NPASS Compound

Structure

CID124172 OpenBabel06191715482D 32 35 0 0 1 0 0 0 0 0999 V2000 -2.8997 6.4073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5932 3.4986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5364 2.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5861 4.8644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 -1.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6902 -0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3747 4.2912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 -1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2251 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6910 1.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5791 6.2303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6883 5.8340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3817 2.9253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6895 -0.9755 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6905 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5358 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2725 3.3216 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2254 1.4621 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8456 1.4631 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3815 1.9503 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 0.4877 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 -2.5361 1.4626 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6813 7.1999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5558 -1.4751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0611 2.7483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0916 1.9617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0202 1.9633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 8 1 0 0 0 0 5 15 1 0 0 0 0 6 7 1 0 0 0 0 6 17 2 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 26 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 1 1 6 0 0 0 16 2 1 1 0 0 0 16 21 1 0 0 0 0 16 24 1 0 0 0 0 17 26 1 0 0 0 0 18 29 1 6 0 0 0 19 7 1 1 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 27 1 6 0 0 0 21 30 1 1 0 0 0 22 24 1 0 0 0 0 22 31 1 6 0 0 0 23 25 1 0 0 0 0 23 32 1 1 0 0 0 24 27 1 6 0 0 0 25 26 1 6 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.33
Volume:	482.637
LogP:	3.3
LogD:	3.3
LogS:	-4.039
# Rotatable Bonds:	6
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	5.083
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.063
MDCK Permeability:	8.40664142742753e-06
Pgp-inhibitor:	0.403
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.366
20% Bioavailability (F20%):	0.815
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.24
Plasma Protein Binding (PPB):	72.92262268066406%
Volume Distribution (VD):	0.967
Pgp-substrate:	9.569832801818848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.343
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.63
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.314
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	10.049
Half-life (T1/2):	0.643

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.397
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.669
Carcinogencity:	0.624
Eye Corrosion:	0.016
Eye Irritation:	0.034
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC124172

Natural Product ID:	NPC124172
*Common Name:**	Helogenin
IUPAC Name:	(3S,8S,9S,10R,11R,13S,14S,16S,17R)-17-[(2S,3S,6R)-3,7-dihydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,11,16-triol
Synonyms:	Helogenin
Standard InCHIKey:	SJLLAOHWHAIKHM-YFCMGWRYSA-N
Standard InCHI:	InChI=1S/C27H46O5/c1-15(14-28)5-8-21(30)16(2)24-22(31)12-20-19-7-6-17-11-18(29)9-10-26(17,3)25(19)23(32)13-27(20,24)4/h6,15-16,18-25,28-32H,5,7-14H2,1-4H3/t15-,16-,18+,19+,20+,21+,22+,23-,24+,25-,26+,27+/m1/s1
SMILES:	OC[C@@H](CC[C@@H]([C@H]([C@H]1[C@@H](O)C[C@@H]2[C@]1(C)C[C@@H](O)[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2088130
PubChem CID:	53466477
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:0002198] Pentahydroxy 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
NPO33234	chamaellirium luteum	Species	n.a.	n.a.	roots	sourced from Botanical Liaisons Ltd. (USA) and Blessed Herbs Ltd. (USA)	n.a.	PMID[22880631]
NPO11520	Homalanthus acuminatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11520	Homalanthus acuminatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2470	Abies spectabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11520	Homalanthus acuminatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10817	Perilla ocymoides	Species	Araneidae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1523	Cell Line	NFF	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[483016]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[483016]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[483016]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[483016]
NPT1524	Cell Line	MM96L	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[483016]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[483016]

☑ 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 NPC124172 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	173
0.1-0.2	1435
0.2-0.3	5741
0.3-0.4	15607
0.4-0.5	7784
0.5-0.6	5134
0.6-0.7	4792
0.7-0.8	1628
0.8-0.85	245
0.85-0.9	125
0.9-0.95	28
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC24277
0.9744	High Similarity	NPC470614
0.9744	High Similarity	NPC1272
0.962	High Similarity	NPC110778
0.9512	High Similarity	NPC470542
0.95	High Similarity	NPC127606
0.95	High Similarity	NPC209802
0.95	High Similarity	NPC475798
0.9487	High Similarity	NPC26117
0.9398	High Similarity	NPC105495
0.9375	High Similarity	NPC477818
0.9375	High Similarity	NPC141941
0.9375	High Similarity	NPC193870
0.9359	High Similarity	NPC1319
0.9268	High Similarity	NPC201273
0.9241	High Similarity	NPC78545
0.9241	High Similarity	NPC71535
0.9231	High Similarity	NPC477522
0.9231	High Similarity	NPC87604
0.9157	High Similarity	NPC271967
0.9125	High Similarity	NPC470383
0.9048	High Similarity	NPC475664
0.9048	High Similarity	NPC2158
0.9036	High Similarity	NPC139724
0.9036	High Similarity	NPC6391
0.9036	High Similarity	NPC293287
0.9036	High Similarity	NPC152808
0.9036	High Similarity	NPC261266
0.9036	High Similarity	NPC6605
0.9012	High Similarity	NPC248886
0.9012	High Similarity	NPC201852
0.9	High Similarity	NPC322313
0.9	High Similarity	NPC102253
0.9	High Similarity	NPC236237
0.8987	High Similarity	NPC477817
0.8987	High Similarity	NPC244385
0.8987	High Similarity	NPC138621
0.8987	High Similarity	NPC275910
0.8987	High Similarity	NPC477819
0.8987	High Similarity	NPC6978
0.8987	High Similarity	NPC167037
0.8974	High Similarity	NPC189883
0.8974	High Similarity	NPC321381
0.8974	High Similarity	NPC107059
0.8974	High Similarity	NPC240604
0.8974	High Similarity	NPC300324
0.8974	High Similarity	NPC321016
0.8974	High Similarity	NPC96319
0.8929	High Similarity	NPC474657
0.8929	High Similarity	NPC186145
0.8916	High Similarity	NPC318390
0.8902	High Similarity	NPC232023
0.8889	High Similarity	NPC474531
0.8889	High Similarity	NPC23852
0.8889	High Similarity	NPC209620
0.8875	High Similarity	NPC80530
0.8875	High Similarity	NPC273410
0.8875	High Similarity	NPC472463
0.8861	High Similarity	NPC318495
0.8861	High Similarity	NPC471798
0.8861	High Similarity	NPC155986
0.8861	High Similarity	NPC198968
0.8861	High Similarity	NPC214570
0.8846	High Similarity	NPC288035
0.8846	High Similarity	NPC257347
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	NPC141071
0.8846	High Similarity	NPC471723
0.8846	High Similarity	NPC134847
0.8846	High Similarity	NPC285893
0.8837	High Similarity	NPC473956
0.8837	High Similarity	NPC107189
0.8837	High Similarity	NPC475751
0.8824	High Similarity	NPC474668
0.881	High Similarity	NPC94462
0.8795	High Similarity	NPC478102
0.8795	High Similarity	NPC255882
0.878	High Similarity	NPC20853
0.878	High Similarity	NPC101462
0.878	High Similarity	NPC30166
0.878	High Similarity	NPC50964
0.8765	High Similarity	NPC236112
0.8765	High Similarity	NPC47149
0.8764	High Similarity	NPC253115
0.8764	High Similarity	NPC304899
0.875	High Similarity	NPC285761
0.875	High Similarity	NPC477514
0.875	High Similarity	NPC474216
0.875	High Similarity	NPC111015
0.875	High Similarity	NPC473943
0.8736	High Similarity	NPC97404
0.8736	High Similarity	NPC41554
0.8734	High Similarity	NPC113733
0.8734	High Similarity	NPC73875
0.8734	High Similarity	NPC46160
0.8734	High Similarity	NPC237460
0.8734	High Similarity	NPC134330
0.8734	High Similarity	NPC129165
0.8734	High Similarity	NPC202642
0.8721	High Similarity	NPC470361
0.8721	High Similarity	NPC109744
0.8706	High Similarity	NPC475313
0.869	High Similarity	NPC474189
0.869	High Similarity	NPC474349
0.8675	High Similarity	NPC207013
0.8675	High Similarity	NPC113978
0.8667	High Similarity	NPC190554
0.8667	High Similarity	NPC475032
0.8667	High Similarity	NPC475033
0.8659	High Similarity	NPC476646
0.8642	High Similarity	NPC47982
0.8642	High Similarity	NPC143182
0.8642	High Similarity	NPC84694
0.8642	High Similarity	NPC24504
0.8642	High Similarity	NPC81306
0.8642	High Similarity	NPC30986
0.8642	High Similarity	NPC109546
0.8642	High Similarity	NPC328714
0.8642	High Similarity	NPC209430
0.8642	High Similarity	NPC28862
0.8636	High Similarity	NPC98193
0.8625	High Similarity	NPC34019
0.8625	High Similarity	NPC130136
0.8621	High Similarity	NPC295668
0.8621	High Similarity	NPC291484
0.8621	High Similarity	NPC3345
0.8621	High Similarity	NPC80561
0.8621	High Similarity	NPC11216
0.8621	High Similarity	NPC329596
0.8621	High Similarity	NPC204188
0.8608	High Similarity	NPC322353
0.8608	High Similarity	NPC121744
0.8608	High Similarity	NPC291503
0.8608	High Similarity	NPC118508
0.8605	High Similarity	NPC471952
0.8605	High Similarity	NPC133588
0.859	High Similarity	NPC474140
0.8588	High Similarity	NPC121981
0.8588	High Similarity	NPC474970
0.8588	High Similarity	NPC299068
0.8571	High Similarity	NPC256567
0.8571	High Similarity	NPC474493
0.8571	High Similarity	NPC205845
0.8571	High Similarity	NPC185568
0.8554	High Similarity	NPC7988
0.8554	High Similarity	NPC470049
0.8554	High Similarity	NPC49964
0.8537	High Similarity	NPC96362
0.8537	High Similarity	NPC234193
0.8537	High Similarity	NPC287749
0.8537	High Similarity	NPC164840
0.8537	High Similarity	NPC241290
0.8537	High Similarity	NPC209944
0.8537	High Similarity	NPC13554
0.8523	High Similarity	NPC210268
0.8519	High Similarity	NPC302041
0.8519	High Similarity	NPC85346
0.8519	High Similarity	NPC18603
0.8519	High Similarity	NPC205455
0.8519	High Similarity	NPC186191
0.8519	High Similarity	NPC472502
0.8519	High Similarity	NPC475
0.8519	High Similarity	NPC307965
0.8519	High Similarity	NPC76931
0.8519	High Similarity	NPC65897
0.8519	High Similarity	NPC472499
0.8519	High Similarity	NPC472500
0.85	High Similarity	NPC470362
0.85	High Similarity	NPC477925
0.85	High Similarity	NPC274079
0.8481	Intermediate Similarity	NPC308440
0.8481	Intermediate Similarity	NPC243342
0.8481	Intermediate Similarity	NPC472503
0.8481	Intermediate Similarity	NPC477138
0.8478	Intermediate Similarity	NPC208358
0.8478	Intermediate Similarity	NPC15390
0.8471	Intermediate Similarity	NPC470360
0.8471	Intermediate Similarity	NPC266511
0.8462	Intermediate Similarity	NPC177818
0.8452	Intermediate Similarity	NPC317458
0.8452	Intermediate Similarity	NPC474634
0.8444	Intermediate Similarity	NPC472485
0.8434	Intermediate Similarity	NPC47761
0.8434	Intermediate Similarity	NPC157655
0.8434	Intermediate Similarity	NPC474759
0.8434	Intermediate Similarity	NPC264245
0.8434	Intermediate Similarity	NPC474683
0.8434	Intermediate Similarity	NPC474752
0.8434	Intermediate Similarity	NPC7505
0.8434	Intermediate Similarity	NPC474731
0.8434	Intermediate Similarity	NPC82986
0.8427	Intermediate Similarity	NPC470376
0.8427	Intermediate Similarity	NPC235126
0.8427	Intermediate Similarity	NPC242419
0.8427	Intermediate Similarity	NPC470375

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 NPC124172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1682
0.2-0.3	4367
0.3-0.4	2104
0.4-0.5	398
0.5-0.6	168
0.6-0.7	128
0.7-0.8	136
0.8-0.85	10
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD7525	Registered
0.8974	High Similarity	NPD3701	Clinical (unspecified phase)
0.8846	High Similarity	NPD6942	Approved
0.8846	High Similarity	NPD7339	Approved
0.8488	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD4785	Approved
0.825	Intermediate Similarity	NPD4784	Approved
0.8228	Intermediate Similarity	NPD4243	Approved
0.814	Intermediate Similarity	NPD4786	Approved
0.8095	Intermediate Similarity	NPD4748	Discontinued
0.8025	Intermediate Similarity	NPD6924	Approved
0.8025	Intermediate Similarity	NPD6926	Approved
0.8022	Intermediate Similarity	NPD4202	Approved
0.7976	Intermediate Similarity	NPD6929	Approved
0.7976	Intermediate Similarity	NPD7645	Phase 2
0.7931	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3667	Approved
0.7889	Intermediate Similarity	NPD5328	Approved
0.7882	Intermediate Similarity	NPD6931	Approved
0.7882	Intermediate Similarity	NPD6930	Phase 2
0.7872	Intermediate Similarity	NPD4755	Approved
0.7831	Intermediate Similarity	NPD6933	Approved
0.7816	Intermediate Similarity	NPD6695	Phase 3
0.7778	Intermediate Similarity	NPD7150	Approved
0.7778	Intermediate Similarity	NPD7151	Approved
0.7778	Intermediate Similarity	NPD7152	Approved
0.7753	Intermediate Similarity	NPD3618	Phase 1
0.775	Intermediate Similarity	NPD6923	Approved
0.775	Intermediate Similarity	NPD6922	Approved
0.7738	Intermediate Similarity	NPD6925	Approved
0.7738	Intermediate Similarity	NPD6932	Approved
0.7738	Intermediate Similarity	NPD5776	Phase 2
0.7727	Intermediate Similarity	NPD3133	Approved
0.7727	Intermediate Similarity	NPD3666	Approved
0.7727	Intermediate Similarity	NPD3665	Phase 1
0.7717	Intermediate Similarity	NPD6079	Approved
0.7711	Intermediate Similarity	NPD5275	Approved
0.7711	Intermediate Similarity	NPD4190	Phase 3
0.7708	Intermediate Similarity	NPD5286	Approved
0.7708	Intermediate Similarity	NPD4700	Approved
0.7708	Intermediate Similarity	NPD5285	Approved
0.7708	Intermediate Similarity	NPD4696	Approved
0.7674	Intermediate Similarity	NPD7509	Discontinued
0.7654	Intermediate Similarity	NPD7144	Approved
0.7654	Intermediate Similarity	NPD7143	Approved
0.7647	Intermediate Similarity	NPD7145	Approved
0.7634	Intermediate Similarity	NPD6399	Phase 3
0.7629	Intermediate Similarity	NPD5223	Approved
0.7604	Intermediate Similarity	NPD7638	Approved
0.7558	Intermediate Similarity	NPD4195	Approved
0.7558	Intermediate Similarity	NPD6683	Phase 2
0.7551	Intermediate Similarity	NPD4633	Approved
0.7551	Intermediate Similarity	NPD5225	Approved
0.7551	Intermediate Similarity	NPD5226	Approved
0.7551	Intermediate Similarity	NPD5224	Approved
0.7551	Intermediate Similarity	NPD5211	Phase 2
0.7526	Intermediate Similarity	NPD7640	Approved
0.7526	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.7475	Intermediate Similarity	NPD5174	Approved
0.7475	Intermediate Similarity	NPD4754	Approved
0.7475	Intermediate Similarity	NPD5175	Approved
0.7473	Intermediate Similarity	NPD7524	Approved
0.7473	Intermediate Similarity	NPD7750	Discontinued
0.7471	Intermediate Similarity	NPD7514	Phase 3
0.7444	Intermediate Similarity	NPD6893	Approved
0.74	Intermediate Similarity	NPD5141	Approved
0.7396	Intermediate Similarity	NPD5222	Approved
0.7396	Intermediate Similarity	NPD5221	Approved
0.7396	Intermediate Similarity	NPD4697	Phase 3
0.7396	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6902	Approved
0.7379	Intermediate Similarity	NPD4634	Approved
0.7353	Intermediate Similarity	NPD6881	Approved
0.7353	Intermediate Similarity	NPD7320	Approved
0.7353	Intermediate Similarity	NPD6899	Approved
0.7333	Intermediate Similarity	NPD3668	Phase 3
0.7327	Intermediate Similarity	NPD4768	Approved
0.7327	Intermediate Similarity	NPD4767	Approved
0.732	Intermediate Similarity	NPD5173	Approved
0.7303	Intermediate Similarity	NPD4221	Approved
0.7303	Intermediate Similarity	NPD4223	Phase 3
0.7282	Intermediate Similarity	NPD6373	Approved
0.7282	Intermediate Similarity	NPD6372	Approved
0.7273	Intermediate Similarity	NPD7332	Phase 2
0.7255	Intermediate Similarity	NPD5697	Approved
0.7255	Intermediate Similarity	NPD5701	Approved
0.7253	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5329	Approved
0.7212	Intermediate Similarity	NPD7102	Approved
0.7212	Intermediate Similarity	NPD6883	Approved
0.7212	Intermediate Similarity	NPD7290	Approved
0.7191	Intermediate Similarity	NPD6898	Phase 1
0.7184	Intermediate Similarity	NPD4729	Approved
0.7184	Intermediate Similarity	NPD4730	Approved
0.7184	Intermediate Similarity	NPD6011	Approved
0.7184	Intermediate Similarity	NPD5128	Approved
0.717	Intermediate Similarity	NPD4632	Approved
0.7158	Intermediate Similarity	NPD7087	Discontinued
0.7158	Intermediate Similarity	NPD7515	Phase 2
0.7157	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD6083	Phase 2
0.7143	Intermediate Similarity	NPD6084	Phase 2
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD6869	Approved
0.7143	Intermediate Similarity	NPD4197	Approved
0.7143	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6649	Approved
0.7143	Intermediate Similarity	NPD6650	Approved
0.7128	Intermediate Similarity	NPD6051	Approved
0.7115	Intermediate Similarity	NPD6013	Approved
0.7115	Intermediate Similarity	NPD6014	Approved
0.7115	Intermediate Similarity	NPD6012	Approved
0.7113	Intermediate Similarity	NPD4629	Approved
0.7113	Intermediate Similarity	NPD5210	Approved
0.7108	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8264	Approved
0.7087	Intermediate Similarity	NPD6412	Phase 2
0.7075	Intermediate Similarity	NPD6882	Approved
0.7075	Intermediate Similarity	NPD8297	Approved
0.7048	Intermediate Similarity	NPD5247	Approved
0.7048	Intermediate Similarity	NPD5248	Approved
0.7048	Intermediate Similarity	NPD5135	Approved
0.7048	Intermediate Similarity	NPD5169	Approved
0.7048	Intermediate Similarity	NPD5249	Phase 3
0.7048	Intermediate Similarity	NPD5250	Approved
0.7048	Intermediate Similarity	NPD5251	Approved
0.7048	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4788	Approved
0.7024	Intermediate Similarity	NPD4787	Phase 1
0.6989	Remote Similarity	NPD7521	Approved
0.6989	Remote Similarity	NPD5330	Approved
0.6989	Remote Similarity	NPD5205	Approved
0.6989	Remote Similarity	NPD6409	Approved
0.6989	Remote Similarity	NPD5279	Phase 3
0.6989	Remote Similarity	NPD6684	Approved
0.6989	Remote Similarity	NPD4693	Phase 3
0.6989	Remote Similarity	NPD4689	Approved
0.6989	Remote Similarity	NPD7334	Approved
0.6989	Remote Similarity	NPD4138	Approved
0.6989	Remote Similarity	NPD4690	Approved
0.6989	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7146	Approved
0.6989	Remote Similarity	NPD4688	Approved
0.6981	Remote Similarity	NPD5127	Approved
0.6981	Remote Similarity	NPD5217	Approved
0.6981	Remote Similarity	NPD5216	Approved
0.6981	Remote Similarity	NPD5215	Approved
0.6979	Remote Similarity	NPD8035	Phase 2
0.6979	Remote Similarity	NPD8034	Phase 2
0.6972	Remote Similarity	NPD6009	Approved
0.6937	Remote Similarity	NPD6059	Approved
0.6937	Remote Similarity	NPD6054	Approved
0.6909	Remote Similarity	NPD7328	Approved
0.6909	Remote Similarity	NPD7327	Approved
0.69	Remote Similarity	NPD5290	Discontinued
0.6889	Remote Similarity	NPD6928	Phase 2
0.6875	Remote Similarity	NPD8033	Approved
0.6863	Remote Similarity	NPD7632	Discontinued
0.6854	Remote Similarity	NPD6697	Approved
0.6854	Remote Similarity	NPD6115	Approved
0.6854	Remote Similarity	NPD6118	Approved
0.6854	Remote Similarity	NPD6114	Approved
0.6847	Remote Similarity	NPD7516	Approved
0.6842	Remote Similarity	NPD4723	Approved
0.6842	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6903	Approved
0.6842	Remote Similarity	NPD4722	Approved
0.6837	Remote Similarity	NPD7748	Approved
0.6814	Remote Similarity	NPD6370	Approved
0.6809	Remote Similarity	NPD5690	Phase 2
0.6809	Remote Similarity	NPD4694	Approved
0.6809	Remote Similarity	NPD5280	Approved
0.6804	Remote Similarity	NPD5284	Approved
0.6804	Remote Similarity	NPD7637	Suspended
0.6804	Remote Similarity	NPD5281	Approved
0.68	Remote Similarity	NPD7902	Approved
0.6789	Remote Similarity	NPD5167	Approved
0.6786	Remote Similarity	NPD8294	Approved
0.6786	Remote Similarity	NPD6319	Approved
0.6786	Remote Similarity	NPD8377	Approved
0.6768	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5695	Phase 3
0.6765	Remote Similarity	NPD4159	Approved
0.6757	Remote Similarity	NPD6335	Approved
0.6754	Remote Similarity	NPD7604	Phase 2
0.6742	Remote Similarity	NPD6116	Phase 1
0.6733	Remote Similarity	NPD5696	Approved
0.6727	Remote Similarity	NPD6274	Approved
0.6726	Remote Similarity	NPD8379	Approved
0.6726	Remote Similarity	NPD8296	Approved
0.6726	Remote Similarity	NPD6015	Approved
0.6726	Remote Similarity	NPD8378	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