NPASS Compound

Structure

CID188079 OpenBabel06191715572D 34 38 0 0 1 0 0 0 0 0999 V2000 6.0622 -1.5000 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 4.3301 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 -0.0000 3.0000 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 1.7321 -3.0000 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 3.4641 -2.0000 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 -0.8660 2.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 2.5981 -0.5000 0.0000 C 0 0 1 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 1.7321 0.0000 0.0000 C 0 0 0 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 33 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 15 1 0 0 0 0 4 10 2 0 0 0 0 4 19 1 0 0 0 0 5 11 2 0 0 0 0 5 18 1 0 0 0 0 6 11 1 0 0 0 0 6 20 2 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 26 1 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 25 1 0 0 0 0 14 9 1 1 0 0 0 14 21 1 0 0 0 0 15 19 2 0 0 0 0 15 28 1 0 0 0 0 16 17 2 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 22 2 0 0 0 0 18 31 1 0 0 0 0 19 33 1 0 0 0 0 20 22 1 0 0 0 0 20 34 1 0 0 0 0 21 10 1 1 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 24 1 0 0 0 0 23 25 2 0 0 0 0 24 32 2 0 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.11
Volume:	448.285
LogP:	2.538
LogD:	1.589
LogS:	-5.339
# Rotatable Bonds:	3
TPSA:	160.07
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.224
Synthetic Accessibility Score:	3.561
Fsp3:	0.12
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.324
MDCK Permeability:	4.659494152292609e-06
Pgp-inhibitor:	0.021
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.873
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	92.31245422363281%
Volume Distribution (VD):	0.552
Pgp-substrate:	9.140830039978027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.576
CYP1A2-substrate:	0.39
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.457
CYP2C9-substrate:	0.575
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	6.863
Half-life (T1/2):	0.893

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.018
Drug-inuced Liver Injury (DILI):	0.637
AMES Toxicity:	0.635
Rat Oral Acute Toxicity:	0.291
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.944
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.882
Respiratory Toxicity:	0.195

Download Data

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

Natural Product: NPC188079

Natural Product ID:	NPC188079
*Common Name:**	Neohydnocarpin
IUPAC Name:	(5R,6R)-2,3,8,10-tetrahydroxy-6-(4-hydroxy-3-methoxyphenyl)-5-(hydroxymethyl)-5,6-dihydrobenzo[c]xanthen-7-one
Synonyms:	Neohydnocarpin
Standard InCHIKey:	KQRVYPVRZSAZBB-QKKBWIMNSA-N
Standard InCHI:	InChI=1S/C25H20O9/c1-33-19-4-10(2-3-15(19)28)21-14(9-26)12-7-16(29)17(30)8-13(12)25-23(21)24(32)22-18(31)5-11(27)6-20(22)34-25/h2-8,14,21,26-31H,9H2,1H3/t14-,21-/m0/s1
SMILES:	OC[C@H]1c2cc(O)c(cc2c2c([C@H]1c1ccc(c(c1)OC)O)c(=O)c1c(o2)cc(cc1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489355
PubChem CID:	44576021
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002044] Phenylnaphthalenes

*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
NPO14784	Hydnocarpus wightiana	Species	Achariaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1800632]
NPO14784	Hydnocarpus wightiana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14784	Hydnocarpus wightiana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14784	Hydnocarpus wightiana	Species	Achariaceae	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	8
Others	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	5
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1490	Cell Line	Ehrlich	Mus musculus	Inhibition	=	43.07	%	PMID[555282]
NPT137	Cell Line	L1210	Mus musculus	ED50	=	3.29	ug ml-1	PMID[555282]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.06	ug ml-1	PMID[555282]
NPT660	Cell Line	SW480	Homo sapiens	ED50	=	2.03	ug ml-1	PMID[555282]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.12	ug ml-1	PMID[555282]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	4.53	ug ml-1	PMID[555282]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.49	ug ml-1	PMID[555282]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	4.07	ug ml-1	PMID[555282]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	85.0	%	PMID[555282]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	79.0	%	PMID[555282]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	60.0	%	PMID[555282]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	6.0	%	PMID[555282]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.05	ug ml-1	PMID[555282]

☑ 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 NPC188079 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	456
0.1-0.2	1794
0.2-0.3	3800
0.3-0.4	9803
0.4-0.5	8642
0.5-0.6	3620
0.6-0.7	5058
0.7-0.8	5253
0.8-0.85	2375
0.85-0.9	1632
0.9-0.95	257
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.939	High Similarity	NPC4200
0.9375	High Similarity	NPC66618
0.9375	High Similarity	NPC84324
0.9375	High Similarity	NPC113163
0.9375	High Similarity	NPC165970
0.9375	High Similarity	NPC288131
0.9375	High Similarity	NPC305987
0.9371	High Similarity	NPC172202
0.9371	High Similarity	NPC284127
0.9371	High Similarity	NPC476410
0.9313	High Similarity	NPC101731
0.9308	High Similarity	NPC183851
0.9308	High Similarity	NPC63454
0.9268	High Similarity	NPC300307
0.9268	High Similarity	NPC475212
0.9268	High Similarity	NPC476637
0.9264	High Similarity	NPC43319
0.9259	High Similarity	NPC186686
0.9259	High Similarity	NPC476295
0.9255	High Similarity	NPC158188
0.9255	High Similarity	NPC142252
0.9255	High Similarity	NPC26326
0.9226	High Similarity	NPC244903
0.9212	High Similarity	NPC279209
0.9212	High Similarity	NPC101107
0.9212	High Similarity	NPC102277
0.9207	High Similarity	NPC476306
0.9207	High Similarity	NPC218226
0.9207	High Similarity	NPC243877
0.9207	High Similarity	NPC474024
0.9202	High Similarity	NPC7154
0.9202	High Similarity	NPC36916
0.9202	High Similarity	NPC156432
0.9202	High Similarity	NPC36
0.9202	High Similarity	NPC125039
0.9202	High Similarity	NPC303174
0.9202	High Similarity	NPC7688
0.9202	High Similarity	NPC58223
0.9202	High Similarity	NPC72787
0.9198	High Similarity	NPC476247
0.9198	High Similarity	NPC474150
0.9198	High Similarity	NPC219927
0.9198	High Similarity	NPC474162
0.9193	High Similarity	NPC297212
0.9193	High Similarity	NPC474960
0.9193	High Similarity	NPC36217
0.9152	High Similarity	NPC475805
0.9146	High Similarity	NPC171985
0.9146	High Similarity	NPC320741
0.9146	High Similarity	NPC272502
0.9141	High Similarity	NPC12461
0.9136	High Similarity	NPC474038
0.9136	High Similarity	NPC278427
0.913	High Similarity	NPC46736
0.913	High Similarity	NPC117418
0.913	High Similarity	NPC53545
0.913	High Similarity	NPC197856
0.9107	High Similarity	NPC216307
0.9091	High Similarity	NPC295082
0.9091	High Similarity	NPC14662
0.9091	High Similarity	NPC260266
0.9091	High Similarity	NPC126204
0.9085	High Similarity	NPC275780
0.9085	High Similarity	NPC239752
0.9085	High Similarity	NPC472450
0.9085	High Similarity	NPC477840
0.9085	High Similarity	NPC293319
0.908	High Similarity	NPC477841
0.908	High Similarity	NPC206605
0.908	High Similarity	NPC201800
0.908	High Similarity	NPC472964
0.908	High Similarity	NPC149389
0.9074	High Similarity	NPC118256
0.9074	High Similarity	NPC321399
0.9074	High Similarity	NPC119209
0.9074	High Similarity	NPC475784
0.9074	High Similarity	NPC192686
0.9074	High Similarity	NPC476280
0.9074	High Similarity	NPC472902
0.9074	High Similarity	NPC471973
0.9068	High Similarity	NPC299520
0.9068	High Similarity	NPC129684
0.9068	High Similarity	NPC112954
0.9068	High Similarity	NPC472598
0.9068	High Similarity	NPC474055
0.9068	High Similarity	NPC183
0.9062	High Similarity	NPC67396
0.9057	High Similarity	NPC472912
0.9057	High Similarity	NPC471982
0.9057	High Similarity	NPC260979
0.9042	High Similarity	NPC257667
0.9042	High Similarity	NPC186847
0.9042	High Similarity	NPC472454
0.9036	High Similarity	NPC107627
0.903	High Similarity	NPC224851
0.903	High Similarity	NPC37870
0.903	High Similarity	NPC39091
0.903	High Similarity	NPC469394
0.903	High Similarity	NPC472449
0.9024	High Similarity	NPC23298
0.9024	High Similarity	NPC7483
0.9024	High Similarity	NPC472625
0.9024	High Similarity	NPC272064
0.9024	High Similarity	NPC270837
0.9024	High Similarity	NPC189473
0.9018	High Similarity	NPC471499
0.9018	High Similarity	NPC289771
0.9018	High Similarity	NPC266314
0.9018	High Similarity	NPC472632
0.9018	High Similarity	NPC472634
0.9018	High Similarity	NPC472906
0.9018	High Similarity	NPC198829
0.9018	High Similarity	NPC87431
0.9012	High Similarity	NPC280680
0.9012	High Similarity	NPC85121
0.9012	High Similarity	NPC210459
0.9012	High Similarity	NPC74178
0.9012	High Similarity	NPC184755
0.9006	High Similarity	NPC35038
0.9006	High Similarity	NPC471985
0.9006	High Similarity	NPC195796
0.9006	High Similarity	NPC278778
0.9006	High Similarity	NPC291878
0.9006	High Similarity	NPC24640
0.9	High Similarity	NPC469550
0.9	High Similarity	NPC18727
0.9	High Similarity	NPC324742
0.8987	High Similarity	NPC287101
0.8987	High Similarity	NPC223579
0.8987	High Similarity	NPC183950
0.8987	High Similarity	NPC177298
0.8987	High Similarity	NPC48479
0.8987	High Similarity	NPC52005
0.8987	High Similarity	NPC137062
0.8976	High Similarity	NPC477154
0.8976	High Similarity	NPC6588
0.8976	High Similarity	NPC117854
0.897	High Similarity	NPC50960
0.897	High Similarity	NPC475888
0.8963	High Similarity	NPC472635
0.8963	High Similarity	NPC211107
0.8963	High Similarity	NPC474034
0.8963	High Similarity	NPC474033
0.8963	High Similarity	NPC294965
0.8963	High Similarity	NPC229632
0.8957	High Similarity	NPC299436
0.8957	High Similarity	NPC282009
0.8957	High Similarity	NPC56085
0.8957	High Similarity	NPC161947
0.8957	High Similarity	NPC472630
0.8957	High Similarity	NPC14353
0.8957	High Similarity	NPC287328
0.8957	High Similarity	NPC470326
0.8957	High Similarity	NPC472631
0.8957	High Similarity	NPC155302
0.8957	High Similarity	NPC174953
0.8957	High Similarity	NPC228785
0.8957	High Similarity	NPC139036
0.8951	High Similarity	NPC469584
0.8951	High Similarity	NPC273843
0.8951	High Similarity	NPC472913
0.8951	High Similarity	NPC136674
0.8951	High Similarity	NPC472910
0.8951	High Similarity	NPC27337
0.8951	High Similarity	NPC291508
0.8951	High Similarity	NPC241904
0.8951	High Similarity	NPC470402
0.8951	High Similarity	NPC473272
0.8951	High Similarity	NPC222814
0.8951	High Similarity	NPC52889
0.8951	High Similarity	NPC472914
0.8951	High Similarity	NPC245758
0.8951	High Similarity	NPC300727
0.8951	High Similarity	NPC472911
0.8951	High Similarity	NPC96167
0.8951	High Similarity	NPC284820
0.8951	High Similarity	NPC472963
0.8944	High Similarity	NPC213622
0.8944	High Similarity	NPC31018
0.8944	High Similarity	NPC146165
0.8944	High Similarity	NPC4455
0.8944	High Similarity	NPC45849
0.8944	High Similarity	NPC200761
0.8944	High Similarity	NPC163780
0.8944	High Similarity	NPC477503
0.8944	High Similarity	NPC2476
0.8944	High Similarity	NPC255807
0.8944	High Similarity	NPC470327
0.8944	High Similarity	NPC138360
0.8944	High Similarity	NPC280339
0.8944	High Similarity	NPC321779
0.8944	High Similarity	NPC80534
0.8944	High Similarity	NPC50715
0.8944	High Similarity	NPC128863
0.8944	High Similarity	NPC183597
0.8944	High Similarity	NPC227325
0.8944	High Similarity	NPC56786
0.8944	High Similarity	NPC201136
0.8944	High Similarity	NPC196439
0.8944	High Similarity	NPC234255

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 NPC188079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	419
0.1-0.2	954
0.2-0.3	1783
0.3-0.4	2669
0.4-0.5	1823
0.5-0.6	924
0.6-0.7	390
0.7-0.8	140
0.8-0.85	23
0.85-0.9	21
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9202	High Similarity	NPD6166	Phase 2
0.9202	High Similarity	NPD6167	Clinical (unspecified phase)
0.9202	High Similarity	NPD6168	Clinical (unspecified phase)
0.8938	High Similarity	NPD1934	Approved
0.8882	High Similarity	NPD2393	Clinical (unspecified phase)
0.8882	High Similarity	NPD2801	Approved
0.881	High Similarity	NPD7054	Approved
0.8802	High Similarity	NPD7473	Discontinued
0.8757	High Similarity	NPD7472	Approved
0.8757	High Similarity	NPD7074	Phase 3
0.8735	High Similarity	NPD6232	Discontinued
0.8675	High Similarity	NPD6959	Discontinued
0.8671	High Similarity	NPD1511	Approved
0.8639	High Similarity	NPD3818	Discontinued
0.8598	High Similarity	NPD3817	Phase 2
0.8596	High Similarity	NPD6797	Phase 2
0.8588	High Similarity	NPD5844	Phase 1
0.858	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD1512	Approved
0.8547	High Similarity	NPD7251	Discontinued
0.8545	High Similarity	NPD4868	Clinical (unspecified phase)
0.8545	High Similarity	NPD3882	Suspended
0.8497	Intermediate Similarity	NPD7808	Phase 3
0.8485	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD5494	Approved
0.8391	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7819	Suspended
0.8276	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD1465	Phase 2
0.8193	Intermediate Similarity	NPD7411	Suspended
0.8166	Intermediate Similarity	NPD7075	Discontinued
0.8144	Intermediate Similarity	NPD6801	Discontinued
0.8129	Intermediate Similarity	NPD7199	Phase 2
0.8092	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1510	Phase 2
0.8025	Intermediate Similarity	NPD3750	Approved
0.8023	Intermediate Similarity	NPD6559	Discontinued
0.8012	Intermediate Similarity	NPD1549	Phase 2
0.8012	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7390	Discontinued
0.7941	Intermediate Similarity	NPD5402	Approved
0.7933	Intermediate Similarity	NPD8313	Approved
0.7933	Intermediate Similarity	NPD8312	Approved
0.7931	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD37	Approved
0.7917	Intermediate Similarity	NPD6599	Discontinued
0.7895	Intermediate Similarity	NPD7768	Phase 2
0.7895	Intermediate Similarity	NPD4966	Approved
0.7895	Intermediate Similarity	NPD4967	Phase 2
0.7895	Intermediate Similarity	NPD4965	Approved
0.7879	Intermediate Similarity	NPD6799	Approved
0.7849	Intermediate Similarity	NPD3749	Approved
0.7844	Intermediate Similarity	NPD5403	Approved
0.7831	Intermediate Similarity	NPD2532	Approved
0.7831	Intermediate Similarity	NPD2534	Approved
0.7831	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD2533	Approved
0.7829	Intermediate Similarity	NPD3926	Phase 2
0.7826	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1607	Approved
0.7799	Intermediate Similarity	NPD1240	Approved
0.7797	Intermediate Similarity	NPD3751	Discontinued
0.7751	Intermediate Similarity	NPD3226	Approved
0.7747	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5401	Approved
0.7716	Intermediate Similarity	NPD3748	Approved
0.7714	Intermediate Similarity	NPD1247	Approved
0.7705	Intermediate Similarity	NPD8150	Discontinued
0.7701	Intermediate Similarity	NPD919	Approved
0.7688	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1613	Approved
0.7688	Intermediate Similarity	NPD943	Approved
0.767	Intermediate Similarity	NPD3787	Discontinued
0.7636	Intermediate Similarity	NPD2800	Approved
0.7636	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3027	Phase 3
0.7607	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD8151	Discontinued
0.759	Intermediate Similarity	NPD4628	Phase 3
0.7582	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6099	Approved
0.7561	Intermediate Similarity	NPD6100	Approved
0.7547	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4908	Phase 1
0.7544	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD6776	Approved
0.7539	Intermediate Similarity	NPD6780	Approved
0.7539	Intermediate Similarity	NPD6781	Approved
0.7539	Intermediate Similarity	NPD6782	Approved
0.7539	Intermediate Similarity	NPD6777	Approved
0.7539	Intermediate Similarity	NPD6779	Approved
0.7539	Intermediate Similarity	NPD6778	Approved
0.7527	Intermediate Similarity	NPD7240	Approved
0.7515	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6651	Approved
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1551	Phase 2
0.7455	Intermediate Similarity	NPD2935	Discontinued
0.7432	Intermediate Similarity	NPD7685	Pre-registration
0.7424	Intermediate Similarity	NPD7783	Phase 2
0.7424	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7435	Discontinued
0.7423	Intermediate Similarity	NPD230	Phase 1
0.7416	Intermediate Similarity	NPD8127	Discontinued
0.741	Intermediate Similarity	NPD2346	Discontinued
0.7385	Intermediate Similarity	NPD7870	Phase 2
0.7385	Intermediate Similarity	NPD7871	Phase 2
0.7384	Intermediate Similarity	NPD1653	Approved
0.7381	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD8166	Discontinued
0.7374	Intermediate Similarity	NPD7229	Phase 3
0.7368	Intermediate Similarity	NPD4360	Phase 2
0.7368	Intermediate Similarity	NPD4363	Phase 3
0.7346	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7458	Discontinued
0.7337	Intermediate Similarity	NPD6190	Approved
0.7333	Intermediate Similarity	NPD7697	Approved
0.7333	Intermediate Similarity	NPD7696	Phase 3
0.7333	Intermediate Similarity	NPD7698	Approved
0.7326	Intermediate Similarity	NPD920	Approved
0.7317	Intermediate Similarity	NPD447	Suspended
0.7305	Intermediate Similarity	NPD2344	Approved
0.7289	Intermediate Similarity	NPD2799	Discontinued
0.7283	Intermediate Similarity	NPD5953	Discontinued
0.7282	Intermediate Similarity	NPD6823	Phase 2
0.7278	Intermediate Similarity	NPD7003	Approved
0.7278	Intermediate Similarity	NPD5710	Approved
0.7278	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5711	Approved
0.7277	Intermediate Similarity	NPD6535	Approved
0.7277	Intermediate Similarity	NPD6534	Approved
0.7273	Intermediate Similarity	NPD7701	Phase 2
0.7273	Intermediate Similarity	NPD8455	Phase 2
0.7267	Intermediate Similarity	NPD6273	Approved
0.725	Intermediate Similarity	NPD7801	Approved
0.7246	Intermediate Similarity	NPD5404	Approved
0.7246	Intermediate Similarity	NPD5406	Approved
0.7246	Intermediate Similarity	NPD5408	Approved
0.7246	Intermediate Similarity	NPD5405	Approved
0.7245	Intermediate Similarity	NPD7680	Approved
0.7219	Intermediate Similarity	NPD1243	Approved
0.7219	Intermediate Similarity	NPD6674	Discontinued
0.7216	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1201	Approved
0.7209	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7549	Discontinued
0.72	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7874	Approved
0.7193	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4625	Phase 3
0.7174	Intermediate Similarity	NPD7286	Phase 2
0.7165	Intermediate Similarity	NPD7699	Phase 2
0.7165	Intermediate Similarity	NPD7700	Phase 2
0.716	Intermediate Similarity	NPD9494	Approved
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.715	Intermediate Similarity	NPD4361	Phase 2
0.715	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1470	Approved
0.7136	Intermediate Similarity	NPD7584	Approved
0.7135	Intermediate Similarity	NPD2309	Approved
0.7135	Intermediate Similarity	NPD4288	Approved
0.7134	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD2313	Discontinued
0.7134	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD8319	Approved
0.7121	Intermediate Similarity	NPD8320	Phase 1
0.712	Intermediate Similarity	NPD7177	Discontinued
0.7108	Intermediate Similarity	NPD1933	Approved
0.7107	Intermediate Similarity	NPD1610	Phase 2
0.7099	Intermediate Similarity	NPD2798	Approved
0.7093	Intermediate Similarity	NPD3300	Phase 2
0.7087	Intermediate Similarity	NPD4665	Approved
0.7087	Intermediate Similarity	NPD4111	Phase 1
0.7083	Intermediate Similarity	NPD7033	Discontinued
0.7079	Intermediate Similarity	NPD5761	Phase 2
0.7079	Intermediate Similarity	NPD5760	Phase 2
0.7056	Intermediate Similarity	NPD2494	Approved
0.7056	Intermediate Similarity	NPD2493	Approved
0.7049	Intermediate Similarity	NPD5242	Approved
0.7048	Intermediate Similarity	NPD3620	Phase 2

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