NPASS Compound

Structure

CID51760 OpenBabel06191715392D 40 45 0 0 1 0 0 0 0 0999 V2000 8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 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 -1.7321 2.0000 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 -1.7321 3.0000 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 0.0000 -3.0000 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 5.1962 -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 7.7942 1.5000 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 -0.8660 1.5000 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 -0.8660 -2.5000 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 -1.7321 -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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 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 -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 1.7321 -1.0000 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 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 -0.8660 4.5000 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 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 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 4 1 0 0 0 0 2 14 2 0 0 0 0 3 5 2 0 0 0 0 3 14 1 0 0 0 0 4 15 2 0 0 0 0 5 15 1 0 0 0 0 6 8 1 0 0 0 0 6 16 2 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 11 24 1 0 0 0 0 12 21 1 0 0 0 0 12 23 1 0 0 0 0 13 22 2 0 0 0 0 13 25 1 0 0 0 0 17 32 1 0 0 0 0 18 26 1 0 0 0 0 18 33 1 0 0 0 0 19 29 2 0 0 0 0 19 34 1 0 0 0 0 20 26 1 0 0 0 0 20 35 2 0 0 0 0 21 27 1 0 0 0 0 21 36 2 0 0 0 0 22 28 1 0 0 0 0 22 37 1 0 0 0 0 23 15 1 6 0 0 0 23 39 1 0 0 0 0 24 16 1 1 0 0 0 24 40 1 0 0 0 0 25 27 2 0 0 0 0 25 39 1 0 0 0 0 26 31 2 0 0 0 0 27 30 1 0 0 0 0 28 29 1 0 0 0 0 28 30 2 0 0 0 0 29 31 1 0 0 0 0 30 38 1 0 0 0 0 31 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	204.19
Volume:	239.69
LogP:	4.968
LogD:	5.206
LogS:	-4.878
# Rotatable Bonds:	1
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.559
Synthetic Accessibility Score:	4.274
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.45
MDCK Permeability:	1.5730414816061966e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.528
30% Bioavailability (F30%):	0.093

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.622
Plasma Protein Binding (PPB):	85.76077270507812%
Volume Distribution (VD):	3.374
Pgp-substrate:	11.614967346191406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.931
CYP1A2-substrate:	0.638
CYP2C19-inhibitor:	0.293
CYP2C19-substrate:	0.897
CYP2C9-inhibitor:	0.1
CYP2C9-substrate:	0.245
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.554
CYP3A4-inhibitor:	0.276
CYP3A4-substrate:	0.369

ADMET: Excretion

Clearance (CL):	14.132
Half-life (T1/2):	0.328

ADMET: Toxicity

hERG Blockers:	0.251
Human Hepatotoxicity (H-HT):	0.346
Drug-inuced Liver Injury (DILI):	0.67
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.58
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.914
Carcinogencity:	0.14
Eye Corrosion:	0.982
Eye Irritation:	0.95
Respiratory Toxicity:	0.815

Download Data

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

Natural Product: NPC51760

Natural Product ID:	NPC51760
*Common Name:**	Rhusflavanone
IUPAC Name:	(2S)-6-[(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-8-yl]-5,7-dihydroxy-2-(4-methylphenyl)-2,3-dihydrochromen-4-one
Synonyms:	Rhusflavanone
Standard InCHIKey:	CBGKJSZVQOWLBY-ZEQRLZLVSA-N
Standard InCHI:	InChI=1S/C31H24O9/c1-14-2-4-15(5-3-14)23-12-21(36)27-25(39-23)13-22(37)28(30(27)38)29-19(34)10-18(33)26-20(35)11-24(40-31(26)29)16-6-8-17(32)9-7-16/h2-10,13,23-24,32-34,37-38H,11-12H2,1H3/t23-,24-/m0/s1
SMILES:	Cc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)cc(c(c2O)c1c(O)cc(c2c1O[C@@H](CC2=O)c1ccc(cc1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458841
PubChem CID:	44559463
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO33250	rhus succedanea	Species	Anacardiaceae	Eukaryota	sap	n.a.	n.a.	PMID[12444713]
NPO33250	rhus succedanea	Species	Anacardiaceae	Eukaryota	seed kernels	Fukuoka, Japan	n.a.	PMID[9322359]
NPO938	Toxicodendron sylvestre	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	<	30.0	%	PMID[520626]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	14.1	%	PMID[520626]

☑ 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 NPC51760 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	409
0.1-0.2	1685
0.2-0.3	3685
0.3-0.4	9782
0.4-0.5	8871
0.5-0.6	3709
0.6-0.7	5769
0.7-0.8	5296
0.8-0.85	2201
0.85-0.9	987
0.9-0.95	281
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC134171
0.98	High Similarity	NPC300668
0.9671	High Similarity	NPC475184
0.9669	High Similarity	NPC182555
0.9669	High Similarity	NPC66441
0.9605	High Similarity	NPC69531
0.9548	High Similarity	NPC15374
0.9542	High Similarity	NPC1796
0.9481	High Similarity	NPC105584
0.9481	High Similarity	NPC51247
0.9477	High Similarity	NPC61112
0.9477	High Similarity	NPC198489
0.9477	High Similarity	NPC32867
0.9474	High Similarity	NPC290830
0.9474	High Similarity	NPC194593
0.9474	High Similarity	NPC303485
0.9474	High Similarity	NPC71061
0.9474	High Similarity	NPC72425
0.9467	High Similarity	NPC3642
0.9419	High Similarity	NPC195136
0.9419	High Similarity	NPC226462
0.9419	High Similarity	NPC42965
0.9419	High Similarity	NPC98023
0.9416	High Similarity	NPC271741
0.9416	High Similarity	NPC257166
0.9416	High Similarity	NPC287789
0.9412	High Similarity	NPC150908
0.9412	High Similarity	NPC100049
0.9412	High Similarity	NPC258474
0.9412	High Similarity	NPC158027
0.9412	High Similarity	NPC248739
0.9412	High Similarity	NPC121649
0.9412	High Similarity	NPC52611
0.9412	High Similarity	NPC205026
0.9412	High Similarity	NPC201227
0.9412	High Similarity	NPC265624
0.9412	High Similarity	NPC215203
0.9412	High Similarity	NPC186227
0.9412	High Similarity	NPC14606
0.9412	High Similarity	NPC159707
0.9408	High Similarity	NPC174086
0.94	High Similarity	NPC122894
0.9359	High Similarity	NPC18380
0.9359	High Similarity	NPC301256
0.9359	High Similarity	NPC312273
0.9355	High Similarity	NPC295090
0.9355	High Similarity	NPC15815
0.9351	High Similarity	NPC309648
0.9346	High Similarity	NPC121568
0.9342	High Similarity	NPC67322
0.9342	High Similarity	NPC222713
0.9342	High Similarity	NPC111112
0.9342	High Similarity	NPC138299
0.9304	High Similarity	NPC469664
0.9304	High Similarity	NPC473010
0.9299	High Similarity	NPC473012
0.9295	High Similarity	NPC186325
0.9295	High Similarity	NPC292863
0.9295	High Similarity	NPC184326
0.9286	High Similarity	NPC37253
0.9286	High Similarity	NPC79375
0.9281	High Similarity	NPC115601
0.9281	High Similarity	NPC78324
0.9281	High Similarity	NPC39154
0.9281	High Similarity	NPC208011
0.9267	High Similarity	NPC470131
0.9267	High Similarity	NPC228779
0.9267	High Similarity	NPC470134
0.9267	High Similarity	NPC470132
0.9267	High Similarity	NPC109183
0.9267	High Similarity	NPC470133
0.9267	High Similarity	NPC473078
0.9245	High Similarity	NPC251336
0.9241	High Similarity	NPC473009
0.9241	High Similarity	NPC38591
0.9241	High Similarity	NPC63438
0.9236	High Similarity	NPC273467
0.9236	High Similarity	NPC137232
0.9236	High Similarity	NPC189552
0.9231	High Similarity	NPC195167
0.9231	High Similarity	NPC123544
0.9231	High Similarity	NPC177650
0.9216	High Similarity	NPC178484
0.9211	High Similarity	NPC473016
0.92	High Similarity	NPC470135
0.92	High Similarity	NPC470136
0.92	High Similarity	NPC39045
0.9177	High Similarity	NPC473011
0.9172	High Similarity	NPC312993
0.9172	High Similarity	NPC121647
0.9167	High Similarity	NPC324358
0.9167	High Similarity	NPC323627
0.9167	High Similarity	NPC318527
0.9167	High Similarity	NPC208258
0.9167	High Similarity	NPC322459
0.9139	High Similarity	NPC472629
0.9125	High Similarity	NPC224851
0.9119	High Similarity	NPC290160
0.9108	High Similarity	NPC18699
0.9108	High Similarity	NPC55443
0.9103	High Similarity	NPC56049
0.9103	High Similarity	NPC54830
0.9097	High Similarity	NPC112701
0.9097	High Similarity	NPC326592
0.9097	High Similarity	NPC109594
0.9091	High Similarity	NPC232645
0.9091	High Similarity	NPC317715
0.9091	High Similarity	NPC316960
0.9091	High Similarity	NPC72958
0.9091	High Similarity	NPC148945
0.9091	High Similarity	NPC309512
0.9091	High Similarity	NPC78835
0.9091	High Similarity	NPC204561
0.9085	High Similarity	NPC132345
0.9085	High Similarity	NPC291746
0.9085	High Similarity	NPC288840
0.9079	High Similarity	NPC308200
0.9079	High Similarity	NPC473077
0.9079	High Similarity	NPC300988
0.9079	High Similarity	NPC10990
0.9079	High Similarity	NPC296998
0.9073	High Similarity	NPC470890
0.9073	High Similarity	NPC124780
0.9073	High Similarity	NPC87486
0.9073	High Similarity	NPC271288
0.9067	High Similarity	NPC324436
0.9067	High Similarity	NPC194432
0.9067	High Similarity	NPC66515
0.9067	High Similarity	NPC328164
0.9067	High Similarity	NPC182852
0.9067	High Similarity	NPC306829
0.9067	High Similarity	NPC228504
0.9067	High Similarity	NPC125855
0.9067	High Similarity	NPC296917
0.9067	High Similarity	NPC64915
0.9067	High Similarity	NPC324134
0.9067	High Similarity	NPC40833
0.9067	High Similarity	NPC166934
0.9067	High Similarity	NPC161506
0.9067	High Similarity	NPC148757
0.9067	High Similarity	NPC37496
0.9067	High Similarity	NPC223500
0.9067	High Similarity	NPC167624
0.9067	High Similarity	NPC107572
0.9067	High Similarity	NPC1089
0.9067	High Similarity	NPC227579
0.9067	High Similarity	NPC78
0.9067	High Similarity	NPC166482
0.9067	High Similarity	NPC220998
0.9067	High Similarity	NPC76338
0.9067	High Similarity	NPC76372
0.9067	High Similarity	NPC177354
0.9067	High Similarity	NPC32739
0.9067	High Similarity	NPC10937
0.9067	High Similarity	NPC265040
0.9038	High Similarity	NPC254351
0.9032	High Similarity	NPC56232
0.9032	High Similarity	NPC150123
0.9032	High Similarity	NPC43345
0.9032	High Similarity	NPC244583
0.9032	High Similarity	NPC475790
0.9032	High Similarity	NPC161881
0.9032	High Similarity	NPC10807
0.9032	High Similarity	NPC87708
0.9026	High Similarity	NPC29777
0.9026	High Similarity	NPC471115
0.9026	High Similarity	NPC472633
0.902	High Similarity	NPC39195
0.902	High Similarity	NPC145467
0.902	High Similarity	NPC161191
0.9018	High Similarity	NPC477529
0.9013	High Similarity	NPC67805
0.9013	High Similarity	NPC176229
0.9013	High Similarity	NPC246948
0.9013	High Similarity	NPC142405
0.9013	High Similarity	NPC290133
0.9013	High Similarity	NPC24136
0.9013	High Similarity	NPC187282
0.9013	High Similarity	NPC20488
0.9013	High Similarity	NPC83357
0.9013	High Similarity	NPC88964
0.9013	High Similarity	NPC214774
0.9013	High Similarity	NPC267375
0.9013	High Similarity	NPC54577
0.9013	High Similarity	NPC301276
0.9013	High Similarity	NPC111786
0.9013	High Similarity	NPC312973
0.9013	High Similarity	NPC195621
0.9013	High Similarity	NPC470647
0.9013	High Similarity	NPC475052
0.9012	High Similarity	NPC300307
0.9012	High Similarity	NPC53252
0.9007	High Similarity	NPC278249
0.9007	High Similarity	NPC125894
0.9007	High Similarity	NPC75049
0.9007	High Similarity	NPC77794
0.9007	High Similarity	NPC164980
0.9007	High Similarity	NPC478086
0.9007	High Similarity	NPC107177
0.9007	High Similarity	NPC68104

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 NPC51760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	974
0.2-0.3	1541
0.3-0.4	2631
0.4-0.5	1919
0.5-0.6	1121
0.6-0.7	398
0.7-0.8	147
0.8-0.85	33
0.85-0.9	17
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.961	High Similarity	NPD6959	Discontinued
0.9161	High Similarity	NPD8443	Clinical (unspecified phase)
0.9062	High Similarity	NPD7852	Clinical (unspecified phase)
0.8846	High Similarity	NPD7411	Suspended
0.8824	High Similarity	NPD4378	Clinical (unspecified phase)
0.8824	High Similarity	NPD7410	Clinical (unspecified phase)
0.8782	High Similarity	NPD4380	Phase 2
0.8742	High Similarity	NPD7768	Phase 2
0.8734	High Similarity	NPD2393	Clinical (unspecified phase)
0.8733	High Similarity	NPD1550	Clinical (unspecified phase)
0.8733	High Similarity	NPD1552	Clinical (unspecified phase)
0.8712	High Similarity	NPD6166	Phase 2
0.8712	High Similarity	NPD6167	Clinical (unspecified phase)
0.8712	High Similarity	NPD6168	Clinical (unspecified phase)
0.8675	High Similarity	NPD1549	Phase 2
0.8571	High Similarity	NPD7075	Discontinued
0.8554	High Similarity	NPD7804	Clinical (unspecified phase)
0.8516	High Similarity	NPD7390	Discontinued
0.85	High Similarity	NPD7819	Suspended
0.8457	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD1934	Approved
0.8421	Intermediate Similarity	NPD2796	Approved
0.8385	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6232	Discontinued
0.8355	Intermediate Similarity	NPD1510	Phase 2
0.8344	Intermediate Similarity	NPD3749	Approved
0.8344	Intermediate Similarity	NPD1607	Approved
0.8333	Intermediate Similarity	NPD5844	Phase 1
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8294	Intermediate Similarity	NPD6559	Discontinued
0.8284	Intermediate Similarity	NPD7074	Phase 3
0.8242	Intermediate Similarity	NPD5494	Approved
0.8225	Intermediate Similarity	NPD7054	Approved
0.8212	Intermediate Similarity	NPD1240	Approved
0.821	Intermediate Similarity	NPD6801	Discontinued
0.8176	Intermediate Similarity	NPD7472	Approved
0.8171	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6797	Phase 2
0.8129	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD8312	Approved
0.8092	Intermediate Similarity	NPD8313	Approved
0.8086	Intermediate Similarity	NPD6599	Discontinued
0.8081	Intermediate Similarity	NPD7251	Discontinued
0.8079	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1511	Approved
0.8049	Intermediate Similarity	NPD2801	Approved
0.8035	Intermediate Similarity	NPD7808	Phase 3
0.8025	Intermediate Similarity	NPD2800	Approved
0.8	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD2532	Approved
0.7975	Intermediate Similarity	NPD3750	Approved
0.795	Intermediate Similarity	NPD1512	Approved
0.7949	Intermediate Similarity	NPD1551	Phase 2
0.7947	Intermediate Similarity	NPD4908	Phase 1
0.7939	Intermediate Similarity	NPD8455	Phase 2
0.7937	Intermediate Similarity	NPD6799	Approved
0.7914	Intermediate Similarity	NPD3226	Approved
0.7892	Intermediate Similarity	NPD3817	Phase 2
0.7888	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD3818	Discontinued
0.7844	Intermediate Similarity	NPD3882	Suspended
0.7805	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD920	Approved
0.7791	Intermediate Similarity	NPD5403	Approved
0.7785	Intermediate Similarity	NPD2344	Approved
0.7771	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6651	Approved
0.775	Intermediate Similarity	NPD4628	Phase 3
0.775	Intermediate Similarity	NPD7003	Approved
0.7736	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD8151	Discontinued
0.7722	Intermediate Similarity	NPD6100	Approved
0.7722	Intermediate Similarity	NPD5404	Approved
0.7722	Intermediate Similarity	NPD6099	Approved
0.7722	Intermediate Similarity	NPD5406	Approved
0.7722	Intermediate Similarity	NPD5408	Approved
0.7722	Intermediate Similarity	NPD5405	Approved
0.7722	Intermediate Similarity	NPD2935	Discontinued
0.7714	Intermediate Similarity	NPD5953	Discontinued
0.7697	Intermediate Similarity	NPD7458	Discontinued
0.7692	Intermediate Similarity	NPD4360	Phase 2
0.7692	Intermediate Similarity	NPD4363	Phase 3
0.7688	Intermediate Similarity	NPD1243	Approved
0.7679	Intermediate Similarity	NPD5402	Approved
0.7673	Intermediate Similarity	NPD2346	Discontinued
0.7669	Intermediate Similarity	NPD5401	Approved
0.7669	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2799	Discontinued
0.7658	Intermediate Similarity	NPD3748	Approved
0.7654	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1465	Phase 2
0.76	Intermediate Similarity	NPD7286	Phase 2
0.7593	Intermediate Similarity	NPD2309	Approved
0.7581	Intermediate Similarity	NPD6781	Approved
0.7581	Intermediate Similarity	NPD6778	Approved
0.7581	Intermediate Similarity	NPD6779	Approved
0.7581	Intermediate Similarity	NPD6776	Approved
0.7581	Intermediate Similarity	NPD6782	Approved
0.7581	Intermediate Similarity	NPD6780	Approved
0.7581	Intermediate Similarity	NPD6777	Approved
0.7561	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7696	Phase 3
0.7553	Intermediate Similarity	NPD7698	Approved
0.7553	Intermediate Similarity	NPD7697	Approved
0.7552	Intermediate Similarity	NPD7783	Phase 2
0.7552	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4625	Phase 3
0.7543	Intermediate Similarity	NPD7177	Discontinued
0.7531	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5711	Approved
0.7514	Intermediate Similarity	NPD5710	Approved
0.7514	Intermediate Similarity	NPD3787	Discontinued
0.7514	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD2313	Discontinued
0.7483	Intermediate Similarity	NPD1610	Phase 2
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3926	Phase 2
0.746	Intermediate Similarity	NPD7435	Discontinued
0.7443	Intermediate Similarity	NPD3751	Discontinued
0.7423	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7229	Phase 3
0.7396	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7701	Phase 2
0.7377	Intermediate Similarity	NPD4287	Approved
0.7372	Intermediate Similarity	NPD6832	Phase 2
0.7363	Intermediate Similarity	NPD8150	Discontinued
0.7358	Intermediate Similarity	NPD5124	Phase 1
0.7358	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD1247	Approved
0.7345	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD919	Approved
0.7329	Intermediate Similarity	NPD7033	Discontinued
0.7316	Intermediate Similarity	NPD6823	Phase 2
0.7312	Intermediate Similarity	NPD6535	Approved
0.7312	Intermediate Similarity	NPD6534	Approved
0.729	Intermediate Similarity	NPD1203	Approved
0.7287	Intermediate Similarity	NPD7700	Phase 2
0.7287	Intermediate Similarity	NPD7699	Phase 2
0.7278	Intermediate Similarity	NPD3268	Approved
0.7273	Intermediate Similarity	NPD4361	Phase 2
0.7273	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7584	Approved
0.7247	Intermediate Similarity	NPD7228	Approved
0.7244	Intermediate Similarity	NPD2798	Approved
0.7239	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7874	Approved
0.7231	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4308	Phase 3
0.7219	Intermediate Similarity	NPD1548	Phase 1
0.7211	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3972	Approved
0.7202	Intermediate Similarity	NPD6273	Approved
0.7194	Intermediate Similarity	NPD7801	Approved
0.7188	Intermediate Similarity	NPD1613	Approved
0.7188	Intermediate Similarity	NPD943	Approved
0.7188	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7213	Phase 3
0.7186	Intermediate Similarity	NPD7212	Phase 2
0.7179	Intermediate Similarity	NPD2797	Approved
0.717	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6798	Discontinued
0.7161	Intermediate Similarity	NPD4749	Approved
0.7159	Intermediate Similarity	NPD7199	Phase 2
0.7151	Intermediate Similarity	NPD37	Approved
0.715	Intermediate Similarity	NPD8319	Approved
0.715	Intermediate Similarity	NPD8320	Phase 1
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD7447	Phase 1
0.7143	Intermediate Similarity	NPD1201	Approved
0.7126	Intermediate Similarity	NPD4966	Approved
0.7126	Intermediate Similarity	NPD4967	Phase 2
0.7126	Intermediate Similarity	NPD4965	Approved
0.712	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5760	Phase 2
0.711	Intermediate Similarity	NPD5761	Phase 2
0.7097	Intermediate Similarity	NPD9717	Approved
0.7089	Intermediate Similarity	NPD2861	Phase 2
0.7081	Intermediate Similarity	NPD8434	Phase 2
0.7079	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6212	Phase 3
0.7074	Intermediate Similarity	NPD6213	Phase 3
0.7072	Intermediate Similarity	NPD1729	Discontinued
0.707	Intermediate Similarity	NPD1470	Approved
0.7069	Intermediate Similarity	NPD2296	Approved
0.7069	Intermediate Similarity	NPD4288	Approved
0.7063	Intermediate Similarity	NPD3764	Approved
0.7055	Intermediate Similarity	NPD7097	Phase 1
0.7052	Intermediate Similarity	NPD7577	Discontinued
0.7052	Intermediate Similarity	NPD6844	Discontinued

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