NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.1
Volume:	264.305
LogP:	2.952
LogD:	2.851
LogS:	-4.16
# Rotatable Bonds:	1
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	2.654
Fsp3:	0.4
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:	-4.631
MDCK Permeability:	2.0882191165583208e-05
Pgp-inhibitor:	0.416
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	91.95093536376953%
Volume Distribution (VD):	0.781
Pgp-substrate:	8.906599044799805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.572
CYP2C19-substrate:	0.561
CYP2C9-inhibitor:	0.353
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.591
CYP2D6-substrate:	0.849
CYP3A4-inhibitor:	0.246
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	10.408
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.915
Drug-inuced Liver Injury (DILI):	0.683
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.267
Maximum Recommended Daily Dose:	0.233
Skin Sensitization:	0.191
Carcinogencity:	0.801
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.139

Download Data

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

Natural Product: NPC270256

Natural Product ID:	NPC270256
*Common Name:**	3',4'-Dihydrobraylin
IUPAC Name:	6-methoxy-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-2-one
Synonyms:
Standard InCHIKey:	BZMZEWWDSNLUOM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O4/c1-15(2)7-6-10-13-9(4-5-12(16)18-13)8-11(17-3)14(10)19-15/h4-5,8H,6-7H2,1-3H3
SMILES:	COc1cc2ccc(=O)oc2c2c1OC(C)(C)CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3235994
PubChem CID:	90655369
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

*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
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597921]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7213	Toddalia asiatica	Species	Rutaceae	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
NPT1464	Individual Protein	Phosphodiesterase 4D	Homo sapiens	IC50	=	1530.0	nM	PMID[549927]

☑ 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 NPC270256 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	489
0.1-0.2	2117
0.2-0.3	5511
0.3-0.4	11498
0.4-0.5	5733
0.5-0.6	4219
0.6-0.7	5760
0.7-0.8	5143
0.8-0.85	1711
0.85-0.9	426
0.9-0.95	84
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC167517
0.947	High Similarity	NPC472522
0.9403	High Similarity	NPC286843
0.9398	High Similarity	NPC147030
0.9398	High Similarity	NPC309953
0.9394	High Similarity	NPC123954
0.9394	High Similarity	NPC137669
0.9389	High Similarity	NPC240722
0.9389	High Similarity	NPC244799
0.9328	High Similarity	NPC234865
0.9323	High Similarity	NPC233018
0.9323	High Similarity	NPC36437
0.9323	High Similarity	NPC241341
0.9313	High Similarity	NPC123127
0.9313	High Similarity	NPC27239
0.9248	High Similarity	NPC319969
0.9185	High Similarity	NPC472521
0.9179	High Similarity	NPC318400
0.9179	High Similarity	NPC471910
0.9179	High Similarity	NPC167111
0.9179	High Similarity	NPC207002
0.9179	High Similarity	NPC133956
0.9179	High Similarity	NPC296624
0.9137	High Similarity	NPC236419
0.9111	High Similarity	NPC18804
0.9111	High Similarity	NPC74655
0.9111	High Similarity	NPC195343
0.9111	High Similarity	NPC319859
0.9111	High Similarity	NPC267412
0.9111	High Similarity	NPC166672
0.9111	High Similarity	NPC100986
0.9111	High Similarity	NPC474600
0.9111	High Similarity	NPC198381
0.9111	High Similarity	NPC260265
0.9111	High Similarity	NPC47163
0.9111	High Similarity	NPC287182
0.9111	High Similarity	NPC164269
0.9111	High Similarity	NPC84894
0.9111	High Similarity	NPC127888
0.9098	High Similarity	NPC19242
0.9084	High Similarity	NPC471826
0.9051	High Similarity	NPC474521
0.9051	High Similarity	NPC474530
0.9051	High Similarity	NPC474540
0.9044	High Similarity	NPC472424
0.9044	High Similarity	NPC471625
0.9044	High Similarity	NPC471909
0.9044	High Similarity	NPC281241
0.9044	High Similarity	NPC86892
0.8993	High Similarity	NPC472520
0.8993	High Similarity	NPC300611
0.8993	High Similarity	NPC279851
0.8986	High Similarity	NPC164148
0.8986	High Similarity	NPC43500
0.8978	High Similarity	NPC471630
0.8978	High Similarity	NPC55615
0.8978	High Similarity	NPC160727
0.8978	High Similarity	NPC177281
0.8978	High Similarity	NPC149320
0.8978	High Similarity	NPC476455
0.8978	High Similarity	NPC128529
0.8978	High Similarity	NPC283019
0.8955	High Similarity	NPC474617
0.8947	High Similarity	NPC474616
0.8944	High Similarity	NPC205361
0.8936	High Similarity	NPC471763
0.8931	High Similarity	NPC111347
0.8913	High Similarity	NPC95162
0.8913	High Similarity	NPC20796
0.8913	High Similarity	NPC76336
0.8913	High Similarity	NPC232246
0.8913	High Similarity	NPC148835
0.8913	High Similarity	NPC153818
0.8913	High Similarity	NPC139548
0.8913	High Similarity	NPC52086
0.8913	High Similarity	NPC20511
0.8905	High Similarity	NPC224941
0.8905	High Similarity	NPC73071
0.8905	High Similarity	NPC240915
0.8905	High Similarity	NPC311430
0.8881	High Similarity	NPC15577
0.8872	High Similarity	NPC474670
0.8865	High Similarity	NPC7439
0.8865	High Similarity	NPC91492
0.8865	High Similarity	NPC256555
0.8865	High Similarity	NPC110067
0.8865	High Similarity	NPC34245
0.8855	High Similarity	NPC472518
0.8849	High Similarity	NPC13067
0.8849	High Similarity	NPC279573
0.8849	High Similarity	NPC211110
0.8841	High Similarity	NPC78746
0.8841	High Similarity	NPC188380
0.8841	High Similarity	NPC82271
0.8841	High Similarity	NPC126682
0.8841	High Similarity	NPC224543
0.8832	High Similarity	NPC55149
0.8832	High Similarity	NPC7163
0.8832	High Similarity	NPC307412
0.8824	High Similarity	NPC14248
0.8815	High Similarity	NPC80170
0.8806	High Similarity	NPC185066
0.8788	High Similarity	NPC201667
0.8788	High Similarity	NPC73413
0.8786	High Similarity	NPC312881
0.8779	High Similarity	NPC194626
0.8779	High Similarity	NPC248429
0.8779	High Similarity	NPC96286
0.8777	High Similarity	NPC184861
0.8777	High Similarity	NPC294456
0.8777	High Similarity	NPC212124
0.8777	High Similarity	NPC225106
0.8777	High Similarity	NPC281014
0.8768	High Similarity	NPC469675
0.8759	High Similarity	NPC30688
0.8759	High Similarity	NPC222036
0.8759	High Similarity	NPC7526
0.8759	High Similarity	NPC176903
0.8741	High Similarity	NPC168710
0.8732	High Similarity	NPC230157
0.8732	High Similarity	NPC138212
0.8731	High Similarity	NPC194841
0.8731	High Similarity	NPC474821
0.8723	High Similarity	NPC152771
0.8723	High Similarity	NPC287286
0.8723	High Similarity	NPC195357
0.8722	High Similarity	NPC471828
0.8722	High Similarity	NPC471827
0.8712	High Similarity	NPC173350
0.8712	High Similarity	NPC290605
0.8712	High Similarity	NPC109675
0.8712	High Similarity	NPC273772
0.8712	High Similarity	NPC154176
0.8707	High Similarity	NPC470264
0.8699	High Similarity	NPC120426
0.8699	High Similarity	NPC294522
0.8699	High Similarity	NPC21184
0.8699	High Similarity	NPC205727
0.8696	High Similarity	NPC62366
0.8696	High Similarity	NPC92830
0.869	High Similarity	NPC96294
0.8681	High Similarity	NPC475872
0.8676	High Similarity	NPC476399
0.8667	High Similarity	NPC474623
0.8667	High Similarity	NPC474651
0.8667	High Similarity	NPC474636
0.8667	High Similarity	NPC199204
0.8657	High Similarity	NPC127604
0.8657	High Similarity	NPC474632
0.8647	High Similarity	NPC291899
0.8647	High Similarity	NPC27671
0.8643	High Similarity	NPC476171
0.8643	High Similarity	NPC155963
0.8643	High Similarity	NPC38874
0.8636	High Similarity	NPC257188
0.8636	High Similarity	NPC13007
0.8633	High Similarity	NPC33986
0.8633	High Similarity	NPC472525
0.8623	High Similarity	NPC277021
0.8623	High Similarity	NPC26673
0.8621	High Similarity	NPC476347
0.8611	High Similarity	NPC476450
0.8601	High Similarity	NPC119640
0.8601	High Similarity	NPC183646
0.8582	High Similarity	NPC151946
0.8581	High Similarity	NPC264875
0.8581	High Similarity	NPC163598
0.8581	High Similarity	NPC120774
0.8571	High Similarity	NPC38099
0.8571	High Similarity	NPC283331
0.8571	High Similarity	NPC114740
0.8571	High Similarity	NPC26954
0.8571	High Similarity	NPC50720
0.8562	High Similarity	NPC187398
0.8562	High Similarity	NPC139839
0.8562	High Similarity	NPC476348
0.8561	High Similarity	NPC213173
0.8561	High Similarity	NPC144418
0.8561	High Similarity	NPC180716
0.8561	High Similarity	NPC253574
0.8561	High Similarity	NPC326600
0.8561	High Similarity	NPC224475
0.8561	High Similarity	NPC204353
0.8561	High Similarity	NPC98179
0.8561	High Similarity	NPC50896
0.8551	High Similarity	NPC19157
0.8551	High Similarity	NPC137949
0.855	High Similarity	NPC222175
0.8542	High Similarity	NPC476457
0.8529	High Similarity	NPC31707
0.8529	High Similarity	NPC472519
0.8529	High Similarity	NPC210674
0.8519	High Similarity	NPC234109
0.8519	High Similarity	NPC188327
0.8514	High Similarity	NPC213197
0.8511	High Similarity	NPC474886
0.8503	High Similarity	NPC313334
0.8503	High Similarity	NPC212670
0.8503	High Similarity	NPC206264
0.8496	Intermediate Similarity	NPC150214

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 NPC270256 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	434
0.1-0.2	1044
0.2-0.3	1948
0.3-0.4	2717
0.4-0.5	1695
0.5-0.6	875
0.6-0.7	303
0.7-0.8	101
0.8-0.85	26
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8503	High Similarity	NPD1653	Approved
0.8099	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD5124	Phase 1
0.8063	Intermediate Similarity	NPD5844	Phase 1
0.8015	Intermediate Similarity	NPD422	Phase 1
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD5494	Approved
0.7959	Intermediate Similarity	NPD1652	Phase 2
0.7929	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1613	Approved
0.7898	Intermediate Similarity	NPD919	Approved
0.7881	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7549	Discontinued
0.7821	Intermediate Similarity	NPD3817	Phase 2
0.7756	Intermediate Similarity	NPD2801	Approved
0.7746	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1247	Approved
0.7667	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1296	Phase 2
0.7626	Intermediate Similarity	NPD1611	Approved
0.7597	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1934	Approved
0.7569	Intermediate Similarity	NPD3027	Phase 3
0.7568	Intermediate Similarity	NPD3748	Approved
0.7554	Intermediate Similarity	NPD3496	Discontinued
0.7552	Intermediate Similarity	NPD3018	Phase 2
0.7536	Intermediate Similarity	NPD5691	Approved
0.7532	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1465	Phase 2
0.7532	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7819	Suspended
0.7517	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD920	Approved
0.7483	Intermediate Similarity	NPD1243	Approved
0.7483	Intermediate Similarity	NPD447	Suspended
0.7448	Intermediate Similarity	NPD4625	Phase 3
0.7447	Intermediate Similarity	NPD2981	Phase 2
0.7424	Intermediate Similarity	NPD1358	Approved
0.7423	Intermediate Similarity	NPD6232	Discontinued
0.7407	Intermediate Similarity	NPD5535	Approved
0.7405	Intermediate Similarity	NPD9697	Approved
0.7403	Intermediate Similarity	NPD1511	Approved
0.74	Intermediate Similarity	NPD2796	Approved
0.74	Intermediate Similarity	NPD2935	Discontinued
0.7397	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4749	Approved
0.7394	Intermediate Similarity	NPD2983	Phase 2
0.7394	Intermediate Similarity	NPD2982	Phase 2
0.7391	Intermediate Similarity	NPD5536	Phase 2
0.7391	Intermediate Similarity	NPD7075	Discontinued
0.7379	Intermediate Similarity	NPD4908	Phase 1
0.7376	Intermediate Similarity	NPD1610	Phase 2
0.7375	Intermediate Similarity	NPD5402	Approved
0.7365	Intermediate Similarity	NPD1933	Approved
0.7358	Intermediate Similarity	NPD6801	Discontinued
0.7357	Intermediate Similarity	NPD4626	Approved
0.7355	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5283	Phase 1
0.7338	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1548	Phase 1
0.7337	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3750	Approved
0.7308	Intermediate Similarity	NPD1512	Approved
0.7301	Intermediate Similarity	NPD5677	Discontinued
0.7297	Intermediate Similarity	NPD4060	Phase 1
0.7296	Intermediate Similarity	NPD7411	Suspended
0.729	Intermediate Similarity	NPD6799	Approved
0.7289	Intermediate Similarity	NPD7473	Discontinued
0.7279	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD7644	Approved
0.7256	Intermediate Similarity	NPD7199	Phase 2
0.7254	Intermediate Similarity	NPD3705	Approved
0.725	Intermediate Similarity	NPD37	Approved
0.7246	Intermediate Similarity	NPD6671	Approved
0.7246	Intermediate Similarity	NPD3818	Discontinued
0.7233	Intermediate Similarity	NPD4380	Phase 2
0.7229	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6166	Phase 2
0.7229	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4966	Approved
0.7222	Intermediate Similarity	NPD4967	Phase 2
0.7222	Intermediate Similarity	NPD3882	Suspended
0.7222	Intermediate Similarity	NPD4965	Approved
0.7202	Intermediate Similarity	NPD7054	Approved
0.7192	Intermediate Similarity	NPD2861	Phase 2
0.719	Intermediate Similarity	NPD2424	Discontinued
0.719	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4307	Phase 2
0.7179	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3266	Approved
0.7172	Intermediate Similarity	NPD2797	Approved
0.7172	Intermediate Similarity	NPD3267	Approved
0.7169	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7472	Approved
0.716	Intermediate Similarity	NPD7074	Phase 3
0.716	Intermediate Similarity	NPD5353	Approved
0.7152	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7134	Intermediate Similarity	NPD6234	Discontinued
0.7134	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD230	Phase 1
0.7125	Intermediate Similarity	NPD6599	Discontinued
0.7124	Intermediate Similarity	NPD7266	Discontinued
0.7118	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7768	Phase 2
0.7103	Intermediate Similarity	NPD8651	Approved
0.7103	Intermediate Similarity	NPD3225	Approved
0.7095	Intermediate Similarity	NPD7095	Approved
0.709	Intermediate Similarity	NPD3134	Approved
0.7081	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1549	Phase 2
0.7076	Intermediate Similarity	NPD6559	Discontinued
0.7073	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5297	Approved
0.707	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5242	Approved
0.7066	Intermediate Similarity	NPD3926	Phase 2
0.7063	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3539	Phase 1
0.7051	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3268	Approved
0.7047	Intermediate Similarity	NPD7985	Registered
0.7044	Intermediate Similarity	NPD5403	Approved
0.7039	Intermediate Similarity	NPD7097	Phase 1
0.7039	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7808	Phase 3
0.7034	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6832	Phase 2
0.7025	Intermediate Similarity	NPD5401	Approved
0.702	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4340	Discontinued
0.7018	Intermediate Similarity	NPD6797	Phase 2
0.7014	Intermediate Similarity	NPD1091	Approved
0.7013	Intermediate Similarity	NPD1375	Discontinued
0.7013	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3540	Phase 1
0.7013	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6233	Phase 2
0.6993	Remote Similarity	NPD1778	Approved
0.6993	Remote Similarity	NPD1510	Phase 2
0.6993	Remote Similarity	NPD17	Approved
0.6993	Remote Similarity	NPD4308	Phase 3
0.6977	Remote Similarity	NPD7251	Discontinued
0.6975	Remote Similarity	NPD5089	Approved
0.6975	Remote Similarity	NPD5090	Approved
0.6974	Remote Similarity	NPD2653	Approved
0.6962	Remote Similarity	NPD4357	Discontinued
0.6959	Remote Similarity	NPD2237	Approved
0.6957	Remote Similarity	NPD228	Approved
0.6948	Remote Similarity	NPD6099	Approved
0.6948	Remote Similarity	NPD6100	Approved
0.6948	Remote Similarity	NPD1551	Phase 2
0.6943	Remote Similarity	NPD6190	Approved
0.6941	Remote Similarity	NPD7228	Approved
0.6933	Remote Similarity	NPD6798	Discontinued
0.6933	Remote Similarity	NPD2313	Discontinued
0.6933	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4481	Phase 3
0.6918	Remote Similarity	NPD2533	Approved
0.6918	Remote Similarity	NPD2534	Approved
0.6918	Remote Similarity	NPD2532	Approved
0.6914	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7229	Phase 3
0.6903	Remote Similarity	NPD2346	Discontinued
0.6903	Remote Similarity	NPD5762	Approved
0.6903	Remote Similarity	NPD5763	Approved
0.6901	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3686	Approved
0.6894	Remote Similarity	NPD3687	Approved
0.6892	Remote Similarity	NPD1019	Discontinued
0.689	Remote Similarity	NPD4585	Approved
0.6883	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD2799	Discontinued
0.6883	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7033	Discontinued
0.6879	Remote Similarity	NPD4628	Phase 3
0.6879	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4110	Phase 3
0.6871	Remote Similarity	NPD6696	Suspended
0.6871	Remote Similarity	NPD6385	Approved
0.6871	Remote Similarity	NPD6386	Approved
0.6867	Remote Similarity	NPD3749	Approved
0.6861	Remote Similarity	NPD2684	Approved
0.6857	Remote Similarity	NPD1241	Discontinued
0.6852	Remote Similarity	NPD3226	Approved
0.6852	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1608	Approved
0.6849	Remote Similarity	NPD9717	Approved
0.6848	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2415	Discontinued
0.6842	Remote Similarity	NPD4140	Approved
0.6842	Remote Similarity	NPD1240	Approved
0.6818	Remote Similarity	NPD4537	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