NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.09
Volume:	252.879
LogP:	3.338
LogD:	3.135
LogS:	-3.293
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.807
Synthetic Accessibility Score:	2.621
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.656
MDCK Permeability:	9.957489965017885e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	96.43353271484375%
Volume Distribution (VD):	1.079
Pgp-substrate:	3.5140552520751953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.708
CYP2C19-inhibitor:	0.964
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.786
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.906
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.807
CYP3A4-substrate:	0.318

ADMET: Excretion

Clearance (CL):	14.73
Half-life (T1/2):	0.794

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.414
Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.923
Carcinogencity:	0.773
Eye Corrosion:	0.034
Eye Irritation:	0.949
Respiratory Toxicity:	0.446

Download Data

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

Natural Product: NPC8283

Natural Product ID:	NPC8283
*Common Name:**	Tupichinol C
IUPAC Name:	(2R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol
Synonyms:	(2R)-7,4'-Dihydroxylflavan; Tupichinol C
Standard InCHIKey:	YXMLGIGHGPSEKA-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C15H14O3/c16-12-5-1-10(2-6-12)14-8-4-11-3-7-13(17)9-15(11)18-14/h1-3,5-7,9,14,16-17H,4,8H2/t14-/m1/s1
SMILES:	Oc1ccc(cc1)[C@H]1CCc2c(O1)cc(cc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463804
PubChem CID:	11064571
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002991] Hydroxyflavonoids [CHEMONTID:0002993] 7-hydroxyflavonoids

*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
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[11575957]
NPO31092	Tupistra chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608845]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19046886]
NPO20812	Soymida febrifuga	Species	Meliaceae	Eukaryota	n.a.	Myanmar	n.a.	PMID[19689125]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20493686]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917310]
NPO31092	Tupistra chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28394	Rohdea chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20812	Soymida febrifuga	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28394	Rohdea chinensis	Species	Asparagaceae	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	7
Others	5

Activity Type	# Activity
Cell Line	4
Individual Protein	4
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	94000.0	nM	PMID[450454]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	50100.0	nM	PMID[450454]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	>	100.0	uM	PMID[450454]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	93400.0	nM	PMID[450454]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	RBA	=	0.048	%	PMID[450455]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	RBA	=	0.021	%	PMID[450455]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	IC50	=	14700.0	nM	PMID[450455]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	IC50	=	26200.0	nM	PMID[450455]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	50.0	%	PMID[450453]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	43900.0	nM	PMID[450454]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[450454]
NPT2	Others	Unspecified		Ratio IC50	=	2.29	n.a.	PMID[450455]

☑ 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 NPC8283 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	458
0.1-0.2	1777
0.2-0.3	5497
0.3-0.4	13470
0.4-0.5	3888
0.5-0.6	4768
0.6-0.7	7597
0.7-0.8	4241
0.8-0.85	717
0.85-0.9	221
0.9-0.95	43
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC93398
1.0	High Similarity	NPC258979
0.9739	High Similarity	NPC36016
0.9739	High Similarity	NPC100099
0.9655	High Similarity	NPC38761
0.9655	High Similarity	NPC76465
0.9652	High Similarity	NPC193364
0.9652	High Similarity	NPC54972
0.9646	High Similarity	NPC74821
0.9573	High Similarity	NPC134195
0.9573	High Similarity	NPC197351
0.9573	High Similarity	NPC106914
0.9573	High Similarity	NPC86502
0.9573	High Similarity	NPC246648
0.9561	High Similarity	NPC295259
0.9492	High Similarity	NPC167571
0.9492	High Similarity	NPC278552
0.9492	High Similarity	NPC285040
0.9492	High Similarity	NPC207179
0.9492	High Similarity	NPC103420
0.9492	High Similarity	NPC17809
0.9492	High Similarity	NPC102540
0.9492	High Similarity	NPC188022
0.9412	High Similarity	NPC262573
0.9412	High Similarity	NPC276212
0.9412	High Similarity	NPC471215
0.9333	High Similarity	NPC149796
0.9316	High Similarity	NPC190454
0.9316	High Similarity	NPC97432
0.9256	High Similarity	NPC222572
0.9256	High Similarity	NPC87224
0.9256	High Similarity	NPC47283
0.9256	High Similarity	NPC274717
0.9256	High Similarity	NPC39064
0.925	High Similarity	NPC26879
0.925	High Similarity	NPC283049
0.925	High Similarity	NPC50315
0.925	High Similarity	NPC230479
0.9224	High Similarity	NPC59561
0.9224	High Similarity	NPC172253
0.913	High Similarity	NPC54507
0.913	High Similarity	NPC85292
0.913	High Similarity	NPC229147
0.9098	High Similarity	NPC38664
0.9098	High Similarity	NPC53986
0.9043	High Similarity	NPC464
0.9043	High Similarity	NPC185541
0.9032	High Similarity	NPC118114
0.9032	High Similarity	NPC129106
0.9032	High Similarity	NPC196765
0.9032	High Similarity	NPC268917
0.9032	High Similarity	NPC206224
0.9032	High Similarity	NPC228369
0.9032	High Similarity	NPC236014
0.9032	High Similarity	NPC207892
0.9032	High Similarity	NPC164574
0.9032	High Similarity	NPC476166
0.9032	High Similarity	NPC280653
0.9032	High Similarity	NPC17343
0.9032	High Similarity	NPC300875
0.9032	High Similarity	NPC162801
0.9032	High Similarity	NPC12875
0.9032	High Similarity	NPC150011
0.9032	High Similarity	NPC103799
0.9032	High Similarity	NPC129784
0.9024	High Similarity	NPC93962
0.8974	High Similarity	NPC131118
0.896	High Similarity	NPC13005
0.896	High Similarity	NPC126029
0.896	High Similarity	NPC219876
0.896	High Similarity	NPC185604
0.896	High Similarity	NPC15658
0.896	High Similarity	NPC61477
0.896	High Similarity	NPC261619
0.896	High Similarity	NPC78770
0.8952	High Similarity	NPC470225
0.8952	High Similarity	NPC27187
0.8889	High Similarity	NPC11060
0.8889	High Similarity	NPC215037
0.8889	High Similarity	NPC85435
0.888	High Similarity	NPC68205
0.888	High Similarity	NPC271945
0.888	High Similarity	NPC244888
0.888	High Similarity	NPC164804
0.888	High Similarity	NPC268266
0.888	High Similarity	NPC42760
0.888	High Similarity	NPC220825
0.888	High Similarity	NPC181497
0.888	High Similarity	NPC268342
0.888	High Similarity	NPC211413
0.888	High Similarity	NPC293203
0.888	High Similarity	NPC118683
0.8871	High Similarity	NPC134360
0.8852	High Similarity	NPC168259
0.8819	High Similarity	NPC223008
0.8819	High Similarity	NPC115335
0.8819	High Similarity	NPC225696
0.8819	High Similarity	NPC124085
0.8819	High Similarity	NPC476615
0.8819	High Similarity	NPC117048
0.8819	High Similarity	NPC473107
0.8819	High Similarity	NPC296915
0.8819	High Similarity	NPC476616
0.8819	High Similarity	NPC476617
0.8819	High Similarity	NPC198154
0.8819	High Similarity	NPC97834
0.8803	High Similarity	NPC150624
0.8803	High Similarity	NPC141090
0.8803	High Similarity	NPC203113
0.879	High Similarity	NPC46274
0.879	High Similarity	NPC226331
0.877	High Similarity	NPC159132
0.877	High Similarity	NPC256015
0.877	High Similarity	NPC270030
0.877	High Similarity	NPC294156
0.875	High Similarity	NPC112246
0.875	High Similarity	NPC61946
0.875	High Similarity	NPC121812
0.875	High Similarity	NPC112939
0.875	High Similarity	NPC151224
0.875	High Similarity	NPC473413
0.875	High Similarity	NPC470356
0.875	High Similarity	NPC474206
0.875	High Similarity	NPC164787
0.875	High Similarity	NPC94750
0.874	High Similarity	NPC77196
0.874	High Similarity	NPC92805
0.873	High Similarity	NPC250727
0.8729	High Similarity	NPC195466
0.8729	High Similarity	NPC50521
0.8729	High Similarity	NPC221549
0.8729	High Similarity	NPC33270
0.8729	High Similarity	NPC474933
0.8729	High Similarity	NPC69261
0.8729	High Similarity	NPC244816
0.8718	High Similarity	NPC808
0.871	High Similarity	NPC250432
0.871	High Similarity	NPC5447
0.871	High Similarity	NPC46978
0.8689	High Similarity	NPC474160
0.8682	High Similarity	NPC302701
0.8682	High Similarity	NPC234952
0.8682	High Similarity	NPC269091
0.8682	High Similarity	NPC227503
0.8682	High Similarity	NPC20829
0.8682	High Similarity	NPC16435
0.8682	High Similarity	NPC474639
0.8682	High Similarity	NPC3049
0.8682	High Similarity	NPC262585
0.8682	High Similarity	NPC18189
0.8682	High Similarity	NPC306441
0.8682	High Similarity	NPC230734
0.8682	High Similarity	NPC471522
0.8678	High Similarity	NPC476633
0.8672	High Similarity	NPC317380
0.8661	High Similarity	NPC202762
0.8661	High Similarity	NPC86655
0.8651	High Similarity	NPC91291
0.8632	High Similarity	NPC22610
0.8632	High Similarity	NPC276737
0.8621	High Similarity	NPC42911
0.8621	High Similarity	NPC280606
0.8621	High Similarity	NPC290353
0.8621	High Similarity	NPC153795
0.8618	High Similarity	NPC138248
0.8618	High Similarity	NPC228503
0.8615	High Similarity	NPC211549
0.8615	High Similarity	NPC102904
0.8615	High Similarity	NPC262328
0.8615	High Similarity	NPC470308
0.8615	High Similarity	NPC474282
0.8615	High Similarity	NPC87777
0.8615	High Similarity	NPC103976
0.8615	High Similarity	NPC326797
0.8615	High Similarity	NPC107551
0.8615	High Similarity	NPC176051
0.8615	High Similarity	NPC474687
0.8615	High Similarity	NPC470307
0.8609	High Similarity	NPC106141
0.8607	High Similarity	NPC57199
0.8607	High Similarity	NPC150026
0.8605	High Similarity	NPC234333
0.8605	High Similarity	NPC47398
0.8605	High Similarity	NPC15109
0.8605	High Similarity	NPC260898
0.8605	High Similarity	NPC125579
0.8605	High Similarity	NPC195022
0.8605	High Similarity	NPC11727
0.8595	High Similarity	NPC102639
0.8594	High Similarity	NPC475840
0.8594	High Similarity	NPC263064
0.8583	High Similarity	NPC184302
0.8571	High Similarity	NPC472797
0.8559	High Similarity	NPC53906
0.8559	High Similarity	NPC167934
0.855	High Similarity	NPC232164
0.855	High Similarity	NPC236306
0.855	High Similarity	NPC295261
0.855	High Similarity	NPC79943
0.855	High Similarity	NPC107586

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 NPC8283 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	973
0.2-0.3	1672
0.3-0.4	2686
0.4-0.5	1637
0.5-0.6	1003
0.6-0.7	621
0.7-0.8	131
0.8-0.85	12
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9652	High Similarity	NPD1610	Phase 2
0.9646	High Similarity	NPD1548	Phase 1
0.9098	High Similarity	NPD4908	Phase 1
0.896	High Similarity	NPD1613	Approved
0.896	High Similarity	NPD1612	Clinical (unspecified phase)
0.8952	High Similarity	NPD4907	Clinical (unspecified phase)
0.879	High Similarity	NPD1529	Clinical (unspecified phase)
0.871	High Similarity	NPD1530	Clinical (unspecified phase)
0.856	High Similarity	NPD2861	Phase 2
0.855	High Similarity	NPD1550	Clinical (unspecified phase)
0.855	High Similarity	NPD1552	Clinical (unspecified phase)
0.8525	High Similarity	NPD422	Phase 1
0.8485	Intermediate Similarity	NPD1549	Phase 2
0.8425	Intermediate Similarity	NPD4625	Phase 3
0.8387	Intermediate Similarity	NPD4749	Approved
0.8261	Intermediate Similarity	NPD968	Approved
0.8217	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD7212	Phase 2
0.8175	Intermediate Similarity	NPD7213	Phase 3
0.814	Intermediate Similarity	NPD3027	Phase 3
0.808	Intermediate Similarity	NPD1091	Approved
0.807	Intermediate Similarity	NPD940	Approved
0.807	Intermediate Similarity	NPD846	Approved
0.8034	Intermediate Similarity	NPD290	Approved
0.803	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD5124	Phase 1
0.7986	Intermediate Similarity	NPD7447	Phase 1
0.7985	Intermediate Similarity	NPD1510	Phase 2
0.7955	Intermediate Similarity	NPD1240	Approved
0.7836	Intermediate Similarity	NPD1607	Approved
0.7826	Intermediate Similarity	NPD3750	Approved
0.7826	Intermediate Similarity	NPD1242	Phase 1
0.7815	Intermediate Similarity	NPD2684	Approved
0.7812	Intermediate Similarity	NPD6583	Phase 3
0.7812	Intermediate Similarity	NPD6582	Phase 2
0.7805	Intermediate Similarity	NPD6671	Approved
0.7794	Intermediate Similarity	NPD2796	Approved
0.7754	Intermediate Similarity	NPD1652	Phase 2
0.773	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1934	Approved
0.7671	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1551	Phase 2
0.7664	Intermediate Similarity	NPD6099	Approved
0.7664	Intermediate Similarity	NPD6100	Approved
0.7655	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD6516	Phase 2
0.7638	Intermediate Similarity	NPD5846	Approved
0.7634	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6584	Phase 3
0.7626	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD3225	Approved
0.7591	Intermediate Similarity	NPD7033	Discontinued
0.7586	Intermediate Similarity	NPD4380	Phase 2
0.7571	Intermediate Similarity	NPD7466	Approved
0.7561	Intermediate Similarity	NPD7843	Approved
0.7561	Intermediate Similarity	NPD821	Approved
0.7561	Intermediate Similarity	NPD5535	Approved
0.7557	Intermediate Similarity	NPD2797	Approved
0.7537	Intermediate Similarity	NPD6798	Discontinued
0.7535	Intermediate Similarity	NPD1511	Approved
0.7534	Intermediate Similarity	NPD7411	Suspended
0.7519	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4538	Approved
0.7518	Intermediate Similarity	NPD4536	Approved
0.7517	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7075	Discontinued
0.7483	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD8651	Approved
0.748	Intermediate Similarity	NPD1894	Discontinued
0.7478	Intermediate Similarity	NPD2859	Approved
0.7478	Intermediate Similarity	NPD2860	Approved
0.7464	Intermediate Similarity	NPD5588	Approved
0.7464	Intermediate Similarity	NPD5960	Phase 3
0.7464	Intermediate Similarity	NPD3748	Approved
0.7459	Intermediate Similarity	NPD5451	Approved
0.745	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1653	Approved
0.7447	Intermediate Similarity	NPD3892	Phase 2
0.7444	Intermediate Similarity	NPD3018	Phase 2
0.7432	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1512	Approved
0.7426	Intermediate Similarity	NPD4060	Phase 1
0.7407	Intermediate Similarity	NPD1296	Phase 2
0.7405	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2200	Suspended
0.7391	Intermediate Similarity	NPD2933	Approved
0.7391	Intermediate Similarity	NPD2934	Approved
0.7388	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1535	Discovery
0.7381	Intermediate Similarity	NPD7157	Approved
0.7381	Intermediate Similarity	NPD2557	Approved
0.7376	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6580	Approved
0.7344	Intermediate Similarity	NPD6581	Approved
0.7339	Intermediate Similarity	NPD228	Approved
0.7338	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7768	Phase 2
0.7328	Intermediate Similarity	NPD1608	Approved
0.7328	Intermediate Similarity	NPD1481	Phase 2
0.7324	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD3596	Phase 2
0.7319	Intermediate Similarity	NPD3052	Approved
0.7319	Intermediate Similarity	NPD3054	Approved
0.7317	Intermediate Similarity	NPD4750	Phase 3
0.7315	Intermediate Similarity	NPD7819	Suspended
0.7293	Intermediate Similarity	NPD1203	Approved
0.7292	Intermediate Similarity	NPD6799	Approved
0.7288	Intermediate Similarity	NPD3020	Approved
0.7287	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3268	Approved
0.7273	Intermediate Similarity	NPD2983	Phase 2
0.7273	Intermediate Similarity	NPD2982	Phase 2
0.7266	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5403	Approved
0.7248	Intermediate Similarity	NPD6801	Discontinued
0.7246	Intermediate Similarity	NPD6355	Discontinued
0.7246	Intermediate Similarity	NPD4340	Discontinued
0.7241	Intermediate Similarity	NPD5401	Approved
0.7239	Intermediate Similarity	NPD3691	Phase 2
0.7239	Intermediate Similarity	NPD3690	Phase 2
0.7231	Intermediate Similarity	NPD1778	Approved
0.7226	Intermediate Similarity	NPD6166	Phase 2
0.7226	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6233	Phase 2
0.7226	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1241	Discontinued
0.7222	Intermediate Similarity	NPD5058	Phase 3
0.7209	Intermediate Similarity	NPD1182	Approved
0.72	Intermediate Similarity	NPD2801	Approved
0.7197	Intermediate Similarity	NPD2981	Phase 2
0.7197	Intermediate Similarity	NPD2235	Phase 2
0.7197	Intermediate Similarity	NPD2231	Phase 2
0.7183	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2238	Phase 2
0.7174	Intermediate Similarity	NPD1558	Phase 1
0.7174	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3749	Approved
0.7154	Intermediate Similarity	NPD3444	Approved
0.7154	Intermediate Similarity	NPD3443	Approved
0.7154	Intermediate Similarity	NPD3445	Approved
0.7154	Intermediate Similarity	NPD3049	Approved
0.7143	Intermediate Similarity	NPD5327	Phase 3
0.7143	Intermediate Similarity	NPD7097	Phase 1
0.7143	Intermediate Similarity	NPD3685	Discontinued
0.7143	Intermediate Similarity	NPD6959	Discontinued
0.7131	Intermediate Similarity	NPD9697	Approved
0.7122	Intermediate Similarity	NPD5735	Approved
0.7115	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6599	Discontinued
0.7113	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3882	Suspended
0.7103	Intermediate Similarity	NPD6666	Approved
0.7103	Intermediate Similarity	NPD6667	Approved
0.7101	Intermediate Similarity	NPD7477	Discontinued
0.7099	Intermediate Similarity	NPD17	Approved
0.7099	Intermediate Similarity	NPD2556	Approved
0.7099	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2554	Approved
0.709	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6696	Suspended
0.7089	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5283	Phase 1
0.7086	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4628	Phase 3
0.708	Intermediate Similarity	NPD6179	Discontinued
0.7068	Intermediate Similarity	NPD1840	Phase 2
0.7063	Intermediate Similarity	NPD2424	Discontinued
0.705	Intermediate Similarity	NPD4140	Approved
0.7045	Intermediate Similarity	NPD3496	Discontinued
0.7045	Intermediate Similarity	NPD3847	Discontinued
0.7044	Intermediate Similarity	NPD7074	Phase 3
0.7037	Intermediate Similarity	NPD3267	Approved
0.7037	Intermediate Similarity	NPD3266	Approved
0.7029	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3818	Discontinued
0.7023	Intermediate Similarity	NPD6382	Discontinued
0.7015	Intermediate Similarity	NPD6542	Approved
0.7015	Intermediate Similarity	NPD6540	Phase 3
0.7015	Intermediate Similarity	NPD6539	Approved
0.7015	Intermediate Similarity	NPD6543	Approved
0.6986	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6815	Approved
0.6983	Remote Similarity	NPD9365	Approved
0.6981	Remote Similarity	NPD7054	Approved
0.6981	Remote Similarity	NPD5844	Phase 1
0.6978	Remote Similarity	NPD6405	Approved
0.6978	Remote Similarity	NPD4062	Phase 3
0.6978	Remote Similarity	NPD6407	Approved
0.6977	Remote Similarity	NPD709	Approved
0.6974	Remote Similarity	NPD1465	Phase 2
0.6974	Remote Similarity	NPD8455	Phase 2
0.6972	Remote Similarity	NPD4308	Phase 3
0.697	Remote Similarity	NPD2668	Approved
0.697	Remote Similarity	NPD4626	Approved
0.697	Remote Similarity	NPD2667	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