NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.07
Volume:	229.714
LogP:	3.681
LogD:	3.206
LogS:	-3.437
# Rotatable Bonds:	0
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.732
Synthetic Accessibility Score:	3.426
Fsp3:	0.231
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:	-4.716
MDCK Permeability:	2.2898046154296026e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	99.29007720947266%
Volume Distribution (VD):	0.681
Pgp-substrate:	4.362236499786377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.874
CYP1A2-substrate:	0.509
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.512
CYP2C9-substrate:	0.678
CYP2D6-inhibitor:	0.77
CYP2D6-substrate:	0.309
CYP3A4-inhibitor:	0.137
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	8.437
Half-life (T1/2):	0.757

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.679
Drug-inuced Liver Injury (DILI):	0.566
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.969
Maximum Recommended Daily Dose:	0.421
Skin Sensitization:	0.687
Carcinogencity:	0.933
Eye Corrosion:	0.004
Eye Irritation:	0.221
Respiratory Toxicity:	0.882

Download Data

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

Natural Product: NPC271681

Natural Product ID:	NPC271681
*Common Name:**	Salfredin B11
IUPAC Name:	5-hydroxy-2,2-dimethyl-8H-furo[3,4-g]chromen-6-one
Synonyms:
Standard InCHIKey:	ZYOUEEMPKPNVQW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H12O4/c1-13(2)4-3-8-9(17-13)5-7-6-16-12(15)10(7)11(8)14/h3-5,14H,6H2,1-2H3
SMILES:	O=C1OCc2c1c(O)c1c(c2)OC(C=C1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609156
PubChem CID:	636462
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO2136	Nigella glandulifera	Species	Ranunculaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[24593120]
NPO2136	Nigella glandulifera	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26227777]
NPO2136	Nigella glandulifera	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2136	Nigella glandulifera	Species	Ranunculaceae	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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	36950.0	nM	PMID[549882]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[549882]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	40000.0	nM	PMID[549882]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24130.0	nM	PMID[549882]

☑ 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 NPC271681 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	351
0.1-0.2	1615
0.2-0.3	3699
0.3-0.4	8232
0.4-0.5	10008
0.5-0.6	3673
0.6-0.7	5380
0.7-0.8	6233
0.8-0.85	2666
0.85-0.9	769
0.9-0.95	70
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9459	High Similarity	NPC119929
0.9456	High Similarity	NPC37139
0.9329	High Similarity	NPC158866
0.9257	High Similarity	NPC137296
0.9252	High Similarity	NPC75694
0.9241	High Similarity	NPC90411
0.9205	High Similarity	NPC273483
0.9172	High Similarity	NPC165172
0.9145	High Similarity	NPC472799
0.9133	High Similarity	NPC291049
0.9133	High Similarity	NPC233267
0.9128	High Similarity	NPC8817
0.9103	High Similarity	NPC275356
0.9079	High Similarity	NPC175978
0.9079	High Similarity	NPC217447
0.9073	High Similarity	NPC179178
0.9073	High Similarity	NPC150928
0.9073	High Similarity	NPC202595
0.9067	High Similarity	NPC105415
0.906	High Similarity	NPC260946
0.906	High Similarity	NPC163846
0.906	High Similarity	NPC470357
0.906	High Similarity	NPC225173
0.9026	High Similarity	NPC146211
0.902	High Similarity	NPC169990
0.902	High Similarity	NPC210942
0.9013	High Similarity	NPC133856
0.9007	High Similarity	NPC198927
0.9	High Similarity	NPC123202
0.9	High Similarity	NPC125801
0.9	High Similarity	NPC22005
0.9	High Similarity	NPC166583
0.9	High Similarity	NPC7943
0.9	High Similarity	NPC53362
0.8974	High Similarity	NPC243701
0.8974	High Similarity	NPC470810
0.8974	High Similarity	NPC143050
0.8968	High Similarity	NPC96342
0.8968	High Similarity	NPC246647
0.8968	High Similarity	NPC212967
0.8968	High Similarity	NPC164110
0.8966	High Similarity	NPC135837
0.8961	High Similarity	NPC149618
0.8961	High Similarity	NPC89625
0.8947	High Similarity	NPC295036
0.8947	High Similarity	NPC470107
0.894	High Similarity	NPC256672
0.894	High Similarity	NPC27221
0.894	High Similarity	NPC7025
0.8926	High Similarity	NPC42540
0.8926	High Similarity	NPC151607
0.8917	High Similarity	NPC117985
0.8903	High Similarity	NPC180924
0.8897	High Similarity	NPC50455
0.8897	High Similarity	NPC158481
0.8896	High Similarity	NPC329844
0.8896	High Similarity	NPC477669
0.8896	High Similarity	NPC477691
0.8889	High Similarity	NPC149526
0.8889	High Similarity	NPC240768
0.8889	High Similarity	NPC474417
0.8889	High Similarity	NPC258249
0.8889	High Similarity	NPC200773
0.8889	High Similarity	NPC478148
0.8882	High Similarity	NPC158338
0.8882	High Similarity	NPC288036
0.8882	High Similarity	NPC97029
0.8882	High Similarity	NPC97028
0.8882	High Similarity	NPC65589
0.8882	High Similarity	NPC70764
0.8882	High Similarity	NPC10027
0.8882	High Similarity	NPC100985
0.8882	High Similarity	NPC65775
0.8874	High Similarity	NPC71055
0.8867	High Similarity	NPC134621
0.8867	High Similarity	NPC316535
0.8867	High Similarity	NPC312789
0.8867	High Similarity	NPC473692
0.8859	High Similarity	NPC469542
0.8859	High Similarity	NPC51106
0.8859	High Similarity	NPC159721
0.8859	High Similarity	NPC472006
0.8854	High Similarity	NPC313368
0.8851	High Similarity	NPC37530
0.8851	High Similarity	NPC1704
0.8851	High Similarity	NPC67650
0.8851	High Similarity	NPC220106
0.8851	High Similarity	NPC149533
0.8846	High Similarity	NPC44199
0.8846	High Similarity	NPC268360
0.8846	High Similarity	NPC263483
0.8839	High Similarity	NPC148938
0.8831	High Similarity	NPC40356
0.8831	High Similarity	NPC154683
0.8831	High Similarity	NPC477690
0.8828	High Similarity	NPC180905
0.8828	High Similarity	NPC182496
0.8824	High Similarity	NPC325983
0.8816	High Similarity	NPC240253
0.8816	High Similarity	NPC470359
0.8816	High Similarity	NPC172329
0.8816	High Similarity	NPC240622
0.8816	High Similarity	NPC471641
0.8816	High Similarity	NPC153417
0.8816	High Similarity	NPC5537
0.8816	High Similarity	NPC2569
0.8816	High Similarity	NPC471642
0.8808	High Similarity	NPC237208
0.8808	High Similarity	NPC267509
0.8808	High Similarity	NPC107625
0.8805	High Similarity	NPC100849
0.88	High Similarity	NPC184702
0.88	High Similarity	NPC95123
0.88	High Similarity	NPC471451
0.88	High Similarity	NPC66404
0.88	High Similarity	NPC470932
0.88	High Similarity	NPC475201
0.8792	High Similarity	NPC474385
0.8792	High Similarity	NPC250755
0.8792	High Similarity	NPC82913
0.8792	High Similarity	NPC94076
0.8792	High Similarity	NPC297985
0.8792	High Similarity	NPC182255
0.8792	High Similarity	NPC105648
0.8792	High Similarity	NPC322112
0.879	High Similarity	NPC474373
0.879	High Similarity	NPC477692
0.8784	High Similarity	NPC99441
0.8784	High Similarity	NPC137009
0.8784	High Similarity	NPC23257
0.8782	High Similarity	NPC4547
0.8782	High Similarity	NPC477674
0.878	High Similarity	NPC312630
0.878	High Similarity	NPC324220
0.8774	High Similarity	NPC280530
0.8774	High Similarity	NPC235333
0.8774	High Similarity	NPC192189
0.8774	High Similarity	NPC135522
0.8774	High Similarity	NPC178964
0.8774	High Similarity	NPC95842
0.8774	High Similarity	NPC301233
0.8767	High Similarity	NPC242712
0.8767	High Similarity	NPC60667
0.8766	High Similarity	NPC215921
0.8766	High Similarity	NPC72958
0.8766	High Similarity	NPC232645
0.8766	High Similarity	NPC290671
0.8766	High Similarity	NPC477672
0.8766	High Similarity	NPC39819
0.8766	High Similarity	NPC70016
0.8766	High Similarity	NPC477673
0.8766	High Similarity	NPC115324
0.8765	High Similarity	NPC477573
0.8765	High Similarity	NPC477571
0.8765	High Similarity	NPC477572
0.8765	High Similarity	NPC17219
0.8759	High Similarity	NPC175943
0.8758	High Similarity	NPC270160
0.8758	High Similarity	NPC237440
0.8758	High Similarity	NPC4423
0.8758	High Similarity	NPC77325
0.8758	High Similarity	NPC76647
0.8758	High Similarity	NPC317492
0.875	High Similarity	NPC202494
0.8742	High Similarity	NPC29577
0.8742	High Similarity	NPC32470
0.8742	High Similarity	NPC472402
0.8742	High Similarity	NPC297788
0.8734	High Similarity	NPC47623
0.8733	High Similarity	NPC472344
0.8733	High Similarity	NPC471731
0.8733	High Similarity	NPC162476
0.8733	High Similarity	NPC84266
0.8726	High Similarity	NPC158542
0.8726	High Similarity	NPC270044
0.8725	High Similarity	NPC471587
0.8725	High Similarity	NPC475730
0.8725	High Similarity	NPC158634
0.8718	High Similarity	NPC279218
0.8718	High Similarity	NPC108937
0.8718	High Similarity	NPC99199
0.8718	High Similarity	NPC297531
0.8718	High Similarity	NPC213936
0.8718	High Similarity	NPC199926
0.8716	High Similarity	NPC32360
0.8716	High Similarity	NPC131130
0.8716	High Similarity	NPC57380
0.8716	High Similarity	NPC88269
0.8716	High Similarity	NPC268052
0.871	High Similarity	NPC473967
0.871	High Similarity	NPC281272
0.871	High Similarity	NPC207624
0.871	High Similarity	NPC87708
0.8701	High Similarity	NPC471115
0.8701	High Similarity	NPC96501
0.8701	High Similarity	NPC472633
0.8701	High Similarity	NPC147735
0.8701	High Similarity	NPC155882
0.8701	High Similarity	NPC476185
0.8701	High Similarity	NPC180351

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 NPC271681 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	972
0.2-0.3	1712
0.3-0.4	2509
0.4-0.5	1840
0.5-0.6	1125
0.6-0.7	445
0.7-0.8	177
0.8-0.85	38
0.85-0.9	6
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9252	High Similarity	NPD2533	Approved
0.9252	High Similarity	NPD2534	Approved
0.9252	High Similarity	NPD2532	Approved
0.8973	High Similarity	NPD970	Clinical (unspecified phase)
0.8654	High Similarity	NPD7819	Suspended
0.8509	High Similarity	NPD6232	Discontinued
0.8509	High Similarity	NPD5711	Approved
0.8509	High Similarity	NPD5710	Approved
0.8506	High Similarity	NPD920	Approved
0.8497	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD2800	Approved
0.8377	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD3749	Approved
0.8354	Intermediate Similarity	NPD7473	Discontinued
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD1551	Phase 2
0.8302	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1243	Approved
0.828	Intermediate Similarity	NPD3226	Approved
0.8278	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1510	Phase 2
0.8255	Intermediate Similarity	NPD1607	Approved
0.8247	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3750	Approved
0.8224	Intermediate Similarity	NPD1549	Phase 2
0.8194	Intermediate Similarity	NPD1511	Approved
0.8176	Intermediate Similarity	NPD7411	Suspended
0.8158	Intermediate Similarity	NPD2346	Discontinued
0.8148	Intermediate Similarity	NPD7075	Discontinued
0.8144	Intermediate Similarity	NPD5844	Phase 1
0.8141	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1934	Approved
0.8121	Intermediate Similarity	NPD1240	Approved
0.8113	Intermediate Similarity	NPD6599	Discontinued
0.8098	Intermediate Similarity	NPD919	Approved
0.8092	Intermediate Similarity	NPD2935	Discontinued
0.8089	Intermediate Similarity	NPD1512	Approved
0.8086	Intermediate Similarity	NPD3882	Suspended
0.8086	Intermediate Similarity	NPD7768	Phase 2
0.8075	Intermediate Similarity	NPD2801	Approved
0.8075	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD3817	Phase 2
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD3818	Discontinued
0.7974	Intermediate Similarity	NPD2796	Approved
0.7964	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD6799	Approved
0.7939	Intermediate Similarity	NPD5494	Approved
0.7908	Intermediate Similarity	NPD3748	Approved
0.7892	Intermediate Similarity	NPD1247	Approved
0.7867	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1465	Phase 2
0.7844	Intermediate Similarity	NPD7229	Phase 3
0.7829	Intermediate Similarity	NPD230	Phase 1
0.7821	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2799	Discontinued
0.7771	Intermediate Similarity	NPD4628	Phase 3
0.7748	Intermediate Similarity	NPD2313	Discontinued
0.7748	Intermediate Similarity	NPD411	Approved
0.7742	Intermediate Similarity	NPD6100	Approved
0.7742	Intermediate Similarity	NPD6099	Approved
0.774	Intermediate Similarity	NPD422	Phase 1
0.7733	Intermediate Similarity	NPD5953	Discontinued
0.7719	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7286	Phase 2
0.7712	Intermediate Similarity	NPD447	Suspended
0.7697	Intermediate Similarity	NPD5402	Approved
0.7697	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2344	Approved
0.7687	Intermediate Similarity	NPD9717	Approved
0.7651	Intermediate Similarity	NPD1203	Approved
0.7647	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6166	Phase 2
0.7644	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3764	Approved
0.7625	Intermediate Similarity	NPD7390	Discontinued
0.7616	Intermediate Similarity	NPD7054	Approved
0.7607	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1283	Approved
0.7578	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD37	Approved
0.7572	Intermediate Similarity	NPD7074	Phase 3
0.7572	Intermediate Similarity	NPD7472	Approved
0.7568	Intermediate Similarity	NPD1608	Approved
0.7566	Intermediate Similarity	NPD4625	Phase 3
0.7564	Intermediate Similarity	NPD7033	Discontinued
0.7564	Intermediate Similarity	NPD4308	Phase 3
0.756	Intermediate Similarity	NPD6234	Discontinued
0.7548	Intermediate Similarity	NPD6651	Approved
0.7545	Intermediate Similarity	NPD4966	Approved
0.7545	Intermediate Similarity	NPD4967	Phase 2
0.7545	Intermediate Similarity	NPD4965	Approved
0.7529	Intermediate Similarity	NPD6797	Phase 2
0.7516	Intermediate Similarity	NPD5406	Approved
0.7516	Intermediate Similarity	NPD5408	Approved
0.7516	Intermediate Similarity	NPD5404	Approved
0.7516	Intermediate Similarity	NPD5405	Approved
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.7486	Intermediate Similarity	NPD7251	Discontinued
0.7485	Intermediate Similarity	NPD5403	Approved
0.7484	Intermediate Similarity	NPD5124	Phase 1
0.7484	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4626	Approved
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7469	Intermediate Similarity	NPD5401	Approved
0.7468	Intermediate Similarity	NPD1471	Phase 3
0.7468	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD9545	Approved
0.7452	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7808	Phase 3
0.7419	Intermediate Similarity	NPD943	Approved
0.7415	Intermediate Similarity	NPD5691	Approved
0.7403	Intermediate Similarity	NPD1296	Phase 2
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4287	Approved
0.7386	Intermediate Similarity	NPD6832	Phase 2
0.7384	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3926	Phase 2
0.7383	Intermediate Similarity	NPD1281	Approved
0.7381	Intermediate Similarity	NPD4288	Approved
0.7374	Intermediate Similarity	NPD8434	Phase 2
0.7368	Intermediate Similarity	NPD1019	Discontinued
0.7365	Intermediate Similarity	NPD17	Approved
0.7365	Intermediate Similarity	NPD1778	Approved
0.7358	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6004	Phase 3
0.7358	Intermediate Similarity	NPD6002	Phase 3
0.7358	Intermediate Similarity	NPD6005	Phase 3
0.7358	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7177	Discontinued
0.733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD9493	Approved
0.7329	Intermediate Similarity	NPD7003	Approved
0.7321	Intermediate Similarity	NPD5761	Phase 2
0.7321	Intermediate Similarity	NPD5760	Phase 2
0.7317	Intermediate Similarity	NPD6273	Approved
0.7308	Intermediate Similarity	NPD2979	Phase 3
0.7308	Intermediate Similarity	NPD4060	Phase 1
0.7308	Intermediate Similarity	NPD4307	Phase 2
0.7305	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1470	Approved
0.7303	Intermediate Similarity	NPD2797	Approved
0.7292	Intermediate Similarity	NPD7783	Phase 2
0.7292	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3268	Approved
0.729	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7435	Discontinued
0.7285	Intermediate Similarity	NPD4749	Approved
0.7278	Intermediate Similarity	NPD8150	Discontinued
0.7273	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD1201	Approved
0.7257	Intermediate Similarity	NPD3751	Discontinued
0.7257	Intermediate Similarity	NPD7228	Approved
0.7237	Intermediate Similarity	NPD6696	Suspended
0.723	Intermediate Similarity	NPD1548	Phase 1
0.7222	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6780	Approved
0.7219	Intermediate Similarity	NPD6777	Approved
0.7219	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD6776	Approved
0.7219	Intermediate Similarity	NPD6778	Approved
0.7219	Intermediate Similarity	NPD6779	Approved
0.7219	Intermediate Similarity	NPD6782	Approved
0.7195	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1164	Approved
0.7189	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4361	Phase 2
0.7188	Intermediate Similarity	NPD4477	Approved
0.7188	Intermediate Similarity	NPD8151	Discontinued
0.7188	Intermediate Similarity	NPD4476	Approved
0.7186	Intermediate Similarity	NPD7458	Discontinued
0.7175	Intermediate Similarity	NPD1729	Discontinued
0.7161	Intermediate Similarity	NPD4908	Phase 1
0.716	Intermediate Similarity	NPD2654	Approved
0.7152	Intermediate Similarity	NPD1611	Approved
0.7143	Intermediate Similarity	NPD2403	Approved
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7128	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3787	Discontinued
0.7124	Intermediate Similarity	NPD3225	Approved
0.7105	Intermediate Similarity	NPD7696	Phase 3

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