NPASS Compound

Structure

CID131039 OpenBabel06191715492D 30 31 0 0 0 0 0 0 0 0999 V2000 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 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 -0.8660 -1.5000 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 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 -8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 -0.5000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 30 1 0 0 0 0 6 9 1 0 0 0 0 6 17 2 0 0 0 0 7 10 1 0 0 0 0 7 18 2 0 0 0 0 8 13 2 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 20 26 2 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 23 25 2 0 0 0 0 24 28 2 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.21
Volume:	449.935
LogP:	6.679
LogD:	4.429
LogS:	-4.358
# Rotatable Bonds:	8
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	2.855
Fsp3:	0.269
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.864
MDCK Permeability:	1.776230419636704e-05
Pgp-inhibitor:	0.628
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.968
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	96.91648864746094%
Volume Distribution (VD):	1.765
Pgp-substrate:	4.542366027832031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.18
CYP2C19-inhibitor:	0.973
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.913
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.926
CYP2D6-substrate:	0.782
CYP3A4-inhibitor:	0.804
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	14.433
Half-life (T1/2):	0.207

ADMET: Toxicity

hERG Blockers:	0.164
Human Hepatotoxicity (H-HT):	0.773
Drug-inuced Liver Injury (DILI):	0.234
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.819
Skin Sensitization:	0.923
Carcinogencity:	0.167
Eye Corrosion:	0.003
Eye Irritation:	0.889
Respiratory Toxicity:	0.86

Download Data

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

Natural Product: NPC131039

Natural Product ID:	NPC131039
*Common Name:**	Abyssinone-Vi-4-O-Methyl Ether
IUPAC Name:	(E)-1-(2,4-dihydroxyphenyl)-3-[4-methoxy-3,5-bis(3-methylbut-2-enyl)phenyl]prop-2-en-1-one
Synonyms:
Standard InCHIKey:	AHQPCANDOCWXDN-MDWZMJQESA-N
Standard InCHI:	InChI=1S/C26H30O4/c1-17(2)6-9-20-14-19(15-21(26(20)30-5)10-7-18(3)4)8-13-24(28)23-12-11-22(27)16-25(23)29/h6-8,11-16,27,29H,9-10H2,1-5H3/b13-8+
SMILES:	COc1c(CC=C(C)C)cc(cc1CC=C(C)C)/C=C/C(=O)c1ccc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470865
PubChem CID:	11995582
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(88)80746-5]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	root barks	n.a.	n.a.	PMID[15689169]
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	root bark	Buea, Southwest Province, Cameroon	1997-JUL	PMID[17125223]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22444	Ceramium boydenii	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27459	Balanophora tobiracola	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27739	Erythrina mildbraedii	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	14800.0	nM	PMID[453491]

☑ 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 NPC131039 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	339
0.1-0.2	1545
0.2-0.3	4019
0.3-0.4	10698
0.4-0.5	7527
0.5-0.6	3727
0.6-0.7	6100
0.7-0.8	5468
0.8-0.85	1895
0.85-0.9	855
0.9-0.95	444
0.95-1	80

Similarity Score	Similarity Level	Natural Product ID
0.9923	High Similarity	NPC168105
0.9923	High Similarity	NPC186838
0.9923	High Similarity	NPC1486
0.9923	High Similarity	NPC274109
0.9923	High Similarity	NPC477242
0.9923	High Similarity	NPC150399
0.9923	High Similarity	NPC41461
0.9923	High Similarity	NPC66349
0.9923	High Similarity	NPC249606
0.9923	High Similarity	NPC25287
0.9923	High Similarity	NPC477243
0.9923	High Similarity	NPC477244
0.9923	High Similarity	NPC98115
0.9923	High Similarity	NPC12165
0.9847	High Similarity	NPC317119
0.9847	High Similarity	NPC153979
0.9847	High Similarity	NPC472419
0.9846	High Similarity	NPC156092
0.9846	High Similarity	NPC13575
0.9773	High Similarity	NPC21350
0.9769	High Similarity	NPC286336
0.9769	High Similarity	NPC103842
0.9699	High Similarity	NPC470211
0.9699	High Similarity	NPC477956
0.9699	High Similarity	NPC472366
0.9692	High Similarity	NPC294593
0.9692	High Similarity	NPC192304
0.9692	High Similarity	NPC312318
0.9692	High Similarity	NPC263670
0.9692	High Similarity	NPC159623
0.9692	High Similarity	NPC472365
0.9692	High Similarity	NPC20560
0.9692	High Similarity	NPC82225
0.9692	High Similarity	NPC204960
0.9692	High Similarity	NPC175098
0.9692	High Similarity	NPC337373
0.9692	High Similarity	NPC188646
0.9692	High Similarity	NPC242294
0.9692	High Similarity	NPC56031
0.9692	High Similarity	NPC27643
0.9692	High Similarity	NPC144051
0.9692	High Similarity	NPC139813
0.9692	High Similarity	NPC28753
0.9692	High Similarity	NPC18877
0.969	High Similarity	NPC262359
0.9627	High Similarity	NPC213659
0.9627	High Similarity	NPC219917
0.9627	High Similarity	NPC11056
0.9627	High Similarity	NPC80962
0.9627	High Similarity	NPC172250
0.9627	High Similarity	NPC48624
0.9627	High Similarity	NPC326109
0.9627	High Similarity	NPC204985
0.9627	High Similarity	NPC259166
0.9627	High Similarity	NPC144118
0.9627	High Similarity	NPC215311
0.9624	High Similarity	NPC471620
0.9624	High Similarity	NPC251681
0.9624	High Similarity	NPC243528
0.9621	High Similarity	NPC213603
0.9615	High Similarity	NPC212631
0.9615	High Similarity	NPC257756
0.9615	High Similarity	NPC129132
0.9615	High Similarity	NPC205468
0.9615	High Similarity	NPC87231
0.9556	High Similarity	NPC470087
0.9556	High Similarity	NPC321980
0.9556	High Similarity	NPC110969
0.9556	High Similarity	NPC469404
0.9556	High Similarity	NPC470089
0.9556	High Similarity	NPC26051
0.9556	High Similarity	NPC268204
0.9556	High Similarity	NPC52789
0.9556	High Similarity	NPC55832
0.9552	High Similarity	NPC295384
0.9552	High Similarity	NPC283429
0.9538	High Similarity	NPC64359
0.9538	High Similarity	NPC112192
0.9538	High Similarity	NPC186097
0.9538	High Similarity	NPC189106
0.9538	High Similarity	NPC313618
0.9538	High Similarity	NPC475009
0.9538	High Similarity	NPC164236
0.9538	High Similarity	NPC308037
0.9538	High Similarity	NPC309717
0.9538	High Similarity	NPC475008
0.9538	High Similarity	NPC66384
0.9538	High Similarity	NPC128348
0.9485	High Similarity	NPC11561
0.9485	High Similarity	NPC226636
0.9485	High Similarity	NPC148545
0.9481	High Similarity	NPC270883
0.9481	High Similarity	NPC261227
0.9481	High Similarity	NPC241100
0.9481	High Similarity	NPC101366
0.9481	High Similarity	NPC69769
0.9481	High Similarity	NPC253822
0.9481	High Similarity	NPC159275
0.9481	High Similarity	NPC235239
0.9481	High Similarity	NPC172986
0.9478	High Similarity	NPC472368
0.9478	High Similarity	NPC124269
0.9474	High Similarity	NPC476333
0.9474	High Similarity	NPC473391
0.9474	High Similarity	NPC472367
0.9474	High Similarity	NPC472364
0.9474	High Similarity	NPC24394
0.947	High Similarity	NPC164136
0.9466	High Similarity	NPC215875
0.9466	High Similarity	NPC15834
0.9416	High Similarity	NPC39329
0.9416	High Similarity	NPC166138
0.9416	High Similarity	NPC164980
0.9416	High Similarity	NPC310130
0.9416	High Similarity	NPC257097
0.9416	High Similarity	NPC68104
0.9416	High Similarity	NPC169591
0.9416	High Similarity	NPC221432
0.9416	High Similarity	NPC150408
0.9416	High Similarity	NPC143896
0.9416	High Similarity	NPC117836
0.9416	High Similarity	NPC106985
0.9416	High Similarity	NPC51887
0.9416	High Similarity	NPC475705
0.9416	High Similarity	NPC301751
0.9416	High Similarity	NPC476178
0.9416	High Similarity	NPC149026
0.9416	High Similarity	NPC75049
0.9416	High Similarity	NPC245482
0.9416	High Similarity	NPC91560
0.9416	High Similarity	NPC18585
0.9416	High Similarity	NPC175504
0.9412	High Similarity	NPC156590
0.9412	High Similarity	NPC205006
0.9412	High Similarity	NPC103362
0.9412	High Similarity	NPC118840
0.9412	High Similarity	NPC147688
0.9412	High Similarity	NPC3188
0.9412	High Similarity	NPC26238
0.9412	High Similarity	NPC64908
0.9412	High Similarity	NPC282300
0.9407	High Similarity	NPC220062
0.9407	High Similarity	NPC109232
0.9407	High Similarity	NPC217186
0.9407	High Similarity	NPC53181
0.9407	High Similarity	NPC55018
0.9407	High Similarity	NPC216978
0.9407	High Similarity	NPC301217
0.9407	High Similarity	NPC303633
0.9407	High Similarity	NPC18260
0.9407	High Similarity	NPC96565
0.9407	High Similarity	NPC78913
0.9403	High Similarity	NPC209560
0.9403	High Similarity	NPC303644
0.9403	High Similarity	NPC188879
0.9403	High Similarity	NPC116632
0.9403	High Similarity	NPC23870
0.9403	High Similarity	NPC181124
0.9403	High Similarity	NPC162680
0.9403	High Similarity	NPC294409
0.9403	High Similarity	NPC7013
0.9394	High Similarity	NPC16197
0.9385	High Similarity	NPC247779
0.9385	High Similarity	NPC84772
0.9348	High Similarity	NPC476055
0.9348	High Similarity	NPC473015
0.9348	High Similarity	NPC234629
0.9348	High Similarity	NPC328623
0.9348	High Similarity	NPC311741
0.9348	High Similarity	NPC197252
0.9348	High Similarity	NPC473013
0.9348	High Similarity	NPC209040
0.9348	High Similarity	NPC236766
0.9343	High Similarity	NPC76372
0.9343	High Similarity	NPC161506
0.9343	High Similarity	NPC32739
0.9343	High Similarity	NPC177354
0.9343	High Similarity	NPC66515
0.9343	High Similarity	NPC328164
0.9343	High Similarity	NPC148757
0.9343	High Similarity	NPC166482
0.9343	High Similarity	NPC194432
0.9343	High Similarity	NPC306829
0.9343	High Similarity	NPC144499
0.9343	High Similarity	NPC40833
0.9343	High Similarity	NPC324436
0.9343	High Similarity	NPC125855
0.9343	High Similarity	NPC324134
0.9343	High Similarity	NPC296917
0.9343	High Similarity	NPC166934
0.9343	High Similarity	NPC228504
0.9343	High Similarity	NPC220998
0.9343	High Similarity	NPC182852
0.9343	High Similarity	NPC297600
0.9343	High Similarity	NPC37496
0.9343	High Similarity	NPC10937
0.9343	High Similarity	NPC64915
0.9343	High Similarity	NPC167624
0.9343	High Similarity	NPC76338
0.9343	High Similarity	NPC107572

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 NPC131039 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	972
0.2-0.3	1434
0.3-0.4	2545
0.4-0.5	1996
0.5-0.6	1244
0.6-0.7	453
0.7-0.8	149
0.8-0.85	37
0.85-0.9	10
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9538	High Similarity	NPD1240	Approved
0.9394	High Similarity	NPD1607	Approved
0.9254	High Similarity	NPD1510	Phase 2
0.9209	High Similarity	NPD4378	Clinical (unspecified phase)
0.9071	High Similarity	NPD7410	Clinical (unspecified phase)
0.9051	High Similarity	NPD1549	Phase 2
0.8978	High Similarity	NPD1550	Clinical (unspecified phase)
0.8978	High Similarity	NPD1552	Clinical (unspecified phase)
0.8889	High Similarity	NPD4380	Phase 2
0.8828	High Similarity	NPD7411	Suspended
0.8768	High Similarity	NPD2796	Approved
0.8768	High Similarity	NPD2935	Discontinued
0.8707	High Similarity	NPD2393	Clinical (unspecified phase)
0.8686	High Similarity	NPD6651	Approved
0.8658	High Similarity	NPD7075	Discontinued
0.8649	High Similarity	NPD8443	Clinical (unspecified phase)
0.8601	High Similarity	NPD6799	Approved
0.8581	High Similarity	NPD7096	Clinical (unspecified phase)
0.8581	High Similarity	NPD7819	Suspended
0.8514	High Similarity	NPD6801	Discontinued
0.8451	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1934	Approved
0.838	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD6599	Discontinued
0.8345	Intermediate Similarity	NPD1511	Approved
0.8344	Intermediate Similarity	NPD7768	Phase 2
0.8344	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD2801	Approved
0.8323	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD2800	Approved
0.8298	Intermediate Similarity	NPD2799	Discontinued
0.8298	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD943	Approved
0.8264	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD3750	Approved
0.8261	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1551	Phase 2
0.8231	Intermediate Similarity	NPD1512	Approved
0.8194	Intermediate Similarity	NPD6232	Discontinued
0.8194	Intermediate Similarity	NPD1243	Approved
0.8182	Intermediate Similarity	NPD2344	Approved
0.8163	Intermediate Similarity	NPD2533	Approved
0.8163	Intermediate Similarity	NPD2532	Approved
0.8163	Intermediate Similarity	NPD2534	Approved
0.8162	Intermediate Similarity	NPD1203	Approved
0.8153	Intermediate Similarity	NPD7473	Discontinued
0.8129	Intermediate Similarity	NPD6959	Discontinued
0.8102	Intermediate Similarity	NPD2798	Approved
0.8074	Intermediate Similarity	NPD3972	Approved
0.8063	Intermediate Similarity	NPD5953	Discontinued
0.8054	Intermediate Similarity	NPD920	Approved
0.8052	Intermediate Similarity	NPD3749	Approved
0.805	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD7286	Phase 2
0.8027	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2313	Discontinued
0.7986	Intermediate Similarity	NPD6832	Phase 2
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD7390	Discontinued
0.7959	Intermediate Similarity	NPD2309	Approved
0.7955	Intermediate Similarity	NPD9493	Approved
0.7949	Intermediate Similarity	NPD5494	Approved
0.7945	Intermediate Similarity	NPD2654	Approved
0.7941	Intermediate Similarity	NPD9717	Approved
0.7933	Intermediate Similarity	NPD5403	Approved
0.7922	Intermediate Similarity	NPD3817	Phase 2
0.7919	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3748	Approved
0.7875	Intermediate Similarity	NPD3818	Discontinued
0.7868	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD5401	Approved
0.7791	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD7074	Phase 3
0.777	Intermediate Similarity	NPD1164	Approved
0.777	Intermediate Similarity	NPD4628	Phase 3
0.7756	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3268	Approved
0.7716	Intermediate Similarity	NPD7054	Approved
0.7712	Intermediate Similarity	NPD3226	Approved
0.7712	Intermediate Similarity	NPD7458	Discontinued
0.7704	Intermediate Similarity	NPD9545	Approved
0.7697	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2346	Discontinued
0.7669	Intermediate Similarity	NPD7472	Approved
0.7658	Intermediate Similarity	NPD919	Approved
0.7651	Intermediate Similarity	NPD7003	Approved
0.7647	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2797	Approved
0.7643	Intermediate Similarity	NPD1470	Approved
0.7622	Intermediate Similarity	NPD6797	Phase 2
0.7619	Intermediate Similarity	NPD6100	Approved
0.7619	Intermediate Similarity	NPD5406	Approved
0.7619	Intermediate Similarity	NPD5404	Approved
0.7619	Intermediate Similarity	NPD5408	Approved
0.7619	Intermediate Similarity	NPD5405	Approved
0.7619	Intermediate Similarity	NPD6099	Approved
0.7609	Intermediate Similarity	NPD422	Phase 1
0.7609	Intermediate Similarity	NPD1201	Approved
0.7607	Intermediate Similarity	NPD5844	Phase 1
0.7606	Intermediate Similarity	NPD4908	Phase 1
0.758	Intermediate Similarity	NPD5402	Approved
0.7578	Intermediate Similarity	NPD3926	Phase 2
0.7576	Intermediate Similarity	NPD7251	Discontinued
0.7574	Intermediate Similarity	NPD1548	Phase 1
0.7571	Intermediate Similarity	NPD1876	Approved
0.7562	Intermediate Similarity	NPD1247	Approved
0.7561	Intermediate Similarity	NPD1729	Discontinued
0.7551	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4308	Phase 3
0.7551	Intermediate Similarity	NPD7033	Discontinued
0.7533	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7808	Phase 3
0.7516	Intermediate Similarity	NPD5711	Approved
0.7516	Intermediate Similarity	NPD5710	Approved
0.7482	Intermediate Similarity	NPD1610	Phase 2
0.7466	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1933	Approved
0.7466	Intermediate Similarity	NPD230	Phase 1
0.7463	Intermediate Similarity	NPD1241	Discontinued
0.7425	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4360	Phase 2
0.7399	Intermediate Similarity	NPD4363	Phase 3
0.7394	Intermediate Similarity	NPD3267	Approved
0.7394	Intermediate Similarity	NPD3266	Approved
0.7391	Intermediate Similarity	NPD1651	Approved
0.7389	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD411	Approved
0.7379	Intermediate Similarity	NPD3764	Approved
0.7376	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2296	Approved
0.7356	Intermediate Similarity	NPD4361	Phase 2
0.7356	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD9266	Approved
0.7348	Intermediate Similarity	NPD74	Approved
0.7347	Intermediate Similarity	NPD447	Suspended
0.7347	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5124	Phase 1
0.7343	Intermediate Similarity	NPD1019	Discontinued
0.7333	Intermediate Similarity	NPD1471	Phase 3
0.7333	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1283	Approved
0.7324	Intermediate Similarity	NPD3225	Approved
0.731	Intermediate Similarity	NPD4625	Phase 3
0.731	Intermediate Similarity	NPD3027	Phase 3
0.7305	Intermediate Similarity	NPD1608	Approved
0.7305	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1465	Phase 2
0.7292	Intermediate Similarity	NPD9494	Approved
0.729	Intermediate Similarity	NPD5049	Phase 3
0.7288	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD940	Approved
0.7287	Intermediate Similarity	NPD846	Approved
0.7286	Intermediate Similarity	NPD3847	Discontinued
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4307	Phase 2
0.7278	Intermediate Similarity	NPD5890	Approved
0.7278	Intermediate Similarity	NPD5889	Approved
0.7273	Intermediate Similarity	NPD9267	Approved
0.7273	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9264	Approved
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9263	Approved
0.7262	Intermediate Similarity	NPD6104	Discontinued
0.7261	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6798	Discontinued
0.726	Intermediate Similarity	NPD1296	Phase 2
0.7255	Intermediate Similarity	NPD2354	Approved
0.7254	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4288	Approved
0.7226	Intermediate Similarity	NPD4661	Approved
0.7226	Intermediate Similarity	NPD4662	Approved
0.7215	Intermediate Similarity	NPD6585	Discontinued
0.7214	Intermediate Similarity	NPD4626	Approved
0.7183	Intermediate Similarity	NPD1481	Phase 2
0.7174	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3140	Approved
0.7162	Intermediate Similarity	NPD3142	Approved
0.7152	Intermediate Similarity	NPD4476	Approved
0.7152	Intermediate Similarity	NPD4477	Approved
0.7143	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3887	Approved
0.7126	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6280	Approved
0.7125	Intermediate Similarity	NPD6279	Approved
0.7123	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5536	Phase 2
0.7115	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6355	Discontinued
0.7113	Intermediate Similarity	NPD1281	Approved
0.7113	Intermediate Similarity	NPD1535	Discovery
0.7105	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2353	Approved
0.7092	Intermediate Similarity	NPD17	Approved
0.7091	Intermediate Similarity	NPD7229	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