NPASS Compound

Structure

CID59453 OpenBabel06191715392D 29 32 0 0 1 0 0 0 0 0999 V2000 -5.8891 2.3377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2544 3.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8066 3.7112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5343 2.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3479 3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8441 -1.4630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6888 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2220 1.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2217 0.4864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7443 3.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6879 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8450 1.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6896 1.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2856 3.2276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3790 2.9229 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6882 -0.9747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6891 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3787 1.9488 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5338 0.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8447 0.4873 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7132 4.0158 0.0000 C 0 0 0 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 -2.5340 1.4614 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5544 -1.4744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 4.9057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 6 11 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 19 2 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 3 1 1 0 0 0 18 22 1 0 0 0 0 19 26 1 0 0 0 0 20 28 1 6 0 0 0 21 8 1 1 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 6 0 0 0 23 27 1 6 0 0 0 24 26 1 6 0 0 0 25 29 2 0 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.33
Volume:	453.63
LogP:	5.97
LogD:	5.481
LogS:	-5.455
# Rotatable Bonds:	5
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	4.284
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.656
MDCK Permeability:	1.3795247468806338e-05
Pgp-inhibitor:	0.971
Pgp-substrate:	0.161
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.77

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.492
Plasma Protein Binding (PPB):	94.07122039794922%
Volume Distribution (VD):	1.327
Pgp-substrate:	1.2172695398330688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.131
CYP1A2-substrate:	0.604
CYP2C19-inhibitor:	0.13
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.309
CYP2C9-substrate:	0.258
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.609
CYP3A4-substrate:	0.519

ADMET: Excretion

Clearance (CL):	8.241
Half-life (T1/2):	0.216

ADMET: Toxicity

hERG Blockers:	0.28
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.585
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.683
Skin Sensitization:	0.916
Carcinogencity:	0.358
Eye Corrosion:	0.043
Eye Irritation:	0.191
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC59453

Natural Product ID:	NPC59453
*Common Name:**	3-Beta-Hydroxycholest-5-En-24-One
IUPAC Name:	(6R)-6-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-one
Synonyms:
Standard InCHIKey:	PGLNLCWHYQYRGQ-ZHHJOTBYSA-N
Standard InCHI:	InChI=1S/C27H44O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-24,28H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
SMILES:	O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CCC(=O)C(C)C)C)C)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL275911
PubChem CID:	11036808
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000260] Monohydroxy bile acids, alcohols 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
NPO12354	Sargassum pallidum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25840	Sargassum fusiforme	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25840	Sargassum fusiforme	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4145	Hijikia fusiforme	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12354	Sargassum pallidum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25840	Sargassum fusiforme	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12354	Sargassum pallidum	Species	Sargassaceae	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
EC50	1
IC50	1
Others	4

Activity Type	# Activity
Individual Protein	3
Organism	1
Others	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1794	Individual Protein	LXR-alpha	Homo sapiens	EC50	=	180.0	nM	PMID[513244]
NPT1794	Individual Protein	LXR-alpha	Homo sapiens	RE	=	1.3	n.a.	PMID[513244]
NPT1794	Individual Protein	LXR-alpha	Homo sapiens	FC	=	2.36	n.a.	PMID[513246]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	>	8000.0	ug.mL-1	PMID[513245]
NPT26790	SINGLE PROTEIN	Oxysterols receptor LXR-beta	Rattus norvegicus	FC	=	3.85	n.a.	PMID[513246]
NPT2	Others	Unspecified		Ratio	=	1.63	n.a.	PMID[513246]

☑ 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 NPC59453 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	155
0.1-0.2	1058
0.2-0.3	4955
0.3-0.4	15363
0.4-0.5	7572
0.5-0.6	5906
0.6-0.7	4596
0.7-0.8	2516
0.8-0.85	360
0.85-0.9	158
0.9-0.95	42
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC221758
0.975	High Similarity	NPC474733
0.975	High Similarity	NPC51014
0.975	High Similarity	NPC474732
0.975	High Similarity	NPC474778
0.975	High Similarity	NPC31564
0.975	High Similarity	NPC145879
0.9744	High Similarity	NPC151519
0.963	High Similarity	NPC475740
0.963	High Similarity	NPC58063
0.9512	High Similarity	NPC328313
0.9506	High Similarity	NPC155011
0.95	High Similarity	NPC214043
0.95	High Similarity	NPC82902
0.95	High Similarity	NPC85774
0.9398	High Similarity	NPC32830
0.9398	High Similarity	NPC186688
0.9398	High Similarity	NPC76879
0.9398	High Similarity	NPC31985
0.9398	High Similarity	NPC26959
0.9398	High Similarity	NPC474245
0.9398	High Similarity	NPC268406
0.9398	High Similarity	NPC1015
0.9383	High Similarity	NPC474218
0.9383	High Similarity	NPC471224
0.9383	High Similarity	NPC469948
0.9375	High Similarity	NPC476082
0.9375	High Similarity	NPC278648
0.9286	High Similarity	NPC48010
0.9277	High Similarity	NPC53911
0.9277	High Similarity	NPC471722
0.9268	High Similarity	NPC118648
0.9268	High Similarity	NPC475022
0.9268	High Similarity	NPC20688
0.9268	High Similarity	NPC222613
0.9268	High Similarity	NPC469994
0.9259	High Similarity	NPC473246
0.9259	High Similarity	NPC472265
0.9167	High Similarity	NPC309603
0.9167	High Similarity	NPC473999
0.9157	High Similarity	NPC474684
0.9157	High Similarity	NPC90652
0.9157	High Similarity	NPC142361
0.9157	High Similarity	NPC317590
0.9146	High Similarity	NPC470574
0.9146	High Similarity	NPC202868
0.9146	High Similarity	NPC474083
0.9048	High Similarity	NPC328539
0.9048	High Similarity	NPC470417
0.9048	High Similarity	NPC193360
0.9036	High Similarity	NPC473168
0.9036	High Similarity	NPC72133
0.9036	High Similarity	NPC94755
0.9024	High Similarity	NPC180834
0.9024	High Similarity	NPC33913
0.9024	High Similarity	NPC329043
0.9024	High Similarity	NPC58841
0.9024	High Similarity	NPC161423
0.9024	High Similarity	NPC227064
0.9024	High Similarity	NPC237712
0.9024	High Similarity	NPC321187
0.9	High Similarity	NPC2482
0.9	High Similarity	NPC472478
0.8987	High Similarity	NPC82635
0.8974	High Similarity	NPC321381
0.8974	High Similarity	NPC107059
0.8974	High Similarity	NPC321016
0.8966	High Similarity	NPC245972
0.8966	High Similarity	NPC196485
0.8953	High Similarity	NPC475806
0.8953	High Similarity	NPC272746
0.8953	High Similarity	NPC473998
0.8941	High Similarity	NPC86319
0.8941	High Similarity	NPC474704
0.8941	High Similarity	NPC477943
0.8941	High Similarity	NPC119416
0.8941	High Similarity	NPC475921
0.8941	High Similarity	NPC275740
0.8941	High Similarity	NPC2983
0.8929	High Similarity	NPC472482
0.8929	High Similarity	NPC96496
0.8929	High Similarity	NPC159046
0.8929	High Similarity	NPC233836
0.8929	High Similarity	NPC472481
0.8929	High Similarity	NPC187376
0.8929	High Similarity	NPC472484
0.8929	High Similarity	NPC93778
0.8889	High Similarity	NPC147066
0.8889	High Similarity	NPC14151
0.8875	High Similarity	NPC215843
0.8864	High Similarity	NPC469599
0.8861	High Similarity	NPC318495
0.8861	High Similarity	NPC155986
0.8861	High Similarity	NPC198968
0.8851	High Similarity	NPC475255
0.8851	High Similarity	NPC12722
0.8851	High Similarity	NPC474736
0.8846	High Similarity	NPC288035
0.8846	High Similarity	NPC304309
0.8846	High Similarity	NPC28657
0.8846	High Similarity	NPC162742
0.8846	High Similarity	NPC230301
0.8846	High Similarity	NPC22105
0.8846	High Similarity	NPC136188
0.8846	High Similarity	NPC285893
0.8846	High Similarity	NPC134847
0.8837	High Similarity	NPC85173
0.8837	High Similarity	NPC320026
0.8837	High Similarity	NPC171441
0.8837	High Similarity	NPC191684
0.8837	High Similarity	NPC69622
0.8837	High Similarity	NPC126993
0.8824	High Similarity	NPC471724
0.8824	High Similarity	NPC143767
0.8824	High Similarity	NPC242864
0.8824	High Similarity	NPC131470
0.881	High Similarity	NPC89077
0.881	High Similarity	NPC327115
0.881	High Similarity	NPC55309
0.881	High Similarity	NPC28252
0.8795	High Similarity	NPC25833
0.8795	High Similarity	NPC165064
0.878	High Similarity	NPC212083
0.878	High Similarity	NPC48362
0.878	High Similarity	NPC328351
0.878	High Similarity	NPC310989
0.878	High Similarity	NPC260956
0.8765	High Similarity	NPC164999
0.875	High Similarity	NPC292793
0.875	High Similarity	NPC474216
0.875	High Similarity	NPC8993
0.875	High Similarity	NPC111015
0.875	High Similarity	NPC477522
0.875	High Similarity	NPC87604
0.875	High Similarity	NPC473943
0.8736	High Similarity	NPC189520
0.8736	High Similarity	NPC110657
0.8736	High Similarity	NPC168027
0.8736	High Similarity	NPC131872
0.8736	High Similarity	NPC212301
0.8736	High Similarity	NPC154101
0.8736	High Similarity	NPC185936
0.8736	High Similarity	NPC262870
0.8736	High Similarity	NPC86266
0.8734	High Similarity	NPC300324
0.8734	High Similarity	NPC113733
0.8734	High Similarity	NPC240604
0.8721	High Similarity	NPC128496
0.8721	High Similarity	NPC84271
0.8721	High Similarity	NPC102414
0.8721	High Similarity	NPC77168
0.8706	High Similarity	NPC136548
0.8706	High Similarity	NPC141292
0.8706	High Similarity	NPC73064
0.869	High Similarity	NPC133954
0.869	High Similarity	NPC197823
0.8675	High Similarity	NPC470046
0.8675	High Similarity	NPC470047
0.8675	High Similarity	NPC475726
0.8675	High Similarity	NPC472743
0.8667	High Similarity	NPC108078
0.8667	High Similarity	NPC190554
0.8659	High Similarity	NPC121984
0.8659	High Similarity	NPC136150
0.8659	High Similarity	NPC3915
0.8659	High Similarity	NPC38350
0.8659	High Similarity	NPC201912
0.8652	High Similarity	NPC271195
0.8652	High Similarity	NPC127063
0.8642	High Similarity	NPC47982
0.8642	High Similarity	NPC143182
0.8642	High Similarity	NPC84694
0.8642	High Similarity	NPC472490
0.8642	High Similarity	NPC81306
0.8642	High Similarity	NPC477371
0.8642	High Similarity	NPC109546
0.8642	High Similarity	NPC328714
0.8642	High Similarity	NPC201459
0.8642	High Similarity	NPC28862
0.8636	High Similarity	NPC470376
0.8636	High Similarity	NPC472942
0.8636	High Similarity	NPC470224
0.8636	High Similarity	NPC109305
0.8636	High Similarity	NPC170220
0.8636	High Similarity	NPC250575
0.8636	High Similarity	NPC141497
0.8636	High Similarity	NPC470375
0.8636	High Similarity	NPC107674
0.8636	High Similarity	NPC69454
0.8625	High Similarity	NPC34019
0.8621	High Similarity	NPC471896
0.8621	High Similarity	NPC183283
0.8608	High Similarity	NPC141071
0.8608	High Similarity	NPC257347
0.8608	High Similarity	NPC471723
0.8605	High Similarity	NPC44181
0.8605	High Similarity	NPC472483
0.8605	High Similarity	NPC474677
0.8605	High Similarity	NPC292491
0.8605	High Similarity	NPC310752

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 NPC59453 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1348
0.2-0.3	4054
0.3-0.4	2485
0.4-0.5	619
0.5-0.6	178
0.6-0.7	104
0.7-0.8	163
0.8-0.85	38
0.85-0.9	13
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4786	Approved
0.9744	High Similarity	NPD3667	Approved
0.9167	High Similarity	NPD5328	Approved
0.9036	High Similarity	NPD3618	Phase 1
0.9024	High Similarity	NPD3666	Approved
0.9024	High Similarity	NPD3665	Phase 1
0.9024	High Similarity	NPD3133	Approved
0.8953	High Similarity	NPD6079	Approved
0.8851	High Similarity	NPD6399	Phase 3
0.8846	High Similarity	NPD6942	Approved
0.8846	High Similarity	NPD7339	Approved
0.8795	High Similarity	NPD3668	Phase 3
0.8636	High Similarity	NPD4202	Approved
0.8588	High Similarity	NPD5279	Phase 3
0.8554	High Similarity	NPD4221	Approved
0.8554	High Similarity	NPD4223	Phase 3
0.8506	High Similarity	NPD4753	Phase 2
0.85	High Similarity	NPD3701	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD5329	Approved
0.8353	Intermediate Similarity	NPD4197	Approved
0.8352	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD5221	Approved
0.8352	Intermediate Similarity	NPD5222	Approved
0.8352	Intermediate Similarity	NPD4697	Phase 3
0.8261	Intermediate Similarity	NPD5173	Approved
0.8261	Intermediate Similarity	NPD4755	Approved
0.8256	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD4788	Approved
0.8161	Intermediate Similarity	NPD4138	Approved
0.8161	Intermediate Similarity	NPD7521	Approved
0.8161	Intermediate Similarity	NPD6409	Approved
0.8161	Intermediate Similarity	NPD4693	Phase 3
0.8161	Intermediate Similarity	NPD5330	Approved
0.8161	Intermediate Similarity	NPD4688	Approved
0.8161	Intermediate Similarity	NPD4689	Approved
0.8161	Intermediate Similarity	NPD7146	Approved
0.8161	Intermediate Similarity	NPD6684	Approved
0.8161	Intermediate Similarity	NPD7334	Approved
0.8161	Intermediate Similarity	NPD4690	Approved
0.8161	Intermediate Similarity	NPD5205	Approved
0.8111	Intermediate Similarity	NPD7515	Phase 2
0.8095	Intermediate Similarity	NPD7525	Registered
0.8085	Intermediate Similarity	NPD5286	Approved
0.8085	Intermediate Similarity	NPD4700	Approved
0.8085	Intermediate Similarity	NPD4696	Approved
0.8085	Intermediate Similarity	NPD5285	Approved
0.8072	Intermediate Similarity	NPD3617	Approved
0.8065	Intermediate Similarity	NPD6083	Phase 2
0.8065	Intermediate Similarity	NPD6084	Phase 2
0.8043	Intermediate Similarity	NPD5210	Approved
0.8043	Intermediate Similarity	NPD4629	Approved
0.8025	Intermediate Similarity	NPD6924	Approved
0.8025	Intermediate Similarity	NPD6926	Approved
0.8	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5223	Approved
0.7978	Intermediate Similarity	NPD5737	Approved
0.7978	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD6672	Approved
0.7978	Intermediate Similarity	NPD6903	Approved
0.7955	Intermediate Similarity	NPD5690	Phase 2
0.7955	Intermediate Similarity	NPD4694	Approved
0.7955	Intermediate Similarity	NPD5280	Approved
0.7917	Intermediate Similarity	NPD5224	Approved
0.7917	Intermediate Similarity	NPD5226	Approved
0.7917	Intermediate Similarity	NPD5225	Approved
0.7917	Intermediate Similarity	NPD4633	Approved
0.7917	Intermediate Similarity	NPD5211	Phase 2
0.7882	Intermediate Similarity	NPD4695	Discontinued
0.7875	Intermediate Similarity	NPD4747	Approved
0.7857	Intermediate Similarity	NPD6675	Approved
0.7857	Intermediate Similarity	NPD6402	Approved
0.7857	Intermediate Similarity	NPD5739	Approved
0.7857	Intermediate Similarity	NPD7128	Approved
0.7835	Intermediate Similarity	NPD5175	Approved
0.7835	Intermediate Similarity	NPD5174	Approved
0.7835	Intermediate Similarity	NPD4754	Approved
0.7831	Intermediate Similarity	NPD6933	Approved
0.7805	Intermediate Similarity	NPD4785	Approved
0.7805	Intermediate Similarity	NPD4784	Approved
0.7791	Intermediate Similarity	NPD4692	Approved
0.7791	Intermediate Similarity	NPD4139	Approved
0.7778	Intermediate Similarity	NPD7151	Approved
0.7778	Intermediate Similarity	NPD7150	Approved
0.7778	Intermediate Similarity	NPD7152	Approved
0.7778	Intermediate Similarity	NPD4243	Approved
0.7765	Intermediate Similarity	NPD4195	Approved
0.7755	Intermediate Similarity	NPD5141	Approved
0.7753	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6098	Approved
0.775	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD4137	Phase 3
0.775	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6923	Approved
0.775	Intermediate Similarity	NPD6922	Approved
0.7742	Intermediate Similarity	NPD7748	Approved
0.77	Intermediate Similarity	NPD7320	Approved
0.77	Intermediate Similarity	NPD6881	Approved
0.77	Intermediate Similarity	NPD6899	Approved
0.7692	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4767	Approved
0.7677	Intermediate Similarity	NPD4768	Approved
0.7667	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD5695	Phase 3
0.7654	Intermediate Similarity	NPD4691	Approved
0.7654	Intermediate Similarity	NPD4789	Approved
0.7654	Intermediate Similarity	NPD7144	Approved
0.7654	Intermediate Similarity	NPD4245	Approved
0.7654	Intermediate Similarity	NPD4244	Approved
0.7654	Intermediate Similarity	NPD7143	Approved
0.7625	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD6372	Approved
0.7624	Intermediate Similarity	NPD6373	Approved
0.7604	Intermediate Similarity	NPD5696	Approved
0.76	Intermediate Similarity	NPD5701	Approved
0.76	Intermediate Similarity	NPD5697	Approved
0.759	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5733	Approved
0.7558	Intermediate Similarity	NPD7645	Phase 2
0.7558	Intermediate Similarity	NPD6929	Approved
0.7556	Intermediate Similarity	NPD4623	Approved
0.7556	Intermediate Similarity	NPD4519	Discontinued
0.7549	Intermediate Similarity	NPD7290	Approved
0.7549	Intermediate Similarity	NPD6883	Approved
0.7549	Intermediate Similarity	NPD7102	Approved
0.7531	Intermediate Similarity	NPD3698	Phase 2
0.7527	Intermediate Similarity	NPD8034	Phase 2
0.7527	Intermediate Similarity	NPD5281	Approved
0.7527	Intermediate Similarity	NPD5284	Approved
0.7527	Intermediate Similarity	NPD8035	Phase 2
0.7525	Intermediate Similarity	NPD4730	Approved
0.7525	Intermediate Similarity	NPD6011	Approved
0.7525	Intermediate Similarity	NPD5168	Approved
0.7525	Intermediate Similarity	NPD4729	Approved
0.7525	Intermediate Similarity	NPD5128	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.7476	Intermediate Similarity	NPD6650	Approved
0.7476	Intermediate Similarity	NPD6617	Approved
0.7476	Intermediate Similarity	NPD6869	Approved
0.7476	Intermediate Similarity	NPD6649	Approved
0.7476	Intermediate Similarity	NPD6847	Approved
0.7476	Intermediate Similarity	NPD8130	Phase 1
0.7476	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6930	Phase 2
0.7471	Intermediate Similarity	NPD6931	Approved
0.7471	Intermediate Similarity	NPD4748	Discontinued
0.7451	Intermediate Similarity	NPD6014	Approved
0.7451	Intermediate Similarity	NPD6012	Approved
0.7451	Intermediate Similarity	NPD6013	Approved
0.7442	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6412	Phase 2
0.7423	Intermediate Similarity	NPD7638	Approved
0.7419	Intermediate Similarity	NPD4096	Approved
0.7412	Intermediate Similarity	NPD6117	Approved
0.7407	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5360	Phase 3
0.7404	Intermediate Similarity	NPD8297	Approved
0.7404	Intermediate Similarity	NPD6882	Approved
0.7391	Intermediate Similarity	NPD4518	Approved
0.7391	Intermediate Similarity	NPD5208	Approved
0.7381	Intermediate Similarity	NPD4058	Approved
0.7381	Intermediate Similarity	NPD4687	Approved
0.7379	Intermediate Similarity	NPD5251	Approved
0.7379	Intermediate Similarity	NPD5247	Approved
0.7379	Intermediate Similarity	NPD5249	Phase 3
0.7379	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5248	Approved
0.7379	Intermediate Similarity	NPD5135	Approved
0.7379	Intermediate Similarity	NPD5169	Approved
0.7379	Intermediate Similarity	NPD5250	Approved
0.7379	Intermediate Similarity	NPD4634	Approved
0.7349	Intermediate Similarity	NPD5276	Approved
0.7347	Intermediate Similarity	NPD7640	Approved
0.7347	Intermediate Similarity	NPD7639	Approved
0.7326	Intermediate Similarity	NPD5776	Phase 2
0.7326	Intermediate Similarity	NPD6932	Approved
0.7326	Intermediate Similarity	NPD6925	Approved
0.7326	Intermediate Similarity	NPD6116	Phase 1
0.7312	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5216	Approved
0.7308	Intermediate Similarity	NPD5217	Approved
0.7308	Intermediate Similarity	NPD5215	Approved
0.7308	Intermediate Similarity	NPD5127	Approved
0.7294	Intermediate Similarity	NPD4190	Phase 3
0.7294	Intermediate Similarity	NPD3703	Phase 2
0.7294	Intermediate Similarity	NPD5275	Approved
0.7292	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD7509	Discontinued
0.7263	Intermediate Similarity	NPD5133	Approved
0.7241	Intermediate Similarity	NPD7145	Approved
0.7241	Intermediate Similarity	NPD6115	Approved
0.7241	Intermediate Similarity	NPD6114	Approved
0.7241	Intermediate Similarity	NPD6697	Approved
0.7241	Intermediate Similarity	NPD6118	Approved
0.7222	Intermediate Similarity	NPD6695	Phase 3
0.7196	Intermediate Similarity	NPD6868	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