NPASS Compound

Structure

NPC173292 OpenBabel07101718322D 30 34 0 0 1 0 0 0 0 0999 V2000 -4.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 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 2.5981 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 -0.8660 -2.5000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 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 -2.4049 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9049 -1.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 -1.8171 -2.8090 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 23 1 0 0 0 0 2 23 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 19 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 28 1 0 0 0 0 11 21 1 0 0 0 0 11 22 2 0 0 0 0 12 15 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 29 1 0 0 0 0 15 28 1 0 0 0 0 16 17 2 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 10 1 6 0 0 0 18 20 1 0 0 0 0 18 30 1 0 0 0 0 19 23 1 1 0 0 0 19 29 1 0 0 0 0 20 12 1 6 0 0 0 20 21 1 0 0 0 0 21 24 2 0 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.15
Volume:	406.658
LogP:	3.59
LogD:	2.909
LogS:	-4.288
# Rotatable Bonds:	3
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.83
Synthetic Accessibility Score:	3.928
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.82
MDCK Permeability:	3.975501749664545e-05
Pgp-inhibitor:	0.953
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.206
Plasma Protein Binding (PPB):	92.83264923095703%
Volume Distribution (VD):	0.756
Pgp-substrate:	9.02302360534668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.589
CYP2C19-inhibitor:	0.705
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.755
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.506
CYP2D6-substrate:	0.748
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.725

ADMET: Excretion

Clearance (CL):	6.062
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.305
Drug-inuced Liver Injury (DILI):	0.677
AMES Toxicity:	0.124
Rat Oral Acute Toxicity:	0.775
Maximum Recommended Daily Dose:	0.762
Skin Sensitization:	0.141
Carcinogencity:	0.221
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.168

Download Data

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

Natural Product: NPC173292

Natural Product ID:	NPC173292
*Common Name:**	Dalpanol
IUPAC Name:	n.a.
Synonyms:	Dalpanol
Standard InCHIKey:	UJRXJHPYROZVGI-AQNXPRMDSA-N
Standard InCHI:	InChI=1S/C23H24O7/c1-23(2,25)19-8-13-14(29-19)6-5-11-21(24)20-12-7-16(26-3)17(27-4)9-15(12)28-10-18(20)30-22(11)13/h5-7,9,18-20,25H,8,10H2,1-4H3/t18-,19-,20+/m1/s1
SMILES:	COc1cc2c(cc1OC)OC[C@@H]1[C@H]2C(=O)c2c(O1)c1C[C@@H](Oc1cc2)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518129
PubChem CID:	182000
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18841906]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28075580]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326318]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350086]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16886	Amorpha fruticosa	Species	Fabaceae	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
ED50	5
IC50	2

Activity Type	# Activity
Cell Line	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	=	0.48	ug ml-1	PMID[469089]
NPT1091	Cell Line	RPMI-7951	Homo sapiens	ED50	=	4.83	ug ml-1	PMID[469089]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.89	ug ml-1	PMID[469089]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.86	ug ml-1	PMID[469089]
NPT672	Cell Line	TE-671	Homo sapiens	ED50	=	0.49	ug ml-1	PMID[469089]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	700.0	nM	PMID[469090]
NPT2	Others	Unspecified		IC50	=	652.0	nM	PMID[469091]

☑ 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 NPC173292 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	424
0.1-0.2	1520
0.2-0.3	3411
0.3-0.4	8769
0.4-0.5	9729
0.5-0.6	3699
0.6-0.7	4877
0.7-0.8	5905
0.8-0.85	2701
0.85-0.9	1429
0.9-0.95	218
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC152477
0.9747	High Similarity	NPC128293
0.9679	High Similarity	NPC298093
0.9627	High Similarity	NPC121333
0.9625	High Similarity	NPC242395
0.962	High Similarity	NPC273959
0.9565	High Similarity	NPC103307
0.95	High Similarity	NPC120593
0.9494	High Similarity	NPC165549
0.9451	High Similarity	NPC156635
0.9444	High Similarity	NPC472276
0.9441	High Similarity	NPC8965
0.9437	High Similarity	NPC234052
0.9383	High Similarity	NPC288813
0.9379	High Similarity	NPC170245
0.9379	High Similarity	NPC235610
0.9375	High Similarity	NPC124038
0.9371	High Similarity	NPC134783
0.9341	High Similarity	NPC473883
0.9329	High Similarity	NPC310794
0.9325	High Similarity	NPC74559
0.9321	High Similarity	NPC477154
0.9321	High Similarity	NPC117854
0.9321	High Similarity	NPC6588
0.9321	High Similarity	NPC150131
0.9317	High Similarity	NPC224280
0.9317	High Similarity	NPC62261
0.9317	High Similarity	NPC300053
0.9317	High Similarity	NPC108433
0.9317	High Similarity	NPC326520
0.9317	High Similarity	NPC472277
0.9313	High Similarity	NPC474162
0.9313	High Similarity	NPC472448
0.9313	High Similarity	NPC83922
0.9313	High Similarity	NPC474034
0.9313	High Similarity	NPC474033
0.9313	High Similarity	NPC81679
0.9313	High Similarity	NPC474150
0.9308	High Similarity	NPC472624
0.9308	High Similarity	NPC471976
0.9304	High Similarity	NPC19097
0.9304	High Similarity	NPC181960
0.9277	High Similarity	NPC67302
0.9268	High Similarity	NPC223375
0.9268	High Similarity	NPC475825
0.9264	High Similarity	NPC177480
0.9259	High Similarity	NPC119589
0.9255	High Similarity	NPC472281
0.9255	High Similarity	NPC236521
0.9255	High Similarity	NPC18100
0.9255	High Similarity	NPC329669
0.9255	High Similarity	NPC473313
0.9255	High Similarity	NPC475985
0.9255	High Similarity	NPC248638
0.9255	High Similarity	NPC152659
0.9255	High Similarity	NPC205265
0.9255	High Similarity	NPC472278
0.925	High Similarity	NPC472632
0.925	High Similarity	NPC3629
0.925	High Similarity	NPC167678
0.925	High Similarity	NPC471210
0.925	High Similarity	NPC266314
0.925	High Similarity	NPC29876
0.9245	High Similarity	NPC95936
0.9245	High Similarity	NPC473990
0.9245	High Similarity	NPC250214
0.9241	High Similarity	NPC303255
0.9207	High Similarity	NPC190351
0.9198	High Similarity	NPC472450
0.9198	High Similarity	NPC275780
0.9198	High Similarity	NPC239752
0.9198	High Similarity	NPC293319
0.9193	High Similarity	NPC261470
0.9193	High Similarity	NPC472402
0.9193	High Similarity	NPC472635
0.9193	High Similarity	NPC220912
0.9193	High Similarity	NPC229632
0.9193	High Similarity	NPC478199
0.9193	High Similarity	NPC25152
0.9187	High Similarity	NPC328102
0.9187	High Similarity	NPC192686
0.9187	High Similarity	NPC119209
0.9187	High Similarity	NPC118256
0.9187	High Similarity	NPC204290
0.9187	High Similarity	NPC174953
0.9187	High Similarity	NPC476980
0.9187	High Similarity	NPC475784
0.9182	High Similarity	NPC475267
0.9182	High Similarity	NPC299520
0.9182	High Similarity	NPC222814
0.9182	High Similarity	NPC469584
0.9182	High Similarity	NPC472910
0.9182	High Similarity	NPC78225
0.9182	High Similarity	NPC474836
0.9182	High Similarity	NPC96167
0.9182	High Similarity	NPC476981
0.9182	High Similarity	NPC223787
0.9182	High Similarity	NPC473272
0.9182	High Similarity	NPC129684
0.9182	High Similarity	NPC472914
0.9182	High Similarity	NPC474208
0.9182	High Similarity	NPC291508
0.9182	High Similarity	NPC99597
0.9182	High Similarity	NPC78071
0.9182	High Similarity	NPC156057
0.9182	High Similarity	NPC245758
0.9182	High Similarity	NPC472913
0.9182	High Similarity	NPC48208
0.9182	High Similarity	NPC162869
0.9182	High Similarity	NPC284820
0.9182	High Similarity	NPC210084
0.9182	High Similarity	NPC262286
0.9182	High Similarity	NPC27337
0.9182	High Similarity	NPC471209
0.9182	High Similarity	NPC36852
0.9182	High Similarity	NPC472911
0.9177	High Similarity	NPC31018
0.9177	High Similarity	NPC37392
0.9177	High Similarity	NPC255807
0.9177	High Similarity	NPC472909
0.9172	High Similarity	NPC40033
0.9172	High Similarity	NPC166201
0.9146	High Similarity	NPC326877
0.9141	High Similarity	NPC39091
0.9141	High Similarity	NPC472449
0.9141	High Similarity	NPC277480
0.9136	High Similarity	NPC41301
0.9136	High Similarity	NPC303460
0.9136	High Similarity	NPC23298
0.9136	High Similarity	NPC186686
0.9136	High Similarity	NPC189473
0.9136	High Similarity	NPC306321
0.913	High Similarity	NPC61010
0.913	High Similarity	NPC474038
0.913	High Similarity	NPC474187
0.913	High Similarity	NPC474186
0.913	High Similarity	NPC173137
0.913	High Similarity	NPC472275
0.913	High Similarity	NPC471212
0.913	High Similarity	NPC259456
0.913	High Similarity	NPC228383
0.913	High Similarity	NPC471211
0.9125	High Similarity	NPC204879
0.9125	High Similarity	NPC187792
0.9125	High Similarity	NPC152904
0.9119	High Similarity	NPC235165
0.9119	High Similarity	NPC195796
0.9119	High Similarity	NPC138243
0.9119	High Similarity	NPC191146
0.9119	High Similarity	NPC470600
0.9119	High Similarity	NPC35038
0.9119	High Similarity	NPC472916
0.9119	High Similarity	NPC278778
0.9119	High Similarity	NPC255106
0.9119	High Similarity	NPC68093
0.9119	High Similarity	NPC291878
0.9114	High Similarity	NPC472408
0.9114	High Similarity	NPC472915
0.9114	High Similarity	NPC128961
0.9112	High Similarity	NPC150977
0.9103	High Similarity	NPC238366
0.9091	High Similarity	NPC131866
0.9091	High Similarity	NPC102277
0.9091	High Similarity	NPC279209
0.9085	High Similarity	NPC14662
0.9085	High Similarity	NPC247973
0.908	High Similarity	NPC473286
0.908	High Similarity	NPC25361
0.908	High Similarity	NPC50960
0.908	High Similarity	NPC37183
0.9074	High Similarity	NPC52204
0.9074	High Similarity	NPC476247
0.9074	High Similarity	NPC329760
0.9068	High Similarity	NPC200746
0.9068	High Similarity	NPC475886
0.9068	High Similarity	NPC56085
0.9068	High Similarity	NPC228785
0.9068	High Similarity	NPC36217
0.9068	High Similarity	NPC474287
0.9068	High Similarity	NPC14353
0.9062	High Similarity	NPC196448
0.9062	High Similarity	NPC472598
0.9062	High Similarity	NPC474681
0.9062	High Similarity	NPC165977
0.9062	High Similarity	NPC52889
0.9062	High Similarity	NPC474055
0.9062	High Similarity	NPC218313
0.9062	High Similarity	NPC217677
0.9057	High Similarity	NPC230149
0.9057	High Similarity	NPC226025
0.9057	High Similarity	NPC152951
0.9057	High Similarity	NPC256925
0.9057	High Similarity	NPC477503
0.9057	High Similarity	NPC113906
0.9057	High Similarity	NPC168247
0.9057	High Similarity	NPC57674
0.9057	High Similarity	NPC45849
0.9057	High Similarity	NPC200761
0.9057	High Similarity	NPC2928
0.9057	High Similarity	NPC117992

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 NPC173292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	912
0.2-0.3	1700
0.3-0.4	2601
0.4-0.5	1894
0.5-0.6	989
0.6-0.7	479
0.7-0.8	159
0.8-0.85	33
0.85-0.9	9
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9679	High Similarity	NPD5494	Approved
0.8994	High Similarity	NPD2393	Clinical (unspecified phase)
0.8931	High Similarity	NPD1934	Approved
0.8875	High Similarity	NPD2801	Approved
0.8765	High Similarity	NPD3882	Suspended
0.8735	High Similarity	NPD6166	Phase 2
0.8735	High Similarity	NPD6167	Clinical (unspecified phase)
0.8735	High Similarity	NPD6168	Clinical (unspecified phase)
0.8631	High Similarity	NPD3818	Discontinued
0.858	High Similarity	NPD5844	Phase 1
0.8571	High Similarity	NPD4380	Phase 2
0.8529	High Similarity	NPD7074	Phase 3
0.8528	High Similarity	NPD7096	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD3817	Phase 2
0.8471	Intermediate Similarity	NPD7054	Approved
0.8443	Intermediate Similarity	NPD1247	Approved
0.8424	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD7472	Approved
0.8415	Intermediate Similarity	NPD7819	Suspended
0.8382	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7075	Discontinued
0.8364	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD1511	Approved
0.8276	Intermediate Similarity	NPD7808	Phase 3
0.8266	Intermediate Similarity	NPD6797	Phase 2
0.8263	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7473	Discontinued
0.8228	Intermediate Similarity	NPD1549	Phase 2
0.8225	Intermediate Similarity	NPD6959	Discontinued
0.8218	Intermediate Similarity	NPD7251	Discontinued
0.8217	Intermediate Similarity	NPD2796	Approved
0.821	Intermediate Similarity	NPD1512	Approved
0.8182	Intermediate Similarity	NPD7411	Suspended
0.8176	Intermediate Similarity	NPD6232	Discontinued
0.8165	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5402	Approved
0.8133	Intermediate Similarity	NPD6801	Discontinued
0.8129	Intermediate Similarity	NPD3926	Phase 2
0.8114	Intermediate Similarity	NPD6559	Discontinued
0.8107	Intermediate Similarity	NPD919	Approved
0.8086	Intermediate Similarity	NPD6799	Approved
0.8084	Intermediate Similarity	NPD1465	Phase 2
0.8057	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.7941	Intermediate Similarity	NPD3749	Approved
0.7933	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1510	Phase 2
0.7874	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD2800	Approved
0.7831	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD920	Approved
0.7818	Intermediate Similarity	NPD2533	Approved
0.7818	Intermediate Similarity	NPD2532	Approved
0.7818	Intermediate Similarity	NPD2534	Approved
0.7814	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7199	Phase 2
0.7802	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1240	Approved
0.7784	Intermediate Similarity	NPD3751	Discontinued
0.7778	Intermediate Similarity	NPD7768	Phase 2
0.7764	Intermediate Similarity	NPD2935	Discontinued
0.7759	Intermediate Similarity	NPD3787	Discontinued
0.7725	Intermediate Similarity	NPD5403	Approved
0.7714	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5401	Approved
0.7711	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD37	Approved
0.7702	Intermediate Similarity	NPD2799	Discontinued
0.7692	Intermediate Similarity	NPD8434	Phase 2
0.7688	Intermediate Similarity	NPD1607	Approved
0.7688	Intermediate Similarity	NPD6234	Discontinued
0.7684	Intermediate Similarity	NPD7228	Approved
0.7674	Intermediate Similarity	NPD4967	Phase 2
0.7674	Intermediate Similarity	NPD4966	Approved
0.7674	Intermediate Similarity	NPD4965	Approved
0.7673	Intermediate Similarity	NPD943	Approved
0.7624	Intermediate Similarity	NPD8312	Approved
0.7624	Intermediate Similarity	NPD8313	Approved
0.7622	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1243	Approved
0.7619	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2346	Discontinued
0.759	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3750	Approved
0.7576	Intermediate Similarity	NPD4628	Phase 3
0.7569	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1613	Approved
0.7561	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3226	Approved
0.7526	Intermediate Similarity	NPD6779	Approved
0.7526	Intermediate Similarity	NPD6781	Approved
0.7526	Intermediate Similarity	NPD6778	Approved
0.7526	Intermediate Similarity	NPD6782	Approved
0.7526	Intermediate Similarity	NPD6776	Approved
0.7526	Intermediate Similarity	NPD6780	Approved
0.7526	Intermediate Similarity	NPD6777	Approved
0.7516	Intermediate Similarity	NPD447	Suspended
0.7514	Intermediate Similarity	NPD7240	Approved
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD3748	Approved
0.7458	Intermediate Similarity	NPD7229	Phase 3
0.744	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6100	Approved
0.7439	Intermediate Similarity	NPD6099	Approved
0.7438	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2313	Discontinued
0.7421	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7435	Discontinued
0.7409	Intermediate Similarity	NPD7696	Phase 3
0.7409	Intermediate Similarity	NPD7697	Approved
0.7409	Intermediate Similarity	NPD7698	Approved
0.7407	Intermediate Similarity	NPD230	Phase 1
0.7407	Intermediate Similarity	NPD1933	Approved
0.7399	Intermediate Similarity	NPD6844	Discontinued
0.7396	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3027	Phase 3
0.7374	Intermediate Similarity	NPD2403	Approved
0.7368	Intermediate Similarity	NPD1653	Approved
0.7365	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5953	Discontinued
0.736	Intermediate Similarity	NPD5710	Approved
0.736	Intermediate Similarity	NPD5711	Approved
0.7358	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD4360	Phase 2
0.7354	Intermediate Similarity	NPD4363	Phase 3
0.7349	Intermediate Similarity	NPD2424	Discontinued
0.7348	Intermediate Similarity	NPD7286	Phase 2
0.7347	Intermediate Similarity	NPD7701	Phase 2
0.7333	Intermediate Similarity	NPD1551	Phase 2
0.7326	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7783	Phase 2
0.7323	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2309	Approved
0.7321	Intermediate Similarity	NPD6190	Approved
0.7318	Intermediate Similarity	NPD5242	Approved
0.7314	Intermediate Similarity	NPD5353	Approved
0.7312	Intermediate Similarity	NPD4908	Phase 1
0.731	Intermediate Similarity	NPD8151	Discontinued
0.7308	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8127	Discontinued
0.7289	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7549	Discontinued
0.7282	Intermediate Similarity	NPD7870	Phase 2
0.7282	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6823	Phase 2
0.7263	Intermediate Similarity	NPD6535	Approved
0.7263	Intermediate Similarity	NPD6534	Approved
0.7257	Intermediate Similarity	NPD8455	Phase 2
0.7257	Intermediate Similarity	NPD5761	Phase 2
0.7257	Intermediate Similarity	NPD5760	Phase 2
0.7256	Intermediate Similarity	NPD6651	Approved
0.725	Intermediate Similarity	NPD2861	Phase 2
0.7241	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7700	Phase 2
0.724	Intermediate Similarity	NPD7699	Phase 2
0.7236	Intermediate Similarity	NPD7801	Approved
0.7235	Intermediate Similarity	NPD7390	Discontinued
0.7225	Intermediate Similarity	NPD7458	Discontinued
0.7208	Intermediate Similarity	NPD7584	Approved
0.7195	Intermediate Similarity	NPD5124	Phase 1
0.7195	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6355	Discontinued
0.7193	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2798	Approved
0.7188	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7874	Approved
0.7175	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7033	Discontinued
0.716	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4665	Approved
0.7157	Intermediate Similarity	NPD4111	Phase 1
0.7151	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD9494	Approved
0.7135	Intermediate Similarity	NPD4361	Phase 2
0.7135	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6674	Discontinued
0.7099	Intermediate Similarity	NPD6832	Phase 2
0.7098	Intermediate Similarity	NPD2974	Approved
0.7098	Intermediate Similarity	NPD2975	Approved
0.7098	Intermediate Similarity	NPD2973	Approved
0.7091	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1610	Phase 2
0.7087	Intermediate Similarity	NPD7907	Approved
0.7083	Intermediate Similarity	NPD1471	Phase 3
0.7077	Intermediate Similarity	NPD4580	Approved
0.7073	Intermediate Similarity	NPD6233	Phase 2
0.7059	Intermediate Similarity	NPD4110	Phase 3
0.7059	Intermediate Similarity	NPD4109	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