NPASS Compound

Structure

NPC104129 OpenBabel07101718312D 32 35 0 0 1 0 0 0 0 0999 V2000 -1.7601 -1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3479 -0.5302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 -0.4954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9781 -3.6048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2871 -2.1510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8080 0.3136 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2147 1.2271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6269 2.0361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6324 1.9316 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6691 -2.1510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2257 1.0181 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9781 -1.1999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4781 -2.7388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4781 -4.4708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2093 1.3317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0337 2.9497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0446 2.7406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7180 -2.4600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9781 -3.6048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3903 -0.3909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9781 -1.1999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7688 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8135 0.2091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 11 1 0 0 0 0 3 4 1 0 0 0 0 3 11 2 0 0 0 0 4 12 1 0 0 0 0 5 10 1 0 0 0 0 5 31 1 0 0 0 0 6 28 1 0 0 0 0 7 20 1 0 0 0 0 7 22 1 0 0 0 0 8 20 1 0 0 0 0 8 29 1 0 0 0 0 9 30 1 0 0 0 0 10 12 1 0 0 0 0 11 21 1 0 0 0 0 12 21 1 6 0 0 0 13 6 1 6 0 0 0 13 14 1 0 0 0 0 13 32 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 1 0 0 0 15 16 1 0 0 0 0 15 24 1 6 0 0 0 16 18 1 0 0 0 0 16 25 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 6 0 0 0 17 26 1 0 0 0 0 18 30 1 6 0 0 0 18 32 1 0 0 0 0 19 28 1 1 0 0 0 19 29 1 0 0 0 0 20 27 1 6 0 0 0 21 9 1 1 0 0 0 21 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.19
Volume:	428.966
LogP:	0.115
LogD:	-0.442
LogS:	-2.713
# Rotatable Bonds:	7
TPSA:	167.53
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.223
Synthetic Accessibility Score:	5.419
Fsp3:	0.81
Lipinski Rule-of-5:	Rejected
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:	-6.302
MDCK Permeability:	3.231947266613133e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.649
Human Intestinal Absorption (HIA):	0.91
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.105
Plasma Protein Binding (PPB):	41.4313850402832%
Volume Distribution (VD):	0.459
Pgp-substrate:	46.47834396362305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.382
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.059

ADMET: Excretion

Clearance (CL):	0.962
Half-life (T1/2):	0.82

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.418
AMES Toxicity:	0.939
Rat Oral Acute Toxicity:	0.694
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.578
Carcinogencity:	0.533
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.193

Download Data

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

Natural Product: NPC104129

Natural Product ID:	NPC104129
*Common Name:**	Patriridoside H
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[[(3aR,6aS)-6-methyl-3-methylidene-3a,4-dihydrocyclopenta[b]furan-6a-yl]methoxy]-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]oxane-3,4,5-triol
Synonyms:	Patriridoside H
Standard InCHIKey:	MCGBJAYWLFYYJH-LRIWWYBNSA-N
Standard InCHI:	InChI=1S/C21H32O11/c1-10-5-31-21(11(2)3-4-12(10)21)9-30-18-16(25)15(24)14(23)13(32-18)6-28-19-17(26)20(27,7-22)8-29-19/h3,12-19,22-27H,1,4-9H2,2H3/t12-,13-,14-,15+,16-,17+,18-,19-,20-,21-/m1/s1
SMILES:	C=C1CO[C@]2(CO[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]4[C@@H]([C@@](CO)(CO4)O)O)O3)O)O)O)C(=CC[C@H]12)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152446
PubChem CID:	71458433
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23002924]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29799195]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[464509]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9400.0	nM	PMID[464509]

☑ 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 NPC104129 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	175
0.1-0.2	1702
0.2-0.3	6583
0.3-0.4	15737
0.4-0.5	9637
0.5-0.6	6728
0.6-0.7	1969
0.7-0.8	161
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC249408
0.9518	High Similarity	NPC470658
0.837	Intermediate Similarity	NPC280390
0.809	Intermediate Similarity	NPC136699
0.809	Intermediate Similarity	NPC220167
0.8081	Intermediate Similarity	NPC86095
0.8	Intermediate Similarity	NPC229655
0.7935	Intermediate Similarity	NPC248312
0.7879	Intermediate Similarity	NPC310804
0.7879	Intermediate Similarity	NPC261117
0.7857	Intermediate Similarity	NPC244878
0.7778	Intermediate Similarity	NPC20673
0.7766	Intermediate Similarity	NPC118078
0.7755	Intermediate Similarity	NPC151093
0.7727	Intermediate Similarity	NPC476701
0.77	Intermediate Similarity	NPC222062
0.77	Intermediate Similarity	NPC250545
0.7692	Intermediate Similarity	NPC266718
0.7684	Intermediate Similarity	NPC9447
0.7677	Intermediate Similarity	NPC255677
0.7677	Intermediate Similarity	NPC306344
0.7677	Intermediate Similarity	NPC22149
0.7667	Intermediate Similarity	NPC20072
0.766	Intermediate Similarity	NPC477748
0.764	Intermediate Similarity	NPC100697
0.7624	Intermediate Similarity	NPC234304
0.7624	Intermediate Similarity	NPC284929
0.7624	Intermediate Similarity	NPC197541
0.7624	Intermediate Similarity	NPC267869
0.7624	Intermediate Similarity	NPC118761
0.76	Intermediate Similarity	NPC298255
0.76	Intermediate Similarity	NPC4637
0.76	Intermediate Similarity	NPC28304
0.76	Intermediate Similarity	NPC219038
0.76	Intermediate Similarity	NPC98859
0.7579	Intermediate Similarity	NPC202886
0.7551	Intermediate Similarity	NPC54731
0.7525	Intermediate Similarity	NPC471599
0.75	Intermediate Similarity	NPC477749
0.75	Intermediate Similarity	NPC277583
0.7447	Intermediate Similarity	NPC125142
0.7444	Intermediate Similarity	NPC127295
0.7444	Intermediate Similarity	NPC163362
0.7431	Intermediate Similarity	NPC100048
0.7431	Intermediate Similarity	NPC476690
0.7423	Intermediate Similarity	NPC472196
0.7423	Intermediate Similarity	NPC472195
0.7423	Intermediate Similarity	NPC238090
0.7404	Intermediate Similarity	NPC33053
0.7396	Intermediate Similarity	NPC327253
0.7379	Intermediate Similarity	NPC93352
0.7374	Intermediate Similarity	NPC306041
0.7374	Intermediate Similarity	NPC241911
0.7364	Intermediate Similarity	NPC10366
0.7363	Intermediate Similarity	NPC246621
0.7358	Intermediate Similarity	NPC170974
0.7358	Intermediate Similarity	NPC103627
0.7358	Intermediate Similarity	NPC191439
0.7356	Intermediate Similarity	NPC472174
0.7353	Intermediate Similarity	NPC13171
0.7353	Intermediate Similarity	NPC195510
0.7347	Intermediate Similarity	NPC159698
0.7327	Intermediate Similarity	NPC130792
0.7315	Intermediate Similarity	NPC469347
0.7315	Intermediate Similarity	NPC469348
0.7312	Intermediate Similarity	NPC475035
0.7312	Intermediate Similarity	NPC98276
0.7312	Intermediate Similarity	NPC259296
0.7308	Intermediate Similarity	NPC476592
0.7308	Intermediate Similarity	NPC239961
0.73	Intermediate Similarity	NPC472290
0.7292	Intermediate Similarity	NPC299527
0.7292	Intermediate Similarity	NPC309310
0.729	Intermediate Similarity	NPC13190
0.7264	Intermediate Similarity	NPC250089
0.7264	Intermediate Similarity	NPC473318
0.7264	Intermediate Similarity	NPC28844
0.7264	Intermediate Similarity	NPC473328
0.7264	Intermediate Similarity	NPC472901
0.7264	Intermediate Similarity	NPC14630
0.7264	Intermediate Similarity	NPC157530
0.7263	Intermediate Similarity	NPC475037
0.7262	Intermediate Similarity	NPC59442
0.7255	Intermediate Similarity	NPC21568
0.7255	Intermediate Similarity	NPC285231
0.7245	Intermediate Similarity	NPC320552
0.7245	Intermediate Similarity	NPC61201
0.7245	Intermediate Similarity	NPC67398
0.7245	Intermediate Similarity	NPC320089
0.7245	Intermediate Similarity	NPC474792
0.7245	Intermediate Similarity	NPC91654
0.7241	Intermediate Similarity	NPC132938
0.7238	Intermediate Similarity	NPC226642
0.7238	Intermediate Similarity	NPC476594
0.7234	Intermediate Similarity	NPC477747
0.7234	Intermediate Similarity	NPC477746
0.7228	Intermediate Similarity	NPC309493
0.7222	Intermediate Similarity	NPC254255
0.7222	Intermediate Similarity	NPC231797
0.7222	Intermediate Similarity	NPC42171
0.7222	Intermediate Similarity	NPC477089
0.7222	Intermediate Similarity	NPC112274
0.7212	Intermediate Similarity	NPC474917
0.72	Intermediate Similarity	NPC256230
0.7196	Intermediate Similarity	NPC247037
0.7196	Intermediate Similarity	NPC141433
0.7196	Intermediate Similarity	NPC65155
0.7188	Intermediate Similarity	NPC137368
0.7172	Intermediate Similarity	NPC256368
0.717	Intermediate Similarity	NPC473069
0.717	Intermediate Similarity	NPC475960
0.7159	Intermediate Similarity	NPC472173
0.7158	Intermediate Similarity	NPC149018
0.7158	Intermediate Similarity	NPC171484
0.7157	Intermediate Similarity	NPC469942
0.7157	Intermediate Similarity	NPC473146
0.7156	Intermediate Similarity	NPC476693
0.7156	Intermediate Similarity	NPC51154
0.7156	Intermediate Similarity	NPC287075
0.7143	Intermediate Similarity	NPC472899
0.7143	Intermediate Similarity	NPC302584
0.7143	Intermediate Similarity	NPC472199
0.7143	Intermediate Similarity	NPC472900
0.7143	Intermediate Similarity	NPC472898
0.7143	Intermediate Similarity	NPC472197
0.7143	Intermediate Similarity	NPC235051
0.7143	Intermediate Similarity	NPC26798
0.7143	Intermediate Similarity	NPC181845
0.713	Intermediate Similarity	NPC473021
0.713	Intermediate Similarity	NPC65034
0.713	Intermediate Similarity	NPC208189
0.713	Intermediate Similarity	NPC472987
0.7117	Intermediate Similarity	NPC203862
0.7117	Intermediate Similarity	NPC20979
0.7115	Intermediate Similarity	NPC473070
0.7115	Intermediate Similarity	NPC213190
0.7113	Intermediate Similarity	NPC22918
0.7113	Intermediate Similarity	NPC50464
0.7105	Intermediate Similarity	NPC43842
0.7103	Intermediate Similarity	NPC128133
0.7103	Intermediate Similarity	NPC40440
0.7103	Intermediate Similarity	NPC42482
0.71	Intermediate Similarity	NPC291709
0.71	Intermediate Similarity	NPC6765
0.71	Intermediate Similarity	NPC93869
0.71	Intermediate Similarity	NPC241407
0.7097	Intermediate Similarity	NPC251026
0.7091	Intermediate Similarity	NPC11548
0.7087	Intermediate Similarity	NPC470434
0.7075	Intermediate Similarity	NPC113044
0.7075	Intermediate Similarity	NPC305423
0.7075	Intermediate Similarity	NPC283829
0.7075	Intermediate Similarity	NPC161676
0.7075	Intermediate Similarity	NPC474285
0.7075	Intermediate Similarity	NPC230507
0.7075	Intermediate Similarity	NPC254538
0.7075	Intermediate Similarity	NPC470432
0.7075	Intermediate Similarity	NPC14704
0.7064	Intermediate Similarity	NPC473567
0.7064	Intermediate Similarity	NPC216595
0.7059	Intermediate Similarity	NPC312325
0.7059	Intermediate Similarity	NPC5358
0.7059	Intermediate Similarity	NPC124181
0.7059	Intermediate Similarity	NPC216260
0.7059	Intermediate Similarity	NPC40182
0.7059	Intermediate Similarity	NPC198422
0.7059	Intermediate Similarity	NPC90819
0.7059	Intermediate Similarity	NPC472015
0.7053	Intermediate Similarity	NPC475034
0.7053	Intermediate Similarity	NPC73166
0.7053	Intermediate Similarity	NPC471494
0.7053	Intermediate Similarity	NPC470124
0.7048	Intermediate Similarity	NPC473068
0.7048	Intermediate Similarity	NPC476595
0.7048	Intermediate Similarity	NPC75608
0.7048	Intermediate Similarity	NPC476593
0.7043	Intermediate Similarity	NPC295133
0.7043	Intermediate Similarity	NPC257207
0.7043	Intermediate Similarity	NPC202261
0.7043	Intermediate Similarity	NPC106589
0.7041	Intermediate Similarity	NPC303451
0.7041	Intermediate Similarity	NPC6414
0.7033	Intermediate Similarity	NPC470944
0.703	Intermediate Similarity	NPC90583
0.7027	Intermediate Similarity	NPC477030
0.7027	Intermediate Similarity	NPC199428
0.7027	Intermediate Similarity	NPC310341
0.7027	Intermediate Similarity	NPC477029
0.7027	Intermediate Similarity	NPC5311
0.7027	Intermediate Similarity	NPC99620
0.7027	Intermediate Similarity	NPC193382
0.7021	Intermediate Similarity	NPC473315
0.7021	Intermediate Similarity	NPC142111
0.7019	Intermediate Similarity	NPC86077
0.7019	Intermediate Similarity	NPC136816
0.7011	Intermediate Similarity	NPC474078
0.701	Intermediate Similarity	NPC148534
0.7009	Intermediate Similarity	NPC476538
0.7009	Intermediate Similarity	NPC476539
0.7009	Intermediate Similarity	NPC98696

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 NPC104129 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	2143
0.2-0.3	4333
0.3-0.4	1818
0.4-0.5	497
0.5-0.6	178
0.6-0.7	33
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6903	Remote Similarity	NPD7327	Approved
0.6903	Remote Similarity	NPD7328	Approved
0.687	Remote Similarity	NPD8033	Approved
0.6842	Remote Similarity	NPD7516	Approved
0.6783	Remote Similarity	NPD8294	Approved
0.6783	Remote Similarity	NPD8377	Approved
0.6724	Remote Similarity	NPD8379	Approved
0.6724	Remote Similarity	NPD8378	Approved
0.6724	Remote Similarity	NPD8296	Approved
0.6724	Remote Similarity	NPD8380	Approved
0.6724	Remote Similarity	NPD8335	Approved
0.67	Remote Similarity	NPD46	Approved
0.67	Remote Similarity	NPD6698	Approved
0.6697	Remote Similarity	NPD6686	Approved
0.6606	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7503	Approved
0.6571	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7507	Approved
0.6441	Remote Similarity	NPD8515	Approved
0.6441	Remote Similarity	NPD8517	Approved
0.6441	Remote Similarity	NPD8516	Approved
0.6441	Remote Similarity	NPD8513	Phase 3
0.64	Remote Similarity	NPD4251	Approved
0.64	Remote Similarity	NPD4250	Approved
0.64	Remote Similarity	NPD7524	Approved
0.6373	Remote Similarity	NPD7838	Discovery
0.6341	Remote Similarity	NPD7319	Approved
0.6306	Remote Similarity	NPD6412	Phase 2
0.63	Remote Similarity	NPD4249	Approved
0.6263	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7332	Phase 2
0.6162	Remote Similarity	NPD6695	Phase 3
0.6147	Remote Similarity	NPD5344	Discontinued
0.614	Remote Similarity	NPD6371	Approved
0.61	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7514	Phase 3
0.6	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD7983	Approved
0.5983	Remote Similarity	NPD8133	Approved
0.596	Remote Similarity	NPD6898	Phase 1
0.5929	Remote Similarity	NPD6640	Phase 3
0.5922	Remote Similarity	NPD7750	Discontinued
0.592	Remote Similarity	NPD8074	Phase 3
0.5904	Remote Similarity	NPD895	Approved
0.5904	Remote Similarity	NPD887	Approved
0.5904	Remote Similarity	NPD889	Approved
0.5904	Remote Similarity	NPD894	Approved
0.5897	Remote Similarity	NPD6053	Discontinued
0.5882	Remote Similarity	NPD2267	Suspended
0.5876	Remote Similarity	NPD5776	Phase 2
0.5876	Remote Similarity	NPD6932	Approved
0.5876	Remote Similarity	NPD6925	Approved
0.5859	Remote Similarity	NPD4821	Approved
0.5859	Remote Similarity	NPD4820	Approved
0.5859	Remote Similarity	NPD6930	Phase 2
0.5859	Remote Similarity	NPD4819	Approved
0.5859	Remote Similarity	NPD4822	Approved
0.5859	Remote Similarity	NPD6931	Approved
0.5854	Remote Similarity	NPD6370	Approved
0.5849	Remote Similarity	NPD7637	Suspended
0.5842	Remote Similarity	NPD6110	Phase 1
0.5816	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4268	Approved
0.5816	Remote Similarity	NPD4271	Approved
0.5816	Remote Similarity	NPD7145	Approved
0.5814	Remote Similarity	NPD8449	Approved
0.581	Remote Similarity	NPD1695	Approved
0.58	Remote Similarity	NPD4790	Discontinued
0.58	Remote Similarity	NPD6902	Approved
0.5794	Remote Similarity	NPD8171	Discontinued
0.5783	Remote Similarity	NPD2269	Approved
0.578	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD6933	Approved
0.5772	Remote Similarity	NPD8444	Approved
0.5769	Remote Similarity	NPD8450	Suspended
0.5766	Remote Similarity	NPD6648	Approved
0.5758	Remote Similarity	NPD6683	Phase 2
0.5758	Remote Similarity	NPD6929	Approved
0.5755	Remote Similarity	NPD3168	Discontinued
0.5741	Remote Similarity	NPD5282	Discontinued
0.573	Remote Similarity	NPD368	Approved
0.5714	Remote Similarity	NPD8451	Approved
0.5701	Remote Similarity	NPD7087	Discontinued
0.5691	Remote Similarity	NPD6054	Approved
0.5691	Remote Similarity	NPD6059	Approved
0.5686	Remote Similarity	NPD5332	Approved
0.5686	Remote Similarity	NPD5331	Approved
0.5686	Remote Similarity	NPD7154	Phase 3
0.568	Remote Similarity	NPD7829	Approved
0.568	Remote Similarity	NPD7830	Approved
0.568	Remote Similarity	NPD7642	Approved
0.5676	Remote Similarity	NPD4225	Approved
0.5669	Remote Similarity	NPD8293	Discontinued
0.5669	Remote Similarity	NPD8448	Approved
0.5663	Remote Similarity	NPD905	Approved
0.5663	Remote Similarity	NPD904	Phase 3
0.5636	Remote Similarity	NPD7839	Suspended
0.5625	Remote Similarity	NPD7736	Approved
0.5612	Remote Similarity	NPD7625	Phase 1
0.56	Remote Similarity	NPD5125	Phase 3
0.56	Remote Similarity	NPD5126	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