NPASS Compound

Structure

CID119589 OpenBabel06191715472D 27 31 0 0 1 0 0 0 0 0999 V2000 4.0905 1.5936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8542 -1.4121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0254 -1.8984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8474 -0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8612 -1.4472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8339 2.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8288 2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1898 -1.4238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 -1.9218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0119 0.0234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8545 -0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5255 -1.4355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6832 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3611 -1.9101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1831 -0.4629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5188 -0.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6832 0.9720 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9720 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.9443 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6643 1.9385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7041 -2.9729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3685 -2.9612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0045 1.0745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6832 1.9443 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 3.3475 0.0117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 8 1 0 0 0 0 4 10 2 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 19 1 0 0 0 0 6 20 1 0 0 0 0 7 19 1 0 0 0 0 7 25 1 0 0 0 0 8 14 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 15 1 0 0 0 0 10 24 1 0 0 0 0 11 13 2 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 16 1 0 0 0 0 14 22 2 0 0 0 0 15 27 1 0 0 0 0 16 27 1 0 0 0 0 17 13 1 1 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 1 0 0 0 18 26 1 0 0 0 0 19 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.08
Volume:	346.264
LogP:	2.281
LogD:	1.927
LogS:	-5.116
# Rotatable Bonds:	2
TPSA:	118.59
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.575
Synthetic Accessibility Score:	4.093
Fsp3:	0.316
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:	-5.503
MDCK Permeability:	1.6812311514513567e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.47
Human Intestinal Absorption (HIA):	0.763
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.69

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	76.35967254638672%
Volume Distribution (VD):	1.171
Pgp-substrate:	19.129451751708984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.585
CYP1A2-substrate:	0.92
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.283
CYP2C9-inhibitor:	0.264
CYP2C9-substrate:	0.36
CYP2D6-inhibitor:	0.134
CYP2D6-substrate:	0.238
CYP3A4-inhibitor:	0.361
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	5.795
Half-life (T1/2):	0.788

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.911
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.748
Rat Oral Acute Toxicity:	0.485
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.42
Carcinogencity:	0.895
Eye Corrosion:	0.003
Eye Irritation:	0.06
Respiratory Toxicity:	0.278

Download Data

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

Natural Product: NPC119589

Natural Product ID:	NPC119589
*Common Name:**	CVWDBIOBFVCYRC-IPMKNSEASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CVWDBIOBFVCYRC-IPMKNSEASA-N
Standard InCHI:	InChI=1S/C19H16O8/c1-24-10-4-2-3-8-14(22)12-9(21)5-11-13(16(12)27-15(8)10)17-18(26-11)19(23,6-20)7-25-17/h2-5,17-18,20-21,23H,6-7H2,1H3/t17-,18+,19+/m0/s1
SMILES:	OC[C@@]1(O)CO[C@@H]2[C@H]1Oc1c2c2oc3c(OC)cccc3c(=O)c2c(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL192424
PubChem CID:	11187889
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO12096	Psorospermum febrifugum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191562]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21682262]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	whole plants	Zhejiang Province, China	2008-AUG	PMID[21682262]
NPO12096	Psorospermum febrifugum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7189773]
NPO12096	Psorospermum febrifugum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12096	Psorospermum febrifugum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15613	Clerodendrum uncinatum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4475	Erythrina costaricensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1645	Sticta pulmonaria	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10519	Angylocalyx vermeulenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7544	Squalus wakiyae	Species	Squalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12096	Psorospermum febrifugum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15236	Leucetta avocado	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13912	Delphinium gracile	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26692	Lophium arboricola	Species	Mytilinidiaceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2641	Cell Line	COLO 320	Homo sapiens	IC50	=	12300.0	nM	PMID[447908]
NPT455	Cell Line	NCI-H522	Homo sapiens	IC50	=	20000.0	nM	PMID[447908]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	36670.0	nM	PMID[447908]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	12260.0	nM	PMID[447908]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	19000.0	nM	PMID[447908]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	30000.0	nM	PMID[447908]

☑ 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 NPC119589 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	444
0.1-0.2	1779
0.2-0.3	3944
0.3-0.4	9914
0.4-0.5	8543
0.5-0.6	4144
0.6-0.7	5530
0.7-0.8	5000
0.8-0.85	2141
0.85-0.9	1184
0.9-0.95	72
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9809	High Similarity	NPC300053
0.9745	High Similarity	NPC124038
0.9682	High Similarity	NPC472635
0.956	High Similarity	NPC108433
0.9554	High Similarity	NPC472624
0.9494	High Similarity	NPC472634
0.9437	High Similarity	NPC472277
0.9434	High Similarity	NPC474033
0.9434	High Similarity	NPC474034
0.943	High Similarity	NPC472631
0.943	High Similarity	NPC475784
0.943	High Similarity	NPC328102
0.943	High Similarity	NPC472630
0.9427	High Similarity	NPC472598
0.9427	High Similarity	NPC27337
0.9427	High Similarity	NPC474055
0.9427	High Similarity	NPC291508
0.9387	High Similarity	NPC121333
0.9383	High Similarity	NPC288813
0.9379	High Similarity	NPC235610
0.9375	High Similarity	NPC205265
0.9375	High Similarity	NPC472281
0.9375	High Similarity	NPC472582
0.9375	High Similarity	NPC18100
0.9371	High Similarity	NPC472632
0.9371	High Similarity	NPC471499
0.9371	High Similarity	NPC26326
0.9371	High Similarity	NPC134783
0.9371	High Similarity	NPC474038
0.9367	High Similarity	NPC473990
0.9363	High Similarity	NPC195796
0.9363	High Similarity	NPC35038
0.9363	High Similarity	NPC278778
0.9363	High Similarity	NPC291878
0.9325	High Similarity	NPC212748
0.9313	High Similarity	NPC476247
0.9313	High Similarity	NPC81679
0.9308	High Similarity	NPC174953
0.9308	High Similarity	NPC192686
0.9308	High Similarity	NPC282009
0.9308	High Similarity	NPC287328
0.9308	High Similarity	NPC470326
0.9308	High Similarity	NPC119209
0.9308	High Similarity	NPC118256
0.9304	High Similarity	NPC284820
0.9304	High Similarity	NPC473272
0.9299	High Similarity	NPC57674
0.9299	High Similarity	NPC230149
0.9299	High Similarity	NPC168247
0.9299	High Similarity	NPC256925
0.9299	High Similarity	NPC200761
0.9299	High Similarity	NPC470327
0.9299	High Similarity	NPC226025
0.9299	High Similarity	NPC45849
0.9299	High Similarity	NPC117992
0.9299	High Similarity	NPC321779
0.9299	High Similarity	NPC477503
0.9299	High Similarity	NPC152951
0.9295	High Similarity	NPC473996
0.9264	High Similarity	NPC152477
0.9264	High Similarity	NPC242395
0.9259	High Similarity	NPC128293
0.9259	High Similarity	NPC170245
0.9259	High Similarity	NPC173292
0.9259	High Similarity	NPC471213
0.9255	High Similarity	NPC472625
0.925	High Similarity	NPC30655
0.925	High Similarity	NPC142252
0.925	High Similarity	NPC74854
0.925	High Similarity	NPC471211
0.925	High Similarity	NPC471210
0.925	High Similarity	NPC45124
0.925	High Similarity	NPC266314
0.925	High Similarity	NPC471212
0.9245	High Similarity	NPC95936
0.9245	High Similarity	NPC117418
0.9245	High Similarity	NPC204879
0.9245	High Similarity	NPC53545
0.9245	High Similarity	NPC187792
0.9245	High Similarity	NPC22192
0.9245	High Similarity	NPC250214
0.9241	High Similarity	NPC472626
0.9241	High Similarity	NPC209614
0.9241	High Similarity	NPC472455
0.9241	High Similarity	NPC470328
0.9236	High Similarity	NPC227337
0.9236	High Similarity	NPC18727
0.9236	High Similarity	NPC70433
0.9236	High Similarity	NPC213896
0.9236	High Similarity	NPC192083
0.9236	High Similarity	NPC49402
0.9236	High Similarity	NPC273462
0.9236	High Similarity	NPC74924
0.9236	High Similarity	NPC33051
0.9231	High Similarity	NPC263384
0.9231	High Similarity	NPC244577
0.9231	High Similarity	NPC472423
0.9231	High Similarity	NPC471676
0.9231	High Similarity	NPC474744
0.9231	High Similarity	NPC474772
0.9231	High Similarity	NPC472580
0.9231	High Similarity	NPC472636
0.9231	High Similarity	NPC472420
0.9231	High Similarity	NPC472422
0.9207	High Similarity	NPC103307
0.9207	High Similarity	NPC102277
0.9207	High Similarity	NPC279209
0.9207	High Similarity	NPC472276
0.9202	High Similarity	NPC150131
0.9198	High Similarity	NPC62261
0.9198	High Similarity	NPC326520
0.9198	High Similarity	NPC50960
0.9193	High Similarity	NPC220912
0.9193	High Similarity	NPC474150
0.9193	High Similarity	NPC83922
0.9193	High Similarity	NPC125991
0.9193	High Similarity	NPC472448
0.9193	High Similarity	NPC472964
0.9193	High Similarity	NPC474162
0.9187	High Similarity	NPC304839
0.9187	High Similarity	NPC471976
0.9187	High Similarity	NPC36217
0.9187	High Similarity	NPC472902
0.9187	High Similarity	NPC220582
0.9187	High Similarity	NPC476980
0.9182	High Similarity	NPC475267
0.9182	High Similarity	NPC299520
0.9182	High Similarity	NPC471209
0.9182	High Similarity	NPC78225
0.9182	High Similarity	NPC476981
0.9182	High Similarity	NPC223787
0.9182	High Similarity	NPC67876
0.9182	High Similarity	NPC129684
0.9182	High Similarity	NPC474208
0.9182	High Similarity	NPC48208
0.9182	High Similarity	NPC162869
0.9182	High Similarity	NPC156057
0.9182	High Similarity	NPC210084
0.9182	High Similarity	NPC262286
0.9182	High Similarity	NPC52530
0.9182	High Similarity	NPC99597
0.9182	High Similarity	NPC474836
0.9182	High Similarity	NPC36852
0.9182	High Similarity	NPC78071
0.9182	High Similarity	NPC218313
0.9182	High Similarity	NPC52889
0.9182	High Similarity	NPC474681
0.9177	High Similarity	NPC31018
0.9177	High Similarity	NPC37392
0.9177	High Similarity	NPC255807
0.9177	High Similarity	NPC234255
0.9177	High Similarity	NPC472280
0.9172	High Similarity	NPC31627
0.9172	High Similarity	NPC219582
0.9172	High Similarity	NPC236637
0.9172	High Similarity	NPC476238
0.9172	High Similarity	NPC477957
0.9172	High Similarity	NPC302950
0.9172	High Similarity	NPC257648
0.9172	High Similarity	NPC327269
0.9172	High Similarity	NPC285623
0.9172	High Similarity	NPC106976
0.9172	High Similarity	NPC477231
0.9167	High Similarity	NPC338131
0.9167	High Similarity	NPC472421
0.9152	High Similarity	NPC235575
0.9141	High Similarity	NPC207575
0.9141	High Similarity	NPC13481
0.9136	High Similarity	NPC475985
0.9136	High Similarity	NPC41301
0.9136	High Similarity	NPC329669
0.9136	High Similarity	NPC273959
0.9136	High Similarity	NPC186686
0.9136	High Similarity	NPC473313
0.9136	High Similarity	NPC472278
0.913	High Similarity	NPC158188
0.913	High Similarity	NPC289771
0.913	High Similarity	NPC3629
0.913	High Similarity	NPC308992
0.913	High Similarity	NPC167678
0.913	High Similarity	NPC29876
0.913	High Similarity	NPC228383
0.9125	High Similarity	NPC74178
0.9125	High Similarity	NPC184755
0.9125	High Similarity	NPC152904
0.9125	High Similarity	NPC55738
0.9119	High Similarity	NPC235165
0.9119	High Similarity	NPC78492
0.9119	High Similarity	NPC5322
0.9119	High Similarity	NPC138243
0.9119	High Similarity	NPC250922
0.9119	High Similarity	NPC470600
0.9119	High Similarity	NPC474638
0.9119	High Similarity	NPC191146
0.9119	High Similarity	NPC472916
0.9119	High Similarity	NPC6633
0.9119	High Similarity	NPC133970
0.9119	High Similarity	NPC13858
0.9119	High Similarity	NPC320825
0.9119	High Similarity	NPC326037

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 NPC119589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	904
0.2-0.3	1837
0.3-0.4	2705
0.4-0.5	1886
0.5-0.6	975
0.6-0.7	316
0.7-0.8	113
0.8-0.85	16
0.85-0.9	19
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9236	High Similarity	NPD2393	Clinical (unspecified phase)
0.9172	High Similarity	NPD1934	Approved
0.9085	High Similarity	NPD3818	Discontinued
0.9	High Similarity	NPD3882	Suspended
0.8963	High Similarity	NPD6168	Clinical (unspecified phase)
0.8963	High Similarity	NPD6166	Phase 2
0.8963	High Similarity	NPD6167	Clinical (unspecified phase)
0.8951	High Similarity	NPD5494	Approved
0.8924	High Similarity	NPD4380	Phase 2
0.8875	High Similarity	NPD2801	Approved
0.875	High Similarity	NPD7074	Phase 3
0.8712	High Similarity	NPD7075	Discontinued
0.869	High Similarity	NPD7054	Approved
0.865	High Similarity	NPD4868	Clinical (unspecified phase)
0.8639	High Similarity	NPD7472	Approved
0.8598	High Similarity	NPD4381	Clinical (unspecified phase)
0.8589	High Similarity	NPD3817	Phase 2
0.8544	High Similarity	NPD1511	Approved
0.8538	High Similarity	NPD6559	Discontinued
0.8528	High Similarity	NPD7096	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8488	Intermediate Similarity	NPD7808	Phase 3
0.8488	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD6797	Phase 2
0.8466	Intermediate Similarity	NPD6801	Discontinued
0.8462	Intermediate Similarity	NPD1549	Phase 2
0.8438	Intermediate Similarity	NPD1512	Approved
0.843	Intermediate Similarity	NPD7251	Discontinued
0.8415	Intermediate Similarity	NPD7819	Suspended
0.8397	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD6232	Discontinued
0.8375	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD5844	Phase 1
0.8353	Intermediate Similarity	NPD7473	Discontinued
0.8293	Intermediate Similarity	NPD7411	Suspended
0.8266	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD6959	Discontinued
0.8225	Intermediate Similarity	NPD1247	Approved
0.8217	Intermediate Similarity	NPD2796	Approved
0.8153	Intermediate Similarity	NPD1510	Phase 2
0.8144	Intermediate Similarity	NPD5402	Approved
0.8129	Intermediate Similarity	NPD3926	Phase 2
0.8107	Intermediate Similarity	NPD919	Approved
0.8086	Intermediate Similarity	NPD6799	Approved
0.8084	Intermediate Similarity	NPD1465	Phase 2
0.8013	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD6234	Discontinued
0.7988	Intermediate Similarity	NPD4967	Phase 2
0.7988	Intermediate Similarity	NPD4966	Approved
0.7988	Intermediate Similarity	NPD4965	Approved
0.7977	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD2800	Approved
0.7941	Intermediate Similarity	NPD3749	Approved
0.7939	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD5403	Approved
0.7933	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD2533	Approved
0.7927	Intermediate Similarity	NPD2532	Approved
0.7927	Intermediate Similarity	NPD2534	Approved
0.7911	Intermediate Similarity	NPD1607	Approved
0.7907	Intermediate Similarity	NPD7199	Phase 2
0.7904	Intermediate Similarity	NPD6599	Discontinued
0.7898	Intermediate Similarity	NPD943	Approved
0.7898	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1613	Approved
0.7886	Intermediate Similarity	NPD7228	Approved
0.7831	Intermediate Similarity	NPD920	Approved
0.7818	Intermediate Similarity	NPD5401	Approved
0.7814	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD37	Approved
0.7807	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7768	Phase 2
0.7764	Intermediate Similarity	NPD2935	Discontinued
0.773	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD3027	Phase 3
0.7705	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8434	Phase 2
0.7684	Intermediate Similarity	NPD3751	Discontinued
0.7683	Intermediate Similarity	NPD4628	Phase 3
0.7667	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5953	Discontinued
0.7651	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6190	Approved
0.7633	Intermediate Similarity	NPD3226	Approved
0.7625	Intermediate Similarity	NPD447	Suspended
0.7625	Intermediate Similarity	NPD230	Phase 1
0.7624	Intermediate Similarity	NPD8312	Approved
0.7624	Intermediate Similarity	NPD8313	Approved
0.7622	Intermediate Similarity	NPD1243	Approved
0.7611	Intermediate Similarity	NPD7685	Pre-registration
0.7607	Intermediate Similarity	NPD2344	Approved
0.759	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3750	Approved
0.7574	Intermediate Similarity	NPD1653	Approved
0.7561	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3787	Discontinued
0.7546	Intermediate Similarity	NPD1551	Phase 2
0.7542	Intermediate Similarity	NPD7286	Phase 2
0.7526	Intermediate Similarity	NPD6778	Approved
0.7526	Intermediate Similarity	NPD6776	Approved
0.7526	Intermediate Similarity	NPD6782	Approved
0.7526	Intermediate Similarity	NPD6777	Approved
0.7526	Intermediate Similarity	NPD6779	Approved
0.7526	Intermediate Similarity	NPD6781	Approved
0.7526	Intermediate Similarity	NPD6780	Approved
0.7514	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2799	Discontinued
0.7474	Intermediate Similarity	NPD7584	Approved
0.747	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6651	Approved
0.746	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5710	Approved
0.7458	Intermediate Similarity	NPD5711	Approved
0.7455	Intermediate Similarity	NPD2424	Discontinued
0.7439	Intermediate Similarity	NPD6100	Approved
0.7439	Intermediate Similarity	NPD6099	Approved
0.7438	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2313	Discontinued
0.7425	Intermediate Similarity	NPD2309	Approved
0.7409	Intermediate Similarity	NPD7435	Discontinued
0.7407	Intermediate Similarity	NPD1933	Approved
0.7398	Intermediate Similarity	NPD8151	Discontinued
0.7378	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7033	Discontinued
0.7365	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD9494	Approved
0.7356	Intermediate Similarity	NPD5761	Phase 2
0.7356	Intermediate Similarity	NPD5760	Phase 2
0.7354	Intermediate Similarity	NPD4360	Phase 2
0.7354	Intermediate Similarity	NPD4363	Phase 3
0.7337	Intermediate Similarity	NPD7390	Discontinued
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7696	Phase 3
0.732	Intermediate Similarity	NPD7697	Approved
0.732	Intermediate Similarity	NPD7698	Approved
0.7308	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7870	Phase 2
0.7282	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD3748	Approved
0.7268	Intermediate Similarity	NPD6823	Phase 2
0.7263	Intermediate Similarity	NPD7229	Phase 3
0.7263	Intermediate Similarity	NPD6535	Approved
0.7263	Intermediate Similarity	NPD6534	Approved
0.7259	Intermediate Similarity	NPD7701	Phase 2
0.7241	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7783	Phase 2
0.7225	Intermediate Similarity	NPD4361	Phase 2
0.7225	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5242	Approved
0.7216	Intermediate Similarity	NPD5353	Approved
0.7215	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8127	Discontinued
0.7205	Intermediate Similarity	NPD4908	Phase 1
0.7205	Intermediate Similarity	NPD6832	Phase 2
0.72	Intermediate Similarity	NPD6844	Discontinued
0.7195	Intermediate Similarity	NPD5124	Phase 1
0.7195	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7874	Approved
0.7182	Intermediate Similarity	NPD2403	Approved
0.7174	Intermediate Similarity	NPD3823	Discontinued
0.716	Intermediate Similarity	NPD4625	Phase 3
0.7159	Intermediate Similarity	NPD8455	Phase 2
0.715	Intermediate Similarity	NPD7700	Phase 2
0.715	Intermediate Similarity	NPD7801	Approved
0.715	Intermediate Similarity	NPD7699	Phase 2
0.7125	Intermediate Similarity	NPD1203	Approved
0.712	Intermediate Similarity	NPD1729	Discontinued
0.7113	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD2163	Approved
0.7092	Intermediate Similarity	NPD5006	Approved
0.7092	Intermediate Similarity	NPD5005	Approved
0.7091	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1610	Phase 2
0.7087	Intermediate Similarity	NPD7907	Approved
0.7085	Intermediate Similarity	NPD7585	Approved
0.7083	Intermediate Similarity	NPD7266	Discontinued
0.7083	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4111	Phase 1
0.7073	Intermediate Similarity	NPD4665	Approved
0.7056	Intermediate Similarity	NPD7680	Approved
0.7053	Intermediate Similarity	NPD4287	Approved
0.7045	Intermediate Similarity	NPD6386	Approved
0.7045	Intermediate Similarity	NPD6385	Approved
0.7044	Intermediate Similarity	NPD7930	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data