NPASS Compound

Structure

CID112009 OpenBabel06191715462D 34 38 0 0 1 0 0 0 0 0999 V2000 7.2618 1.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5377 1.8135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5058 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0186 0.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1252 -0.5890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0154 -1.5421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0464 -1.4402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7611 0.4407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3821 1.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7301 0.3389 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4117 -0.6520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3648 -0.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6876 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5315 2.4359 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0889 -1.1014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3352 0.8604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3753 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9870 -2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6363 -0.0663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9327 -0.6142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 26 1 0 0 0 0 18 17 1 6 0 0 0 18 34 1 0 0 0 0 19 20 1 1 0 0 0 19 21 1 0 0 0 0 20 25 1 0 0 0 0 21 29 1 6 0 0 0 22 27 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 31 1 1 0 0 0 25 32 2 0 0 0 0 25 34 1 0 0 0 0 26 33 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	5.501
LogD:	4.904
LogS:	-4.857
# Rotatable Bonds:	3
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.452
Synthetic Accessibility Score:	4.833
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.063
MDCK Permeability:	2.8281740014790557e-05
Pgp-inhibitor:	0.099
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	94.66427612304688%
Volume Distribution (VD):	1.261
Pgp-substrate:	2.3453121185302734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.778
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.93
CYP2C9-inhibitor:	0.176
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.12
CYP3A4-substrate:	0.352

ADMET: Excretion

Clearance (CL):	5.02
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.23
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.55
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.54
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.895

Download Data

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

Natural Product: NPC112009

Natural Product ID:	NPC112009
*Common Name:**	Gypensapogenin E
IUPAC Name:	(2S)-2-(2-hydroxy-2-methylpropyl)-4-[(3S,5R,8R,9R,10R,13R,14R,17S)-3-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms:	Gypensapogenin E
Standard InCHIKey:	QDAUOBHGLHSXJU-CFJKEVLMSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-26(2,33)17-18-16-20(25(32)34-18)19-10-14-29(6)21(19)8-9-23-28(5)13-12-24(31)27(3,4)22(28)11-15-30(23,29)7/h16,18-19,21-24,31,33H,8-15,17H2,1-7H3/t18-,19-,21-,22+,23-,24+,28+,29-,30-/m1/s1
SMILES:	O=C1O[C@H](C=C1[C@H]1CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)CC(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2313421
PubChem CID:	71517216
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20104880]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342101]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25895106]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	23000.0	nM	PMID[501233]

☑ 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 NPC112009 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	196
0.1-0.2	1156
0.2-0.3	4031
0.3-0.4	9046
0.4-0.5	12361
0.5-0.6	5513
0.6-0.7	6276
0.7-0.8	3678
0.8-0.85	368
0.85-0.9	67
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC180204
0.9684	High Similarity	NPC201406
0.9053	High Similarity	NPC139692
0.9038	High Similarity	NPC470063
0.8958	High Similarity	NPC201725
0.8922	High Similarity	NPC131665
0.8922	High Similarity	NPC255387
0.8878	High Similarity	NPC253826
0.8824	High Similarity	NPC266570
0.8812	High Similarity	NPC476237
0.8812	High Similarity	NPC97487
0.8812	High Similarity	NPC187302
0.8812	High Similarity	NPC189588
0.8812	High Similarity	NPC10232
0.8812	High Similarity	NPC196471
0.88	High Similarity	NPC222875
0.88	High Similarity	NPC25177
0.88	High Similarity	NPC295110
0.88	High Similarity	NPC268829
0.88	High Similarity	NPC471412
0.88	High Similarity	NPC247701
0.8788	High Similarity	NPC57079
0.8788	High Similarity	NPC108368
0.8785	High Similarity	NPC469794
0.8785	High Similarity	NPC72772
0.8776	High Similarity	NPC242848
0.8776	High Similarity	NPC234993
0.8776	High Similarity	NPC134072
0.8737	High Similarity	NPC174342
0.8713	High Similarity	NPC114540
0.8713	High Similarity	NPC476081
0.8713	High Similarity	NPC32577
0.8713	High Similarity	NPC155332
0.87	High Similarity	NPC117685
0.87	High Similarity	NPC476299
0.87	High Similarity	NPC474012
0.87	High Similarity	NPC251680
0.87	High Similarity	NPC476303
0.87	High Similarity	NPC471413
0.8687	High Similarity	NPC231751
0.8673	High Similarity	NPC279974
0.8667	High Similarity	NPC16270
0.8667	High Similarity	NPC179642
0.866	High Similarity	NPC472871
0.8646	High Similarity	NPC302280
0.8641	High Similarity	NPC189863
0.8641	High Similarity	NPC119855
0.8641	High Similarity	NPC220217
0.8627	High Similarity	NPC160583
0.8627	High Similarity	NPC120321
0.8627	High Similarity	NPC36688
0.8627	High Similarity	NPC297617
0.8627	High Similarity	NPC176883
0.8611	High Similarity	NPC196931
0.86	High Similarity	NPC119036
0.86	High Similarity	NPC98868
0.86	High Similarity	NPC218107
0.8598	High Similarity	NPC122056
0.8558	High Similarity	NPC475294
0.8542	High Similarity	NPC475921
0.8542	High Similarity	NPC474704
0.8529	High Similarity	NPC162973
0.8519	High Similarity	NPC147912
0.8519	High Similarity	NPC67259
0.8505	High Similarity	NPC69291
0.85	High Similarity	NPC175351
0.85	High Similarity	NPC121402
0.85	High Similarity	NPC132753
0.85	High Similarity	NPC151681
0.85	High Similarity	NPC224356
0.8485	Intermediate Similarity	NPC476174
0.8476	Intermediate Similarity	NPC472825
0.8469	Intermediate Similarity	NPC38232
0.8469	Intermediate Similarity	NPC470224
0.8469	Intermediate Similarity	NPC472303
0.8469	Intermediate Similarity	NPC476304
0.8468	Intermediate Similarity	NPC470312
0.8462	Intermediate Similarity	NPC34768
0.8462	Intermediate Similarity	NPC186668
0.8454	Intermediate Similarity	NPC126993
0.8454	Intermediate Similarity	NPC78973
0.8454	Intermediate Similarity	NPC471896
0.8447	Intermediate Similarity	NPC329345
0.8447	Intermediate Similarity	NPC472821
0.8447	Intermediate Similarity	NPC476889
0.8447	Intermediate Similarity	NPC475526
0.8447	Intermediate Similarity	NPC478057
0.8447	Intermediate Similarity	NPC72151
0.8447	Intermediate Similarity	NPC473283
0.8447	Intermediate Similarity	NPC222153
0.8438	Intermediate Similarity	NPC104560
0.8431	Intermediate Similarity	NPC235142
0.8431	Intermediate Similarity	NPC282524
0.8431	Intermediate Similarity	NPC115899
0.8426	Intermediate Similarity	NPC73050
0.8421	Intermediate Similarity	NPC131813
0.8416	Intermediate Similarity	NPC252295
0.8411	Intermediate Similarity	NPC474315
0.84	Intermediate Similarity	NPC472363
0.84	Intermediate Similarity	NPC472362
0.84	Intermediate Similarity	NPC471039
0.84	Intermediate Similarity	NPC195366
0.84	Intermediate Similarity	NPC307164
0.84	Intermediate Similarity	NPC114743
0.84	Intermediate Similarity	NPC29952
0.84	Intermediate Similarity	NPC250757
0.84	Intermediate Similarity	NPC327788
0.84	Intermediate Similarity	NPC154526
0.84	Intermediate Similarity	NPC301534
0.8396	Intermediate Similarity	NPC5475
0.8396	Intermediate Similarity	NPC173905
0.8396	Intermediate Similarity	NPC475030
0.8396	Intermediate Similarity	NPC284828
0.8396	Intermediate Similarity	NPC475065
0.8396	Intermediate Similarity	NPC472216
0.8384	Intermediate Similarity	NPC476186
0.8384	Intermediate Similarity	NPC471720
0.8384	Intermediate Similarity	NPC91010
0.8381	Intermediate Similarity	NPC263729
0.8381	Intermediate Similarity	NPC329048
0.8381	Intermediate Similarity	NPC187435
0.8381	Intermediate Similarity	NPC67321
0.8381	Intermediate Similarity	NPC179380
0.8381	Intermediate Similarity	NPC330011
0.8381	Intermediate Similarity	NPC302788
0.8367	Intermediate Similarity	NPC289479
0.8367	Intermediate Similarity	NPC472814
0.8367	Intermediate Similarity	NPC74296
0.8367	Intermediate Similarity	NPC110923
0.8367	Intermediate Similarity	NPC177037
0.8367	Intermediate Similarity	NPC329842
0.8367	Intermediate Similarity	NPC72845
0.8365	Intermediate Similarity	NPC189616
0.8364	Intermediate Similarity	NPC167606
0.8364	Intermediate Similarity	NPC20302
0.8364	Intermediate Similarity	NPC286528
0.8364	Intermediate Similarity	NPC140055
0.8351	Intermediate Similarity	NPC262858
0.8351	Intermediate Similarity	NPC5509
0.8351	Intermediate Similarity	NPC285982
0.8351	Intermediate Similarity	NPC472240
0.835	Intermediate Similarity	NPC22388
0.835	Intermediate Similarity	NPC40918
0.835	Intermediate Similarity	NPC165250
0.835	Intermediate Similarity	NPC136289
0.835	Intermediate Similarity	NPC476890
0.835	Intermediate Similarity	NPC320447
0.8333	Intermediate Similarity	NPC142361
0.8333	Intermediate Similarity	NPC472826
0.8333	Intermediate Similarity	NPC266955
0.8333	Intermediate Similarity	NPC470906
0.8333	Intermediate Similarity	NPC470074
0.8333	Intermediate Similarity	NPC100267
0.8333	Intermediate Similarity	NPC475524
0.8333	Intermediate Similarity	NPC474684
0.8333	Intermediate Similarity	NPC476274
0.8333	Intermediate Similarity	NPC476767
0.8333	Intermediate Similarity	NPC471041
0.8317	Intermediate Similarity	NPC156546
0.8317	Intermediate Similarity	NPC210337
0.8317	Intermediate Similarity	NPC51499
0.8317	Intermediate Similarity	NPC110937
0.8317	Intermediate Similarity	NPC2049
0.8317	Intermediate Similarity	NPC108078
0.8316	Intermediate Similarity	NPC106416
0.8316	Intermediate Similarity	NPC474013
0.8316	Intermediate Similarity	NPC65661
0.8316	Intermediate Similarity	NPC86316
0.8304	Intermediate Similarity	NPC41123
0.8304	Intermediate Similarity	NPC145074
0.8304	Intermediate Similarity	NPC114939
0.8302	Intermediate Similarity	NPC220155
0.8302	Intermediate Similarity	NPC275539
0.8302	Intermediate Similarity	NPC189075
0.8302	Intermediate Similarity	NPC475418
0.8302	Intermediate Similarity	NPC177064
0.8302	Intermediate Similarity	NPC318363
0.8302	Intermediate Similarity	NPC473482
0.8302	Intermediate Similarity	NPC306265
0.83	Intermediate Similarity	NPC33473
0.83	Intermediate Similarity	NPC180950
0.83	Intermediate Similarity	NPC276110
0.83	Intermediate Similarity	NPC183012
0.83	Intermediate Similarity	NPC84383
0.83	Intermediate Similarity	NPC293052
0.8288	Intermediate Similarity	NPC50774
0.8288	Intermediate Similarity	NPC709
0.8288	Intermediate Similarity	NPC146786
0.8288	Intermediate Similarity	NPC257457
0.8288	Intermediate Similarity	NPC311554
0.8286	Intermediate Similarity	NPC60681
0.8286	Intermediate Similarity	NPC472818
0.8286	Intermediate Similarity	NPC173172
0.8286	Intermediate Similarity	NPC475414
0.8283	Intermediate Similarity	NPC205034
0.8283	Intermediate Similarity	NPC294263
0.8283	Intermediate Similarity	NPC162615
0.8283	Intermediate Similarity	NPC115021
0.8283	Intermediate Similarity	NPC152778
0.8269	Intermediate Similarity	NPC171014

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 NPC112009 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1346
0.2-0.3	3627
0.3-0.4	2639
0.4-0.5	837
0.5-0.6	194
0.6-0.7	162
0.7-0.8	159
0.8-0.85	22
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8788	High Similarity	NPD7638	Approved
0.87	High Similarity	NPD7639	Approved
0.87	High Similarity	NPD7640	Approved
0.8364	Intermediate Similarity	NPD7115	Discovery
0.8302	Intermediate Similarity	NPD7320	Approved
0.8302	Intermediate Similarity	NPD6899	Approved
0.8302	Intermediate Similarity	NPD6881	Approved
0.8286	Intermediate Similarity	NPD6675	Approved
0.8286	Intermediate Similarity	NPD7128	Approved
0.8286	Intermediate Similarity	NPD6402	Approved
0.8286	Intermediate Similarity	NPD5739	Approved
0.8208	Intermediate Similarity	NPD5697	Approved
0.8148	Intermediate Similarity	NPD6883	Approved
0.8148	Intermediate Similarity	NPD7102	Approved
0.8148	Intermediate Similarity	NPD7290	Approved
0.8137	Intermediate Similarity	NPD6083	Phase 2
0.8137	Intermediate Similarity	NPD6084	Phase 2
0.8103	Intermediate Similarity	NPD7507	Approved
0.8073	Intermediate Similarity	NPD6869	Approved
0.8073	Intermediate Similarity	NPD6650	Approved
0.8073	Intermediate Similarity	NPD6649	Approved
0.8073	Intermediate Similarity	NPD6847	Approved
0.8073	Intermediate Similarity	NPD8130	Phase 1
0.8073	Intermediate Similarity	NPD6617	Approved
0.8056	Intermediate Similarity	NPD6372	Approved
0.8056	Intermediate Similarity	NPD6373	Approved
0.8056	Intermediate Similarity	NPD6013	Approved
0.8056	Intermediate Similarity	NPD6014	Approved
0.8056	Intermediate Similarity	NPD6012	Approved
0.8037	Intermediate Similarity	NPD5701	Approved
0.802	Intermediate Similarity	NPD7748	Approved
0.8	Intermediate Similarity	NPD6079	Approved
0.8	Intermediate Similarity	NPD7515	Phase 2
0.8	Intermediate Similarity	NPD6882	Approved
0.8	Intermediate Similarity	NPD8297	Approved
0.8	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7632	Discontinued
0.798	Intermediate Similarity	NPD5328	Approved
0.7963	Intermediate Similarity	NPD6011	Approved
0.7938	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD6399	Phase 3
0.7899	Intermediate Similarity	NPD7319	Approved
0.7885	Intermediate Similarity	NPD4225	Approved
0.7857	Intermediate Similarity	NPD3618	Phase 1
0.783	Intermediate Similarity	NPD5211	Phase 2
0.7822	Intermediate Similarity	NPD8034	Phase 2
0.7822	Intermediate Similarity	NPD8035	Phase 2
0.781	Intermediate Similarity	NPD4696	Approved
0.781	Intermediate Similarity	NPD5285	Approved
0.781	Intermediate Similarity	NPD5286	Approved
0.7807	Intermediate Similarity	NPD7328	Approved
0.7807	Intermediate Similarity	NPD7327	Approved
0.7798	Intermediate Similarity	NPD6686	Approved
0.7788	Intermediate Similarity	NPD4755	Approved
0.7788	Intermediate Similarity	NPD7902	Approved
0.7767	Intermediate Similarity	NPD5695	Phase 3
0.7767	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD4202	Approved
0.7739	Intermediate Similarity	NPD7516	Approved
0.7727	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5696	Approved
0.77	Intermediate Similarity	NPD6903	Approved
0.77	Intermediate Similarity	NPD6672	Approved
0.77	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5737	Approved
0.7692	Intermediate Similarity	NPD5221	Approved
0.7692	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5222	Approved
0.7685	Intermediate Similarity	NPD5141	Approved
0.7677	Intermediate Similarity	NPD6409	Approved
0.7677	Intermediate Similarity	NPD5330	Approved
0.7677	Intermediate Similarity	NPD7146	Approved
0.7677	Intermediate Similarity	NPD7521	Approved
0.7677	Intermediate Similarity	NPD7334	Approved
0.7677	Intermediate Similarity	NPD6684	Approved
0.7672	Intermediate Similarity	NPD8294	Approved
0.7672	Intermediate Similarity	NPD8377	Approved
0.7664	Intermediate Similarity	NPD5226	Approved
0.7664	Intermediate Similarity	NPD5224	Approved
0.7664	Intermediate Similarity	NPD5225	Approved
0.7664	Intermediate Similarity	NPD4633	Approved
0.7653	Intermediate Similarity	NPD4786	Approved
0.7647	Intermediate Similarity	NPD5693	Phase 1
0.7642	Intermediate Similarity	NPD4700	Approved
0.7632	Intermediate Similarity	NPD6274	Approved
0.7624	Intermediate Similarity	NPD4753	Phase 2
0.7619	Intermediate Similarity	NPD5173	Approved
0.7607	Intermediate Similarity	NPD8033	Approved
0.7607	Intermediate Similarity	NPD8380	Approved
0.7607	Intermediate Similarity	NPD8335	Approved
0.7607	Intermediate Similarity	NPD8379	Approved
0.7607	Intermediate Similarity	NPD8378	Approved
0.7607	Intermediate Similarity	NPD8296	Approved
0.7604	Intermediate Similarity	NPD7525	Registered
0.7593	Intermediate Similarity	NPD5174	Approved
0.7593	Intermediate Similarity	NPD5175	Approved
0.7586	Intermediate Similarity	NPD7101	Approved
0.7586	Intermediate Similarity	NPD7100	Approved
0.757	Intermediate Similarity	NPD5223	Approved
0.7524	Intermediate Similarity	NPD4697	Phase 3
0.7522	Intermediate Similarity	NPD6053	Discontinued
0.75	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD7900	Approved
0.7478	Intermediate Similarity	NPD6868	Approved
0.7475	Intermediate Similarity	NPD3665	Phase 1
0.7475	Intermediate Similarity	NPD3133	Approved
0.7475	Intermediate Similarity	NPD3666	Approved
0.7456	Intermediate Similarity	NPD4632	Approved
0.7455	Intermediate Similarity	NPD6008	Approved
0.7451	Intermediate Similarity	NPD6051	Approved
0.7451	Intermediate Similarity	NPD6673	Approved
0.7451	Intermediate Similarity	NPD6080	Approved
0.7451	Intermediate Similarity	NPD6904	Approved
0.7449	Intermediate Similarity	NPD3667	Approved
0.7429	Intermediate Similarity	NPD5210	Approved
0.7429	Intermediate Similarity	NPD4629	Approved
0.7417	Intermediate Similarity	NPD7492	Approved
0.7414	Intermediate Similarity	NPD6317	Approved
0.74	Intermediate Similarity	NPD1694	Approved
0.7377	Intermediate Similarity	NPD7736	Approved
0.7374	Intermediate Similarity	NPD4788	Approved
0.7373	Intermediate Similarity	NPD6319	Approved
0.7373	Intermediate Similarity	NPD6054	Approved
0.7368	Intermediate Similarity	NPD6117	Approved
0.7355	Intermediate Similarity	NPD6616	Approved
0.735	Intermediate Similarity	NPD6314	Approved
0.735	Intermediate Similarity	NPD6313	Approved
0.7333	Intermediate Similarity	NPD6001	Approved
0.7327	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5128	Approved
0.7321	Intermediate Similarity	NPD4730	Approved
0.7321	Intermediate Similarity	NPD4729	Approved
0.7311	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6908	Approved
0.7311	Intermediate Similarity	NPD6909	Approved
0.7297	Intermediate Similarity	NPD4768	Approved
0.7297	Intermediate Similarity	NPD4767	Approved
0.7295	Intermediate Similarity	NPD7078	Approved
0.7292	Intermediate Similarity	NPD6116	Phase 1
0.7273	Intermediate Similarity	NPD4754	Approved
0.7273	Intermediate Similarity	NPD4221	Approved
0.7273	Intermediate Similarity	NPD4223	Phase 3
0.7265	Intermediate Similarity	NPD6009	Approved
0.7255	Intermediate Similarity	NPD3573	Approved
0.725	Intermediate Similarity	NPD6370	Approved
0.7232	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5329	Approved
0.7227	Intermediate Similarity	NPD6059	Approved
0.7216	Intermediate Similarity	NPD6115	Approved
0.7216	Intermediate Similarity	NPD6114	Approved
0.7216	Intermediate Similarity	NPD6697	Approved
0.7216	Intermediate Similarity	NPD6118	Approved
0.7212	Intermediate Similarity	NPD5785	Approved
0.7193	Intermediate Similarity	NPD5249	Phase 3
0.7193	Intermediate Similarity	NPD5248	Approved
0.7193	Intermediate Similarity	NPD5250	Approved
0.7193	Intermediate Similarity	NPD5247	Approved
0.7193	Intermediate Similarity	NPD5251	Approved
0.7193	Intermediate Similarity	NPD4634	Approved
0.719	Intermediate Similarity	NPD7604	Phase 2
0.7184	Intermediate Similarity	NPD5208	Approved
0.7167	Intermediate Similarity	NPD5983	Phase 2
0.7167	Intermediate Similarity	NPD6015	Approved
0.7167	Intermediate Similarity	NPD7503	Approved
0.7167	Intermediate Similarity	NPD6016	Approved
0.7158	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6098	Approved
0.7157	Intermediate Similarity	NPD5279	Phase 3
0.7155	Intermediate Similarity	NPD8133	Approved
0.7154	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD7637	Suspended
0.7143	Intermediate Similarity	NPD5281	Approved
0.7143	Intermediate Similarity	NPD5284	Approved
0.7143	Intermediate Similarity	NPD6050	Approved
0.713	Intermediate Similarity	NPD5217	Approved
0.713	Intermediate Similarity	NPD5216	Approved
0.713	Intermediate Similarity	NPD5215	Approved
0.7129	Intermediate Similarity	NPD4197	Approved
0.7107	Intermediate Similarity	NPD5988	Approved
0.708	Intermediate Similarity	NPD6412	Phase 2
0.7073	Intermediate Similarity	NPD6336	Discontinued
0.7048	Intermediate Similarity	NPD5207	Approved
0.7048	Intermediate Similarity	NPD5692	Phase 3
0.7043	Intermediate Similarity	NPD5135	Approved
0.7043	Intermediate Similarity	NPD5169	Approved
0.7043	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5362	Discontinued
0.7018	Intermediate Similarity	NPD5168	Approved
0.699	Remote Similarity	NPD4138	Approved
0.699	Remote Similarity	NPD4693	Phase 3
0.699	Remote Similarity	NPD5690	Phase 2
0.699	Remote Similarity	NPD4688	Approved
0.699	Remote Similarity	NPD4689	Approved
0.699	Remote Similarity	NPD4690	Approved
0.699	Remote Similarity	NPD5205	Approved
0.6983	Remote Similarity	NPD5127	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