NPASS Compound

Structure

NPC253822 OpenBabel07101719512D 27 29 0 0 0 0 0 0 0 0999 V2000 -6.0622 -1.5000 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 4.3301 -1.5000 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 -4.3301 -0.5000 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 2.5981 -0.5000 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 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 -5.1962 -2.0000 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 2.5981 -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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 26 1 0 0 0 0 4 5 1 0 0 0 0 4 11 2 0 0 0 0 5 12 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 13 1 0 0 0 0 8 19 2 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 15 2 0 0 0 0 10 27 1 0 0 0 0 12 16 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 17 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 21 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.13
Volume:	375.116
LogP:	4.893
LogD:	3.05
LogS:	-3.221
# Rotatable Bonds:	4
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.6
Synthetic Accessibility Score:	2.828
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.881
MDCK Permeability:	1.04508399090264e-05
Pgp-inhibitor:	0.088
Pgp-substrate:	0.441
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.921
30% Bioavailability (F30%):	0.645

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	95.1478042602539%
Volume Distribution (VD):	0.625
Pgp-substrate:	4.194186687469482%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.661
CYP2C19-inhibitor:	0.887
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.84
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.919
CYP2D6-substrate:	0.793
CYP3A4-inhibitor:	0.393
CYP3A4-substrate:	0.104

ADMET: Excretion

Clearance (CL):	8.068
Half-life (T1/2):	0.559

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.695
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.26
Maximum Recommended Daily Dose:	0.844
Skin Sensitization:	0.905
Carcinogencity:	0.055
Eye Corrosion:	0.004
Eye Irritation:	0.921
Respiratory Toxicity:	0.201

Download Data

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

Natural Product: NPC253822

Natural Product ID:	NPC253822
*Common Name:**	5,2',4'-Trihydroxy-7-Methoxy-5'-(3-Methylbuten-2-Yl)Isoflavone
IUPAC Name:	3-[2,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5-hydroxy-7-methoxychromen-4-one
Synonyms:
Standard InCHIKey:	FDGOXOKMOFWQKA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O6/c1-11(2)4-5-12-6-14(17(23)9-16(12)22)15-10-27-19-8-13(26-3)7-18(24)20(19)21(15)25/h4,6-10,22-24H,5H2,1-3H3
SMILES:	COc1cc(O)c2c(c1)occ(c2=O)c1cc(CC=C(C)C)c(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079060
PubChem CID:	44481781
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002602] 7-O-methylated isoflavonoids [CHEMONTID:0002689] 7-O-methylisoflavones

*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
NPO12590	Erythrina poeppigiana	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[12803562]
NPO12590	Erythrina poeppigiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19705860]
NPO12590	Erythrina poeppigiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12590	Erythrina poeppigiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12590	Erythrina poeppigiana	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
Others	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	RBA	=	0.15	%	PMID[470396]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	RBA	=	0.21	%	PMID[470396]
NPT2	Others	Unspecified		Ratio IC50	=	0.7	n.a.	PMID[470396]

☑ 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 NPC253822 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	396
0.1-0.2	1728
0.2-0.3	4078
0.3-0.4	10239
0.4-0.5	8221
0.5-0.6	3875
0.6-0.7	5541
0.7-0.8	4370
0.8-0.85	2012
0.85-0.9	1728
0.9-0.95	424
0.95-1	85

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC52789
0.9926	High Similarity	NPC26051
0.9926	High Similarity	NPC55832
0.9926	High Similarity	NPC268204
0.9852	High Similarity	NPC213659
0.9852	High Similarity	NPC219917
0.9852	High Similarity	NPC204985
0.9852	High Similarity	NPC48624
0.9852	High Similarity	NPC259166
0.9852	High Similarity	NPC101366
0.9852	High Similarity	NPC80962
0.9852	High Similarity	NPC172250
0.9852	High Similarity	NPC326109
0.9852	High Similarity	NPC144118
0.9852	High Similarity	NPC215311
0.9779	High Similarity	NPC469404
0.9778	High Similarity	NPC283429
0.9778	High Similarity	NPC295384
0.971	High Similarity	NPC476055
0.9704	High Similarity	NPC12175
0.9704	High Similarity	NPC278323
0.9704	High Similarity	NPC55162
0.9704	High Similarity	NPC90665
0.9704	High Similarity	NPC309154
0.9704	High Similarity	NPC279668
0.9638	High Similarity	NPC475705
0.9638	High Similarity	NPC476178
0.9638	High Similarity	NPC51887
0.9638	High Similarity	NPC117836
0.9632	High Similarity	NPC477956
0.963	High Similarity	NPC7013
0.963	High Similarity	NPC181124
0.963	High Similarity	NPC116632
0.963	High Similarity	NPC472419
0.963	High Similarity	NPC294409
0.963	High Similarity	NPC162680
0.963	High Similarity	NPC209560
0.963	High Similarity	NPC303644
0.9568	High Similarity	NPC234629
0.9568	High Similarity	NPC311741
0.9559	High Similarity	NPC21350
0.9556	High Similarity	NPC98115
0.9556	High Similarity	NPC477243
0.9556	High Similarity	NPC1486
0.9556	High Similarity	NPC186838
0.9556	High Similarity	NPC477242
0.9556	High Similarity	NPC87545
0.9556	High Similarity	NPC168105
0.9556	High Similarity	NPC235428
0.9556	High Similarity	NPC274109
0.9556	High Similarity	NPC66349
0.9556	High Similarity	NPC477244
0.9556	High Similarity	NPC12165
0.9556	High Similarity	NPC150399
0.9556	High Similarity	NPC41461
0.9556	High Similarity	NPC25287
0.9556	High Similarity	NPC249606
0.9504	High Similarity	NPC266572
0.9493	High Similarity	NPC470087
0.9493	High Similarity	NPC321980
0.9493	High Similarity	NPC110969
0.9493	High Similarity	NPC470089
0.9489	High Similarity	NPC470211
0.9485	High Similarity	NPC317119
0.9485	High Similarity	NPC153979
0.9481	High Similarity	NPC131039
0.9481	High Similarity	NPC234560
0.9481	High Similarity	NPC156092
0.9481	High Similarity	NPC39426
0.9481	High Similarity	NPC13575
0.9437	High Similarity	NPC317492
0.9433	High Similarity	NPC237635
0.9433	High Similarity	NPC79469
0.9433	High Similarity	NPC104406
0.9433	High Similarity	NPC222298
0.9433	High Similarity	NPC201731
0.9433	High Similarity	NPC24673
0.9433	High Similarity	NPC97716
0.9433	High Similarity	NPC51070
0.9429	High Similarity	NPC224714
0.9424	High Similarity	NPC226636
0.9424	High Similarity	NPC11561
0.942	High Similarity	NPC172986
0.942	High Similarity	NPC270883
0.942	High Similarity	NPC159275
0.942	High Similarity	NPC261227
0.942	High Similarity	NPC241100
0.942	High Similarity	NPC11056
0.9416	High Similarity	NPC471620
0.9416	High Similarity	NPC251681
0.9416	High Similarity	NPC243528
0.9412	High Similarity	NPC193792
0.9407	High Similarity	NPC103842
0.9407	High Similarity	NPC286336
0.9366	High Similarity	NPC168085
0.9366	High Similarity	NPC6511
0.9366	High Similarity	NPC166036
0.9366	High Similarity	NPC39195
0.9366	High Similarity	NPC203077
0.9366	High Similarity	NPC238279
0.9357	High Similarity	NPC169591
0.9357	High Similarity	NPC39329
0.9357	High Similarity	NPC149026
0.9357	High Similarity	NPC257097
0.9357	High Similarity	NPC310130
0.9357	High Similarity	NPC150408
0.9357	High Similarity	NPC106985
0.9357	High Similarity	NPC166138
0.9357	High Similarity	NPC68104
0.9357	High Similarity	NPC301751
0.9357	High Similarity	NPC18585
0.9357	High Similarity	NPC91560
0.9357	High Similarity	NPC143896
0.9357	High Similarity	NPC75049
0.9357	High Similarity	NPC164980
0.9357	High Similarity	NPC175504
0.9357	High Similarity	NPC221432
0.9357	High Similarity	NPC245482
0.9353	High Similarity	NPC96408
0.9353	High Similarity	NPC17170
0.9353	High Similarity	NPC156190
0.9353	High Similarity	NPC156590
0.9353	High Similarity	NPC147688
0.9353	High Similarity	NPC103362
0.9353	High Similarity	NPC258630
0.9353	High Similarity	NPC205006
0.9353	High Similarity	NPC279650
0.9353	High Similarity	NPC118840
0.9353	High Similarity	NPC166689
0.9353	High Similarity	NPC64908
0.9353	High Similarity	NPC282300
0.9353	High Similarity	NPC3188
0.9348	High Similarity	NPC78913
0.9348	High Similarity	NPC472366
0.9348	High Similarity	NPC217186
0.9348	High Similarity	NPC301217
0.9348	High Similarity	NPC220062
0.9348	High Similarity	NPC216978
0.9348	High Similarity	NPC303633
0.9348	High Similarity	NPC53181
0.9348	High Similarity	NPC18260
0.9348	High Similarity	NPC55018
0.9348	High Similarity	NPC96565
0.9343	High Similarity	NPC212767
0.9333	High Similarity	NPC18877
0.9333	High Similarity	NPC56031
0.9333	High Similarity	NPC27643
0.9333	High Similarity	NPC192304
0.9333	High Similarity	NPC139813
0.9333	High Similarity	NPC159623
0.9333	High Similarity	NPC337373
0.9333	High Similarity	NPC188646
0.9333	High Similarity	NPC175098
0.9333	High Similarity	NPC82225
0.9333	High Similarity	NPC472365
0.9333	High Similarity	NPC28753
0.9333	High Similarity	NPC20560
0.9333	High Similarity	NPC144051
0.9333	High Similarity	NPC263670
0.9333	High Similarity	NPC294593
0.9333	High Similarity	NPC242294
0.9333	High Similarity	NPC223354
0.9333	High Similarity	NPC312318
0.9333	High Similarity	NPC204960
0.9301	High Similarity	NPC171916
0.9301	High Similarity	NPC38545
0.9296	High Similarity	NPC296998
0.9296	High Similarity	NPC473077
0.9296	High Similarity	NPC23728
0.9296	High Similarity	NPC308200
0.9296	High Similarity	NPC110303
0.9291	High Similarity	NPC319752
0.9291	High Similarity	NPC197252
0.9291	High Similarity	NPC209040
0.9291	High Similarity	NPC473013
0.9291	High Similarity	NPC236766
0.9291	High Similarity	NPC473015
0.9291	High Similarity	NPC273538
0.9291	High Similarity	NPC271288
0.9291	High Similarity	NPC216538
0.9291	High Similarity	NPC470890
0.9286	High Similarity	NPC32739
0.9286	High Similarity	NPC161506
0.9286	High Similarity	NPC297600
0.9286	High Similarity	NPC306829
0.9286	High Similarity	NPC78
0.9286	High Similarity	NPC66515
0.9286	High Similarity	NPC194432
0.9286	High Similarity	NPC265040
0.9286	High Similarity	NPC220998
0.9286	High Similarity	NPC177354
0.9286	High Similarity	NPC125855
0.9286	High Similarity	NPC182852
0.9286	High Similarity	NPC296917
0.9286	High Similarity	NPC107572
0.9286	High Similarity	NPC167624
0.9286	High Similarity	NPC166482
0.9286	High Similarity	NPC76372
0.9286	High Similarity	NPC228504
0.9286	High Similarity	NPC148757

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 NPC253822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	974
0.2-0.3	1623
0.3-0.4	2630
0.4-0.5	1913
0.5-0.6	1109
0.6-0.7	355
0.7-0.8	111
0.8-0.85	46
0.85-0.9	22
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9481	High Similarity	NPD1510	Phase 2
0.9291	High Similarity	NPD4378	Clinical (unspecified phase)
0.9185	High Similarity	NPD1240	Approved
0.9103	High Similarity	NPD4380	Phase 2
0.9051	High Similarity	NPD1607	Approved
0.9021	High Similarity	NPD7410	Clinical (unspecified phase)
0.9	High Similarity	NPD1549	Phase 2
0.8993	High Similarity	NPD2796	Approved
0.8929	High Similarity	NPD1552	Clinical (unspecified phase)
0.8929	High Similarity	NPD1550	Clinical (unspecified phase)
0.8792	High Similarity	NPD2393	Clinical (unspecified phase)
0.8784	High Similarity	NPD7411	Suspended
0.8742	High Similarity	NPD7075	Discontinued
0.8733	High Similarity	NPD8443	Clinical (unspecified phase)
0.8667	High Similarity	NPD7819	Suspended
0.8667	High Similarity	NPD7096	Clinical (unspecified phase)
0.86	High Similarity	NPD6801	Discontinued
0.8543	High Similarity	NPD2801	Approved
0.8511	High Similarity	NPD6651	Approved
0.8497	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1934	Approved
0.8472	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD2935	Discontinued
0.8435	Intermediate Similarity	NPD1511	Approved
0.8435	Intermediate Similarity	NPD6799	Approved
0.8431	Intermediate Similarity	NPD3882	Suspended
0.8431	Intermediate Similarity	NPD7768	Phase 2
0.8414	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD2800	Approved
0.8408	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD2532	Approved
0.8378	Intermediate Similarity	NPD2534	Approved
0.8378	Intermediate Similarity	NPD2533	Approved
0.8356	Intermediate Similarity	NPD3750	Approved
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8322	Intermediate Similarity	NPD1512	Approved
0.8288	Intermediate Similarity	NPD1243	Approved
0.828	Intermediate Similarity	NPD6232	Discontinued
0.8267	Intermediate Similarity	NPD920	Approved
0.825	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7473	Discontinued
0.8224	Intermediate Similarity	NPD6599	Discontinued
0.8207	Intermediate Similarity	NPD1551	Phase 2
0.8187	Intermediate Similarity	NPD3818	Discontinued
0.8153	Intermediate Similarity	NPD5494	Approved
0.8148	Intermediate Similarity	NPD5953	Discontinued
0.8141	Intermediate Similarity	NPD3749	Approved
0.8138	Intermediate Similarity	NPD2799	Discontinued
0.8133	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3817	Phase 2
0.8121	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD943	Approved
0.8099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD2313	Discontinued
0.8077	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD2798	Approved
0.8063	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6166	Phase 2
0.8063	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD2344	Approved
0.8026	Intermediate Similarity	NPD5403	Approved
0.8025	Intermediate Similarity	NPD7286	Phase 2
0.8014	Intermediate Similarity	NPD3748	Approved
0.7947	Intermediate Similarity	NPD7390	Discontinued
0.7914	Intermediate Similarity	NPD7054	Approved
0.7898	Intermediate Similarity	NPD5402	Approved
0.7895	Intermediate Similarity	NPD5401	Approved
0.7879	Intermediate Similarity	NPD6559	Discontinued
0.7866	Intermediate Similarity	NPD7472	Approved
0.7866	Intermediate Similarity	NPD7074	Phase 3
0.7847	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6797	Phase 2
0.7815	Intermediate Similarity	NPD2309	Approved
0.7806	Intermediate Similarity	NPD3226	Approved
0.78	Intermediate Similarity	NPD2654	Approved
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.7764	Intermediate Similarity	NPD1247	Approved
0.775	Intermediate Similarity	NPD919	Approved
0.7748	Intermediate Similarity	NPD4628	Phase 3
0.7746	Intermediate Similarity	NPD1203	Approved
0.7725	Intermediate Similarity	NPD7808	Phase 3
0.7725	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6099	Approved
0.7718	Intermediate Similarity	NPD6100	Approved
0.7716	Intermediate Similarity	NPD5711	Approved
0.7716	Intermediate Similarity	NPD5710	Approved
0.7714	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4908	Phase 1
0.7708	Intermediate Similarity	NPD6832	Phase 2
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7692	Intermediate Similarity	NPD7458	Discontinued
0.7687	Intermediate Similarity	NPD230	Phase 1
0.7681	Intermediate Similarity	NPD1548	Phase 1
0.7677	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2346	Discontinued
0.766	Intermediate Similarity	NPD3972	Approved
0.7651	Intermediate Similarity	NPD7033	Discontinued
0.7632	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1470	Approved
0.7605	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3268	Approved
0.7589	Intermediate Similarity	NPD1610	Phase 2
0.7586	Intermediate Similarity	NPD4360	Phase 2
0.7586	Intermediate Similarity	NPD4363	Phase 3
0.7561	Intermediate Similarity	NPD3926	Phase 2
0.7554	Intermediate Similarity	NPD9545	Approved
0.7543	Intermediate Similarity	NPD4361	Phase 2
0.7543	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD9493	Approved
0.7535	Intermediate Similarity	NPD9717	Approved
0.7533	Intermediate Similarity	NPD4308	Phase 3
0.7516	Intermediate Similarity	NPD7003	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD1164	Approved
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5404	Approved
0.7483	Intermediate Similarity	NPD5408	Approved
0.7483	Intermediate Similarity	NPD5406	Approved
0.7483	Intermediate Similarity	NPD3764	Approved
0.7483	Intermediate Similarity	NPD5405	Approved
0.7471	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD422	Phase 1
0.7465	Intermediate Similarity	NPD1201	Approved
0.745	Intermediate Similarity	NPD5124	Phase 1
0.745	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1729	Discontinued
0.7417	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4288	Approved
0.7333	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD37	Approved
0.732	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3225	Approved
0.731	Intermediate Similarity	NPD1876	Approved
0.7297	Intermediate Similarity	NPD4625	Phase 3
0.7297	Intermediate Similarity	NPD3027	Phase 3
0.7289	Intermediate Similarity	NPD7229	Phase 3
0.7279	Intermediate Similarity	NPD9494	Approved
0.7267	Intermediate Similarity	NPD5889	Approved
0.7267	Intermediate Similarity	NPD4307	Phase 2
0.7267	Intermediate Similarity	NPD5890	Approved
0.7261	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3266	Approved
0.726	Intermediate Similarity	NPD3267	Approved
0.7257	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2296	Approved
0.7228	Intermediate Similarity	NPD7584	Approved
0.7222	Intermediate Similarity	NPD6844	Discontinued
0.7219	Intermediate Similarity	NPD447	Suspended
0.7219	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1933	Approved
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6234	Discontinued
0.7208	Intermediate Similarity	NPD1471	Phase 3
0.7195	Intermediate Similarity	NPD4966	Approved
0.7195	Intermediate Similarity	NPD4965	Approved
0.7195	Intermediate Similarity	NPD4967	Phase 2
0.7194	Intermediate Similarity	NPD1241	Discontinued
0.7182	Intermediate Similarity	NPD6777	Approved
0.7182	Intermediate Similarity	NPD6781	Approved
0.7182	Intermediate Similarity	NPD6778	Approved
0.7182	Intermediate Similarity	NPD6782	Approved
0.7182	Intermediate Similarity	NPD6776	Approved
0.7182	Intermediate Similarity	NPD6780	Approved
0.7182	Intermediate Similarity	NPD6779	Approved
0.7172	Intermediate Similarity	NPD1608	Approved
0.7168	Intermediate Similarity	NPD8313	Approved
0.7168	Intermediate Similarity	NPD8312	Approved
0.7162	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4287	Approved
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1613	Approved
0.7151	Intermediate Similarity	NPD8151	Discontinued
0.7151	Intermediate Similarity	NPD6104	Discontinued
0.7134	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD1296	Phase 2
0.7133	Intermediate Similarity	NPD1651	Approved
0.7133	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD411	Approved
0.7123	Intermediate Similarity	NPD4749	Approved
0.7123	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3751	Discontinued
0.7117	Intermediate Similarity	NPD6280	Approved
0.7117	Intermediate Similarity	NPD6279	Approved
0.7114	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2403	Approved
0.7101	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6585	Discontinued
0.7095	Intermediate Similarity	NPD1019	Discontinued
0.7095	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1283	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