NPASS Compound

Structure

NPC289700 OpenBabel07101719152D 41 46 0 0 1 0 0 0 0 0999 V2000 2.1913 3.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 4.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4980 5.4543 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 0.8660 2.5000 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 4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.1910 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 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 3.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 3.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 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 -5.1962 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4762 5.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7852 6.6132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 0.5865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 4.9190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 3 2 0 0 0 0 2 16 1 0 0 0 0 3 22 1 0 0 0 0 4 9 1 0 0 0 0 4 17 1 0 0 0 0 5 8 1 0 0 0 0 5 19 1 0 0 0 0 6 10 1 0 0 0 0 6 20 1 0 0 0 0 7 11 1 0 0 0 0 7 18 1 0 0 0 0 8 27 1 0 0 0 0 9 28 1 0 0 0 0 10 29 1 0 0 0 0 11 30 1 0 0 0 0 12 17 1 0 0 0 0 12 29 1 0 0 0 0 13 31 1 0 0 0 0 14 16 2 0 0 0 0 14 39 1 0 0 0 0 15 28 1 0 0 0 0 15 32 2 0 0 0 0 16 18 1 0 0 0 0 17 40 1 1 0 0 0 18 27 1 1 0 0 0 19 20 1 0 0 0 0 19 28 1 1 0 0 0 20 30 1 6 0 0 0 21 13 1 6 0 0 0 21 23 1 0 0 0 0 21 41 1 0 0 0 0 22 33 2 0 0 0 0 22 39 1 0 0 0 0 23 24 1 0 0 0 0 23 34 1 1 0 0 0 24 25 1 0 0 0 0 24 35 1 6 0 0 0 25 26 1 0 0 0 0 25 36 1 1 0 0 0 26 40 1 6 0 0 0 26 41 1 0 0 0 0 27 30 1 1 0 0 0 28 29 1 1 0 0 0 29 37 1 1 0 0 0 30 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.27
Volume:	562.244
LogP:	0.105
LogD:	-0.18
LogS:	-2.861
# Rotatable Bonds:	5
TPSA:	187.12
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	5.248
Fsp3:	0.8
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.504
MDCK Permeability:	5.080594200990163e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.947
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.241
Plasma Protein Binding (PPB):	44.810142517089844%
Volume Distribution (VD):	0.476
Pgp-substrate:	23.519437789916992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.686
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	1.892
Half-life (T1/2):	0.477

ADMET: Toxicity

hERG Blockers:	0.224
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.479
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.554
Carcinogencity:	0.926
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC289700

Natural Product ID:	NPC289700
*Common Name:**	5Beta,14Beta-Dihydroxy-19-Oxo-3Beta-[(Beta-D-Glucopyranosyl)Oxy)]Bufa-20,22-Dienolide
IUPAC Name:	(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(6-oxopyran-3-yl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms:
Standard InCHIKey:	AXUYMUBJXHVZEL-DBOUUHTQSA-N
Standard InCHI:	InChI=1S/C30H42O11/c1-27-8-5-19-20(30(27,38)11-7-18(27)16-2-3-22(33)39-14-16)6-10-29(37)12-17(4-9-28(19,29)15-32)40-26-25(36)24(35)23(34)21(13-31)41-26/h2-3,14-15,17-21,23-26,31,34-38H,4-13H2,1H3/t17-,18+,19-,20+,21+,23+,24-,25+,26+,27+,28-,29-,30-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@](C2)(O)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3c2ccc(=O)oc2)C)C=O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446052
PubChem CID:	3055779
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001557] Bufanolides and derivatives

*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
NPO6205	Helleborus orientalis	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12608856]

☑ 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
NPT924	Cell Line	HSC-2	Homo sapiens	IC50	=	0.0029	ug.mL-1	PMID[540285]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	0.0086	ug.mL-1	PMID[540285]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	0.23	ug.mL-1	PMID[540285]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.082	ug.mL-1	PMID[540285]

☑ 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 NPC289700 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	416
0.1-0.2	1541
0.2-0.3	3023
0.3-0.4	5807
0.4-0.5	9750
0.5-0.6	9346
0.6-0.7	9199
0.7-0.8	3271
0.8-0.85	230
0.85-0.9	85
0.9-0.95	25
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC62172
0.9841	High Similarity	NPC75616
0.952	High Similarity	NPC155529
0.937	High Similarity	NPC248703
0.9297	High Similarity	NPC158350
0.9225	High Similarity	NPC127656
0.9206	High Similarity	NPC86159
0.9206	High Similarity	NPC471358
0.9206	High Similarity	NPC471361
0.9206	High Similarity	NPC9499
0.9206	High Similarity	NPC469751
0.9206	High Similarity	NPC471352
0.9206	High Similarity	NPC469754
0.9206	High Similarity	NPC251866
0.9206	High Similarity	NPC197707
0.9206	High Similarity	NPC180079
0.9206	High Similarity	NPC70542
0.9206	High Similarity	NPC219085
0.9206	High Similarity	NPC471360
0.9206	High Similarity	NPC17896
0.9206	High Similarity	NPC469753
0.9206	High Similarity	NPC284406
0.9206	High Similarity	NPC10823
0.9206	High Similarity	NPC469755
0.9206	High Similarity	NPC471359
0.9206	High Similarity	NPC89514
0.9206	High Similarity	NPC469752
0.9206	High Similarity	NPC6108
0.9141	High Similarity	NPC469749
0.9141	High Similarity	NPC146857
0.9141	High Similarity	NPC247190
0.9141	High Similarity	NPC116075
0.9141	High Similarity	NPC32793
0.9113	High Similarity	NPC55602
0.907	High Similarity	NPC329636
0.9048	High Similarity	NPC471356
0.9048	High Similarity	NPC471357
0.9048	High Similarity	NPC179412
0.9048	High Similarity	NPC117702
0.9048	High Similarity	NPC146456
0.9048	High Similarity	NPC469757
0.9	High Similarity	NPC194716
0.8968	High Similarity	NPC250556
0.8968	High Similarity	NPC469750
0.8931	High Similarity	NPC59288
0.8931	High Similarity	NPC329675
0.8915	High Similarity	NPC93416
0.8906	High Similarity	NPC125077
0.8906	High Similarity	NPC329986
0.8906	High Similarity	NPC276838
0.8906	High Similarity	NPC232785
0.8906	High Similarity	NPC188234
0.8906	High Similarity	NPC140092
0.8871	High Similarity	NPC184555
0.8837	High Similarity	NPC173347
0.8837	High Similarity	NPC253456
0.8837	High Similarity	NPC16569
0.8837	High Similarity	NPC159338
0.881	High Similarity	NPC27363
0.8769	High Similarity	NPC42670
0.8769	High Similarity	NPC19124
0.876	High Similarity	NPC91
0.875	High Similarity	NPC329784
0.875	High Similarity	NPC240070
0.8702	High Similarity	NPC225385
0.8702	High Similarity	NPC157817
0.8702	High Similarity	NPC298783
0.8702	High Similarity	NPC104585
0.8702	High Similarity	NPC477709
0.8702	High Similarity	NPC476221
0.8682	High Similarity	NPC245094
0.8682	High Similarity	NPC311534
0.8615	High Similarity	NPC476966
0.8594	High Similarity	NPC233041
0.8571	High Similarity	NPC114939
0.8571	High Similarity	NPC145074
0.8571	High Similarity	NPC171619
0.8571	High Similarity	NPC41123
0.8561	High Similarity	NPC142756
0.8561	High Similarity	NPC88668
0.8527	High Similarity	NPC179261
0.8527	High Similarity	NPC159499
0.8485	Intermediate Similarity	NPC231240
0.8485	Intermediate Similarity	NPC471855
0.8473	Intermediate Similarity	NPC221414
0.845	Intermediate Similarity	NPC318135
0.8425	Intermediate Similarity	NPC470312
0.8425	Intermediate Similarity	NPC281840
0.8425	Intermediate Similarity	NPC257610
0.8421	Intermediate Similarity	NPC316915
0.8387	Intermediate Similarity	NPC73050
0.8372	Intermediate Similarity	NPC41129
0.8359	Intermediate Similarity	NPC233500
0.8333	Intermediate Similarity	NPC243196
0.8333	Intermediate Similarity	NPC471354
0.8333	Intermediate Similarity	NPC474483
0.8333	Intermediate Similarity	NPC27507
0.8333	Intermediate Similarity	NPC196429
0.8333	Intermediate Similarity	NPC471351
0.8333	Intermediate Similarity	NPC471353
0.8333	Intermediate Similarity	NPC474418
0.8333	Intermediate Similarity	NPC142066
0.8333	Intermediate Similarity	NPC309034
0.8333	Intermediate Similarity	NPC34390
0.8333	Intermediate Similarity	NPC84987
0.8333	Intermediate Similarity	NPC158344
0.8333	Intermediate Similarity	NPC99728
0.8333	Intermediate Similarity	NPC50305
0.8333	Intermediate Similarity	NPC77319
0.8333	Intermediate Similarity	NPC231529
0.8333	Intermediate Similarity	NPC244402
0.8333	Intermediate Similarity	NPC471355
0.8333	Intermediate Similarity	NPC157376
0.8333	Intermediate Similarity	NPC471407
0.8333	Intermediate Similarity	NPC87250
0.8333	Intermediate Similarity	NPC473852
0.8308	Intermediate Similarity	NPC241456
0.8308	Intermediate Similarity	NPC32868
0.8295	Intermediate Similarity	NPC196130
0.8281	Intermediate Similarity	NPC476150
0.8281	Intermediate Similarity	NPC475629
0.8281	Intermediate Similarity	NPC475136
0.8281	Intermediate Similarity	NPC476127
0.8281	Intermediate Similarity	NPC475556
0.8281	Intermediate Similarity	NPC474466
0.8271	Intermediate Similarity	NPC213634
0.8268	Intermediate Similarity	NPC13710
0.8268	Intermediate Similarity	NPC473617
0.8268	Intermediate Similarity	NPC83287
0.8268	Intermediate Similarity	NPC473828
0.8258	Intermediate Similarity	NPC473620
0.8258	Intermediate Similarity	NPC477490
0.8258	Intermediate Similarity	NPC473888
0.8258	Intermediate Similarity	NPC114306
0.8254	Intermediate Similarity	NPC199428
0.8254	Intermediate Similarity	NPC72772
0.8254	Intermediate Similarity	NPC99620
0.8254	Intermediate Similarity	NPC5311
0.8254	Intermediate Similarity	NPC469794
0.8254	Intermediate Similarity	NPC310341
0.8254	Intermediate Similarity	NPC193382
0.8235	Intermediate Similarity	NPC190065
0.8235	Intermediate Similarity	NPC471089
0.8235	Intermediate Similarity	NPC141215
0.8231	Intermediate Similarity	NPC204812
0.8231	Intermediate Similarity	NPC6193
0.8217	Intermediate Similarity	NPC170084
0.8217	Intermediate Similarity	NPC173555
0.8217	Intermediate Similarity	NPC46570
0.8217	Intermediate Similarity	NPC476204
0.8217	Intermediate Similarity	NPC314535
0.8209	Intermediate Similarity	NPC477195
0.8203	Intermediate Similarity	NPC236973
0.8203	Intermediate Similarity	NPC219656
0.8203	Intermediate Similarity	NPC469756
0.8203	Intermediate Similarity	NPC329905
0.8203	Intermediate Similarity	NPC292467
0.8203	Intermediate Similarity	NPC470897
0.8203	Intermediate Similarity	NPC32177
0.8203	Intermediate Similarity	NPC55532
0.8203	Intermediate Similarity	NPC30483
0.8201	Intermediate Similarity	NPC48414
0.8201	Intermediate Similarity	NPC5153
0.8195	Intermediate Similarity	NPC473593
0.8189	Intermediate Similarity	NPC93883
0.8189	Intermediate Similarity	NPC152615
0.8182	Intermediate Similarity	NPC42399
0.8182	Intermediate Similarity	NPC287423
0.8182	Intermediate Similarity	NPC298841
0.8175	Intermediate Similarity	NPC140045
0.8175	Intermediate Similarity	NPC84949
0.8175	Intermediate Similarity	NPC295885
0.8175	Intermediate Similarity	NPC31354
0.8175	Intermediate Similarity	NPC69576
0.8175	Intermediate Similarity	NPC596
0.8175	Intermediate Similarity	NPC471633
0.8162	Intermediate Similarity	NPC279915
0.8162	Intermediate Similarity	NPC110700
0.8162	Intermediate Similarity	NPC262813
0.8154	Intermediate Similarity	NPC107493
0.8154	Intermediate Similarity	NPC264336
0.8154	Intermediate Similarity	NPC269642
0.8154	Intermediate Similarity	NPC28532
0.8148	Intermediate Similarity	NPC476779
0.814	Intermediate Similarity	NPC112936
0.814	Intermediate Similarity	NPC72260
0.814	Intermediate Similarity	NPC476962
0.814	Intermediate Similarity	NPC135369
0.8134	Intermediate Similarity	NPC300655
0.8134	Intermediate Similarity	NPC43589
0.8134	Intermediate Similarity	NPC222951
0.8134	Intermediate Similarity	NPC477493
0.8134	Intermediate Similarity	NPC311178
0.8125	Intermediate Similarity	NPC239293
0.8125	Intermediate Similarity	NPC471249
0.8125	Intermediate Similarity	NPC146786
0.8125	Intermediate Similarity	NPC45475
0.812	Intermediate Similarity	NPC23020
0.812	Intermediate Similarity	NPC472269
0.812	Intermediate Similarity	NPC112492

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 NPC289700 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	875
0.2-0.3	1865
0.3-0.4	2740
0.4-0.5	2058
0.5-0.6	920
0.6-0.7	286
0.7-0.8	55
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9206	High Similarity	NPD7319	Approved
0.8968	High Similarity	NPD7507	Approved
0.88	High Similarity	NPD7503	Approved
0.8268	Intermediate Similarity	NPD7327	Approved
0.8268	Intermediate Similarity	NPD7328	Approved
0.8217	Intermediate Similarity	NPD8378	Approved
0.8217	Intermediate Similarity	NPD8380	Approved
0.8217	Intermediate Similarity	NPD8296	Approved
0.8217	Intermediate Similarity	NPD8379	Approved
0.8217	Intermediate Similarity	NPD8335	Approved
0.8203	Intermediate Similarity	NPD7516	Approved
0.814	Intermediate Similarity	NPD8377	Approved
0.814	Intermediate Similarity	NPD8294	Approved
0.812	Intermediate Similarity	NPD7736	Approved
0.8077	Intermediate Similarity	NPD8033	Approved
0.7879	Intermediate Similarity	NPD6370	Approved
0.784	Intermediate Similarity	NPD6686	Approved
0.7812	Intermediate Similarity	NPD8133	Approved
0.7803	Intermediate Similarity	NPD8513	Phase 3
0.7761	Intermediate Similarity	NPD7492	Approved
0.7727	Intermediate Similarity	NPD6319	Approved
0.7727	Intermediate Similarity	NPD6054	Approved
0.7704	Intermediate Similarity	NPD6616	Approved
0.7687	Intermediate Similarity	NPD8328	Phase 3
0.7669	Intermediate Similarity	NPD8515	Approved
0.7669	Intermediate Similarity	NPD8517	Approved
0.7669	Intermediate Similarity	NPD8516	Approved
0.7647	Intermediate Similarity	NPD7078	Approved
0.7647	Intermediate Similarity	NPD8293	Discontinued
0.7634	Intermediate Similarity	NPD7115	Discovery
0.7619	Intermediate Similarity	NPD6412	Phase 2
0.7597	Intermediate Similarity	NPD6882	Approved
0.7537	Intermediate Similarity	NPD6015	Approved
0.7537	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD6009	Approved
0.7481	Intermediate Similarity	NPD5988	Approved
0.7463	Intermediate Similarity	NPD6059	Approved
0.7462	Intermediate Similarity	NPD8297	Approved
0.7405	Intermediate Similarity	NPD4632	Approved
0.7368	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7638	Approved
0.7287	Intermediate Similarity	NPD6899	Approved
0.7287	Intermediate Similarity	NPD6881	Approved
0.728	Intermediate Similarity	NPD7640	Approved
0.728	Intermediate Similarity	NPD7639	Approved
0.7252	Intermediate Similarity	NPD6650	Approved
0.7252	Intermediate Similarity	NPD6649	Approved
0.7209	Intermediate Similarity	NPD5697	Approved
0.7197	Intermediate Similarity	NPD6053	Discontinued
0.7176	Intermediate Similarity	NPD4634	Approved
0.7176	Intermediate Similarity	NPD7102	Approved
0.7176	Intermediate Similarity	NPD7290	Approved
0.7176	Intermediate Similarity	NPD6883	Approved
0.7154	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6402	Approved
0.7132	Intermediate Similarity	NPD5739	Approved
0.7132	Intermediate Similarity	NPD7128	Approved
0.7132	Intermediate Similarity	NPD6675	Approved
0.7121	Intermediate Similarity	NPD6617	Approved
0.7121	Intermediate Similarity	NPD6847	Approved
0.7121	Intermediate Similarity	NPD8130	Phase 1
0.7121	Intermediate Similarity	NPD6869	Approved
0.7099	Intermediate Similarity	NPD6013	Approved
0.7099	Intermediate Similarity	NPD6373	Approved
0.7099	Intermediate Similarity	NPD6012	Approved
0.7099	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6372	Approved
0.7099	Intermediate Similarity	NPD6014	Approved
0.705	Intermediate Similarity	NPD7604	Phase 2
0.7029	Intermediate Similarity	NPD5983	Phase 2
0.7023	Intermediate Similarity	NPD7320	Approved
0.7023	Intermediate Similarity	NPD6011	Approved
0.6972	Remote Similarity	NPD6033	Approved
0.697	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6336	Discontinued
0.6947	Remote Similarity	NPD5701	Approved
0.6928	Remote Similarity	NPD7799	Discontinued
0.6923	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8074	Phase 3
0.6899	Remote Similarity	NPD5211	Phase 2
0.6875	Remote Similarity	NPD5286	Approved
0.6875	Remote Similarity	NPD5285	Approved
0.6875	Remote Similarity	NPD4696	Approved
0.6797	Remote Similarity	NPD4225	Approved
0.6794	Remote Similarity	NPD5141	Approved
0.6791	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7632	Discontinued
0.6769	Remote Similarity	NPD5225	Approved
0.6769	Remote Similarity	NPD4633	Approved
0.6769	Remote Similarity	NPD5224	Approved
0.6769	Remote Similarity	NPD5226	Approved
0.6763	Remote Similarity	NPD7100	Approved
0.6763	Remote Similarity	NPD7101	Approved
0.6753	Remote Similarity	NPD7625	Phase 1
0.6742	Remote Similarity	NPD6008	Approved
0.6741	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4755	Approved
0.6718	Remote Similarity	NPD5175	Approved
0.6718	Remote Similarity	NPD5174	Approved
0.6712	Remote Similarity	NPD7260	Phase 2
0.6692	Remote Similarity	NPD5223	Approved
0.6691	Remote Similarity	NPD6335	Approved
0.669	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6642	Remote Similarity	NPD4730	Approved
0.6642	Remote Similarity	NPD4729	Approved
0.6619	Remote Similarity	NPD6317	Approved
0.6615	Remote Similarity	NPD4700	Approved
0.6597	Remote Similarity	NPD8451	Approved
0.6589	Remote Similarity	NPD6083	Phase 2
0.6589	Remote Similarity	NPD6084	Phase 2
0.6587	Remote Similarity	NPD7637	Suspended
0.6587	Remote Similarity	NPD6079	Approved
0.6573	Remote Similarity	NPD7829	Approved
0.6573	Remote Similarity	NPD7830	Approved
0.6571	Remote Similarity	NPD6314	Approved
0.6571	Remote Similarity	NPD6313	Approved
0.6567	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8448	Approved
0.6544	Remote Similarity	NPD5250	Approved
0.6544	Remote Similarity	NPD5251	Approved
0.6544	Remote Similarity	NPD5247	Approved
0.6544	Remote Similarity	NPD5249	Phase 3
0.6544	Remote Similarity	NPD5248	Approved
0.6538	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD8391	Approved
0.6531	Remote Similarity	NPD5956	Approved
0.6531	Remote Similarity	NPD8392	Approved
0.6531	Remote Similarity	NPD8390	Approved
0.6493	Remote Similarity	NPD4768	Approved
0.6493	Remote Similarity	NPD4767	Approved
0.649	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7748	Approved
0.6463	Remote Similarity	NPD5761	Phase 2
0.6463	Remote Similarity	NPD5760	Phase 2
0.6462	Remote Similarity	NPD7902	Approved
0.6458	Remote Similarity	NPD7642	Approved
0.6457	Remote Similarity	NPD6411	Approved
0.6457	Remote Similarity	NPD7983	Approved
0.6457	Remote Similarity	NPD7515	Phase 2
0.6456	Remote Similarity	NPD7236	Approved
0.6443	Remote Similarity	NPD8338	Approved
0.6439	Remote Similarity	NPD5344	Discontinued
0.6434	Remote Similarity	NPD6909	Approved
0.6434	Remote Similarity	NPD6908	Approved
0.6434	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5328	Approved
0.6414	Remote Similarity	NPD8341	Approved
0.6414	Remote Similarity	NPD8299	Approved
0.6414	Remote Similarity	NPD8340	Approved
0.6414	Remote Similarity	NPD8342	Approved
0.6406	Remote Similarity	NPD4202	Approved
0.6406	Remote Similarity	NPD5779	Approved
0.6406	Remote Similarity	NPD5778	Approved
0.6397	Remote Similarity	NPD5128	Approved
0.6385	Remote Similarity	NPD5221	Approved
0.6385	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD5222	Approved
0.6385	Remote Similarity	NPD4697	Phase 3
0.6378	Remote Similarity	NPD46	Approved
0.6378	Remote Similarity	NPD6698	Approved
0.6377	Remote Similarity	NPD5217	Approved
0.6377	Remote Similarity	NPD5215	Approved
0.6377	Remote Similarity	NPD5216	Approved
0.6364	Remote Similarity	NPD6648	Approved
0.6358	Remote Similarity	NPD7239	Suspended
0.6349	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD4754	Approved
0.6338	Remote Similarity	NPD7641	Discontinued
0.6336	Remote Similarity	NPD5173	Approved
0.6333	Remote Similarity	NPD6845	Suspended
0.6328	Remote Similarity	NPD8034	Phase 2
0.6328	Remote Similarity	NPD8035	Phase 2
0.6328	Remote Similarity	NPD5284	Approved
0.6328	Remote Similarity	NPD5281	Approved
0.6312	Remote Similarity	NPD6868	Approved
0.6308	Remote Similarity	NPD5695	Phase 3
0.6304	Remote Similarity	NPD5169	Approved
0.6304	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5135	Approved
0.6299	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6101	Approved
0.6288	Remote Similarity	NPD5696	Approved
0.6284	Remote Similarity	NPD8337	Approved
0.6284	Remote Similarity	NPD8336	Approved
0.6279	Remote Similarity	NPD6399	Phase 3
0.6279	Remote Similarity	NPD8171	Discontinued
0.627	Remote Similarity	NPD3573	Approved
0.6259	Remote Similarity	NPD5127	Approved
0.625	Remote Similarity	NPD7838	Discovery
0.625	Remote Similarity	NPD5785	Approved
0.624	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD6334	Approved
0.6234	Remote Similarity	NPD6333	Approved
0.6231	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7900	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