NPASS Compound

Structure

NPC276212 OpenBabel07101718312D 26 28 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 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 0.8660 -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 -3.4641 -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 -2.5981 0.5000 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 -0.8660 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 -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 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 25 1 0 0 0 0 3 7 1 0 0 0 0 3 13 2 0 0 0 0 4 9 2 0 0 0 0 4 14 1 0 0 0 0 5 10 1 0 0 0 0 5 14 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 14 21 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 16 1 6 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	371.599
LogP:	3.157
LogD:	3.064
LogS:	-3.496
# Rotatable Bonds:	5
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.713
Synthetic Accessibility Score:	3.298
Fsp3:	0.333
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:	-4.716
MDCK Permeability:	1.5093007277755532e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.17
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	97.07730865478516%
Volume Distribution (VD):	0.467
Pgp-substrate:	2.0457699298858643%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.812
CYP2C19-substrate:	0.326
CYP2C9-inhibitor:	0.534
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.887
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.64
CYP3A4-substrate:	0.426

ADMET: Excretion

Clearance (CL):	11.946
Half-life (T1/2):	0.823

ADMET: Toxicity

hERG Blockers:	0.109
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.206
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.949
Carcinogencity:	0.357
Eye Corrosion:	0.003
Eye Irritation:	0.631
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC276212

Natural Product ID:	NPC276212
*Common Name:**	Morusyunnansins E
IUPAC Name:	4-[(2S)-8-[(E)-4-hydroxy-3-methylbut-2-enyl]-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzene-1,3-diol
Synonyms:	Morusyunnansins E
Standard InCHIKey:	ZWYKFLRPPQSGJI-BBYTVTEQSA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-13(12-22)3-7-17-19(25-2)9-4-14-5-10-20(26-21(14)17)16-8-6-15(23)11-18(16)24/h3-4,6,8-9,11,20,22-24H,5,7,10,12H2,1-2H3/b13-3+/t20-/m0/s1
SMILES:	OC/C(=C/Cc1c(OC)ccc2c1O[C@@H](CC2)c1ccc(cc1O)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1951403
PubChem CID:	57333039
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans

*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
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22165973]
NPO5877	Morus yunnanensis	Species	Moraceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	1430.0	nM	PMID[521174]

☑ 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 NPC276212 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	348
0.1-0.2	1435
0.2-0.3	4354
0.3-0.4	12630
0.4-0.5	5699
0.5-0.6	4324
0.6-0.7	7349
0.7-0.8	5104
0.8-0.85	1064
0.85-0.9	255
0.9-0.95	116
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.9916	High Similarity	NPC17809
0.9916	High Similarity	NPC285040
0.9916	High Similarity	NPC188022
0.9916	High Similarity	NPC102540
0.9916	High Similarity	NPC103420
0.9835	High Similarity	NPC274717
0.9832	High Similarity	NPC86502
0.9832	High Similarity	NPC197351
0.9832	High Similarity	NPC134195
0.9832	High Similarity	NPC246648
0.9832	High Similarity	NPC106914
0.9748	High Similarity	NPC38761
0.9748	High Similarity	NPC76465
0.9664	High Similarity	NPC100099
0.9664	High Similarity	NPC36016
0.9597	High Similarity	NPC103799
0.959	High Similarity	NPC149796
0.9512	High Similarity	NPC38664
0.9512	High Similarity	NPC53986
0.944	High Similarity	NPC280653
0.944	High Similarity	NPC17343
0.944	High Similarity	NPC300875
0.944	High Similarity	NPC118114
0.944	High Similarity	NPC129784
0.944	High Similarity	NPC228369
0.944	High Similarity	NPC129106
0.944	High Similarity	NPC196765
0.944	High Similarity	NPC164574
0.944	High Similarity	NPC206224
0.944	High Similarity	NPC476166
0.944	High Similarity	NPC268917
0.944	High Similarity	NPC150011
0.944	High Similarity	NPC207892
0.944	High Similarity	NPC236014
0.944	High Similarity	NPC12875
0.9435	High Similarity	NPC93962
0.9417	High Similarity	NPC54972
0.9412	High Similarity	NPC8283
0.9412	High Similarity	NPC258979
0.9412	High Similarity	NPC93398
0.9365	High Similarity	NPC13005
0.936	High Similarity	NPC470225
0.936	High Similarity	NPC27187
0.9355	High Similarity	NPC222572
0.9355	High Similarity	NPC87224
0.935	High Similarity	NPC283049
0.935	High Similarity	NPC50315
0.935	High Similarity	NPC230479
0.935	High Similarity	NPC26879
0.9328	High Similarity	NPC172253
0.9328	High Similarity	NPC59561
0.9291	High Similarity	NPC85435
0.9286	High Similarity	NPC293203
0.9286	High Similarity	NPC244888
0.9286	High Similarity	NPC211413
0.9286	High Similarity	NPC68205
0.9286	High Similarity	NPC271945
0.9286	High Similarity	NPC164804
0.9286	High Similarity	NPC181497
0.9286	High Similarity	NPC118683
0.928	High Similarity	NPC134360
0.9268	High Similarity	NPC167571
0.9268	High Similarity	NPC278552
0.9268	High Similarity	NPC207179
0.9244	High Similarity	NPC131118
0.9219	High Similarity	NPC115335
0.9219	High Similarity	NPC198154
0.9219	High Similarity	NPC97834
0.9219	High Similarity	NPC296915
0.9219	High Similarity	NPC473107
0.9219	High Similarity	NPC124085
0.9219	High Similarity	NPC117048
0.9219	High Similarity	NPC223008
0.9219	High Similarity	NPC225696
0.92	High Similarity	NPC47283
0.92	High Similarity	NPC39064
0.9187	High Similarity	NPC159132
0.9167	High Similarity	NPC295259
0.9147	High Similarity	NPC473413
0.9141	High Similarity	NPC92805
0.9141	High Similarity	NPC77196
0.9134	High Similarity	NPC162801
0.9098	High Similarity	NPC193364
0.9098	High Similarity	NPC476633
0.9084	High Similarity	NPC475836
0.9083	High Similarity	NPC74821
0.9077	High Similarity	NPC262585
0.9077	High Similarity	NPC470802
0.9077	High Similarity	NPC3049
0.9077	High Similarity	NPC471522
0.9077	High Similarity	NPC18189
0.9077	High Similarity	NPC20829
0.9076	High Similarity	NPC85292
0.9076	High Similarity	NPC229147
0.9076	High Similarity	NPC54507
0.904	High Similarity	NPC262573
0.904	High Similarity	NPC471215
0.9008	High Similarity	NPC470307
0.9008	High Similarity	NPC470308
0.9008	High Similarity	NPC474687
0.9	High Similarity	NPC61946
0.8992	High Similarity	NPC215037
0.8992	High Similarity	NPC464
0.8992	High Similarity	NPC11060
0.8992	High Similarity	NPC185541
0.896	High Similarity	NPC81641
0.8952	High Similarity	NPC474160
0.8947	High Similarity	NPC5155
0.8943	High Similarity	NPC190454
0.8943	High Similarity	NPC97432
0.8939	High Similarity	NPC32630
0.8931	High Similarity	NPC16435
0.8931	High Similarity	NPC306441
0.8923	High Similarity	NPC476616
0.8923	High Similarity	NPC476617
0.8923	High Similarity	NPC476615
0.8906	High Similarity	NPC32463
0.8881	High Similarity	NPC230718
0.8881	High Similarity	NPC128337
0.8881	High Similarity	NPC84207
0.8881	High Similarity	NPC5253
0.8881	High Similarity	NPC139976
0.8881	High Similarity	NPC49542
0.888	High Similarity	NPC294156
0.888	High Similarity	NPC256015
0.8871	High Similarity	NPC150026
0.8864	High Similarity	NPC87777
0.8864	High Similarity	NPC262328
0.8855	High Similarity	NPC121812
0.8855	High Similarity	NPC234333
0.8855	High Similarity	NPC260898
0.8855	High Similarity	NPC470356
0.8855	High Similarity	NPC47398
0.8855	High Similarity	NPC164787
0.8855	High Similarity	NPC112246
0.8855	High Similarity	NPC125579
0.8855	High Similarity	NPC112939
0.8855	High Similarity	NPC474206
0.8855	High Similarity	NPC94750
0.8855	High Similarity	NPC151224
0.8846	High Similarity	NPC475840
0.8846	High Similarity	NPC263064
0.8806	High Similarity	NPC265075
0.8806	High Similarity	NPC100482
0.8806	High Similarity	NPC277331
0.8797	High Similarity	NPC35501
0.8797	High Similarity	NPC37428
0.8797	High Similarity	NPC144512
0.8797	High Similarity	NPC471388
0.8797	High Similarity	NPC260741
0.8797	High Similarity	NPC137262
0.8797	High Similarity	NPC47040
0.8797	High Similarity	NPC278600
0.8797	High Similarity	NPC70682
0.8788	High Similarity	NPC230734
0.8788	High Similarity	NPC269091
0.8788	High Similarity	NPC227503
0.8788	High Similarity	NPC302701
0.8788	High Similarity	NPC234952
0.8788	High Similarity	NPC474639
0.8779	High Similarity	NPC317380
0.8779	High Similarity	NPC131950
0.8769	High Similarity	NPC78770
0.8769	High Similarity	NPC61477
0.8769	High Similarity	NPC261619
0.8769	High Similarity	NPC185604
0.8769	High Similarity	NPC219876
0.8769	High Similarity	NPC15658
0.8769	High Similarity	NPC126029
0.875	High Similarity	NPC225445
0.8739	High Similarity	NPC153795
0.8739	High Similarity	NPC290353
0.8739	High Similarity	NPC42911
0.873	High Similarity	NPC270030
0.8722	High Similarity	NPC477938
0.8722	High Similarity	NPC474282
0.8722	High Similarity	NPC211549
0.8722	High Similarity	NPC107551
0.8722	High Similarity	NPC326797
0.8722	High Similarity	NPC102904
0.8722	High Similarity	NPC176051
0.8722	High Similarity	NPC103976
0.872	High Similarity	NPC18128
0.872	High Similarity	NPC77789
0.872	High Similarity	NPC57199
0.8712	High Similarity	NPC195022
0.8702	High Similarity	NPC177712
0.8702	High Similarity	NPC24913
0.8702	High Similarity	NPC31849
0.8692	High Similarity	NPC160623
0.8692	High Similarity	NPC220825
0.8692	High Similarity	NPC42760
0.8692	High Similarity	NPC250727
0.8692	High Similarity	NPC268266
0.8692	High Similarity	NPC268342
0.8689	High Similarity	NPC69261
0.8689	High Similarity	NPC474933
0.8689	High Similarity	NPC33270
0.8682	High Similarity	NPC472796
0.8682	High Similarity	NPC472795

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 NPC276212 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	878
0.2-0.3	1644
0.3-0.4	2675
0.4-0.5	1740
0.5-0.6	1035
0.6-0.7	675
0.7-0.8	175
0.8-0.85	12
0.85-0.9	3
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.936	High Similarity	NPD4907	Clinical (unspecified phase)
0.92	High Similarity	NPD4908	Phase 1
0.9098	High Similarity	NPD1610	Phase 2
0.9083	High Similarity	NPD1548	Phase 1
0.8769	High Similarity	NPD1612	Clinical (unspecified phase)
0.8769	High Similarity	NPD1613	Approved
0.8682	High Similarity	NPD4625	Phase 3
0.8561	High Similarity	NPD5124	Phase 1
0.8561	High Similarity	NPD5123	Clinical (unspecified phase)
0.8473	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD3027	Phase 3
0.8385	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD2861	Phase 2
0.8359	Intermediate Similarity	NPD4749	Approved
0.8333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD7212	Phase 2
0.8286	Intermediate Similarity	NPD7213	Phase 3
0.8248	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8203	Intermediate Similarity	NPD422	Phase 1
0.8188	Intermediate Similarity	NPD1549	Phase 2
0.8129	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD7447	Phase 1
0.8062	Intermediate Similarity	NPD1091	Approved
0.8029	Intermediate Similarity	NPD4538	Approved
0.8029	Intermediate Similarity	NPD4536	Approved
0.8029	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD8651	Approved
0.8014	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7951	Intermediate Similarity	NPD2684	Approved
0.7945	Intermediate Similarity	NPD4380	Phase 2
0.7899	Intermediate Similarity	NPD846	Approved
0.7899	Intermediate Similarity	NPD940	Approved
0.7895	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD7411	Suspended
0.7872	Intermediate Similarity	NPD1652	Phase 2
0.7869	Intermediate Similarity	NPD290	Approved
0.7867	Intermediate Similarity	NPD7075	Discontinued
0.7847	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD7033	Discontinued
0.7842	Intermediate Similarity	NPD5588	Approved
0.7842	Intermediate Similarity	NPD5960	Phase 3
0.784	Intermediate Similarity	NPD7843	Approved
0.781	Intermediate Similarity	NPD4060	Phase 1
0.7803	Intermediate Similarity	NPD6582	Phase 2
0.7803	Intermediate Similarity	NPD6583	Phase 3
0.7803	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD6671	Approved
0.7787	Intermediate Similarity	NPD968	Approved
0.7786	Intermediate Similarity	NPD2796	Approved
0.7785	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6801	Discontinued
0.7718	Intermediate Similarity	NPD1934	Approved
0.7714	Intermediate Similarity	NPD1510	Phase 2
0.7708	Intermediate Similarity	NPD5058	Phase 3
0.7698	Intermediate Similarity	NPD5535	Approved
0.7692	Intermediate Similarity	NPD3750	Approved
0.7682	Intermediate Similarity	NPD7768	Phase 2
0.7681	Intermediate Similarity	NPD1240	Approved
0.7667	Intermediate Similarity	NPD7819	Suspended
0.7664	Intermediate Similarity	NPD6798	Discontinued
0.766	Intermediate Similarity	NPD6100	Approved
0.766	Intermediate Similarity	NPD6099	Approved
0.7656	Intermediate Similarity	NPD7157	Approved
0.7634	Intermediate Similarity	NPD6516	Phase 2
0.7634	Intermediate Similarity	NPD5846	Approved
0.7632	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6584	Phase 3
0.763	Intermediate Similarity	NPD3691	Phase 2
0.763	Intermediate Similarity	NPD3690	Phase 2
0.7574	Intermediate Similarity	NPD3018	Phase 2
0.7571	Intermediate Similarity	NPD1607	Approved
0.7569	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7466	Approved
0.7569	Intermediate Similarity	NPD3892	Phase 2
0.7556	Intermediate Similarity	NPD2797	Approved
0.7552	Intermediate Similarity	NPD2424	Discontinued
0.7532	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6959	Discontinued
0.7483	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3225	Approved
0.7479	Intermediate Similarity	NPD2860	Approved
0.7479	Intermediate Similarity	NPD2859	Approved
0.7466	Intermediate Similarity	NPD6666	Approved
0.7466	Intermediate Similarity	NPD6667	Approved
0.7465	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD5451	Approved
0.7452	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6166	Phase 2
0.7452	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1653	Approved
0.7448	Intermediate Similarity	NPD4535	Phase 3
0.7447	Intermediate Similarity	NPD3052	Approved
0.7447	Intermediate Similarity	NPD3054	Approved
0.7422	Intermediate Similarity	NPD821	Approved
0.7421	Intermediate Similarity	NPD5844	Phase 1
0.7415	Intermediate Similarity	NPD6799	Approved
0.7413	Intermediate Similarity	NPD1551	Phase 2
0.741	Intermediate Similarity	NPD3268	Approved
0.7407	Intermediate Similarity	NPD3685	Discontinued
0.7407	Intermediate Similarity	NPD2983	Phase 2
0.7407	Intermediate Similarity	NPD2982	Phase 2
0.74	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD2933	Approved
0.7395	Intermediate Similarity	NPD2934	Approved
0.7394	Intermediate Similarity	NPD7097	Phase 1
0.7394	Intermediate Similarity	NPD2200	Suspended
0.7391	Intermediate Similarity	NPD6559	Discontinued
0.7385	Intermediate Similarity	NPD2557	Approved
0.7383	Intermediate Similarity	NPD5403	Approved
0.7379	Intermediate Similarity	NPD6674	Discontinued
0.7377	Intermediate Similarity	NPD1242	Phase 1
0.7376	Intermediate Similarity	NPD6355	Discontinued
0.7376	Intermediate Similarity	NPD5735	Approved
0.7361	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6002	Phase 3
0.7361	Intermediate Similarity	NPD6005	Phase 3
0.7361	Intermediate Similarity	NPD6004	Phase 3
0.7357	Intermediate Similarity	NPD6407	Approved
0.7357	Intermediate Similarity	NPD6233	Phase 2
0.7357	Intermediate Similarity	NPD6405	Approved
0.7353	Intermediate Similarity	NPD6696	Suspended
0.7348	Intermediate Similarity	NPD6581	Approved
0.7348	Intermediate Similarity	NPD6580	Approved
0.7343	Intermediate Similarity	NPD3748	Approved
0.7333	Intermediate Similarity	NPD2981	Phase 2
0.7329	Intermediate Similarity	NPD4628	Phase 3
0.7328	Intermediate Similarity	NPD3596	Phase 2
0.7323	Intermediate Similarity	NPD4750	Phase 3
0.732	Intermediate Similarity	NPD8455	Phase 2
0.732	Intermediate Similarity	NPD2801	Approved
0.7305	Intermediate Similarity	NPD4140	Approved
0.7305	Intermediate Similarity	NPD2238	Phase 2
0.7303	Intermediate Similarity	NPD6072	Discontinued
0.7297	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7041	Phase 2
0.7297	Intermediate Similarity	NPD1511	Approved
0.7295	Intermediate Similarity	NPD3020	Approved
0.7293	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2935	Discontinued
0.7279	Intermediate Similarity	NPD5327	Phase 3
0.7273	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7074	Phase 3
0.7266	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD37	Approved
0.7254	Intermediate Similarity	NPD4340	Discontinued
0.7248	Intermediate Similarity	NPD5401	Approved
0.7241	Intermediate Similarity	NPD5763	Approved
0.7241	Intermediate Similarity	NPD5762	Approved
0.7239	Intermediate Similarity	NPD4626	Approved
0.7239	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6599	Discontinued
0.7231	Intermediate Similarity	NPD5283	Phase 1
0.7226	Intermediate Similarity	NPD4965	Approved
0.7226	Intermediate Similarity	NPD4967	Phase 2
0.7226	Intermediate Similarity	NPD4966	Approved
0.7226	Intermediate Similarity	NPD3882	Suspended
0.7218	Intermediate Similarity	NPD7741	Discontinued
0.7218	Intermediate Similarity	NPD1894	Discontinued
0.7215	Intermediate Similarity	NPD7229	Phase 3
0.7206	Intermediate Similarity	NPD2235	Phase 2
0.7206	Intermediate Similarity	NPD2231	Phase 2
0.7205	Intermediate Similarity	NPD7054	Approved
0.7203	Intermediate Similarity	NPD4097	Suspended
0.72	Intermediate Similarity	NPD1512	Approved
0.7197	Intermediate Similarity	NPD5494	Approved
0.7185	Intermediate Similarity	NPD3496	Discontinued
0.7185	Intermediate Similarity	NPD3847	Discontinued
0.7183	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4476	Approved
0.7172	Intermediate Similarity	NPD4477	Approved
0.7171	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD3444	Approved
0.7164	Intermediate Similarity	NPD3443	Approved
0.7164	Intermediate Similarity	NPD5691	Approved
0.7164	Intermediate Similarity	NPD3049	Approved
0.7164	Intermediate Similarity	NPD3445	Approved
0.7163	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1296	Phase 2
0.716	Intermediate Similarity	NPD7472	Approved
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD2800	Approved
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7134	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6234	Discontinued
0.7132	Intermediate Similarity	NPD1535	Discovery
0.7132	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7030	Discontinued
0.7121	Intermediate Similarity	NPD6387	Discontinued
0.7117	Intermediate Similarity	NPD6797	Phase 2
0.7113	Intermediate Similarity	NPD4062	Phase 3
0.7113	Intermediate Similarity	NPD7477	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