NPASS Compound

Structure

CID21835 OpenBabel06191715342D 22 24 0 0 1 0 0 0 0 0999 V2000 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 1 6 2 0 0 0 0 1 7 1 0 0 0 0 2 6 1 0 0 0 0 2 8 2 0 0 0 0 3 7 2 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 11 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 14 21 1 6 0 0 0 15 6 1 1 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.06
Volume:	285.403
LogP:	0.457
LogD:	-0.019
LogS:	-2.413
# Rotatable Bonds:	1
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	3.659
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.109
MDCK Permeability:	4.39500718130148e-06
Pgp-inhibitor:	0.012
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.961
30% Bioavailability (F30%):	0.904

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	73.19464874267578%
Volume Distribution (VD):	1.36
Pgp-substrate:	22.083208084106445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.271
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.179
CYP2D6-substrate:	0.298
CYP3A4-inhibitor:	0.604
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	9.054
Half-life (T1/2):	0.883

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.887
AMES Toxicity:	0.1
Rat Oral Acute Toxicity:	0.187
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.926
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.881
Respiratory Toxicity:	0.37

Download Data

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

Natural Product: NPC21835

Natural Product ID:	NPC21835
*Common Name:**	(2R,3R)-3,3',5,5',7-Pentahydroxy Flavanonol
IUPAC Name:	(2R,3R)-2-(3,5-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	SRHDEHLQIMAWNV-LSDHHAIUSA-N
Standard InCHI:	InChI=1S/C15H12O7/c16-7-1-6(2-8(17)3-7)15-14(21)13(20)12-10(19)4-9(18)5-11(12)22-15/h1-5,14-19,21H/t14-,15+/m0/s1
SMILES:	Oc1cc(O)cc(c1)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3634574
PubChem CID:	5320468
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones [CHEMONTID:0001362] Flavanonols

*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]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9729	Hovenia dulcis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	10.0	%	PMID[542479]
NPT35	Others	n.a.		EC50	>	100000.0	nM	PMID[542479]

☑ 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 NPC21835 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	426
0.1-0.2	1712
0.2-0.3	4348
0.3-0.4	9992
0.4-0.5	7896
0.5-0.6	3686
0.6-0.7	4972
0.7-0.8	5437
0.8-0.85	2611
0.85-0.9	1376
0.9-0.95	209
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC218569
0.9716	High Similarity	NPC306607
0.9716	High Similarity	NPC62290
0.9716	High Similarity	NPC49130
0.9716	High Similarity	NPC208176
0.9716	High Similarity	NPC142731
0.9716	High Similarity	NPC279417
0.9716	High Similarity	NPC326506
0.9716	High Similarity	NPC4152
0.9655	High Similarity	NPC19721
0.9655	High Similarity	NPC9743
0.9655	High Similarity	NPC61506
0.9655	High Similarity	NPC260491
0.9655	High Similarity	NPC36835
0.9655	High Similarity	NPC240476
0.9655	High Similarity	NPC246162
0.9648	High Similarity	NPC148011
0.9648	High Similarity	NPC1940
0.9589	High Similarity	NPC256346
0.9589	High Similarity	NPC27532
0.9589	High Similarity	NPC246328
0.9589	High Similarity	NPC325028
0.958	High Similarity	NPC40086
0.958	High Similarity	NPC3779
0.958	High Similarity	NPC122828
0.958	High Similarity	NPC44721
0.958	High Similarity	NPC211466
0.958	High Similarity	NPC476182
0.958	High Similarity	NPC176869
0.9571	High Similarity	NPC182421
0.9459	High Similarity	NPC326037
0.9459	High Similarity	NPC201837
0.9459	High Similarity	NPC320825
0.9459	High Similarity	NPC13858
0.9459	High Similarity	NPC250922
0.9452	High Similarity	NPC254412
0.9452	High Similarity	NPC262038
0.9452	High Similarity	NPC262039
0.9452	High Similarity	NPC278476
0.9452	High Similarity	NPC319910
0.9437	High Similarity	NPC73028
0.9396	High Similarity	NPC52530
0.9388	High Similarity	NPC171651
0.9388	High Similarity	NPC216035
0.9388	High Similarity	NPC243171
0.9388	High Similarity	NPC138288
0.9388	High Similarity	NPC217149
0.9388	High Similarity	NPC35567
0.9384	High Similarity	NPC105136
0.9379	High Similarity	NPC321011
0.9379	High Similarity	NPC294852
0.9379	High Similarity	NPC188679
0.9375	High Similarity	NPC229190
0.9366	High Similarity	NPC150023
0.9333	High Similarity	NPC22192
0.9329	High Similarity	NPC471500
0.9324	High Similarity	NPC293286
0.9324	High Similarity	NPC141212
0.9324	High Similarity	NPC244250
0.9324	High Similarity	NPC268193
0.9324	High Similarity	NPC20907
0.9315	High Similarity	NPC183959
0.9315	High Similarity	NPC1612
0.9315	High Similarity	NPC277032
0.931	High Similarity	NPC472918
0.9272	High Similarity	NPC470326
0.9272	High Similarity	NPC282009
0.9272	High Similarity	NPC287328
0.9272	High Similarity	NPC263449
0.9272	High Similarity	NPC470183
0.9267	High Similarity	NPC471479
0.9267	High Similarity	NPC471515
0.9262	High Similarity	NPC304745
0.9262	High Similarity	NPC304207
0.9262	High Similarity	NPC111341
0.9262	High Similarity	NPC217706
0.9262	High Similarity	NPC48579
0.9262	High Similarity	NPC207809
0.9262	High Similarity	NPC259710
0.9257	High Similarity	NPC219582
0.9257	High Similarity	NPC236637
0.9257	High Similarity	NPC302950
0.9252	High Similarity	NPC338131
0.9252	High Similarity	NPC267117
0.9241	High Similarity	NPC24136
0.9241	High Similarity	NPC290133
0.9241	High Similarity	NPC187282
0.922	High Similarity	NPC296490
0.922	High Similarity	NPC243083
0.922	High Similarity	NPC287246
0.922	High Similarity	NPC107586
0.922	High Similarity	NPC79943
0.922	High Similarity	NPC12296
0.922	High Similarity	NPC32441
0.922	High Similarity	NPC295261
0.922	High Similarity	NPC13768
0.9211	High Similarity	NPC308992
0.9211	High Similarity	NPC289771
0.9211	High Similarity	NPC471499
0.92	High Similarity	NPC215917
0.92	High Similarity	NPC208152
0.92	High Similarity	NPC20530
0.92	High Similarity	NPC10754
0.92	High Similarity	NPC78492
0.92	High Similarity	NPC474638
0.9195	High Similarity	NPC18727
0.9195	High Similarity	NPC180301
0.9195	High Similarity	NPC203080
0.9195	High Similarity	NPC248793
0.9189	High Similarity	NPC471677
0.9189	High Similarity	NPC244577
0.9189	High Similarity	NPC471676
0.9189	High Similarity	NPC263384
0.9189	High Similarity	NPC204515
0.9189	High Similarity	NPC472420
0.9189	High Similarity	NPC471229
0.9189	High Similarity	NPC328740
0.9189	High Similarity	NPC474021
0.9189	High Similarity	NPC472422
0.9189	High Similarity	NPC289774
0.9189	High Similarity	NPC474023
0.9189	High Similarity	NPC209846
0.9189	High Similarity	NPC477897
0.9184	High Similarity	NPC477941
0.9178	High Similarity	NPC85773
0.9172	High Similarity	NPC470890
0.9155	High Similarity	NPC147686
0.9155	High Similarity	NPC472460
0.9155	High Similarity	NPC329225
0.915	High Similarity	NPC211107
0.9145	High Similarity	NPC471744
0.9139	High Similarity	NPC472598
0.9139	High Similarity	NPC67876
0.9139	High Similarity	NPC474055
0.9133	High Similarity	NPC200761
0.9133	High Similarity	NPC477503
0.9133	High Similarity	NPC321779
0.9133	High Similarity	NPC45849
0.9133	High Similarity	NPC470327
0.9128	High Similarity	NPC56232
0.9128	High Similarity	NPC210597
0.9128	High Similarity	NPC106976
0.9128	High Similarity	NPC475790
0.9128	High Similarity	NPC161881
0.9128	High Similarity	NPC244583
0.9128	High Similarity	NPC10807
0.9128	High Similarity	NPC150123
0.9116	High Similarity	NPC119059
0.9116	High Similarity	NPC3036
0.9116	High Similarity	NPC10097
0.911	High Similarity	NPC20791
0.911	High Similarity	NPC169749
0.911	High Similarity	NPC179271
0.911	High Similarity	NPC472629
0.9091	High Similarity	NPC310135
0.9091	High Similarity	NPC265871
0.9091	High Similarity	NPC222342
0.9091	High Similarity	NPC150648
0.9091	High Similarity	NPC329203
0.9091	High Similarity	NPC225153
0.9091	High Similarity	NPC474240
0.9091	High Similarity	NPC316480
0.9091	High Similarity	NPC274784
0.9091	High Similarity	NPC472625
0.9091	High Similarity	NPC20709
0.9091	High Similarity	NPC140890
0.9085	High Similarity	NPC112418
0.9085	High Similarity	NPC287068
0.9085	High Similarity	NPC173137
0.9085	High Similarity	NPC84585
0.9085	High Similarity	NPC476480
0.9079	High Similarity	NPC53545
0.9079	High Similarity	NPC123544
0.9079	High Similarity	NPC55738
0.9079	High Similarity	NPC152904
0.9079	High Similarity	NPC117418
0.9079	High Similarity	NPC473990
0.9073	High Similarity	NPC195796
0.9073	High Similarity	NPC235165
0.9073	High Similarity	NPC209614
0.9073	High Similarity	NPC35038
0.9073	High Similarity	NPC472626
0.9073	High Similarity	NPC255106
0.9073	High Similarity	NPC278778
0.9073	High Similarity	NPC470328
0.9073	High Similarity	NPC261866
0.9073	High Similarity	NPC291878
0.9067	High Similarity	NPC326592
0.9067	High Similarity	NPC472583
0.9067	High Similarity	NPC298692
0.9067	High Similarity	NPC213896
0.9067	High Similarity	NPC209760
0.9067	High Similarity	NPC311579
0.9067	High Similarity	NPC109594
0.9067	High Similarity	NPC112701
0.9067	High Similarity	NPC236756
0.9067	High Similarity	NPC100134
0.9067	High Similarity	NPC7989
0.9067	High Similarity	NPC223701
0.9067	High Similarity	NPC192083

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 NPC21835 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	420
0.1-0.2	910
0.2-0.3	1872
0.3-0.4	2566
0.4-0.5	1739
0.5-0.6	1024
0.6-0.7	428
0.7-0.8	140
0.8-0.85	29
0.85-0.9	14
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9257	High Similarity	NPD1934	Approved
0.922	High Similarity	NPD1550	Clinical (unspecified phase)
0.922	High Similarity	NPD1552	Clinical (unspecified phase)
0.9155	High Similarity	NPD1549	Phase 2
0.911	High Similarity	NPD1512	Approved
0.9067	High Similarity	NPD2393	Clinical (unspecified phase)
0.9032	High Similarity	NPD6168	Clinical (unspecified phase)
0.9032	High Similarity	NPD6167	Clinical (unspecified phase)
0.9032	High Similarity	NPD6166	Phase 2
0.8993	High Similarity	NPD4380	Phase 2
0.8973	High Similarity	NPD1511	Approved
0.8912	High Similarity	NPD4378	Clinical (unspecified phase)
0.8889	High Similarity	NPD4381	Clinical (unspecified phase)
0.8889	High Similarity	NPD7075	Discontinued
0.8816	High Similarity	NPD7096	Clinical (unspecified phase)
0.8811	High Similarity	NPD1510	Phase 2
0.8701	High Similarity	NPD3882	Suspended
0.8693	High Similarity	NPD2801	Approved
0.8636	High Similarity	NPD3817	Phase 2
0.8634	High Similarity	NPD6797	Phase 2
0.8627	High Similarity	NPD6801	Discontinued
0.8625	High Similarity	NPD7804	Clinical (unspecified phase)
0.8591	High Similarity	NPD6799	Approved
0.8581	High Similarity	NPD4868	Clinical (unspecified phase)
0.858	High Similarity	NPD7251	Discontinued
0.8571	High Similarity	NPD7074	Phase 3
0.8562	High Similarity	NPD3818	Discontinued
0.8531	High Similarity	NPD1240	Approved
0.8528	High Similarity	NPD7808	Phase 3
0.8528	High Similarity	NPD4338	Clinical (unspecified phase)
0.8516	High Similarity	NPD5402	Approved
0.8509	High Similarity	NPD7054	Approved
0.8493	Intermediate Similarity	NPD2796	Approved
0.8457	Intermediate Similarity	NPD7472	Approved
0.8421	Intermediate Similarity	NPD5403	Approved
0.8414	Intermediate Similarity	NPD1607	Approved
0.8411	Intermediate Similarity	NPD5401	Approved
0.8405	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD6599	Discontinued
0.8365	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD7819	Suspended
0.8276	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1613	Approved
0.8255	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6559	Discontinued
0.8205	Intermediate Similarity	NPD7411	Suspended
0.8187	Intermediate Similarity	NPD5494	Approved
0.817	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1551	Phase 2
0.8101	Intermediate Similarity	NPD1465	Phase 2
0.8056	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD943	Approved
0.8026	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2800	Approved
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.795	Intermediate Similarity	NPD3749	Approved
0.7914	Intermediate Similarity	NPD1247	Approved
0.7908	Intermediate Similarity	NPD4628	Phase 3
0.7901	Intermediate Similarity	NPD919	Approved
0.7887	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6232	Discontinued
0.7866	Intermediate Similarity	NPD3787	Discontinued
0.7831	Intermediate Similarity	NPD7473	Discontinued
0.7821	Intermediate Similarity	NPD2533	Approved
0.7821	Intermediate Similarity	NPD2532	Approved
0.7821	Intermediate Similarity	NPD2534	Approved
0.7778	Intermediate Similarity	NPD7768	Phase 2
0.777	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2935	Discontinued
0.7763	Intermediate Similarity	NPD6099	Approved
0.7763	Intermediate Similarity	NPD6100	Approved
0.7762	Intermediate Similarity	NPD1610	Phase 2
0.7733	Intermediate Similarity	NPD230	Phase 1
0.7727	Intermediate Similarity	NPD1243	Approved
0.7727	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD920	Approved
0.7714	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3926	Phase 2
0.7707	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3748	Approved
0.7697	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1203	Approved
0.7606	Intermediate Similarity	NPD1548	Phase 1
0.7597	Intermediate Similarity	NPD2344	Approved
0.7595	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3027	Phase 3
0.7566	Intermediate Similarity	NPD6651	Approved
0.7558	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2313	Discontinued
0.7533	Intermediate Similarity	NPD6798	Discontinued
0.7517	Intermediate Similarity	NPD4908	Phase 1
0.7516	Intermediate Similarity	NPD6190	Approved
0.7516	Intermediate Similarity	NPD3226	Approved
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD447	Suspended
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7468	Intermediate Similarity	NPD7033	Discontinued
0.7453	Intermediate Similarity	NPD1653	Approved
0.7452	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5953	Discontinued
0.743	Intermediate Similarity	NPD4360	Phase 2
0.743	Intermediate Similarity	NPD4363	Phase 3
0.7427	Intermediate Similarity	NPD7286	Phase 2
0.7421	Intermediate Similarity	NPD7390	Discontinued
0.7418	Intermediate Similarity	NPD6779	Approved
0.7418	Intermediate Similarity	NPD6782	Approved
0.7418	Intermediate Similarity	NPD6778	Approved
0.7418	Intermediate Similarity	NPD6776	Approved
0.7418	Intermediate Similarity	NPD6777	Approved
0.7418	Intermediate Similarity	NPD6780	Approved
0.7418	Intermediate Similarity	NPD6781	Approved
0.7417	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2309	Approved
0.7396	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1652	Phase 2
0.7386	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8434	Phase 2
0.7386	Intermediate Similarity	NPD6355	Discontinued
0.7381	Intermediate Similarity	NPD7199	Phase 2
0.7368	Intermediate Similarity	NPD6233	Phase 2
0.7355	Intermediate Similarity	NPD2799	Discontinued
0.7347	Intermediate Similarity	NPD1608	Approved
0.7347	Intermediate Similarity	NPD9717	Approved
0.7337	Intermediate Similarity	NPD5710	Approved
0.7337	Intermediate Similarity	NPD5711	Approved
0.7333	Intermediate Similarity	NPD2861	Phase 2
0.7301	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7435	Discontinued
0.7288	Intermediate Similarity	NPD8150	Discontinued
0.7285	Intermediate Similarity	NPD6832	Phase 2
0.7279	Intermediate Similarity	NPD1201	Approved
0.7279	Intermediate Similarity	NPD422	Phase 1
0.7273	Intermediate Similarity	NPD6844	Discontinued
0.7273	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD7584	Approved
0.7273	Intermediate Similarity	NPD1933	Approved
0.7262	Intermediate Similarity	NPD6234	Discontinued
0.7251	Intermediate Similarity	NPD2403	Approved
0.7246	Intermediate Similarity	NPD4967	Phase 2
0.7246	Intermediate Similarity	NPD4966	Approved
0.7246	Intermediate Similarity	NPD4965	Approved
0.7232	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8455	Phase 2
0.7228	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD9494	Approved
0.7215	Intermediate Similarity	NPD2424	Discontinued
0.7212	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4060	Phase 1
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7697	Approved
0.7204	Intermediate Similarity	NPD7698	Approved
0.7204	Intermediate Similarity	NPD7696	Phase 3
0.72	Intermediate Similarity	NPD1470	Approved
0.7196	Intermediate Similarity	NPD8151	Discontinued
0.719	Intermediate Similarity	NPD411	Approved
0.719	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3268	Approved
0.7188	Intermediate Similarity	NPD2354	Approved
0.7181	Intermediate Similarity	NPD4749	Approved
0.717	Intermediate Similarity	NPD2654	Approved
0.7168	Intermediate Similarity	NPD7228	Approved
0.7166	Intermediate Similarity	NPD7871	Phase 2
0.7166	Intermediate Similarity	NPD7870	Phase 2
0.7162	Intermediate Similarity	NPD1091	Approved
0.7161	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5124	Phase 1
0.716	Intermediate Similarity	NPD4662	Approved
0.716	Intermediate Similarity	NPD4661	Approved
0.7152	Intermediate Similarity	NPD2798	Approved
0.7152	Intermediate Similarity	NPD1471	Phase 3
0.7151	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD6535	Approved
0.7143	Intermediate Similarity	NPD6534	Approved
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7133	Intermediate Similarity	NPD3225	Approved
0.7124	Intermediate Similarity	NPD4625	Phase 3
0.7123	Intermediate Similarity	NPD9545	Approved
0.7114	Intermediate Similarity	NPD9269	Phase 2
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD4361	Phase 2
0.7104	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2797	Approved
0.7083	Intermediate Similarity	NPD4288	Approved
0.7081	Intermediate Similarity	NPD3887	Approved
0.7078	Intermediate Similarity	NPD1296	Phase 2
0.7068	Intermediate Similarity	NPD7874	Approved
0.7068	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5698	Clinical (unspecified phase)

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