NPASS Compound

Structure

NPC227906 OpenBabel07101718272D 48 51 0 0 1 0 0 0 0 0999 V2000 11.8228 5.1586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4215 6.1766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 -4.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5000 -3.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0594 2.7315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8948 1.3225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3681 -3.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2459 4.5586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8838 1.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2405 4.4541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 -2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6582 3.7496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 -0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4771 2.0270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2961 0.3044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7137 -0.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7192 -0.2955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.0000 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 4.9504 -2.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8282 5.2631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -3.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0649 2.8360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3015 0.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9559 -2.7226 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 5.1314 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5382 -2.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 4.1369 -1.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5327 -2.1226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 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 28 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 32 1 0 0 0 0 8 33 1 0 0 0 0 9 34 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 14 25 1 0 0 0 0 15 28 2 0 0 0 0 16 29 2 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 30 2 0 0 0 0 20 32 1 0 0 0 0 21 31 2 0 0 0 0 22 23 1 0 0 0 0 22 32 2 0 0 0 0 23 35 1 0 0 0 0 24 26 2 0 0 0 0 24 36 1 0 0 0 0 25 44 1 0 0 0 0 26 44 1 0 0 0 0 27 33 2 0 0 0 0 27 37 1 0 0 0 0 33 38 1 0 0 0 0 34 39 2 0 0 0 0 34 40 1 0 0 0 0 35 37 2 0 0 0 0 35 41 1 0 0 0 0 36 42 2 0 0 0 0 36 43 1 0 0 0 0 37 45 1 0 0 0 0 38 39 1 0 0 0 0 38 41 2 0 0 0 0 39 42 1 0 0 0 0 40 43 2 0 0 0 0 40 46 1 0 0 0 0 41 47 1 0 0 0 0 42 47 1 0 0 0 0 43 48 1 0 0 0 0 44 10 1 1 0 0 0 44 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	650.43
Volume:	738.877
LogP:	11.688
LogD:	7.198
LogS:	-4.868
# Rotatable Bonds:	14
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.17
Synthetic Accessibility Score:	4.435
Fsp3:	0.455
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.179
MDCK Permeability:	1.4214416296454147e-05
Pgp-inhibitor:	0.24
Pgp-substrate:	0.817
Human Intestinal Absorption (HIA):	0.067
20% Bioavailability (F20%):	0.941
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	103.0304946899414%
Volume Distribution (VD):	3.019
Pgp-substrate:	2.9943981170654297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.175
CYP1A2-substrate:	0.161
CYP2C19-inhibitor:	0.575
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.737
CYP2C9-substrate:	0.985
CYP2D6-inhibitor:	0.354
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.172
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	4.679
Half-life (T1/2):	0.018

ADMET: Toxicity

hERG Blockers:	0.203
Human Hepatotoxicity (H-HT):	0.99
Drug-inuced Liver Injury (DILI):	0.75
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.957
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.273
Respiratory Toxicity:	0.606

Download Data

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

Natural Product: NPC227906

Natural Product ID:	NPC227906
*Common Name:**	Albatrelin D
IUPAC Name:	(3R)-3-[(3E)-4,8-dimethylnona-3,7-dienyl]-3,6,7-trimethyl-10-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]-[1]benzofuro[2,3-f]chromene-5,9-diol
Synonyms:	Albatrelin D
Standard InCHIKey:	URKKJJQZOARVCY-IMZRLPGDSA-N
Standard InCHI:	InChI=1S/C44H58O4/c1-28(2)15-11-17-30(5)19-13-20-32(7)22-23-35-37(45)27-33(8)38-39-34(9)40(46)43-36(42(39)47-41(35)38)24-26-44(10,48-43)25-14-21-31(6)18-12-16-29(3)4/h15-16,19,21-22,24,26-27,45-46H,11-14,17-18,20,23,25H2,1-10H3/b30-19+,31-21+,32-22+/t44-/m1/s1
SMILES:	CC(=CCC/C(=C/CC/C(=C/Cc1c(cc(C)c2c3c(C)c(c4c(C=C[C@@](C)(CC/C=C(C)/CCC=C(C)C)O4)c3oc12)O)O)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332226
PubChem CID:	71524351
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23305465]
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[538496]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[538496]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[538496]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	40000.0	nM	PMID[538496]

☑ 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 NPC227906 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	479
0.1-0.2	1852
0.2-0.3	4161
0.3-0.4	11222
0.4-0.5	7074
0.5-0.6	3783
0.6-0.7	5401
0.7-0.8	5935
0.8-0.85	1713
0.85-0.9	931
0.9-0.95	145
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.939	High Similarity	NPC37870
0.9387	High Similarity	NPC270837
0.9341	High Similarity	NPC310794
0.9333	High Similarity	NPC126204
0.9329	High Similarity	NPC39306
0.9325	High Similarity	NPC294965
0.9273	High Similarity	NPC39091
0.9268	High Similarity	NPC207690
0.9268	High Similarity	NPC23298
0.9268	High Similarity	NPC236132
0.9268	High Similarity	NPC133065
0.9268	High Similarity	NPC189473
0.9264	High Similarity	NPC66288
0.9231	High Similarity	NPC49667
0.9231	High Similarity	NPC8127
0.9222	High Similarity	NPC101107
0.9217	High Similarity	NPC247973
0.9212	High Similarity	NPC472450
0.9212	High Similarity	NPC239752
0.9212	High Similarity	NPC275780
0.9207	High Similarity	NPC84515
0.9207	High Similarity	NPC312056
0.9202	High Similarity	NPC119224
0.9202	High Similarity	NPC320359
0.9176	High Similarity	NPC77179
0.9176	High Similarity	NPC23553
0.9162	High Similarity	NPC475805
0.9162	High Similarity	NPC476637
0.9157	High Similarity	NPC277480
0.9157	High Similarity	NPC170245
0.9157	High Similarity	NPC472449
0.9146	High Similarity	NPC40491
0.9146	High Similarity	NPC61010
0.9146	High Similarity	NPC188486
0.9146	High Similarity	NPC278052
0.9141	High Similarity	NPC100123
0.9118	High Similarity	NPC216307
0.9112	High Similarity	NPC82217
0.9112	High Similarity	NPC65885
0.9112	High Similarity	NPC216842
0.9112	High Similarity	NPC476640
0.9112	High Similarity	NPC473834
0.9102	High Similarity	NPC50394
0.9102	High Similarity	NPC218226
0.9102	High Similarity	NPC470704
0.9096	High Similarity	NPC326520
0.9096	High Similarity	NPC37183
0.9091	High Similarity	NPC25152
0.9091	High Similarity	NPC329760
0.9091	High Similarity	NPC229632
0.9085	High Similarity	NPC56085
0.9085	High Similarity	NPC471973
0.9085	High Similarity	NPC14353
0.9085	High Similarity	NPC204290
0.9085	High Similarity	NPC139036
0.9085	High Similarity	NPC228785
0.9085	High Similarity	NPC476980
0.908	High Similarity	NPC136674
0.908	High Similarity	NPC268360
0.908	High Similarity	NPC236796
0.9064	High Similarity	NPC221820
0.9059	High Similarity	NPC287243
0.9053	High Similarity	NPC54098
0.9053	High Similarity	NPC230619
0.9053	High Similarity	NPC174700
0.9048	High Similarity	NPC247136
0.9042	High Similarity	NPC43319
0.9036	High Similarity	NPC7483
0.9036	High Similarity	NPC152659
0.9036	High Similarity	NPC236521
0.9036	High Similarity	NPC248638
0.9036	High Similarity	NPC475985
0.9036	High Similarity	NPC197168
0.9036	High Similarity	NPC220313
0.9034	High Similarity	NPC60848
0.903	High Similarity	NPC474351
0.903	High Similarity	NPC259456
0.903	High Similarity	NPC278427
0.903	High Similarity	NPC475883
0.903	High Similarity	NPC29876
0.903	High Similarity	NPC167678
0.903	High Similarity	NPC474187
0.9024	High Similarity	NPC196879
0.9024	High Similarity	NPC474290
0.9024	High Similarity	NPC16935
0.9024	High Similarity	NPC476242
0.9018	High Similarity	NPC191146
0.9018	High Similarity	NPC68093
0.9018	High Similarity	NPC274730
0.9018	High Similarity	NPC142339
0.9017	High Similarity	NPC246153
0.9017	High Similarity	NPC240508
0.9017	High Similarity	NPC228209
0.9012	High Similarity	NPC476631
0.8994	High Similarity	NPC476641
0.8994	High Similarity	NPC131866
0.8982	High Similarity	NPC25361
0.8982	High Similarity	NPC36320
0.8982	High Similarity	NPC303174
0.8982	High Similarity	NPC45449
0.8982	High Similarity	NPC156432
0.8976	High Similarity	NPC83922
0.8976	High Similarity	NPC81679
0.8976	High Similarity	NPC472448
0.8976	High Similarity	NPC470694
0.8976	High Similarity	NPC201800
0.897	High Similarity	NPC235018
0.897	High Similarity	NPC200746
0.897	High Similarity	NPC80375
0.897	High Similarity	NPC474287
0.897	High Similarity	NPC475886
0.897	High Similarity	NPC45146
0.8963	High Similarity	NPC476981
0.8963	High Similarity	NPC300727
0.8963	High Similarity	NPC165977
0.8963	High Similarity	NPC246647
0.8963	High Similarity	NPC217677
0.8963	High Similarity	NPC273843
0.8963	High Similarity	NPC96342
0.8963	High Similarity	NPC212967
0.8963	High Similarity	NPC164110
0.8963	High Similarity	NPC476630
0.8963	High Similarity	NPC78225
0.8963	High Similarity	NPC241904
0.8963	High Similarity	NPC218871
0.8957	High Similarity	NPC472280
0.8957	High Similarity	NPC297531
0.8957	High Similarity	NPC99199
0.8957	High Similarity	NPC213936
0.8953	High Similarity	NPC297807
0.8951	High Similarity	NPC249570
0.8929	High Similarity	NPC53640
0.8922	High Similarity	NPC59295
0.8922	High Similarity	NPC477689
0.8922	High Similarity	NPC303460
0.8922	High Similarity	NPC1706
0.8922	High Similarity	NPC306321
0.8922	High Similarity	NPC1755
0.8922	High Similarity	NPC263092
0.8922	High Similarity	NPC186686
0.8922	High Similarity	NPC39305
0.8922	High Similarity	NPC146134
0.8916	High Similarity	NPC258331
0.8916	High Similarity	NPC32694
0.8916	High Similarity	NPC474186
0.8916	High Similarity	NPC311740
0.8909	High Similarity	NPC235448
0.8908	High Similarity	NPC150977
0.8908	High Similarity	NPC8927
0.8902	High Similarity	NPC183843
0.8902	High Similarity	NPC13779
0.8902	High Similarity	NPC45131
0.8902	High Similarity	NPC180924
0.8902	High Similarity	NPC475799
0.8902	High Similarity	NPC476273
0.8902	High Similarity	NPC472455
0.8902	High Similarity	NPC138243
0.8902	High Similarity	NPC471985
0.8902	High Similarity	NPC472907
0.8902	High Similarity	NPC276444
0.8896	High Similarity	NPC69394
0.8896	High Similarity	NPC235333
0.8896	High Similarity	NPC231018
0.8896	High Similarity	NPC472462
0.8896	High Similarity	NPC47781
0.8896	High Similarity	NPC72370
0.8896	High Similarity	NPC160951
0.8896	High Similarity	NPC176775
0.8896	High Similarity	NPC22519
0.8896	High Similarity	NPC183878
0.8896	High Similarity	NPC145379
0.8896	High Similarity	NPC274327
0.8896	High Similarity	NPC89474
0.8896	High Similarity	NPC255350
0.8895	High Similarity	NPC164384
0.8889	High Similarity	NPC30550
0.8889	High Similarity	NPC261471
0.8882	High Similarity	NPC78830
0.8882	High Similarity	NPC472276
0.8882	High Similarity	NPC109827
0.8882	High Similarity	NPC124470
0.8882	High Similarity	NPC218533
0.8876	High Similarity	NPC6588
0.8876	High Similarity	NPC477154
0.8876	High Similarity	NPC117854
0.887	High Similarity	NPC295436
0.8869	High Similarity	NPC29411
0.8869	High Similarity	NPC473286
0.8869	High Similarity	NPC26386
0.8869	High Similarity	NPC293319
0.8864	High Similarity	NPC240808
0.8862	High Similarity	NPC238995
0.8862	High Similarity	NPC474162
0.8862	High Similarity	NPC472402
0.8862	High Similarity	NPC261470
0.8862	High Similarity	NPC474150
0.8862	High Similarity	NPC272722
0.8857	High Similarity	NPC476170
0.8855	High Similarity	NPC328102
0.8855	High Similarity	NPC246478

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 NPC227906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	421
0.1-0.2	1008
0.2-0.3	1709
0.3-0.4	2827
0.4-0.5	1758
0.5-0.6	904
0.6-0.7	362
0.7-0.8	136
0.8-0.85	15
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8896	High Similarity	NPD2801	Approved
0.8706	High Similarity	NPD7473	Discontinued
0.8639	High Similarity	NPD6232	Discontinued
0.8554	High Similarity	NPD2393	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD1934	Approved
0.8457	Intermediate Similarity	NPD1511	Approved
0.8452	Intermediate Similarity	NPD3882	Suspended
0.8412	Intermediate Similarity	NPD5494	Approved
0.8391	Intermediate Similarity	NPD5844	Phase 1
0.8354	Intermediate Similarity	NPD1512	Approved
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8256	Intermediate Similarity	NPD1247	Approved
0.8218	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD6166	Phase 2
0.8218	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD3749	Approved
0.8182	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6959	Discontinued
0.8146	Intermediate Similarity	NPD6559	Discontinued
0.8132	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7819	Suspended
0.8079	Intermediate Similarity	NPD7054	Approved
0.8072	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3817	Phase 2
0.8057	Intermediate Similarity	NPD3926	Phase 2
0.8034	Intermediate Similarity	NPD7074	Phase 3
0.8034	Intermediate Similarity	NPD7472	Approved
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD2533	Approved
0.7964	Intermediate Similarity	NPD2532	Approved
0.7964	Intermediate Similarity	NPD2534	Approved
0.7941	Intermediate Similarity	NPD4380	Phase 2
0.7931	Intermediate Similarity	NPD919	Approved
0.7919	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7808	Phase 3
0.7874	Intermediate Similarity	NPD7075	Discontinued
0.7845	Intermediate Similarity	NPD7251	Discontinued
0.7803	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2800	Approved
0.7758	Intermediate Similarity	NPD2344	Approved
0.7754	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7768	Phase 2
0.7692	Intermediate Similarity	NPD7390	Discontinued
0.7676	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3226	Approved
0.767	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1243	Approved
0.7661	Intermediate Similarity	NPD920	Approved
0.7651	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6801	Discontinued
0.7636	Intermediate Similarity	NPD1510	Phase 2
0.7636	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD8434	Phase 2
0.763	Intermediate Similarity	NPD6599	Discontinued
0.7627	Intermediate Similarity	NPD6234	Discontinued
0.7622	Intermediate Similarity	NPD1607	Approved
0.7619	Intermediate Similarity	NPD3750	Approved
0.7611	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD943	Approved
0.7605	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1549	Phase 2
0.7596	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6099	Approved
0.759	Intermediate Similarity	NPD2796	Approved
0.759	Intermediate Similarity	NPD6100	Approved
0.7586	Intermediate Similarity	NPD7411	Suspended
0.7574	Intermediate Similarity	NPD2309	Approved
0.7557	Intermediate Similarity	NPD5402	Approved
0.7545	Intermediate Similarity	NPD2346	Discontinued
0.7544	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD1240	Approved
0.7485	Intermediate Similarity	NPD6799	Approved
0.7485	Intermediate Similarity	NPD2935	Discontinued
0.7474	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD8312	Approved
0.7473	Intermediate Similarity	NPD8313	Approved
0.7459	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD7783	Phase 2
0.745	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD37	Approved
0.7442	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7228	Approved
0.7427	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4625	Phase 3
0.7416	Intermediate Similarity	NPD4967	Phase 2
0.7416	Intermediate Similarity	NPD4965	Approved
0.7416	Intermediate Similarity	NPD4966	Approved
0.7403	Intermediate Similarity	NPD7229	Phase 3
0.7403	Intermediate Similarity	NPD5711	Approved
0.7403	Intermediate Similarity	NPD5710	Approved
0.7362	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD8150	Discontinued
0.735	Intermediate Similarity	NPD8151	Discontinued
0.7337	Intermediate Similarity	NPD3751	Discontinued
0.7326	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7870	Phase 2
0.7323	Intermediate Similarity	NPD7871	Phase 2
0.7321	Intermediate Similarity	NPD3748	Approved
0.731	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3787	Discontinued
0.7301	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6781	Approved
0.7296	Intermediate Similarity	NPD6777	Approved
0.7296	Intermediate Similarity	NPD6776	Approved
0.7296	Intermediate Similarity	NPD6782	Approved
0.7296	Intermediate Similarity	NPD6780	Approved
0.7296	Intermediate Similarity	NPD6778	Approved
0.7296	Intermediate Similarity	NPD6779	Approved
0.7283	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4287	Approved
0.7273	Intermediate Similarity	NPD7697	Approved
0.7273	Intermediate Similarity	NPD7435	Discontinued
0.7273	Intermediate Similarity	NPD7698	Approved
0.7273	Intermediate Similarity	NPD7696	Phase 3
0.7251	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD447	Suspended
0.7243	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1471	Phase 3
0.7219	Intermediate Similarity	NPD2799	Discontinued
0.7214	Intermediate Similarity	NPD7701	Phase 2
0.7212	Intermediate Similarity	NPD7907	Approved
0.7209	Intermediate Similarity	NPD4628	Phase 3
0.7186	Intermediate Similarity	NPD1613	Approved
0.7186	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7685	Pre-registration
0.7176	Intermediate Similarity	NPD5408	Approved
0.7176	Intermediate Similarity	NPD1551	Phase 2
0.7176	Intermediate Similarity	NPD5406	Approved
0.7176	Intermediate Similarity	NPD5404	Approved
0.7176	Intermediate Similarity	NPD5405	Approved
0.7169	Intermediate Similarity	NPD2313	Discontinued
0.7159	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7874	Approved
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7136	Intermediate Similarity	NPD6823	Phase 2
0.7112	Intermediate Similarity	NPD7286	Phase 2
0.7111	Intermediate Similarity	NPD5760	Phase 2
0.7111	Intermediate Similarity	NPD5761	Phase 2
0.7108	Intermediate Similarity	NPD3027	Phase 3
0.7108	Intermediate Similarity	NPD7801	Approved
0.7107	Intermediate Similarity	NPD7700	Phase 2
0.7107	Intermediate Similarity	NPD7699	Phase 2
0.7101	Intermediate Similarity	NPD6651	Approved
0.7079	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2296	Approved
0.7066	Intermediate Similarity	NPD3764	Approved
0.7066	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5401	Approved
0.7045	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6535	Approved
0.7041	Intermediate Similarity	NPD6534	Approved
0.7037	Intermediate Similarity	NPD5953	Discontinued
0.7035	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4111	Phase 1
0.7033	Intermediate Similarity	NPD4665	Approved
0.7022	Intermediate Similarity	NPD1653	Approved
0.7012	Intermediate Similarity	NPD6696	Suspended
0.7	Intermediate Similarity	NPD7240	Approved
0.6979	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6190	Approved
0.697	Remote Similarity	NPD1470	Approved
0.6964	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD2403	Approved
0.6933	Remote Similarity	NPD1201	Approved
0.6931	Remote Similarity	NPD7680	Approved
0.6919	Remote Similarity	NPD4361	Phase 2
0.6919	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4308	Phase 3
0.6915	Remote Similarity	NPD2494	Approved
0.6915	Remote Similarity	NPD2493	Approved
0.6914	Remote Similarity	NPD7003	Approved
0.6914	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7458	Discontinued
0.6887	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD9494	Approved
0.6882	Remote Similarity	NPD8127	Discontinued
0.6878	Remote Similarity	NPD7177	Discontinued
0.6869	Remote Similarity	NPD4360	Phase 2
0.6869	Remote Similarity	NPD4363	Phase 3
0.6864	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3268	Approved
0.6848	Remote Similarity	NPD4749	Approved
0.6848	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4908	Phase 1
0.6842	Remote Similarity	NPD1933	Approved
0.6836	Remote Similarity	NPD3300	Phase 2
0.6832	Remote Similarity	NPD3452	Approved
0.6832	Remote Similarity	NPD3450	Approved
0.6831	Remote Similarity	NPD8455	Phase 2
0.6829	Remote Similarity	NPD7584	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