NPASS Compound

Structure

CID139554 OpenBabel06191715492D 21 22 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 20 1 0 0 0 0 5 8 1 0 0 0 0 5 10 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 9 21 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 18 2 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.12
Volume:	296.312
LogP:	2.648
LogD:	2.15
LogS:	-3.132
# Rotatable Bonds:	4
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.846
Synthetic Accessibility Score:	3.448
Fsp3:	0.312
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:	-4.783
MDCK Permeability:	1.3055892850388773e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.525
30% Bioavailability (F30%):	0.274

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	80.6231460571289%
Volume Distribution (VD):	1.339
Pgp-substrate:	20.14339828491211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.666
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.869
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.597
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.463

ADMET: Excretion

Clearance (CL):	8.619
Half-life (T1/2):	0.529

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.746
AMES Toxicity:	0.362
Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.256
Skin Sensitization:	0.219
Carcinogencity:	0.162
Eye Corrosion:	0.003
Eye Irritation:	0.112
Respiratory Toxicity:	0.392

Download Data

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

Natural Product: NPC139554

Natural Product ID:	NPC139554
*Common Name:**	Perforamone B
IUPAC Name:	5-hydroxy-8-(1-hydroxy-3-methylbut-3-enyl)-7-methoxy-2-methylchromen-4-one
Synonyms:	Perforamone B
Standard InCHIKey:	NECCMSLPKRWTRS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H18O5/c1-8(2)5-10(17)15-13(20-4)7-12(19)14-11(18)6-9(3)21-16(14)15/h6-7,10,17,19H,1,5H2,2-4H3
SMILES:	C=C(C)CC(c1c(cc(c2c(=O)cc(C)oc12)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204371
PubChem CID:	11608981
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[16394547]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23688954]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21362	Harrisonia perforata	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	25.0	ug.mL-1	PMID[497257]

☑ 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 NPC139554 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	355
0.1-0.2	1553
0.2-0.3	4152
0.3-0.4	10641
0.4-0.5	7884
0.5-0.6	4038
0.6-0.7	5853
0.7-0.8	4430
0.8-0.85	2080
0.85-0.9	1209
0.9-0.95	487
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9774	High Similarity	NPC174999
0.9704	High Similarity	NPC23257
0.9699	High Similarity	NPC60667
0.9638	High Similarity	NPC224714
0.9632	High Similarity	NPC471587
0.963	High Similarity	NPC131130
0.9627	High Similarity	NPC156910
0.9627	High Similarity	NPC470397
0.9624	High Similarity	NPC125920
0.9562	High Similarity	NPC258630
0.9562	High Similarity	NPC17170
0.9562	High Similarity	NPC96408
0.9562	High Similarity	NPC156190
0.9562	High Similarity	NPC279650
0.9562	High Similarity	NPC166689
0.9559	High Similarity	NPC471697
0.9549	High Similarity	NPC223457
0.9549	High Similarity	NPC108113
0.9549	High Similarity	NPC93756
0.9496	High Similarity	NPC470890
0.9496	High Similarity	NPC319752
0.9493	High Similarity	NPC78
0.9493	High Similarity	NPC194432
0.9493	High Similarity	NPC324436
0.9493	High Similarity	NPC223500
0.9493	High Similarity	NPC227579
0.9493	High Similarity	NPC177354
0.9493	High Similarity	NPC10937
0.9493	High Similarity	NPC228504
0.9493	High Similarity	NPC296917
0.9493	High Similarity	NPC328164
0.9493	High Similarity	NPC182852
0.9493	High Similarity	NPC66515
0.9493	High Similarity	NPC166482
0.9493	High Similarity	NPC148757
0.9493	High Similarity	NPC40833
0.9493	High Similarity	NPC1089
0.9493	High Similarity	NPC125855
0.9493	High Similarity	NPC324134
0.9493	High Similarity	NPC107572
0.9493	High Similarity	NPC306829
0.9493	High Similarity	NPC76372
0.9493	High Similarity	NPC161506
0.9493	High Similarity	NPC32739
0.9493	High Similarity	NPC37496
0.9493	High Similarity	NPC166934
0.9493	High Similarity	NPC167624
0.9493	High Similarity	NPC64915
0.9493	High Similarity	NPC76338
0.9493	High Similarity	NPC220998
0.9493	High Similarity	NPC265040
0.9489	High Similarity	NPC241100
0.9489	High Similarity	NPC159275
0.9485	High Similarity	NPC470669
0.9485	High Similarity	NPC470668
0.9481	High Similarity	NPC470398
0.9478	High Similarity	NPC144027
0.9478	High Similarity	NPC236974
0.9474	High Similarity	NPC203817
0.9474	High Similarity	NPC10971
0.9433	High Similarity	NPC10097
0.9429	High Similarity	NPC470458
0.9429	High Similarity	NPC83357
0.9429	High Similarity	NPC20488
0.9429	High Similarity	NPC474161
0.9429	High Similarity	NPC142405
0.9429	High Similarity	NPC301276
0.9429	High Similarity	NPC267375
0.9429	High Similarity	NPC312973
0.9429	High Similarity	NPC214774
0.9429	High Similarity	NPC111786
0.9429	High Similarity	NPC67805
0.9429	High Similarity	NPC176229
0.9429	High Similarity	NPC195621
0.9429	High Similarity	NPC476088
0.9429	High Similarity	NPC472629
0.9429	High Similarity	NPC470647
0.9429	High Similarity	NPC88964
0.9429	High Similarity	NPC475052
0.9429	High Similarity	NPC54577
0.9429	High Similarity	NPC246948
0.9424	High Similarity	NPC175504
0.9424	High Similarity	NPC149026
0.9424	High Similarity	NPC214166
0.9424	High Similarity	NPC77794
0.9424	High Similarity	NPC91560
0.9424	High Similarity	NPC223812
0.9424	High Similarity	NPC478086
0.9424	High Similarity	NPC185276
0.9424	High Similarity	NPC316816
0.9424	High Similarity	NPC75049
0.9424	High Similarity	NPC143896
0.9424	High Similarity	NPC310130
0.9424	High Similarity	NPC107177
0.9424	High Similarity	NPC169591
0.9424	High Similarity	NPC125894
0.9424	High Similarity	NPC68104
0.9424	High Similarity	NPC150408
0.9424	High Similarity	NPC81697
0.9424	High Similarity	NPC164980
0.9424	High Similarity	NPC85162
0.9424	High Similarity	NPC221432
0.9424	High Similarity	NPC257097
0.9424	High Similarity	NPC39329
0.9424	High Similarity	NPC278249
0.942	High Similarity	NPC213322
0.942	High Similarity	NPC110038
0.942	High Similarity	NPC4743
0.942	High Similarity	NPC282300
0.942	High Similarity	NPC110969
0.942	High Similarity	NPC312391
0.942	High Similarity	NPC248372
0.942	High Similarity	NPC324386
0.9416	High Similarity	NPC303633
0.9416	High Similarity	NPC217186
0.9416	High Similarity	NPC140890
0.9416	High Similarity	NPC18260
0.9416	High Similarity	NPC37206
0.9416	High Similarity	NPC220062
0.9416	High Similarity	NPC96565
0.9416	High Similarity	NPC53181
0.9416	High Similarity	NPC78913
0.9416	High Similarity	NPC470211
0.9416	High Similarity	NPC55018
0.9416	High Similarity	NPC216978
0.9416	High Similarity	NPC301217
0.9407	High Similarity	NPC101752
0.9407	High Similarity	NPC84699
0.9398	High Similarity	NPC475589
0.9398	High Similarity	NPC31872
0.9398	High Similarity	NPC473584
0.9366	High Similarity	NPC307052
0.9366	High Similarity	NPC139966
0.9366	High Similarity	NPC5173
0.9362	High Similarity	NPC470670
0.9362	High Similarity	NPC85773
0.9362	High Similarity	NPC110303
0.9362	High Similarity	NPC472627
0.9362	High Similarity	NPC296998
0.9362	High Similarity	NPC473133
0.9362	High Similarity	NPC202494
0.9362	High Similarity	NPC283234
0.9362	High Similarity	NPC91902
0.9362	High Similarity	NPC47388
0.9362	High Similarity	NPC473077
0.9362	High Similarity	NPC23728
0.9357	High Similarity	NPC473013
0.9357	High Similarity	NPC297788
0.9357	High Similarity	NPC87486
0.9357	High Similarity	NPC209040
0.9357	High Similarity	NPC131579
0.9357	High Similarity	NPC197252
0.9357	High Similarity	NPC473014
0.9357	High Similarity	NPC235217
0.9357	High Similarity	NPC124780
0.9357	High Similarity	NPC131568
0.9357	High Similarity	NPC236766
0.9357	High Similarity	NPC473015
0.9353	High Similarity	NPC325346
0.9353	High Similarity	NPC294432
0.9353	High Similarity	NPC11561
0.9353	High Similarity	NPC226636
0.9348	High Similarity	NPC188243
0.9348	High Similarity	NPC270883
0.9348	High Similarity	NPC172986
0.9348	High Similarity	NPC261227
0.9348	High Similarity	NPC16455
0.9348	High Similarity	NPC6407
0.9348	High Similarity	NPC110228
0.9348	High Similarity	NPC307990
0.9348	High Similarity	NPC150522
0.9343	High Similarity	NPC474504
0.9343	High Similarity	NPC470399
0.9343	High Similarity	NPC474487
0.9343	High Similarity	NPC470672
0.9343	High Similarity	NPC470671
0.9343	High Similarity	NPC201395
0.9343	High Similarity	NPC124269
0.9338	High Similarity	NPC121243
0.9338	High Similarity	NPC187826
0.9338	High Similarity	NPC240147
0.9333	High Similarity	NPC164136
0.9328	High Similarity	NPC25937
0.9323	High Similarity	NPC5515
0.9323	High Similarity	NPC270369
0.9301	High Similarity	NPC61258
0.9301	High Similarity	NPC37348
0.9296	High Similarity	NPC132592
0.9296	High Similarity	NPC168085
0.9296	High Similarity	NPC321623
0.9296	High Similarity	NPC161191
0.9296	High Similarity	NPC160821
0.9296	High Similarity	NPC189087
0.9296	High Similarity	NPC470460
0.9296	High Similarity	NPC6511
0.9291	High Similarity	NPC470133
0.9291	High Similarity	NPC109183
0.9291	High Similarity	NPC290133
0.9291	High Similarity	NPC24136
0.9291	High Similarity	NPC470132

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 NPC139554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	949
0.2-0.3	1679
0.3-0.4	2681
0.4-0.5	1848
0.5-0.6	1139
0.6-0.7	371
0.7-0.8	113
0.8-0.85	33
0.85-0.9	18
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.922	High Similarity	NPD4378	Clinical (unspecified phase)
0.913	High Similarity	NPD1550	Clinical (unspecified phase)
0.913	High Similarity	NPD1552	Clinical (unspecified phase)
0.9065	High Similarity	NPD1549	Phase 2
0.8951	High Similarity	NPD7410	Clinical (unspecified phase)
0.8921	High Similarity	NPD2796	Approved
0.8904	High Similarity	NPD4380	Phase 2
0.8851	High Similarity	NPD2393	Clinical (unspecified phase)
0.8849	High Similarity	NPD1510	Phase 2
0.8832	High Similarity	NPD1240	Approved
0.8792	High Similarity	NPD8443	Clinical (unspecified phase)
0.8784	High Similarity	NPD6801	Discontinued
0.8716	High Similarity	NPD7411	Suspended
0.8705	High Similarity	NPD1607	Approved
0.8675	High Similarity	NPD7075	Discontinued
0.8601	High Similarity	NPD2800	Approved
0.86	High Similarity	NPD7096	Clinical (unspecified phase)
0.8571	High Similarity	NPD6651	Approved
0.8553	High Similarity	NPD4381	Clinical (unspecified phase)
0.8533	High Similarity	NPD1934	Approved
0.8531	High Similarity	NPD970	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD6799	Approved
0.8477	Intermediate Similarity	NPD7819	Suspended
0.8418	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD6959	Discontinued
0.8367	Intermediate Similarity	NPD1511	Approved
0.8355	Intermediate Similarity	NPD2801	Approved
0.8345	Intermediate Similarity	NPD1243	Approved
0.8345	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD2534	Approved
0.8311	Intermediate Similarity	NPD2533	Approved
0.8311	Intermediate Similarity	NPD2532	Approved
0.8288	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD6599	Discontinued
0.8255	Intermediate Similarity	NPD1512	Approved
0.8247	Intermediate Similarity	NPD7768	Phase 2
0.8247	Intermediate Similarity	NPD3882	Suspended
0.8228	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6166	Phase 2
0.8228	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD920	Approved
0.82	Intermediate Similarity	NPD5403	Approved
0.8176	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD3750	Approved
0.8138	Intermediate Similarity	NPD1551	Phase 2
0.8125	Intermediate Similarity	NPD3818	Discontinued
0.8098	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7054	Approved
0.8067	Intermediate Similarity	NPD5401	Approved
0.8067	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD3817	Phase 2
0.8025	Intermediate Similarity	NPD7074	Phase 3
0.8025	Intermediate Similarity	NPD7472	Approved
0.8014	Intermediate Similarity	NPD2935	Discontinued
0.7986	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD5124	Phase 1
0.7975	Intermediate Similarity	NPD6797	Phase 2
0.7975	Intermediate Similarity	NPD5953	Discontinued
0.7975	Intermediate Similarity	NPD5494	Approved
0.7963	Intermediate Similarity	NPD7286	Phase 2
0.7945	Intermediate Similarity	NPD2799	Discontinued
0.7945	Intermediate Similarity	NPD7033	Discontinued
0.7927	Intermediate Similarity	NPD7251	Discontinued
0.7927	Intermediate Similarity	NPD6559	Discontinued
0.7919	Intermediate Similarity	NPD4628	Phase 3
0.7899	Intermediate Similarity	NPD422	Phase 1
0.7898	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7808	Phase 3
0.7852	Intermediate Similarity	NPD2654	Approved
0.7848	Intermediate Similarity	NPD3749	Approved
0.7842	Intermediate Similarity	NPD9717	Approved
0.7838	Intermediate Similarity	NPD2344	Approved
0.7834	Intermediate Similarity	NPD5402	Approved
0.7823	Intermediate Similarity	NPD3748	Approved
0.7801	Intermediate Similarity	NPD1203	Approved
0.7799	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD2313	Discontinued
0.7778	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6099	Approved
0.777	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6100	Approved
0.7764	Intermediate Similarity	NPD6232	Discontinued
0.7762	Intermediate Similarity	NPD6832	Phase 2
0.7744	Intermediate Similarity	NPD5844	Phase 1
0.7737	Intermediate Similarity	NPD1548	Phase 1
0.7733	Intermediate Similarity	NPD4363	Phase 3
0.7733	Intermediate Similarity	NPD4360	Phase 2
0.773	Intermediate Similarity	NPD7473	Discontinued
0.7703	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1247	Approved
0.7682	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3268	Approved
0.7654	Intermediate Similarity	NPD5710	Approved
0.7654	Intermediate Similarity	NPD5711	Approved
0.7644	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4908	Phase 1
0.7632	Intermediate Similarity	NPD2309	Approved
0.7609	Intermediate Similarity	NPD9545	Approved
0.759	Intermediate Similarity	NPD1729	Discontinued
0.7586	Intermediate Similarity	NPD4361	Phase 2
0.7586	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD2797	Approved
0.7551	Intermediate Similarity	NPD943	Approved
0.7545	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1296	Phase 2
0.7532	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7390	Discontinued
0.7518	Intermediate Similarity	NPD1610	Phase 2
0.7516	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD2798	Approved
0.7464	Intermediate Similarity	NPD9493	Approved
0.7434	Intermediate Similarity	NPD2424	Discontinued
0.7415	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6104	Discontinued
0.7394	Intermediate Similarity	NPD3926	Phase 2
0.7386	Intermediate Similarity	NPD1652	Phase 2
0.7379	Intermediate Similarity	NPD1019	Discontinued
0.7372	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6004	Phase 3
0.7368	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2346	Discontinued
0.7368	Intermediate Similarity	NPD6005	Phase 3
0.7368	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6002	Phase 3
0.7361	Intermediate Similarity	NPD3225	Approved
0.7351	Intermediate Similarity	NPD4308	Phase 3
0.7343	Intermediate Similarity	NPD3972	Approved
0.7315	Intermediate Similarity	NPD1613	Approved
0.7315	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3267	Approved
0.731	Intermediate Similarity	NPD3266	Approved
0.7305	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6798	Discontinued
0.7297	Intermediate Similarity	NPD411	Approved
0.7296	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4749	Approved
0.7268	Intermediate Similarity	NPD7584	Approved
0.7267	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD447	Suspended
0.7261	Intermediate Similarity	NPD4661	Approved
0.7261	Intermediate Similarity	NPD4662	Approved
0.7246	Intermediate Similarity	NPD2403	Approved
0.723	Intermediate Similarity	NPD3027	Phase 3
0.723	Intermediate Similarity	NPD4625	Phase 3
0.7222	Intermediate Similarity	NPD1465	Phase 2
0.7222	Intermediate Similarity	NPD1608	Approved
0.7216	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5889	Approved
0.7205	Intermediate Similarity	NPD5890	Approved
0.72	Intermediate Similarity	NPD3142	Approved
0.72	Intermediate Similarity	NPD3140	Approved
0.7188	Intermediate Similarity	NPD7458	Discontinued
0.7178	Intermediate Similarity	NPD4288	Approved
0.717	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6844	Discontinued
0.716	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7124	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5761	Phase 2
0.7117	Intermediate Similarity	NPD5760	Phase 2
0.711	Intermediate Similarity	NPD8312	Approved
0.711	Intermediate Similarity	NPD8313	Approved
0.7095	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7212	Phase 2
0.7089	Intermediate Similarity	NPD7213	Phase 3
0.7086	Intermediate Similarity	NPD4307	Phase 2
0.7078	Intermediate Similarity	NPD4476	Approved
0.7078	Intermediate Similarity	NPD4477	Approved
0.7075	Intermediate Similarity	NPD1164	Approved
0.7073	Intermediate Similarity	NPD2296	Approved
0.707	Intermediate Similarity	NPD3887	Approved
0.7067	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7199	Phase 2
0.7059	Intermediate Similarity	NPD3751	Discontinued
0.7055	Intermediate Similarity	NPD37	Approved
0.7047	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6585	Discontinued
0.7034	Intermediate Similarity	NPD1091	Approved
0.7034	Intermediate Similarity	NPD1201	Approved
0.7032	Intermediate Similarity	NPD1471	Phase 3
0.703	Intermediate Similarity	NPD4965	Approved
0.703	Intermediate Similarity	NPD4966	Approved
0.703	Intermediate Similarity	NPD4967	Phase 2
0.7027	Intermediate Similarity	NPD5647	Approved
0.7024	Intermediate Similarity	NPD3787	Discontinued
0.702	Intermediate Similarity	NPD6233	Phase 2
0.7019	Intermediate Similarity	NPD1653	Approved
0.7014	Intermediate Similarity	NPD1778	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