NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	746.24
Volume:	691.102
LogP:	1.436
LogD:	0.506
LogS:	-3.263
# Rotatable Bonds:	13
TPSA:	249.59
# H-Bond Aceptor:	17
# H-Bond Donor:	7
# Rings:	10
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.127
Synthetic Accessibility Score:	6.671
Fsp3:	0.611
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.704
MDCK Permeability:	5.08E-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.943
20% Bioavailability (F20%):	0.833
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	55.97%
Volume Distribution (VD):	0.622
Pgp-substrate:	8.62%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.15
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.083
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	1.139
Half-life (T1/2):	0.829

ADMET: Toxicity

hERG Blockers:	0.449
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.897
AMES Toxicity:	0.368
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.624
Carcinogencity:	0.321
Eye Corrosion:	0.003
Eye Irritation:	0.178
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC477623

Natural Product ID:	NPC477623
*Common Name:**	Paeoniflorin B
IUPAC Name:	[(2R,3S,4R,5R,6S)-6-[[(1R,2S,3R,5R,6R,8S)-2-(benzoyloxymethyl)-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-3-yl]oxy]-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
Synonyms:	Paeoniflorin B
Standard InCHIKey:	QREQQDSOBGSTFM-XXBRTPTLSA-N
Standard InCHI:	InChI=1S/C36H42O17/c1-33-15-35(45)21-12-36(33,34(21,32(52-33)53-35)16-47-29(44)18-10-6-3-7-11-18)51-31-26(42)24(40)27(50-30-25(41)23(39)22(38)19(13-37)48-30)20(49-31)14-46-28(43)17-8-4-2-5-9-17/h2-11,19-27,30-32,37-42,45H,12-16H2,1H3/t19-,20-,21-,22-,23+,24-,25-,26-,27-,30+,31+,32-,33+,34+,35-,36+/m1/s1
SMILES:	C[C@]12C[C@@]3([C@@H]4C[C@]1([C@@]4([C@H](O2)O3)COC(=O)C5=CC=CC=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)COC(=O)C7=CC=CC=C7)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	71452334
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	31250	nM	PMID[23067550]

☑ 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 NPC477623 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	367
0.1-0.2	1325
0.2-0.3	2722
0.3-0.4	5888
0.4-0.5	10664
0.5-0.6	13974
0.6-0.7	6438
0.7-0.8	991
0.8-0.85	203
0.85-0.9	95
0.9-0.95	18
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.973	High Similarity	NPC469422
0.973	High Similarity	NPC469398
0.9597	High Similarity	NPC34066
0.9527	High Similarity	NPC469415
0.9459	High Similarity	NPC222102
0.9459	High Similarity	NPC303429
0.9329	High Similarity	NPC469448
0.9187	High Similarity	NPC469421
0.9177	High Similarity	NPC469420
0.9156	High Similarity	NPC469399
0.913	High Similarity	NPC477617
0.9051	High Similarity	NPC473557
0.9051	High Similarity	NPC473468
0.9051	High Similarity	NPC475567
0.9032	High Similarity	NPC476784
0.902	High Similarity	NPC469477
0.902	High Similarity	NPC133430
0.9	High Similarity	NPC469459
0.8994	High Similarity	NPC475198
0.8994	High Similarity	NPC475175
0.8994	High Similarity	NPC475531
0.8968	High Similarity	NPC469417
0.8961	High Similarity	NPC5115
0.8933	High Similarity	NPC476973
0.8933	High Similarity	NPC96903
0.8933	High Similarity	NPC472571
0.8933	High Similarity	NPC472572
0.8933	High Similarity	NPC200471
0.8933	High Similarity	NPC174982
0.8933	High Similarity	NPC472575
0.8933	High Similarity	NPC184817
0.8933	High Similarity	NPC29704
0.8933	High Similarity	NPC70403
0.8933	High Similarity	NPC470159
0.8933	High Similarity	NPC472568
0.8933	High Similarity	NPC158663
0.8933	High Similarity	NPC470157
0.8933	High Similarity	NPC469349
0.8933	High Similarity	NPC473088
0.8933	High Similarity	NPC177940
0.8933	High Similarity	NPC471104
0.8933	High Similarity	NPC171525
0.8882	High Similarity	NPC471101
0.8882	High Similarity	NPC477471
0.8882	High Similarity	NPC477469
0.8882	High Similarity	NPC477473
0.8882	High Similarity	NPC477466
0.8882	High Similarity	NPC270590
0.8882	High Similarity	NPC92293
0.8882	High Similarity	NPC469396
0.8882	High Similarity	NPC149002
0.8882	High Similarity	NPC469458
0.8882	High Similarity	NPC266265
0.8882	High Similarity	NPC88176
0.8882	High Similarity	NPC301556
0.8867	High Similarity	NPC125106
0.8867	High Similarity	NPC472573
0.8867	High Similarity	NPC470152
0.8867	High Similarity	NPC472569
0.8867	High Similarity	NPC475759
0.8867	High Similarity	NPC188865
0.8867	High Similarity	NPC476974
0.8867	High Similarity	NPC25768
0.8867	High Similarity	NPC57628
0.8867	High Similarity	NPC241951
0.8867	High Similarity	NPC472570
0.8867	High Similarity	NPC475122
0.8867	High Similarity	NPC95265
0.8867	High Similarity	NPC163719
0.8867	High Similarity	NPC11685
0.8867	High Similarity	NPC95810
0.8867	High Similarity	NPC70716
0.8816	High Similarity	NPC281717
0.88	High Similarity	NPC163087
0.8792	High Similarity	NPC118080
0.8792	High Similarity	NPC16912
0.8792	High Similarity	NPC41481
0.8792	High Similarity	NPC291599
0.8792	High Similarity	NPC87448
0.8792	High Similarity	NPC27377
0.8792	High Similarity	NPC472576
0.8792	High Similarity	NPC97947
0.879	High Similarity	NPC319404
0.8774	High Similarity	NPC472658
0.8774	High Similarity	NPC472657
0.8765	High Similarity	NPC477488
0.8758	High Similarity	NPC476975
0.875	High Similarity	NPC474935
0.875	High Similarity	NPC117943
0.875	High Similarity	NPC293568
0.8742	High Similarity	NPC478124
0.8726	High Similarity	NPC322048
0.8726	High Similarity	NPC477735
0.8726	High Similarity	NPC318447
0.8725	High Similarity	NPC171207
0.8725	High Similarity	NPC97667
0.8725	High Similarity	NPC90614
0.8725	High Similarity	NPC100913
0.8725	High Similarity	NPC275592
0.871	High Similarity	NPC472548
0.871	High Similarity	NPC477905
0.8704	High Similarity	NPC102465
0.8701	High Similarity	NPC473214
0.8701	High Similarity	NPC470245
0.8696	High Similarity	NPC477491
0.8688	High Similarity	NPC329960
0.8688	High Similarity	NPC150893
0.8688	High Similarity	NPC295408
0.8684	High Similarity	NPC472556
0.8671	High Similarity	NPC477736
0.8667	High Similarity	NPC148185
0.8662	High Similarity	NPC323001
0.8662	High Similarity	NPC326235
0.8654	High Similarity	NPC471135
0.8645	High Similarity	NPC470153
0.8642	High Similarity	NPC120012
0.8636	High Similarity	NPC473215
0.8631	High Similarity	NPC195114
0.8623	High Similarity	NPC469397
0.8616	High Similarity	NPC323356
0.8616	High Similarity	NPC326328
0.8616	High Similarity	NPC471138
0.8616	High Similarity	NPC309991
0.8609	High Similarity	NPC34012
0.86	High Similarity	NPC473613
0.86	High Similarity	NPC4341
0.86	High Similarity	NPC473109
0.86	High Similarity	NPC472547
0.86	High Similarity	NPC473081
0.86	High Similarity	NPC184747
0.86	High Similarity	NPC476094
0.86	High Similarity	NPC211137
0.86	High Similarity	NPC473758
0.86	High Similarity	NPC473085
0.86	High Similarity	NPC43241
0.86	High Similarity	NPC48017
0.86	High Similarity	NPC147880
0.86	High Similarity	NPC473112
0.86	High Similarity	NPC473060
0.86	High Similarity	NPC200592
0.8599	High Similarity	NPC472549
0.8589	High Similarity	NPC265600
0.8581	High Similarity	NPC476173
0.8571	High Similarity	NPC80360
0.8571	High Similarity	NPC478125
0.8553	High Similarity	NPC91703
0.8553	High Similarity	NPC473673
0.8553	High Similarity	NPC147217
0.8553	High Similarity	NPC246480
0.8553	High Similarity	NPC270498
0.8553	High Similarity	NPC177340
0.8553	High Similarity	NPC191082
0.8553	High Similarity	NPC475429
0.8553	High Similarity	NPC139067
0.8544	High Similarity	NPC475548
0.8544	High Similarity	NPC290683
0.8544	High Similarity	NPC475638
0.8543	High Similarity	NPC224491
0.8533	High Similarity	NPC214550
0.8533	High Similarity	NPC210591
0.8533	High Similarity	NPC475652
0.8519	High Similarity	NPC471493
0.8506	High Similarity	NPC478263
0.8506	High Similarity	NPC240115
0.8506	High Similarity	NPC469513
0.8497	Intermediate Similarity	NPC38696
0.8497	Intermediate Similarity	NPC67777
0.8497	Intermediate Similarity	NPC51314
0.8487	Intermediate Similarity	NPC473755
0.8487	Intermediate Similarity	NPC475513
0.8481	Intermediate Similarity	NPC469456
0.8471	Intermediate Similarity	NPC188217
0.8467	Intermediate Similarity	NPC39549
0.8467	Intermediate Similarity	NPC283375
0.8467	Intermediate Similarity	NPC183122
0.8462	Intermediate Similarity	NPC260300
0.8457	Intermediate Similarity	NPC66193
0.8456	Intermediate Similarity	NPC195647
0.8456	Intermediate Similarity	NPC472577
0.8456	Intermediate Similarity	NPC66761
0.8456	Intermediate Similarity	NPC473399
0.8456	Intermediate Similarity	NPC473216
0.8456	Intermediate Similarity	NPC291638
0.8456	Intermediate Similarity	NPC17877
0.8452	Intermediate Similarity	NPC473760
0.8442	Intermediate Similarity	NPC478264
0.8428	Intermediate Similarity	NPC106895
0.8424	Intermediate Similarity	NPC469419
0.8405	Intermediate Similarity	NPC471134
0.84	Intermediate Similarity	NPC472551
0.84	Intermediate Similarity	NPC472545
0.8389	Intermediate Similarity	NPC474608
0.8387	Intermediate Similarity	NPC209592
0.8387	Intermediate Similarity	NPC48599
0.8387	Intermediate Similarity	NPC20255
0.8387	Intermediate Similarity	NPC473602
0.8377	Intermediate Similarity	NPC470231
0.8377	Intermediate Similarity	NPC111466
0.8377	Intermediate Similarity	NPC34943
0.8366	Intermediate Similarity	NPC472546

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 NPC477623 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	781
0.2-0.3	1762
0.3-0.4	3174
0.4-0.5	2226
0.5-0.6	738
0.6-0.7	146
0.7-0.8	18
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
0.8214	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7799	Discontinued
0.7829	Intermediate Similarity	NPD8407	Phase 2
0.7759	Intermediate Similarity	NPD8368	Discontinued
0.7647	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7228	Approved
0.7557	Intermediate Similarity	NPD7240	Approved
0.7542	Intermediate Similarity	NPD8434	Phase 2
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD8312	Approved
0.7472	Intermediate Similarity	NPD8313	Approved
0.7459	Intermediate Similarity	NPD8435	Approved
0.7459	Intermediate Similarity	NPD8361	Approved
0.7459	Intermediate Similarity	NPD8360	Approved
0.7423	Intermediate Similarity	NPD7236	Approved
0.7396	Intermediate Similarity	NPD8455	Phase 2
0.7377	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4966	Approved
0.731	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD4965	Approved
0.7305	Intermediate Similarity	NPD7239	Suspended
0.7287	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6234	Discontinued
0.7222	Intermediate Similarity	NPD7266	Discontinued
0.7219	Intermediate Similarity	NPD5125	Phase 3
0.7219	Intermediate Similarity	NPD5126	Approved
0.7167	Intermediate Similarity	NPD7685	Pre-registration
0.7151	Intermediate Similarity	NPD7074	Phase 3
0.7135	Intermediate Similarity	NPD8319	Approved
0.7135	Intermediate Similarity	NPD8320	Phase 1
0.7135	Intermediate Similarity	NPD37	Approved
0.7128	Intermediate Similarity	NPD8485	Approved
0.7095	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7700	Phase 2
0.709	Intermediate Similarity	NPD7699	Phase 2
0.7072	Intermediate Similarity	NPD6559	Discontinued
0.7065	Intermediate Similarity	NPD8150	Discontinued
0.7059	Intermediate Similarity	NPD7458	Discontinued
0.7056	Intermediate Similarity	NPD7472	Approved
0.7033	Intermediate Similarity	NPD7808	Phase 3
0.7024	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7054	Approved
0.6988	Remote Similarity	NPD4628	Phase 3
0.6978	Remote Similarity	NPD7251	Discontinued
0.6971	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8127	Discontinued
0.6931	Remote Similarity	NPD6535	Approved
0.6931	Remote Similarity	NPD6534	Approved
0.6923	Remote Similarity	NPD6797	Phase 2
0.6914	Remote Similarity	NPD7058	Phase 2
0.6914	Remote Similarity	NPD7057	Phase 3
0.6907	Remote Similarity	NPD7680	Approved
0.6907	Remote Similarity	NPD7435	Discontinued
0.6906	Remote Similarity	NPD5844	Phase 1
0.6898	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8166	Discontinued
0.6884	Remote Similarity	NPD8462	Phase 1
0.6875	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7008	Discontinued
0.686	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7199	Phase 2
0.6851	Remote Similarity	NPD3818	Discontinued
0.6821	Remote Similarity	NPD7698	Approved
0.6821	Remote Similarity	NPD7697	Approved
0.6821	Remote Similarity	NPD2629	Approved
0.6821	Remote Similarity	NPD7696	Phase 3
0.6818	Remote Similarity	NPD8151	Discontinued
0.68	Remote Similarity	NPD7819	Suspended
0.6784	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7874	Approved
0.6784	Remote Similarity	NPD6273	Approved
0.6769	Remote Similarity	NPD6823	Phase 2
0.6768	Remote Similarity	NPD7701	Phase 2
0.6765	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6778	Approved
0.6753	Remote Similarity	NPD6776	Approved
0.6753	Remote Similarity	NPD6781	Approved
0.6753	Remote Similarity	NPD6780	Approved
0.6753	Remote Similarity	NPD6782	Approved
0.6753	Remote Similarity	NPD7741	Discontinued
0.6753	Remote Similarity	NPD6777	Approved
0.6753	Remote Similarity	NPD6779	Approved
0.675	Remote Similarity	NPD7783	Phase 2
0.675	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD8404	Phase 2
0.6746	Remote Similarity	NPD6190	Approved
0.6744	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7497	Discontinued
0.6728	Remote Similarity	NPD3764	Approved
0.6724	Remote Similarity	NPD4380	Phase 2
0.6723	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.671	Remote Similarity	NPD8378	Approved
0.671	Remote Similarity	NPD8335	Approved
0.671	Remote Similarity	NPD8296	Approved
0.671	Remote Similarity	NPD8380	Approved
0.671	Remote Similarity	NPD8379	Approved
0.6707	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD5494	Approved
0.6701	Remote Similarity	NPD7870	Phase 2
0.6701	Remote Similarity	NPD7871	Phase 2
0.6687	Remote Similarity	NPD7961	Discontinued
0.6685	Remote Similarity	NPD7075	Discontinued
0.6685	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD7999	Approved
0.6667	Remote Similarity	NPD7801	Approved
0.6667	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD8377	Approved
0.6645	Remote Similarity	NPD8294	Approved
0.6629	Remote Similarity	NPD7028	Phase 2
0.6628	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6212	Phase 3
0.6615	Remote Similarity	NPD6213	Phase 3
0.6603	Remote Similarity	NPD8515	Approved
0.6603	Remote Similarity	NPD8033	Approved
0.6603	Remote Similarity	NPD8516	Approved
0.6603	Remote Similarity	NPD8513	Phase 3
0.6603	Remote Similarity	NPD8517	Approved
0.6601	Remote Similarity	NPD5951	Approved
0.6588	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7003	Approved
0.6581	Remote Similarity	NPD7516	Approved
0.6579	Remote Similarity	NPD8133	Approved
0.6577	Remote Similarity	NPD6686	Approved
0.6576	Remote Similarity	NPD3751	Discontinued
0.6573	Remote Similarity	NPD5402	Approved
0.6571	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6166	Phase 2
0.6557	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7507	Approved
0.6538	Remote Similarity	NPD3787	Discontinued
0.6534	Remote Similarity	NPD6599	Discontinued
0.6529	Remote Similarity	NPD6674	Discontinued
0.6527	Remote Similarity	NPD7097	Phase 1
0.6524	Remote Similarity	NPD6764	Approved
0.6524	Remote Similarity	NPD6765	Approved
0.6522	Remote Similarity	NPD7319	Approved
0.6522	Remote Similarity	NPD7473	Discontinued
0.6517	Remote Similarity	NPD5761	Phase 2
0.6517	Remote Similarity	NPD5760	Phase 2
0.6516	Remote Similarity	NPD7327	Approved
0.6516	Remote Similarity	NPD7328	Approved
0.6513	Remote Similarity	NPD969	Suspended
0.6497	Remote Similarity	NPD7503	Approved
0.6488	Remote Similarity	NPD7930	Approved
0.648	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD6801	Discontinued
0.6459	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5403	Approved
0.6456	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD6232	Discontinued
0.6444	Remote Similarity	NPD7768	Phase 2
0.6437	Remote Similarity	NPD5401	Approved
0.6425	Remote Similarity	NPD1465	Phase 2
0.6425	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2182	Approved
0.6421	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1653	Approved
0.6418	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD2346	Discontinued
0.6407	Remote Similarity	NPD6355	Discontinued
0.6404	Remote Similarity	NPD7411	Suspended
0.6395	Remote Similarity	NPD3750	Approved
0.6393	Remote Similarity	NPD6959	Discontinued
0.6389	Remote Similarity	NPD3817	Phase 2
0.6387	Remote Similarity	NPD6785	Approved
0.6387	Remote Similarity	NPD6784	Approved
0.6386	Remote Similarity	NPD7715	Approved
0.6386	Remote Similarity	NPD7714	Approved
0.6386	Remote Similarity	NPD6663	Approved
0.6378	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD6287	Discontinued
0.6374	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD1934	Approved
0.6353	Remote Similarity	NPD2935	Discontinued
0.6343	Remote Similarity	NPD2534	Approved
0.6343	Remote Similarity	NPD2533	Approved
0.6343	Remote Similarity	NPD2532	Approved
0.634	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6002	Phase 3
0.6316	Remote Similarity	NPD6005	Phase 3
0.6316	Remote Similarity	NPD6004	Phase 3
0.6316	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD8328	Phase 3
0.631	Remote Similarity	NPD230	Phase 1

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