☑ 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	3
MIC	6
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	IC50	=	2400.0	nM	PMID[575412]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	31100.0	nM	PMID[575413]
NPT27	Others	Unspecified		IC50	=	49400.0	nM	PMID[575412]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[575413]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[575413]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[575413]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[575413]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[575413]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[575413]
NPT2	Others	Unspecified		IC50	=	133200.0	nM	PMID[575413]

☑ 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 NPC275539 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	210
0.1-0.2	1239
0.2-0.3	3730
0.3-0.4	7092
0.4-0.5	12956
0.5-0.6	6343
0.6-0.7	6013
0.7-0.8	4348
0.8-0.85	630
0.85-0.9	123
0.9-0.95	6
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC189075
0.9899	High Similarity	NPC110496
0.9612	High Similarity	NPC194951
0.9612	High Similarity	NPC12046
0.9596	High Similarity	NPC254202
0.9519	High Similarity	NPC157441
0.9216	High Similarity	NPC469607
0.9151	High Similarity	NPC25909
0.9135	High Similarity	NPC112457
0.9109	High Similarity	NPC165250
0.9057	High Similarity	NPC277769
0.901	High Similarity	NPC471412
0.8922	High Similarity	NPC31058
0.8922	High Similarity	NPC162973
0.8922	High Similarity	NPC469606
0.8922	High Similarity	NPC273005
0.8911	High Similarity	NPC47024
0.8911	High Similarity	NPC471413
0.89	High Similarity	NPC175351
0.89	High Similarity	NPC121402
0.89	High Similarity	NPC132753
0.89	High Similarity	NPC151681
0.89	High Similarity	NPC224356
0.8899	High Similarity	NPC473968
0.8879	High Similarity	NPC4573
0.8879	High Similarity	NPC269530
0.8879	High Similarity	NPC90952
0.8846	High Similarity	NPC478208
0.8835	High Similarity	NPC471208
0.8835	High Similarity	NPC95585
0.8835	High Similarity	NPC478057
0.8835	High Similarity	NPC282233
0.8835	High Similarity	NPC95899
0.8812	High Similarity	NPC23364
0.8812	High Similarity	NPC216478
0.88	High Similarity	NPC472363
0.88	High Similarity	NPC472362
0.88	High Similarity	NPC154526
0.8788	High Similarity	NPC250075
0.875	High Similarity	NPC222161
0.8739	High Similarity	NPC476529
0.8739	High Similarity	NPC475775
0.8738	High Similarity	NPC136289
0.8738	High Similarity	NPC476081
0.8727	High Similarity	NPC134430
0.8725	High Similarity	NPC471041
0.8713	High Similarity	NPC474343
0.87	High Similarity	NPC183012
0.8679	High Similarity	NPC476802
0.8679	High Similarity	NPC325054
0.8679	High Similarity	NPC89171
0.8667	High Similarity	NPC102352
0.8661	High Similarity	NPC109607
0.8661	High Similarity	NPC107338
0.8654	High Similarity	NPC36688
0.8641	High Similarity	NPC81530
0.8641	High Similarity	NPC63249
0.8627	High Similarity	NPC478056
0.8627	High Similarity	NPC260149
0.8627	High Similarity	NPC58942
0.8614	High Similarity	NPC29952
0.8611	High Similarity	NPC469655
0.8611	High Similarity	NPC474846
0.8611	High Similarity	NPC469656
0.86	High Similarity	NPC57117
0.8598	High Similarity	NPC478210
0.8598	High Similarity	NPC474243
0.8586	High Similarity	NPC233345
0.8586	High Similarity	NPC186363
0.8585	High Similarity	NPC144854
0.8585	High Similarity	NPC230541
0.8585	High Similarity	NPC3316
0.8571	High Similarity	NPC77689
0.8571	High Similarity	NPC473636
0.8571	High Similarity	NPC475041
0.8559	High Similarity	NPC473590
0.8559	High Similarity	NPC284068
0.8559	High Similarity	NPC475809
0.8558	High Similarity	NPC134077
0.8558	High Similarity	NPC476769
0.8544	High Similarity	NPC477972
0.8544	High Similarity	NPC477971
0.8544	High Similarity	NPC117685
0.8544	High Similarity	NPC219285
0.8544	High Similarity	NPC161527
0.8544	High Similarity	NPC476767
0.8544	High Similarity	NPC228251
0.8544	High Similarity	NPC477968
0.8544	High Similarity	NPC251680
0.8544	High Similarity	NPC20113
0.8529	High Similarity	NPC189880
0.8519	High Similarity	NPC197428
0.8519	High Similarity	NPC478211
0.8519	High Similarity	NPC253906
0.8519	High Similarity	NPC5103
0.8519	High Similarity	NPC478209
0.8519	High Similarity	NPC472666
0.8515	High Similarity	NPC473240
0.8515	High Similarity	NPC157686
0.8515	High Similarity	NPC259042
0.8505	High Similarity	NPC277017
0.8505	High Similarity	NPC154608
0.8505	High Similarity	NPC476479
0.8505	High Similarity	NPC192813
0.8491	Intermediate Similarity	NPC231530
0.8491	Intermediate Similarity	NPC278628
0.8491	Intermediate Similarity	NPC478052
0.8491	Intermediate Similarity	NPC127609
0.8485	Intermediate Similarity	NPC158488
0.8476	Intermediate Similarity	NPC275583
0.8476	Intermediate Similarity	NPC120321
0.8462	Intermediate Similarity	NPC235142
0.8462	Intermediate Similarity	NPC472637
0.8455	Intermediate Similarity	NPC469454
0.8455	Intermediate Similarity	NPC469463
0.8455	Intermediate Similarity	NPC469496
0.8447	Intermediate Similarity	NPC234617
0.8447	Intermediate Similarity	NPC476806
0.8447	Intermediate Similarity	NPC124703
0.8447	Intermediate Similarity	NPC475876
0.8447	Intermediate Similarity	NPC476807
0.844	Intermediate Similarity	NPC188738
0.844	Intermediate Similarity	NPC132790
0.844	Intermediate Similarity	NPC97939
0.844	Intermediate Similarity	NPC100329
0.844	Intermediate Similarity	NPC247031
0.8435	Intermediate Similarity	NPC67251
0.8435	Intermediate Similarity	NPC469789
0.8431	Intermediate Similarity	NPC29410
0.8431	Intermediate Similarity	NPC476318
0.8431	Intermediate Similarity	NPC200054
0.8431	Intermediate Similarity	NPC476327
0.8431	Intermediate Similarity	NPC134072
0.8431	Intermediate Similarity	NPC234993
0.8426	Intermediate Similarity	NPC472534
0.8426	Intermediate Similarity	NPC31522
0.8426	Intermediate Similarity	NPC141350
0.8426	Intermediate Similarity	NPC143706
0.8416	Intermediate Similarity	NPC148000
0.8416	Intermediate Similarity	NPC469596
0.8416	Intermediate Similarity	NPC91010
0.8416	Intermediate Similarity	NPC225474
0.8411	Intermediate Similarity	NPC301666
0.8411	Intermediate Similarity	NPC187435
0.8411	Intermediate Similarity	NPC67321
0.8407	Intermediate Similarity	NPC473839
0.8407	Intermediate Similarity	NPC476960
0.8407	Intermediate Similarity	NPC211093
0.84	Intermediate Similarity	NPC72845
0.8396	Intermediate Similarity	NPC118911
0.8396	Intermediate Similarity	NPC96268
0.8393	Intermediate Similarity	NPC469684
0.8393	Intermediate Similarity	NPC98249
0.8393	Intermediate Similarity	NPC53396
0.8384	Intermediate Similarity	NPC116620
0.8381	Intermediate Similarity	NPC295791
0.8381	Intermediate Similarity	NPC137430
0.8381	Intermediate Similarity	NPC235369
0.8378	Intermediate Similarity	NPC474181
0.8378	Intermediate Similarity	NPC473798
0.8365	Intermediate Similarity	NPC476274
0.8365	Intermediate Similarity	NPC201406
0.8365	Intermediate Similarity	NPC474012
0.8365	Intermediate Similarity	NPC476299
0.8364	Intermediate Similarity	NPC476801
0.8364	Intermediate Similarity	NPC472002
0.8364	Intermediate Similarity	NPC470063
0.8362	Intermediate Similarity	NPC8369
0.8362	Intermediate Similarity	NPC470922
0.8362	Intermediate Similarity	NPC24651
0.835	Intermediate Similarity	NPC51499
0.835	Intermediate Similarity	NPC473963
0.835	Intermediate Similarity	NPC70145
0.835	Intermediate Similarity	NPC170131
0.835	Intermediate Similarity	NPC91695
0.835	Intermediate Similarity	NPC84335
0.835	Intermediate Similarity	NPC38530
0.835	Intermediate Similarity	NPC253826
0.8348	Intermediate Similarity	NPC269642
0.8333	Intermediate Similarity	NPC90946
0.8333	Intermediate Similarity	NPC476961
0.8333	Intermediate Similarity	NPC300614
0.8333	Intermediate Similarity	NPC474727
0.8333	Intermediate Similarity	NPC476962
0.8333	Intermediate Similarity	NPC475263
0.8333	Intermediate Similarity	NPC139570
0.8333	Intermediate Similarity	NPC94529
0.8333	Intermediate Similarity	NPC90014
0.8333	Intermediate Similarity	NPC473483
0.8333	Intermediate Similarity	NPC98639
0.8319	Intermediate Similarity	NPC284707
0.8318	Intermediate Similarity	NPC88349
0.8318	Intermediate Similarity	NPC34768
0.8317	Intermediate Similarity	NPC474436
0.8317	Intermediate Similarity	NPC475657
0.8317	Intermediate Similarity	NPC139692
0.8317	Intermediate Similarity	NPC49776
0.8317	Intermediate Similarity	NPC63118
0.8304	Intermediate Similarity	NPC49492
0.8304	Intermediate Similarity	NPC268954

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 NPC275539 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1418
0.2-0.3	3496
0.3-0.4	2558
0.4-0.5	923
0.5-0.6	266
0.6-0.7	162
0.7-0.8	146
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8627	High Similarity	NPD7638	Approved
0.8544	High Similarity	NPD7640	Approved
0.8544	High Similarity	NPD7639	Approved
0.8173	Intermediate Similarity	NPD7902	Approved
0.8058	Intermediate Similarity	NPD7748	Approved
0.8039	Intermediate Similarity	NPD7515	Phase 2
0.7982	Intermediate Similarity	NPD6008	Approved
0.7925	Intermediate Similarity	NPD4225	Approved
0.7913	Intermediate Similarity	NPD7115	Discovery
0.7885	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD7900	Approved
0.787	Intermediate Similarity	NPD7632	Discontinued
0.7838	Intermediate Similarity	NPD6881	Approved
0.7838	Intermediate Similarity	NPD6899	Approved
0.7838	Intermediate Similarity	NPD6686	Approved
0.7833	Intermediate Similarity	NPD7507	Approved
0.7818	Intermediate Similarity	NPD6402	Approved
0.7818	Intermediate Similarity	NPD7128	Approved
0.7818	Intermediate Similarity	NPD5739	Approved
0.7818	Intermediate Similarity	NPD6675	Approved
0.7788	Intermediate Similarity	NPD6650	Approved
0.7788	Intermediate Similarity	NPD6649	Approved
0.7788	Intermediate Similarity	NPD6399	Phase 3
0.7768	Intermediate Similarity	NPD6372	Approved
0.7768	Intermediate Similarity	NPD6373	Approved
0.7768	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD5697	Approved
0.7699	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD7102	Approved
0.7699	Intermediate Similarity	NPD7290	Approved
0.7699	Intermediate Similarity	NPD6883	Approved
0.7692	Intermediate Similarity	NPD6079	Approved
0.7679	Intermediate Similarity	NPD6011	Approved
0.7679	Intermediate Similarity	NPD7320	Approved
0.767	Intermediate Similarity	NPD5328	Approved
0.7652	Intermediate Similarity	NPD4632	Approved
0.7642	Intermediate Similarity	NPD7319	Approved
0.7632	Intermediate Similarity	NPD8130	Phase 1
0.7632	Intermediate Similarity	NPD6617	Approved
0.7632	Intermediate Similarity	NPD6869	Approved
0.7632	Intermediate Similarity	NPD6847	Approved
0.7624	Intermediate Similarity	NPD1694	Approved
0.7611	Intermediate Similarity	NPD6013	Approved
0.7611	Intermediate Similarity	NPD6012	Approved
0.7611	Intermediate Similarity	NPD6014	Approved
0.7589	Intermediate Similarity	NPD5701	Approved
0.7565	Intermediate Similarity	NPD6053	Discontinued
0.7565	Intermediate Similarity	NPD6882	Approved
0.7565	Intermediate Similarity	NPD8297	Approved
0.7561	Intermediate Similarity	NPD7736	Approved
0.7549	Intermediate Similarity	NPD3618	Phase 1
0.7524	Intermediate Similarity	NPD8034	Phase 2
0.7524	Intermediate Similarity	NPD8035	Phase 2
0.7521	Intermediate Similarity	NPD8328	Phase 3
0.75	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD3573	Approved
0.7459	Intermediate Similarity	NPD7492	Approved
0.7458	Intermediate Similarity	NPD6009	Approved
0.7434	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6319	Approved
0.7417	Intermediate Similarity	NPD6054	Approved
0.7407	Intermediate Similarity	NPD5221	Approved
0.7407	Intermediate Similarity	NPD4697	Phase 3
0.7407	Intermediate Similarity	NPD5222	Approved
0.7407	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6616	Approved
0.7387	Intermediate Similarity	NPD5211	Phase 2
0.7377	Intermediate Similarity	NPD7604	Phase 2
0.7368	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD5285	Approved
0.7364	Intermediate Similarity	NPD5286	Approved
0.7364	Intermediate Similarity	NPD4696	Approved
0.7355	Intermediate Similarity	NPD5983	Phase 2
0.7339	Intermediate Similarity	NPD7078	Approved
0.7339	Intermediate Similarity	NPD5173	Approved
0.7339	Intermediate Similarity	NPD4755	Approved
0.7315	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5223	Approved
0.7295	Intermediate Similarity	NPD6370	Approved
0.729	Intermediate Similarity	NPD5778	Approved
0.729	Intermediate Similarity	NPD5779	Approved
0.7282	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6412	Phase 2
0.7273	Intermediate Similarity	NPD6059	Approved
0.7258	Intermediate Similarity	NPD6336	Discontinued
0.7257	Intermediate Similarity	NPD5141	Approved
0.725	Intermediate Similarity	NPD7327	Approved
0.725	Intermediate Similarity	NPD7328	Approved
0.725	Intermediate Similarity	NPD6335	Approved
0.7232	Intermediate Similarity	NPD4633	Approved
0.7232	Intermediate Similarity	NPD5226	Approved
0.7232	Intermediate Similarity	NPD5225	Approved
0.7232	Intermediate Similarity	NPD5224	Approved
0.7227	Intermediate Similarity	NPD6868	Approved
0.7227	Intermediate Similarity	NPD6274	Approved
0.7213	Intermediate Similarity	NPD8033	Approved
0.7213	Intermediate Similarity	NPD8517	Approved
0.7213	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6016	Approved
0.7213	Intermediate Similarity	NPD8516	Approved
0.7213	Intermediate Similarity	NPD8515	Approved
0.7213	Intermediate Similarity	NPD8513	Phase 3
0.7213	Intermediate Similarity	NPD6015	Approved
0.7212	Intermediate Similarity	NPD6684	Approved
0.7212	Intermediate Similarity	NPD6409	Approved
0.7212	Intermediate Similarity	NPD7146	Approved
0.7212	Intermediate Similarity	NPD5330	Approved
0.7212	Intermediate Similarity	NPD7521	Approved
0.7212	Intermediate Similarity	NPD7334	Approved
0.7207	Intermediate Similarity	NPD4700	Approved
0.72	Intermediate Similarity	NPD8293	Discontinued
0.7196	Intermediate Similarity	NPD6411	Approved
0.719	Intermediate Similarity	NPD7101	Approved
0.719	Intermediate Similarity	NPD7516	Approved
0.719	Intermediate Similarity	NPD7100	Approved
0.7184	Intermediate Similarity	NPD4786	Approved
0.7182	Intermediate Similarity	NPD6083	Phase 2
0.7182	Intermediate Similarity	NPD6084	Phase 2
0.7168	Intermediate Similarity	NPD5175	Approved
0.7168	Intermediate Similarity	NPD5174	Approved
0.7167	Intermediate Similarity	NPD6317	Approved
0.7157	Intermediate Similarity	NPD3667	Approved
0.7156	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5988	Approved
0.7131	Intermediate Similarity	NPD8377	Approved
0.7131	Intermediate Similarity	NPD8294	Approved
0.713	Intermediate Similarity	NPD4202	Approved
0.7109	Intermediate Similarity	NPD7260	Phase 2
0.7107	Intermediate Similarity	NPD6313	Approved
0.7107	Intermediate Similarity	NPD6314	Approved
0.7103	Intermediate Similarity	NPD46	Approved
0.7103	Intermediate Similarity	NPD6698	Approved
0.7094	Intermediate Similarity	NPD4634	Approved
0.7075	Intermediate Similarity	NPD6672	Approved
0.7075	Intermediate Similarity	NPD5737	Approved
0.7075	Intermediate Similarity	NPD6903	Approved
0.7073	Intermediate Similarity	NPD8379	Approved
0.7073	Intermediate Similarity	NPD8296	Approved
0.7073	Intermediate Similarity	NPD8378	Approved
0.7073	Intermediate Similarity	NPD8380	Approved
0.7073	Intermediate Similarity	NPD8335	Approved
0.7073	Intermediate Similarity	NPD7503	Approved
0.7059	Intermediate Similarity	NPD8133	Approved
0.7019	Intermediate Similarity	NPD3133	Approved
0.7019	Intermediate Similarity	NPD3666	Approved
0.7019	Intermediate Similarity	NPD3665	Phase 1
0.7018	Intermediate Similarity	NPD4754	Approved
0.7009	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6101	Approved
0.6991	Remote Similarity	NPD5344	Discontinued
0.6964	Remote Similarity	NPD5696	Approved
0.6949	Remote Similarity	NPD6371	Approved
0.6944	Remote Similarity	NPD5785	Approved
0.6935	Remote Similarity	NPD6909	Approved
0.6935	Remote Similarity	NPD6908	Approved
0.6923	Remote Similarity	NPD4729	Approved
0.6923	Remote Similarity	NPD5128	Approved
0.6923	Remote Similarity	NPD4730	Approved
0.6923	Remote Similarity	NPD6845	Suspended
0.6897	Remote Similarity	NPD4767	Approved
0.6897	Remote Similarity	NPD4768	Approved
0.6887	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5693	Phase 1
0.6875	Remote Similarity	NPD6033	Approved
0.6863	Remote Similarity	NPD7645	Phase 2
0.6847	Remote Similarity	NPD5695	Phase 3
0.6838	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6067	Discontinued
0.6807	Remote Similarity	NPD5248	Approved
0.6807	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5247	Approved
0.6807	Remote Similarity	NPD5135	Approved
0.6807	Remote Similarity	NPD5249	Phase 3
0.6807	Remote Similarity	NPD5169	Approved
0.6807	Remote Similarity	NPD5251	Approved
0.6807	Remote Similarity	NPD5250	Approved
0.6797	Remote Similarity	NPD8074	Phase 3
0.6796	Remote Similarity	NPD7525	Registered
0.6796	Remote Similarity	NPD4695	Discontinued
0.6786	Remote Similarity	NPD7614	Phase 1
0.678	Remote Similarity	NPD5168	Approved
0.6765	Remote Similarity	NPD6115	Approved
0.6765	Remote Similarity	NPD6118	Approved
0.6765	Remote Similarity	NPD6697	Approved
0.6765	Remote Similarity	NPD6114	Approved
0.6757	Remote Similarity	NPD6001	Approved
0.6754	Remote Similarity	NPD6648	Approved
0.675	Remote Similarity	NPD5215	Approved
0.675	Remote Similarity	NPD5216	Approved
0.675	Remote Similarity	NPD5217	Approved
0.675	Remote Similarity	NPD5127	Approved
0.675	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5284	Approved
0.6727	Remote Similarity	NPD5281	Approved
0.6727	Remote Similarity	NPD7637	Suspended

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data