NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	186.03
Volume:	183.695
LogP:	2.079
LogD:	2.44
LogS:	-3.314
# Rotatable Bonds:	0
TPSA:	43.35
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	2.37
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.729
MDCK Permeability:	2.228853918495588e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.678
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.968
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	91.2712173461914%
Volume Distribution (VD):	1.423
Pgp-substrate:	10.868365287780762%

ADMET: Metabolism

CYP1A2-inhibitor:	0.992
CYP1A2-substrate:	0.775
CYP2C19-inhibitor:	0.443
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.123
CYP2C9-substrate:	0.813
CYP2D6-inhibitor:	0.81
CYP2D6-substrate:	0.842
CYP3A4-inhibitor:	0.698
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	12.228
Half-life (T1/2):	0.637

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.273
Rat Oral Acute Toxicity:	0.7
Maximum Recommended Daily Dose:	0.124
Skin Sensitization:	0.113
Carcinogencity:	0.899
Eye Corrosion:	0.053
Eye Irritation:	0.926
Respiratory Toxicity:	0.723

Download Data

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

Natural Product: NPC166858

Natural Product ID:	NPC166858
*Common Name:**	Bakuchicin
IUPAC Name:	furo[2,3-f]chromen-7-one
Synonyms:	Bakuchicin
Standard InCHIKey:	HMUJHZNYHJMOHR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H6O3/c12-10-4-2-8-9(14-10)3-1-7-5-6-13-11(7)8/h1-6H
SMILES:	O=c1ccc2c(o1)ccc1c2occ1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499847
PubChem CID:	3083848
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002568] Angular furanocoumarins

*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
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20663508]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24507928]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544566]
NPO1470	Fructus psoraleae corylifoliae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28809	Cullen corylifolium	Species	Fabaceae	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
Others	3

Activity Type	# Activity
Individual Protein	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	404000.0	nM	PMID[476267]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	35700.0	nM	PMID[476268]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	5440.0	nM	PMID[476268]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	=	1780.0	nM	PMID[476268]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Activity	=	37.8	%	PMID[476268]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	Activity	=	18.6	%	PMID[476268]
NPT2	Others	Unspecified		Ratio IC50	=	3.1	n.a.	PMID[476268]

☑ 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 NPC166858 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	597
0.1-0.2	2310
0.2-0.3	5820
0.3-0.4	11969
0.4-0.5	5510
0.5-0.6	5498
0.6-0.7	5408
0.7-0.8	4501
0.8-0.85	755
0.85-0.9	275
0.9-0.95	46
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC51146
0.9855	High Similarity	NPC246903
0.9645	High Similarity	NPC266743
0.9577	High Similarity	NPC88445
0.9574	High Similarity	NPC304443
0.9574	High Similarity	NPC74539
0.951	High Similarity	NPC191104
0.9496	High Similarity	NPC254010
0.9493	High Similarity	NPC262635
0.9429	High Similarity	NPC313036
0.9375	High Similarity	NPC155882
0.9315	High Similarity	NPC131725
0.9296	High Similarity	NPC208584
0.9231	High Similarity	NPC190572
0.9128	High Similarity	NPC269495
0.9122	High Similarity	NPC295608
0.9122	High Similarity	NPC250769
0.9122	High Similarity	NPC278010
0.9103	High Similarity	NPC306788
0.9067	High Similarity	NPC33320
0.9048	High Similarity	NPC98028
0.9034	High Similarity	NPC198427
0.9014	High Similarity	NPC470856
0.9007	High Similarity	NPC243509
0.9007	High Similarity	NPC49009
0.9007	High Similarity	NPC169
0.9007	High Similarity	NPC36414
0.9	High Similarity	NPC29638
0.9	High Similarity	NPC270044
0.898	High Similarity	NPC135303
0.898	High Similarity	NPC148423
0.8958	High Similarity	NPC17262
0.8947	High Similarity	NPC216092
0.8947	High Similarity	NPC14822
0.8944	High Similarity	NPC136095
0.8936	High Similarity	NPC253616
0.8919	High Similarity	NPC472407
0.8882	High Similarity	NPC303210
0.8882	High Similarity	NPC95472
0.8882	High Similarity	NPC239270
0.8865	High Similarity	NPC268081
0.8865	High Similarity	NPC472516
0.8859	High Similarity	NPC130015
0.8859	High Similarity	NPC38361
0.8851	High Similarity	NPC472406
0.8831	High Similarity	NPC179464
0.8831	High Similarity	NPC15819
0.8811	High Similarity	NPC472515
0.8803	High Similarity	NPC103001
0.88	High Similarity	NPC41719
0.8792	High Similarity	NPC116604
0.8786	High Similarity	NPC247743
0.8774	High Similarity	NPC179015
0.8774	High Similarity	NPC173149
0.8766	High Similarity	NPC234536
0.8766	High Similarity	NPC78612
0.8742	High Similarity	NPC233776
0.8733	High Similarity	NPC263676
0.8718	High Similarity	NPC210460
0.8718	High Similarity	NPC155264
0.8718	High Similarity	NPC193881
0.8718	High Similarity	NPC67450
0.8714	High Similarity	NPC229646
0.8707	High Similarity	NPC300267
0.8707	High Similarity	NPC51641
0.8699	High Similarity	NPC225884
0.8681	High Similarity	NPC473209
0.8675	High Similarity	NPC122365
0.8658	High Similarity	NPC296030
0.8658	High Similarity	NPC39929
0.8652	High Similarity	NPC292998
0.8649	High Similarity	NPC130581
0.8649	High Similarity	NPC12148
0.8643	High Similarity	NPC175159
0.863	High Similarity	NPC53192
0.8623	High Similarity	NPC50583
0.8621	High Similarity	NPC28337
0.8609	High Similarity	NPC253872
0.8601	High Similarity	NPC254741
0.8591	High Similarity	NPC272194
0.8591	High Similarity	NPC135325
0.8581	High Similarity	NPC210826
0.8571	High Similarity	NPC472517
0.8571	High Similarity	NPC302181
0.8562	High Similarity	NPC19860
0.8562	High Similarity	NPC160015
0.8562	High Similarity	NPC247677
0.8553	High Similarity	NPC473194
0.8553	High Similarity	NPC51404
0.8552	High Similarity	NPC137009
0.8543	High Similarity	NPC290671
0.8543	High Similarity	NPC156244
0.8542	High Similarity	NPC38153
0.8542	High Similarity	NPC332594
0.8533	High Similarity	NPC37226
0.8533	High Similarity	NPC226644
0.8533	High Similarity	NPC221868
0.8533	High Similarity	NPC37208
0.8516	High Similarity	NPC115432
0.8516	High Similarity	NPC260296
0.8514	High Similarity	NPC230943
0.8514	High Similarity	NPC171656
0.8511	High Similarity	NPC284424
0.8506	High Similarity	NPC296957
0.8506	High Similarity	NPC260902
0.8497	Intermediate Similarity	NPC474542
0.8493	Intermediate Similarity	NPC472409
0.8487	Intermediate Similarity	NPC67654
0.8487	Intermediate Similarity	NPC41326
0.8472	Intermediate Similarity	NPC161196
0.8467	Intermediate Similarity	NPC168085
0.8462	Intermediate Similarity	NPC264293
0.8462	Intermediate Similarity	NPC229128
0.8462	Intermediate Similarity	NPC66705
0.8456	Intermediate Similarity	NPC470322
0.8456	Intermediate Similarity	NPC154217
0.8456	Intermediate Similarity	NPC473927
0.8452	Intermediate Similarity	NPC244750
0.8452	Intermediate Similarity	NPC476350
0.8452	Intermediate Similarity	NPC476349
0.8451	Intermediate Similarity	NPC55147
0.8451	Intermediate Similarity	NPC182428
0.8447	Intermediate Similarity	NPC72455
0.8447	Intermediate Similarity	NPC233956
0.8442	Intermediate Similarity	NPC470625
0.8438	Intermediate Similarity	NPC281835
0.8438	Intermediate Similarity	NPC144288
0.8435	Intermediate Similarity	NPC22467
0.8431	Intermediate Similarity	NPC213608
0.8431	Intermediate Similarity	NPC1477
0.8425	Intermediate Similarity	NPC37206
0.8425	Intermediate Similarity	NPC11566
0.8421	Intermediate Similarity	NPC170169
0.8417	Intermediate Similarity	NPC475496
0.8417	Intermediate Similarity	NPC49852
0.8414	Intermediate Similarity	NPC157855
0.8414	Intermediate Similarity	NPC259685
0.8411	Intermediate Similarity	NPC317492
0.8411	Intermediate Similarity	NPC164299
0.8408	Intermediate Similarity	NPC193998
0.8403	Intermediate Similarity	NPC60667
0.8403	Intermediate Similarity	NPC151113
0.8403	Intermediate Similarity	NPC46869
0.84	Intermediate Similarity	NPC282335
0.84	Intermediate Similarity	NPC218300
0.8392	Intermediate Similarity	NPC223354
0.8389	Intermediate Similarity	NPC196137
0.8389	Intermediate Similarity	NPC155144
0.8389	Intermediate Similarity	NPC469953
0.8389	Intermediate Similarity	NPC179970
0.8389	Intermediate Similarity	NPC1886
0.8389	Intermediate Similarity	NPC294365
0.8387	Intermediate Similarity	NPC65504
0.838	Intermediate Similarity	NPC278556
0.8378	Intermediate Similarity	NPC36181
0.8377	Intermediate Similarity	NPC198490
0.8377	Intermediate Similarity	NPC473193
0.8377	Intermediate Similarity	NPC108937
0.8377	Intermediate Similarity	NPC279218
0.8366	Intermediate Similarity	NPC5871
0.8365	Intermediate Similarity	NPC323137
0.8357	Intermediate Similarity	NPC473907
0.8356	Intermediate Similarity	NPC17848
0.8355	Intermediate Similarity	NPC474735
0.8355	Intermediate Similarity	NPC230713
0.8355	Intermediate Similarity	NPC78335
0.8354	Intermediate Similarity	NPC155640
0.8354	Intermediate Similarity	NPC65846
0.8345	Intermediate Similarity	NPC234109
0.8345	Intermediate Similarity	NPC188327
0.8344	Intermediate Similarity	NPC304387
0.8344	Intermediate Similarity	NPC107244
0.8344	Intermediate Similarity	NPC325176
0.8333	Intermediate Similarity	NPC255073
0.8333	Intermediate Similarity	NPC125920
0.8333	Intermediate Similarity	NPC181388
0.8333	Intermediate Similarity	NPC125269
0.8323	Intermediate Similarity	NPC475797
0.8323	Intermediate Similarity	NPC474738
0.8323	Intermediate Similarity	NPC78554
0.8323	Intermediate Similarity	NPC321372
0.8323	Intermediate Similarity	NPC474609
0.8323	Intermediate Similarity	NPC469936
0.8323	Intermediate Similarity	NPC13879
0.8323	Intermediate Similarity	NPC109967
0.8323	Intermediate Similarity	NPC129053
0.8322	Intermediate Similarity	NPC87609
0.8322	Intermediate Similarity	NPC112791
0.8322	Intermediate Similarity	NPC59522
0.8322	Intermediate Similarity	NPC196459
0.8322	Intermediate Similarity	NPC184702
0.8322	Intermediate Similarity	NPC188632
0.8322	Intermediate Similarity	NPC94794
0.8322	Intermediate Similarity	NPC473655
0.8322	Intermediate Similarity	NPC54503
0.8322	Intermediate Similarity	NPC101294
0.8322	Intermediate Similarity	NPC470296
0.8313	Intermediate Similarity	NPC167479
0.8313	Intermediate Similarity	NPC320789
0.8312	Intermediate Similarity	NPC183874

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 NPC166858 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	506
0.1-0.2	1024
0.2-0.3	1866
0.3-0.4	2797
0.4-0.5	1811
0.5-0.6	800
0.6-0.7	231
0.7-0.8	88
0.8-0.85	16
0.85-0.9	6
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD643	Clinical (unspecified phase)
0.9855	High Similarity	NPD642	Clinical (unspecified phase)
0.9574	High Similarity	NPD920	Approved
0.9493	High Similarity	NPD1243	Approved
0.9067	High Similarity	NPD919	Approved
0.8601	High Similarity	NPD2796	Approved
0.8462	Intermediate Similarity	NPD1247	Approved
0.8276	Intermediate Similarity	NPD1510	Phase 2
0.8269	Intermediate Similarity	NPD3749	Approved
0.8231	Intermediate Similarity	NPD1549	Phase 2
0.8219	Intermediate Similarity	NPD1551	Phase 2
0.82	Intermediate Similarity	NPD6799	Approved
0.8194	Intermediate Similarity	NPD7819	Suspended
0.8194	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7411	Suspended
0.8163	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD3748	Approved
0.8146	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6801	Discontinued
0.8125	Intermediate Similarity	NPD1240	Approved
0.8038	Intermediate Similarity	NPD7075	Discontinued
0.8014	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD6599	Discontinued
0.7919	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6559	Discontinued
0.7885	Intermediate Similarity	NPD4380	Phase 2
0.7881	Intermediate Similarity	NPD3750	Approved
0.7867	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7768	Phase 2
0.7853	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD6832	Phase 2
0.7826	Intermediate Similarity	NPD5494	Approved
0.7815	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2344	Approved
0.7799	Intermediate Similarity	NPD3817	Phase 2
0.7792	Intermediate Similarity	NPD5401	Approved
0.774	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1296	Phase 2
0.774	Intermediate Similarity	NPD2313	Discontinued
0.7736	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1511	Approved
0.7702	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2800	Approved
0.7692	Intermediate Similarity	NPD5403	Approved
0.7688	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3926	Phase 2
0.7677	Intermediate Similarity	NPD2533	Approved
0.7677	Intermediate Similarity	NPD2534	Approved
0.7677	Intermediate Similarity	NPD2532	Approved
0.7667	Intermediate Similarity	NPD2799	Discontinued
0.7651	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3882	Suspended
0.7639	Intermediate Similarity	NPD1203	Approved
0.7628	Intermediate Similarity	NPD1512	Approved
0.7597	Intermediate Similarity	NPD2309	Approved
0.7586	Intermediate Similarity	NPD1019	Discontinued
0.7584	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1934	Approved
0.7552	Intermediate Similarity	NPD9717	Approved
0.7545	Intermediate Similarity	NPD3818	Discontinued
0.7515	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7483	Intermediate Similarity	NPD422	Phase 1
0.7469	Intermediate Similarity	NPD5402	Approved
0.7468	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1471	Phase 3
0.741	Intermediate Similarity	NPD6808	Phase 2
0.7407	Intermediate Similarity	NPD2801	Approved
0.74	Intermediate Similarity	NPD4307	Phase 2
0.7397	Intermediate Similarity	NPD3266	Approved
0.7397	Intermediate Similarity	NPD3267	Approved
0.7396	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7286	Phase 2
0.7396	Intermediate Similarity	NPD5844	Phase 1
0.7375	Intermediate Similarity	NPD3226	Approved
0.7355	Intermediate Similarity	NPD2654	Approved
0.7349	Intermediate Similarity	NPD6959	Discontinued
0.7346	Intermediate Similarity	NPD6280	Approved
0.7346	Intermediate Similarity	NPD6279	Approved
0.7343	Intermediate Similarity	NPD17	Approved
0.7338	Intermediate Similarity	NPD1241	Discontinued
0.7326	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4628	Phase 3
0.7305	Intermediate Similarity	NPD6232	Discontinued
0.7301	Intermediate Similarity	NPD1465	Phase 2
0.7278	Intermediate Similarity	NPD7473	Discontinued
0.7273	Intermediate Similarity	NPD4287	Approved
0.7267	Intermediate Similarity	NPD411	Approved
0.7251	Intermediate Similarity	NPD1729	Discontinued
0.7248	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1933	Approved
0.723	Intermediate Similarity	NPD2798	Approved
0.7226	Intermediate Similarity	NPD2346	Discontinued
0.7208	Intermediate Similarity	NPD7033	Discontinued
0.7208	Intermediate Similarity	NPD4308	Phase 3
0.7203	Intermediate Similarity	NPD9545	Approved
0.7192	Intermediate Similarity	NPD1608	Approved
0.719	Intermediate Similarity	NPD6651	Approved
0.7178	Intermediate Similarity	NPD5890	Approved
0.7178	Intermediate Similarity	NPD5889	Approved
0.7162	Intermediate Similarity	NPD1164	Approved
0.7162	Intermediate Similarity	NPD2797	Approved
0.7152	Intermediate Similarity	NPD4288	Approved
0.7152	Intermediate Similarity	NPD3268	Approved
0.7132	Intermediate Similarity	NPD9697	Approved
0.7126	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5124	Phase 1
0.7124	Intermediate Similarity	NPD447	Suspended
0.7118	Intermediate Similarity	NPD6166	Phase 2
0.7118	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5710	Approved
0.7101	Intermediate Similarity	NPD5711	Approved
0.7101	Intermediate Similarity	NPD7229	Phase 3
0.7095	Intermediate Similarity	NPD3225	Approved
0.7093	Intermediate Similarity	NPD7054	Approved
0.7083	Intermediate Similarity	NPD1548	Phase 1
0.7075	Intermediate Similarity	NPD3972	Approved
0.7063	Intermediate Similarity	NPD9493	Approved
0.7062	Intermediate Similarity	NPD8434	Phase 2
0.7059	Intermediate Similarity	NPD943	Approved
0.7052	Intermediate Similarity	NPD7074	Phase 3
0.7052	Intermediate Similarity	NPD7472	Approved
0.7048	Intermediate Similarity	NPD2296	Approved
0.7024	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD230	Phase 1
0.7012	Intermediate Similarity	NPD6585	Discontinued
0.7011	Intermediate Similarity	NPD6797	Phase 2
0.7007	Intermediate Similarity	NPD1610	Phase 2
0.7007	Intermediate Similarity	NPD1281	Approved
0.6987	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9261	Approved
0.6981	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1876	Approved
0.6971	Remote Similarity	NPD7251	Discontinued
0.6951	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.694	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3887	Approved
0.6932	Remote Similarity	NPD7808	Phase 3
0.6928	Remote Similarity	NPD3764	Approved
0.6919	Remote Similarity	NPD2403	Approved
0.6914	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2353	Approved
0.6885	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4361	Phase 2
0.6875	Remote Similarity	NPD7003	Approved
0.6871	Remote Similarity	NPD6273	Approved
0.6867	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1283	Approved
0.6849	Remote Similarity	NPD1894	Discontinued
0.6848	Remote Similarity	NPD7458	Discontinued
0.6845	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7199	Phase 2
0.6839	Remote Similarity	NPD3140	Approved
0.6839	Remote Similarity	NPD3142	Approved
0.6835	Remote Similarity	NPD4477	Approved
0.6835	Remote Similarity	NPD4476	Approved
0.6832	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1652	Phase 2
0.6803	Remote Similarity	NPD5691	Approved
0.6803	Remote Similarity	NPD1651	Approved
0.6795	Remote Similarity	NPD6355	Discontinued
0.6792	Remote Similarity	NPD6004	Phase 3
0.6792	Remote Similarity	NPD6005	Phase 3
0.6792	Remote Similarity	NPD6002	Phase 3
0.6792	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD9267	Approved
0.6786	Remote Similarity	NPD9263	Approved
0.6786	Remote Similarity	NPD5760	Phase 2
0.6786	Remote Similarity	NPD5761	Phase 2
0.6786	Remote Similarity	NPD9264	Approved
0.6763	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5242	Approved
0.6757	Remote Similarity	NPD1778	Approved
0.6748	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4360	Phase 2
0.6739	Remote Similarity	NPD4363	Phase 3
0.6738	Remote Similarity	NPD9266	Approved
0.6738	Remote Similarity	NPD74	Approved
0.6731	Remote Similarity	NPD2979	Phase 3
0.673	Remote Similarity	NPD6099	Approved
0.673	Remote Similarity	NPD5406	Approved
0.673	Remote Similarity	NPD6100	Approved
0.673	Remote Similarity	NPD5405	Approved
0.673	Remote Similarity	NPD5408	Approved
0.673	Remote Similarity	NPD5404	Approved
0.6728	Remote Similarity	NPD2354	Approved
0.6711	Remote Similarity	NPD1049	Clinical (unspecified phase)

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