NPASS Compound

Structure

NPC134077 OpenBabel07101718222D 32 36 0 0 1 0 0 0 0 0999 V2000 -1.3685 -1.2248 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 7.2350 -1.6340 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 3.2709 -2.5000 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 2.4049 -2.0000 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 -0.6994 -1.9680 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 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 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 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 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 C 0 0 0 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 2 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0084 -2.9190 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 0.2788 -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 1 16 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 17 2 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 24 1 0 0 0 0 12 27 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 29 2 0 0 0 0 16 31 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 18 27 1 1 0 0 0 19 25 1 1 0 0 0 19 26 1 0 0 0 0 20 25 1 1 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 21 26 1 1 0 0 0 22 30 2 0 0 0 0 22 32 1 0 0 0 0 23 31 1 6 0 0 0 23 32 1 0 0 0 0 25 4 1 1 0 0 0 26 5 1 1 0 0 0 27 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.29
Volume:	468.808
LogP:	4.964
LogD:	3.842
LogS:	-4.902
# Rotatable Bonds:	3
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.606
Synthetic Accessibility Score:	4.925
Fsp3:	0.852
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:	-4.703
MDCK Permeability:	3.1052044505486265e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	86.81269073486328%
Volume Distribution (VD):	1.637
Pgp-substrate:	9.704606056213379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.399
CYP2C9-inhibitor:	0.183
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.788
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.823
CYP3A4-substrate:	0.327

ADMET: Excretion

Clearance (CL):	6.751
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.657
Drug-inuced Liver Injury (DILI):	0.069
AMES Toxicity:	0.311
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.958
Carcinogencity:	0.825
Eye Corrosion:	0.787
Eye Irritation:	0.176
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC134077

Natural Product ID:	NPC134077
*Common Name:**	[(1R,5As,5Bs,7As,11Ar,11Bs,13As,13Br)-11A-(Hydroxymethyl)-5B,8,8,13A-Tetramethyl-3-Oxo-5,5A,6,7,7A,9,10,11,11B,12,13,13B-Dodecahydro-1H-Phenanthro[1,2-G][2]Benzofuran-1-Yl] Acetate
IUPAC Name:	[(1R,5aS,5bS,7aS,11aR,11bS,13aS,13bR)-11a-(hydroxymethyl)-5b,8,8,13a-tetramethyl-3-oxo-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[1,2-g][2]benzofuran-1-yl] acetate
Synonyms:
Standard InCHIKey:	HZNSTAFUGUGFAZ-JMJANOEMSA-N
Standard InCHI:	InChI=1S/C27H40O5/c1-16(29)31-23-21-17(22(30)32-23)7-8-19-25(4)13-9-18-24(2,3)11-6-12-27(18,15-28)20(25)10-14-26(19,21)5/h7,18-21,23,28H,6,8-15H2,1-5H3/t18-,19-,20-,21+,23+,25-,26-,27+/m0/s1
SMILES:	CC(=O)O[C@H]1[C@H]2C(=CC[C@H]3[C@]4(C)CC[C@H]5C(C)(C)CCC[C@]5(CO)[C@H]4CC[C@]23C)C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL573400
PubChem CID:	25159223
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
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497955]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
MIC	6
Others	1

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	22.5	ug.mL-1	PMID[492584]
NPT4391	Individual Protein	Isocitrate lyase	Magnaporthe oryzae (strain 70-15 / FGSC 8958) (Rice blast fungus)(Pyricularia oryzae)	IC50	>	100.0	ug.mL-1	PMID[492584]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[492584]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	1.56	ug.mL-1	PMID[492584]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	3.12	ug.mL-1	PMID[492584]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[492584]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	6.25	ug.mL-1	PMID[492584]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[492584]

☑ 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 NPC134077 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	199
0.1-0.2	1217
0.2-0.3	4320
0.3-0.4	10822
0.4-0.5	10728
0.5-0.6	6387
0.6-0.7	5953
0.7-0.8	2947
0.8-0.85	99
0.85-0.9	19
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC63249
0.9574	High Similarity	NPC204054
0.9574	High Similarity	NPC257726
0.9149	High Similarity	NPC166346
0.9043	High Similarity	NPC65513
0.9038	High Similarity	NPC157441
0.8969	High Similarity	NPC76266
0.8942	High Similarity	NPC12046
0.8942	High Similarity	NPC194951
0.8842	High Similarity	NPC165904
0.8842	High Similarity	NPC179517
0.8788	High Similarity	NPC477720
0.8687	High Similarity	NPC473154
0.8654	High Similarity	NPC112457
0.8646	High Similarity	NPC477783
0.8632	High Similarity	NPC168131
0.8558	High Similarity	NPC275539
0.8558	High Similarity	NPC189075
0.8557	High Similarity	NPC470656
0.8557	High Similarity	NPC267266
0.8557	High Similarity	NPC277721
0.8542	High Similarity	NPC477782
0.8511	High Similarity	NPC173917
0.8485	Intermediate Similarity	NPC325960
0.8485	Intermediate Similarity	NPC319692
0.8485	Intermediate Similarity	NPC112654
0.8462	Intermediate Similarity	NPC110496
0.8447	Intermediate Similarity	NPC222161
0.8438	Intermediate Similarity	NPC251528
0.8438	Intermediate Similarity	NPC174342
0.8404	Intermediate Similarity	NPC217394
0.84	Intermediate Similarity	NPC175351
0.84	Intermediate Similarity	NPC121402
0.84	Intermediate Similarity	NPC132753
0.84	Intermediate Similarity	NPC151681
0.84	Intermediate Similarity	NPC224356
0.8381	Intermediate Similarity	NPC325054
0.8367	Intermediate Similarity	NPC151722
0.8351	Intermediate Similarity	NPC159748
0.8351	Intermediate Similarity	NPC101651
0.835	Intermediate Similarity	NPC471208
0.8333	Intermediate Similarity	NPC471075
0.8316	Intermediate Similarity	NPC118266
0.8302	Intermediate Similarity	NPC476759
0.83	Intermediate Similarity	NPC472363
0.83	Intermediate Similarity	NPC472362
0.83	Intermediate Similarity	NPC154526
0.8288	Intermediate Similarity	NPC475834
0.8288	Intermediate Similarity	NPC474179
0.8283	Intermediate Similarity	NPC476415
0.8265	Intermediate Similarity	NPC141831
0.8247	Intermediate Similarity	NPC477973
0.8247	Intermediate Similarity	NPC5509
0.8247	Intermediate Similarity	NPC293044
0.8235	Intermediate Similarity	NPC477971
0.8235	Intermediate Similarity	NPC228251
0.8235	Intermediate Similarity	NPC20113
0.8235	Intermediate Similarity	NPC477968
0.8235	Intermediate Similarity	NPC477972
0.8235	Intermediate Similarity	NPC161527
0.8235	Intermediate Similarity	NPC219285
0.8218	Intermediate Similarity	NPC475709
0.8211	Intermediate Similarity	NPC106416
0.8211	Intermediate Similarity	NPC65661
0.8211	Intermediate Similarity	NPC86316
0.8208	Intermediate Similarity	NPC300614
0.8208	Intermediate Similarity	NPC177524
0.8208	Intermediate Similarity	NPC219900
0.8208	Intermediate Similarity	NPC392
0.8208	Intermediate Similarity	NPC90946
0.82	Intermediate Similarity	NPC183012
0.8198	Intermediate Similarity	NPC475913
0.8191	Intermediate Similarity	NPC22611
0.8191	Intermediate Similarity	NPC469
0.819	Intermediate Similarity	NPC127790
0.8182	Intermediate Similarity	NPC472303
0.8173	Intermediate Similarity	NPC254202
0.8163	Intermediate Similarity	NPC281942
0.8163	Intermediate Similarity	NPC232426
0.8137	Intermediate Similarity	NPC478056
0.8131	Intermediate Similarity	NPC31522
0.8125	Intermediate Similarity	NPC474062
0.8105	Intermediate Similarity	NPC71626
0.81	Intermediate Similarity	NPC298973
0.81	Intermediate Similarity	NPC324078
0.81	Intermediate Similarity	NPC469697
0.81	Intermediate Similarity	NPC474554
0.81	Intermediate Similarity	NPC104925
0.8081	Intermediate Similarity	NPC289479
0.8081	Intermediate Similarity	NPC186363
0.8081	Intermediate Similarity	NPC233345
0.8077	Intermediate Similarity	NPC165250
0.8077	Intermediate Similarity	NPC31058
0.8077	Intermediate Similarity	NPC469606
0.8077	Intermediate Similarity	NPC476769
0.8077	Intermediate Similarity	NPC273005
0.8058	Intermediate Similarity	NPC476767
0.8058	Intermediate Similarity	NPC477721
0.8058	Intermediate Similarity	NPC477716
0.8056	Intermediate Similarity	NPC476766
0.8056	Intermediate Similarity	NPC235014
0.8039	Intermediate Similarity	NPC170131
0.8039	Intermediate Similarity	NPC474343
0.8039	Intermediate Similarity	NPC477718
0.8039	Intermediate Similarity	NPC477719
0.8037	Intermediate Similarity	NPC476765
0.8037	Intermediate Similarity	NPC469844
0.8021	Intermediate Similarity	NPC473251
0.8021	Intermediate Similarity	NPC42586
0.8021	Intermediate Similarity	NPC30984
0.802	Intermediate Similarity	NPC473369
0.8019	Intermediate Similarity	NPC252296
0.8	Intermediate Similarity	NPC476889
0.8	Intermediate Similarity	NPC476416
0.8	Intermediate Similarity	NPC169343
0.8	Intermediate Similarity	NPC472440
0.8	Intermediate Similarity	NPC471364
0.8	Intermediate Similarity	NPC471365
0.8	Intermediate Similarity	NPC132395
0.7981	Intermediate Similarity	NPC235142
0.7981	Intermediate Similarity	NPC477717
0.798	Intermediate Similarity	NPC212679
0.798	Intermediate Similarity	NPC253186
0.798	Intermediate Similarity	NPC198818
0.798	Intermediate Similarity	NPC469595
0.798	Intermediate Similarity	NPC220454
0.798	Intermediate Similarity	NPC51486
0.7979	Intermediate Similarity	NPC229584
0.7979	Intermediate Similarity	NPC40228
0.7979	Intermediate Similarity	NPC14203
0.7961	Intermediate Similarity	NPC124703
0.7961	Intermediate Similarity	NPC194196
0.7961	Intermediate Similarity	NPC23364
0.7961	Intermediate Similarity	NPC234617
0.7961	Intermediate Similarity	NPC98868
0.7959	Intermediate Similarity	NPC226863
0.7946	Intermediate Similarity	NPC474483
0.7946	Intermediate Similarity	NPC473968
0.7944	Intermediate Similarity	NPC91034
0.7944	Intermediate Similarity	NPC184512
0.7944	Intermediate Similarity	NPC301666
0.7941	Intermediate Similarity	NPC470801
0.7941	Intermediate Similarity	NPC240673
0.7941	Intermediate Similarity	NPC8954
0.7941	Intermediate Similarity	NPC162346
0.7941	Intermediate Similarity	NPC73858
0.7941	Intermediate Similarity	NPC311166
0.7941	Intermediate Similarity	NPC17578
0.7941	Intermediate Similarity	NPC235053
0.7941	Intermediate Similarity	NPC94905
0.7925	Intermediate Similarity	NPC476764
0.7925	Intermediate Similarity	NPC476763
0.7921	Intermediate Similarity	NPC477129
0.7921	Intermediate Similarity	NPC477130
0.7921	Intermediate Similarity	NPC91010
0.7905	Intermediate Similarity	NPC476081
0.7905	Intermediate Similarity	NPC40918
0.7905	Intermediate Similarity	NPC476890
0.7905	Intermediate Similarity	NPC136289
0.7905	Intermediate Similarity	NPC238397
0.7905	Intermediate Similarity	NPC471363
0.79	Intermediate Similarity	NPC72845
0.79	Intermediate Similarity	NPC477122
0.7895	Intermediate Similarity	NPC186276
0.7895	Intermediate Similarity	NPC470312
0.7895	Intermediate Similarity	NPC200513
0.7885	Intermediate Similarity	NPC201406
0.7885	Intermediate Similarity	NPC474012
0.7885	Intermediate Similarity	NPC476299
0.7885	Intermediate Similarity	NPC47024
0.7881	Intermediate Similarity	NPC45606
0.7881	Intermediate Similarity	NPC220838
0.7879	Intermediate Similarity	NPC474396
0.7879	Intermediate Similarity	NPC470734
0.7879	Intermediate Similarity	NPC50488
0.7872	Intermediate Similarity	NPC195424
0.7872	Intermediate Similarity	NPC104545
0.787	Intermediate Similarity	NPC473483
0.7864	Intermediate Similarity	NPC98112
0.7864	Intermediate Similarity	NPC253826
0.7864	Intermediate Similarity	NPC476768
0.7864	Intermediate Similarity	NPC476253
0.7857	Intermediate Similarity	NPC44170
0.7857	Intermediate Similarity	NPC268954
0.7857	Intermediate Similarity	NPC312561
0.7857	Intermediate Similarity	NPC477228
0.785	Intermediate Similarity	NPC476760
0.785	Intermediate Similarity	NPC127609
0.785	Intermediate Similarity	NPC476761
0.785	Intermediate Similarity	NPC469607
0.785	Intermediate Similarity	NPC172867
0.785	Intermediate Similarity	NPC218158
0.785	Intermediate Similarity	NPC476762
0.7843	Intermediate Similarity	NPC477970
0.7843	Intermediate Similarity	NPC477969
0.7843	Intermediate Similarity	NPC209355
0.7843	Intermediate Similarity	NPC293052
0.7843	Intermediate Similarity	NPC100892
0.7843	Intermediate Similarity	NPC135224
0.7838	Intermediate Similarity	NPC474410

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 NPC134077 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1390
0.2-0.3	3704
0.3-0.4	2602
0.4-0.5	786
0.5-0.6	227
0.6-0.7	195
0.7-0.8	79
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8208	Intermediate Similarity	NPD6686	Approved
0.7895	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7902	Approved
0.7647	Intermediate Similarity	NPD6399	Phase 3
0.7619	Intermediate Similarity	NPD7638	Approved
0.7615	Intermediate Similarity	NPD6412	Phase 2
0.7573	Intermediate Similarity	NPD7748	Approved
0.7549	Intermediate Similarity	NPD7515	Phase 2
0.7547	Intermediate Similarity	NPD7640	Approved
0.7547	Intermediate Similarity	NPD7639	Approved
0.7478	Intermediate Similarity	NPD7115	Discovery
0.7453	Intermediate Similarity	NPD4225	Approved
0.7426	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7507	Approved
0.7404	Intermediate Similarity	NPD7900	Approved
0.7404	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6083	Phase 2
0.7358	Intermediate Similarity	NPD6084	Phase 2
0.73	Intermediate Similarity	NPD1694	Approved
0.7281	Intermediate Similarity	NPD6882	Approved
0.7255	Intermediate Similarity	NPD6672	Approved
0.7255	Intermediate Similarity	NPD5737	Approved
0.7236	Intermediate Similarity	NPD7319	Approved
0.7228	Intermediate Similarity	NPD5330	Approved
0.7228	Intermediate Similarity	NPD6684	Approved
0.7228	Intermediate Similarity	NPD7334	Approved
0.7228	Intermediate Similarity	NPD7521	Approved
0.7228	Intermediate Similarity	NPD7146	Approved
0.7228	Intermediate Similarity	NPD6409	Approved
0.72	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD7736	Approved
0.713	Intermediate Similarity	NPD5696	Approved
0.7119	Intermediate Similarity	NPD7328	Approved
0.7119	Intermediate Similarity	NPD7327	Approved
0.7107	Intermediate Similarity	NPD8328	Phase 3
0.7087	Intermediate Similarity	NPD6903	Approved
0.7083	Intermediate Similarity	NPD7503	Approved
0.7083	Intermediate Similarity	NPD8033	Approved
0.708	Intermediate Similarity	NPD6899	Approved
0.708	Intermediate Similarity	NPD6881	Approved
0.7069	Intermediate Similarity	NPD8133	Approved
0.7059	Intermediate Similarity	NPD7516	Approved
0.7059	Intermediate Similarity	NPD3618	Phase 1
0.7054	Intermediate Similarity	NPD7128	Approved
0.7054	Intermediate Similarity	NPD5739	Approved
0.7054	Intermediate Similarity	NPD6675	Approved
0.7054	Intermediate Similarity	NPD6402	Approved
0.7048	Intermediate Similarity	NPD8034	Phase 2
0.7048	Intermediate Similarity	NPD8035	Phase 2
0.7048	Intermediate Similarity	NPD5693	Phase 1
0.7043	Intermediate Similarity	NPD6650	Approved
0.7043	Intermediate Similarity	NPD6649	Approved
0.703	Intermediate Similarity	NPD3666	Approved
0.703	Intermediate Similarity	NPD4786	Approved
0.703	Intermediate Similarity	NPD3665	Phase 1
0.703	Intermediate Similarity	NPD3133	Approved
0.7018	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6373	Approved
0.7018	Intermediate Similarity	NPD6372	Approved
0.7009	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5695	Phase 3
0.7009	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3667	Approved
0.7	Intermediate Similarity	NPD8377	Approved
0.7	Intermediate Similarity	NPD8294	Approved
0.6991	Remote Similarity	NPD5697	Approved
0.697	Remote Similarity	NPD4695	Discontinued
0.6957	Remote Similarity	NPD7290	Approved
0.6957	Remote Similarity	NPD6883	Approved
0.6957	Remote Similarity	NPD7102	Approved
0.6952	Remote Similarity	NPD5785	Approved
0.6942	Remote Similarity	NPD8378	Approved
0.6942	Remote Similarity	NPD8335	Approved
0.6942	Remote Similarity	NPD8380	Approved
0.6942	Remote Similarity	NPD8379	Approved
0.6942	Remote Similarity	NPD8296	Approved
0.6937	Remote Similarity	NPD7632	Discontinued
0.693	Remote Similarity	NPD7320	Approved
0.693	Remote Similarity	NPD6011	Approved
0.6897	Remote Similarity	NPD6617	Approved
0.6897	Remote Similarity	NPD8130	Phase 1
0.6897	Remote Similarity	NPD6869	Approved
0.6897	Remote Similarity	NPD6847	Approved
0.6891	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5281	Approved
0.6887	Remote Similarity	NPD6079	Approved
0.6887	Remote Similarity	NPD5284	Approved
0.6885	Remote Similarity	NPD6370	Approved
0.687	Remote Similarity	NPD6012	Approved
0.687	Remote Similarity	NPD6014	Approved
0.687	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6013	Approved
0.6857	Remote Similarity	NPD6080	Approved
0.6857	Remote Similarity	NPD4753	Phase 2
0.6857	Remote Similarity	NPD6904	Approved
0.6857	Remote Similarity	NPD6673	Approved
0.6857	Remote Similarity	NPD5328	Approved
0.6852	Remote Similarity	NPD5210	Approved
0.6852	Remote Similarity	NPD4629	Approved
0.6842	Remote Similarity	NPD5701	Approved
0.6838	Remote Similarity	NPD6053	Discontinued
0.6838	Remote Similarity	NPD8297	Approved
0.6827	Remote Similarity	NPD3573	Approved
0.681	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD8513	Phase 3
0.6803	Remote Similarity	NPD8515	Approved
0.6803	Remote Similarity	NPD8517	Approved
0.6803	Remote Similarity	NPD8516	Approved
0.68	Remote Similarity	NPD8293	Discontinued
0.6796	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7614	Phase 1
0.6774	Remote Similarity	NPD7492	Approved
0.6754	Remote Similarity	NPD6008	Approved
0.6752	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6009	Approved
0.6731	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4623	Approved
0.6731	Remote Similarity	NPD4519	Discontinued
0.6729	Remote Similarity	NPD6411	Approved
0.6721	Remote Similarity	NPD6054	Approved
0.672	Remote Similarity	NPD6616	Approved
0.6698	Remote Similarity	NPD6051	Approved
0.6694	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7078	Approved
0.6637	Remote Similarity	NPD5211	Phase 2
0.6636	Remote Similarity	NPD5207	Approved
0.6636	Remote Similarity	NPD6698	Approved
0.6636	Remote Similarity	NPD5221	Approved
0.6636	Remote Similarity	NPD5222	Approved
0.6636	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4697	Phase 3
0.6636	Remote Similarity	NPD7732	Phase 3
0.6636	Remote Similarity	NPD46	Approved
0.6635	Remote Similarity	NPD5329	Approved
0.6633	Remote Similarity	NPD8039	Approved
0.6607	Remote Similarity	NPD5286	Approved
0.6607	Remote Similarity	NPD5285	Approved
0.6607	Remote Similarity	NPD4696	Approved
0.6607	Remote Similarity	NPD6404	Discontinued
0.6606	Remote Similarity	NPD6001	Approved
0.6604	Remote Similarity	NPD5208	Approved
0.6602	Remote Similarity	NPD4788	Approved
0.6585	Remote Similarity	NPD6059	Approved
0.6577	Remote Similarity	NPD4755	Approved
0.6577	Remote Similarity	NPD5173	Approved
0.6574	Remote Similarity	NPD6050	Approved
0.6571	Remote Similarity	NPD6098	Approved
0.6571	Remote Similarity	NPD5279	Phase 3
0.6557	Remote Similarity	NPD6335	Approved
0.6552	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5223	Approved
0.6542	Remote Similarity	NPD6101	Approved
0.6542	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4197	Approved
0.6538	Remote Similarity	NPD3668	Phase 3
0.6532	Remote Similarity	NPD6016	Approved
0.6532	Remote Similarity	NPD6015	Approved
0.6532	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6274	Approved
0.6529	Remote Similarity	NPD6868	Approved
0.6525	Remote Similarity	NPD6371	Approved
0.6522	Remote Similarity	NPD5141	Approved
0.6514	Remote Similarity	NPD5778	Approved
0.6514	Remote Similarity	NPD5779	Approved
0.6504	Remote Similarity	NPD7101	Approved
0.6504	Remote Similarity	NPD7100	Approved
0.65	Remote Similarity	NPD4632	Approved
0.6491	Remote Similarity	NPD5226	Approved
0.6491	Remote Similarity	NPD5225	Approved
0.6491	Remote Similarity	NPD5224	Approved
0.6491	Remote Similarity	NPD4633	Approved
0.6489	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5692	Phase 3
0.648	Remote Similarity	NPD5988	Approved
0.6476	Remote Similarity	NPD5363	Approved
0.6475	Remote Similarity	NPD6317	Approved
0.646	Remote Similarity	NPD4700	Approved
0.6436	Remote Similarity	NPD3617	Approved
0.6435	Remote Similarity	NPD6052	Approved
0.6435	Remote Similarity	NPD5174	Approved
0.6435	Remote Similarity	NPD5175	Approved
0.6423	Remote Similarity	NPD6313	Approved
0.6423	Remote Similarity	NPD6314	Approved
0.6422	Remote Similarity	NPD5694	Approved
0.6422	Remote Similarity	NPD7637	Suspended
0.6415	Remote Similarity	NPD4693	Phase 3
0.6415	Remote Similarity	NPD4688	Approved
0.6415	Remote Similarity	NPD4138	Approved
0.6415	Remote Similarity	NPD4690	Approved
0.6415	Remote Similarity	NPD5690	Phase 2
0.6415	Remote Similarity	NPD5205	Approved
0.6415	Remote Similarity	NPD4689	Approved
0.641	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7645	Phase 2

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