NPASS Compound

Structure

NPC474021 OpenBabel07101718282D 31 34 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.3660 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 1.0000 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 -1.7321 -2.0000 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 -6.9282 -3.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -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 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 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 -2.0000 0.0000 C 0 0 1 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 3 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 -0.8660 -0.5000 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 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 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 -4.3301 -1.5000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 13 2 0 0 0 0 6 14 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 16 1 0 0 0 0 9 22 1 0 0 0 0 10 17 2 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 11 21 2 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 14 24 1 0 0 0 0 16 24 2 0 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 19 28 2 0 0 0 0 20 15 1 6 0 0 0 20 30 1 0 0 0 0 21 23 1 0 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 29 1 0 0 0 0 24 31 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.19
Volume:	438.38
LogP:	5.48
LogD:	3.742
LogS:	-2.993
# Rotatable Bonds:	3
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	3.961
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.797
MDCK Permeability:	1.4016384739079513e-05
Pgp-inhibitor:	0.171
Pgp-substrate:	0.954
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.827
30% Bioavailability (F30%):	0.094

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	97.22342681884766%
Volume Distribution (VD):	1.082
Pgp-substrate:	3.7988576889038086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.328
CYP1A2-substrate:	0.2
CYP2C19-inhibitor:	0.87
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.91
CYP2D6-substrate:	0.251
CYP3A4-inhibitor:	0.616
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	13.913
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.857
Drug-inuced Liver Injury (DILI):	0.681
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.755
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.782
Carcinogencity:	0.441
Eye Corrosion:	0.003
Eye Irritation:	0.104
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC474021

Natural Product ID:	NPC474021
*Common Name:**	(2S)-3',5,7-Trihydroxy-2',2'-Dimethyl-8'-(3-Methylbut-2-Enyl)-2,6'-Bichroman-4-One
IUPAC Name:	(2S)-5,7-dihydroxy-2-[3-hydroxy-2,2-dimethyl-8-(3-methylbut-2-enyl)-3,4-dihydrochromen-6-yl]-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	WJBWITXUNBMVLF-AIBWNMTMSA-N
Standard InCHI:	InChI=1S/C25H28O6/c1-13(2)5-6-14-7-15(8-16-9-22(29)25(3,4)31-24(14)16)20-12-19(28)23-18(27)10-17(26)11-21(23)30-20/h5,7-8,10-11,20,22,26-27,29H,6,9,12H2,1-4H3/t20-,22?/m0/s1
SMILES:	CC(=CCC1=CC(=CC2=C1OC(C(C2)O)(C)C)C3CC(=O)C4=C(C=C(C=C4O3)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458555
PubChem CID:	44589132
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003643] 3'-prenylated flavans [CHEMONTID:0003506] 3'-prenylated flavanones

*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
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8526	Erythrina abyssinica	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	=	14900.0	nM	PMID[541823]

☑ 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 NPC474021 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	376
0.1-0.2	1476
0.2-0.3	3552
0.3-0.4	8816
0.4-0.5	9867
0.5-0.6	3604
0.6-0.7	5337
0.7-0.8	5359
0.8-0.85	2584
0.85-0.9	1191
0.9-0.95	457
0.95-1	78

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474023
0.9931	High Similarity	NPC475790
0.9796	High Similarity	NPC477958
0.9728	High Similarity	NPC472583
0.9728	High Similarity	NPC223701
0.9728	High Similarity	NPC469405
0.9728	High Similarity	NPC7989
0.9726	High Similarity	NPC471677
0.9726	High Similarity	NPC263384
0.9726	High Similarity	NPC472422
0.9726	High Similarity	NPC472420
0.9726	High Similarity	NPC471676
0.9726	High Similarity	NPC244577
0.9662	High Similarity	NPC259710
0.9662	High Similarity	NPC304207
0.9662	High Similarity	NPC217706
0.9662	High Similarity	NPC207809
0.9662	High Similarity	NPC48579
0.966	High Similarity	NPC161881
0.966	High Similarity	NPC10807
0.966	High Similarity	NPC56232
0.966	High Similarity	NPC150123
0.966	High Similarity	NPC244583
0.96	High Similarity	NPC473990
0.9595	High Similarity	NPC326592
0.9595	High Similarity	NPC112701
0.9595	High Similarity	NPC109594
0.9595	High Similarity	NPC180301
0.9595	High Similarity	NPC248793
0.9592	High Similarity	NPC262038
0.9592	High Similarity	NPC254412
0.9592	High Similarity	NPC319910
0.9592	High Similarity	NPC472636
0.9592	High Similarity	NPC328740
0.9592	High Similarity	NPC289774
0.9592	High Similarity	NPC278476
0.9592	High Similarity	NPC209846
0.9592	High Similarity	NPC477897
0.9592	High Similarity	NPC262039
0.9589	High Similarity	NPC472628
0.9586	High Similarity	NPC472627
0.9586	High Similarity	NPC85773
0.9586	High Similarity	NPC473133
0.9586	High Similarity	NPC47388
0.9586	High Similarity	NPC470670
0.9586	High Similarity	NPC91902
0.9583	High Similarity	NPC470890
0.9536	High Similarity	NPC471976
0.9536	High Similarity	NPC174953
0.953	High Similarity	NPC304745
0.953	High Similarity	NPC470681
0.953	High Similarity	NPC111341
0.9527	High Similarity	NPC35567
0.9527	High Similarity	NPC243171
0.9527	High Similarity	NPC473996
0.9527	High Similarity	NPC216035
0.9527	High Similarity	NPC138288
0.9527	High Similarity	NPC217149
0.9527	High Similarity	NPC171651
0.9524	High Similarity	NPC105136
0.9521	High Similarity	NPC10097
0.9517	High Similarity	NPC474302
0.9517	High Similarity	NPC472629
0.9474	High Similarity	NPC3629
0.9474	High Similarity	NPC472632
0.9467	High Similarity	NPC20530
0.9467	High Similarity	NPC78492
0.9467	High Similarity	NPC208152
0.9467	High Similarity	NPC215917
0.9467	High Similarity	NPC10754
0.9463	High Similarity	NPC311579
0.9463	High Similarity	NPC268193
0.9463	High Similarity	NPC293286
0.9463	High Similarity	NPC20907
0.9463	High Similarity	NPC236756
0.9463	High Similarity	NPC244250
0.9459	High Similarity	NPC474772
0.9459	High Similarity	NPC474744
0.9459	High Similarity	NPC472423
0.9459	High Similarity	NPC472580
0.9459	High Similarity	NPC471675
0.9456	High Similarity	NPC5173
0.9456	High Similarity	NPC89442
0.9456	High Similarity	NPC307052
0.9456	High Similarity	NPC473016
0.9456	High Similarity	NPC139966
0.9452	High Similarity	NPC473077
0.9452	High Similarity	NPC296998
0.9448	High Similarity	NPC87486
0.9448	High Similarity	NPC224714
0.9448	High Similarity	NPC124780
0.9412	High Similarity	NPC474033
0.9412	High Similarity	NPC474034
0.9408	High Similarity	NPC475784
0.9404	High Similarity	NPC471209
0.94	High Similarity	NPC476169
0.94	High Similarity	NPC477530
0.9396	High Similarity	NPC256141
0.9396	High Similarity	NPC327269
0.9396	High Similarity	NPC210597
0.9396	High Similarity	NPC477957
0.9396	High Similarity	NPC285623
0.9396	High Similarity	NPC476238
0.9396	High Similarity	NPC31627
0.9392	High Similarity	NPC124478
0.9392	High Similarity	NPC177308
0.9392	High Similarity	NPC472421
0.9392	High Similarity	NPC472633
0.9384	High Similarity	NPC67805
0.9384	High Similarity	NPC312973
0.9384	High Similarity	NPC83357
0.9384	High Similarity	NPC176229
0.9384	High Similarity	NPC195621
0.9384	High Similarity	NPC316769
0.9384	High Similarity	NPC187282
0.9384	High Similarity	NPC214774
0.9384	High Similarity	NPC142405
0.9384	High Similarity	NPC267375
0.9384	High Similarity	NPC475052
0.9384	High Similarity	NPC88964
0.9384	High Similarity	NPC301276
0.9384	High Similarity	NPC470647
0.9384	High Similarity	NPC290133
0.9384	High Similarity	NPC246948
0.9384	High Similarity	NPC54577
0.9384	High Similarity	NPC111786
0.9384	High Similarity	NPC20488
0.9384	High Similarity	NPC24136
0.9379	High Similarity	NPC478086
0.9379	High Similarity	NPC112749
0.9379	High Similarity	NPC316816
0.9379	High Similarity	NPC214166
0.9379	High Similarity	NPC18886
0.9375	High Similarity	NPC96408
0.9375	High Similarity	NPC258630
0.9375	High Similarity	NPC17170
0.9375	High Similarity	NPC156190
0.9375	High Similarity	NPC279650
0.9375	High Similarity	NPC166689
0.9346	High Similarity	NPC471211
0.9346	High Similarity	NPC474038
0.9346	High Similarity	NPC134783
0.9346	High Similarity	NPC471212
0.9346	High Similarity	NPC471210
0.9338	High Similarity	NPC146636
0.9333	High Similarity	NPC88983
0.9333	High Similarity	NPC74924
0.9333	High Similarity	NPC209760
0.9333	High Similarity	NPC203080
0.9333	High Similarity	NPC100134
0.932	High Similarity	NPC3779
0.932	High Similarity	NPC44721
0.932	High Similarity	NPC23728
0.932	High Similarity	NPC211466
0.932	High Similarity	NPC476182
0.932	High Similarity	NPC40086
0.932	High Similarity	NPC472918
0.932	High Similarity	NPC283234
0.932	High Similarity	NPC202494
0.932	High Similarity	NPC122828
0.932	High Similarity	NPC176869
0.932	High Similarity	NPC51070
0.932	High Similarity	NPC110303
0.932	High Similarity	NPC222298
0.9315	High Similarity	NPC131579
0.9315	High Similarity	NPC131568
0.9315	High Similarity	NPC209040
0.931	High Similarity	NPC194432
0.931	High Similarity	NPC227579
0.931	High Similarity	NPC64915
0.931	High Similarity	NPC166482
0.931	High Similarity	NPC107572
0.931	High Similarity	NPC76372
0.931	High Similarity	NPC223500
0.931	High Similarity	NPC78
0.931	High Similarity	NPC125855
0.931	High Similarity	NPC228504
0.931	High Similarity	NPC32739
0.931	High Similarity	NPC76338
0.931	High Similarity	NPC324134
0.931	High Similarity	NPC167624
0.931	High Similarity	NPC161506
0.931	High Similarity	NPC328164
0.931	High Similarity	NPC148757
0.931	High Similarity	NPC296917
0.931	High Similarity	NPC324436
0.931	High Similarity	NPC66515
0.931	High Similarity	NPC177354
0.931	High Similarity	NPC37496
0.931	High Similarity	NPC182852
0.931	High Similarity	NPC40833
0.931	High Similarity	NPC166934
0.931	High Similarity	NPC306829
0.931	High Similarity	NPC220998
0.931	High Similarity	NPC265040
0.931	High Similarity	NPC10937
0.931	High Similarity	NPC1089
0.9286	High Similarity	NPC44947
0.9286	High Similarity	NPC259834
0.9281	High Similarity	NPC118256

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 NPC474021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	875
0.2-0.3	1730
0.3-0.4	2623
0.4-0.5	1856
0.5-0.6	1093
0.6-0.7	445
0.7-0.8	148
0.8-0.85	34
0.85-0.9	17
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9392	High Similarity	NPD4380	Phase 2
0.9205	High Similarity	NPD2393	Clinical (unspecified phase)
0.9054	High Similarity	NPD4378	Clinical (unspecified phase)
0.9026	High Similarity	NPD7075	Discontinued
0.9026	High Similarity	NPD4381	Clinical (unspecified phase)
0.9013	High Similarity	NPD1934	Approved
0.8994	High Similarity	NPD7804	Clinical (unspecified phase)
0.8966	High Similarity	NPD1550	Clinical (unspecified phase)
0.8966	High Similarity	NPD1552	Clinical (unspecified phase)
0.8954	High Similarity	NPD7096	Clinical (unspecified phase)
0.8924	High Similarity	NPD6167	Clinical (unspecified phase)
0.8924	High Similarity	NPD6166	Phase 2
0.8924	High Similarity	NPD6168	Clinical (unspecified phase)
0.8904	High Similarity	NPD1549	Phase 2
0.8896	High Similarity	NPD8443	Clinical (unspecified phase)
0.88	High Similarity	NPD7410	Clinical (unspecified phase)
0.8766	High Similarity	NPD6801	Discontinued
0.8734	High Similarity	NPD6959	Discontinued
0.8704	High Similarity	NPD7074	Phase 3
0.8701	High Similarity	NPD7411	Suspended
0.8642	High Similarity	NPD7054	Approved
0.8639	High Similarity	NPD2796	Approved
0.859	High Similarity	NPD2801	Approved
0.8589	High Similarity	NPD7472	Approved
0.8571	High Similarity	NPD1510	Phase 2
0.8553	High Similarity	NPD5494	Approved
0.8537	High Similarity	NPD6797	Phase 2
0.8487	Intermediate Similarity	NPD6799	Approved
0.8487	Intermediate Similarity	NPD1511	Approved
0.8485	Intermediate Similarity	NPD7251	Discontinued
0.8481	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7819	Suspended
0.8434	Intermediate Similarity	NPD7808	Phase 3
0.8425	Intermediate Similarity	NPD1240	Approved
0.8377	Intermediate Similarity	NPD1512	Approved
0.8373	Intermediate Similarity	NPD6559	Discontinued
0.8365	Intermediate Similarity	NPD3882	Suspended
0.8354	Intermediate Similarity	NPD3818	Discontinued
0.8344	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5403	Approved
0.8311	Intermediate Similarity	NPD1607	Approved
0.8302	Intermediate Similarity	NPD3817	Phase 2
0.828	Intermediate Similarity	NPD6599	Discontinued
0.825	Intermediate Similarity	NPD7768	Phase 2
0.8224	Intermediate Similarity	NPD2800	Approved
0.8214	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD5401	Approved
0.8193	Intermediate Similarity	NPD5844	Phase 1
0.8187	Intermediate Similarity	NPD5402	Approved
0.8105	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD3749	Approved
0.8052	Intermediate Similarity	NPD3750	Approved
0.8052	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD6232	Discontinued
0.7964	Intermediate Similarity	NPD7473	Discontinued
0.7962	Intermediate Similarity	NPD2533	Approved
0.7962	Intermediate Similarity	NPD2532	Approved
0.7962	Intermediate Similarity	NPD2534	Approved
0.7947	Intermediate Similarity	NPD6651	Approved
0.7922	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2935	Discontinued
0.7908	Intermediate Similarity	NPD1551	Phase 2
0.7901	Intermediate Similarity	NPD1465	Phase 2
0.7895	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1243	Approved
0.7862	Intermediate Similarity	NPD920	Approved
0.7853	Intermediate Similarity	NPD4360	Phase 2
0.7853	Intermediate Similarity	NPD4363	Phase 3
0.7841	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1613	Approved
0.7815	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6100	Approved
0.7792	Intermediate Similarity	NPD6099	Approved
0.7785	Intermediate Similarity	NPD4908	Phase 1
0.7778	Intermediate Similarity	NPD5953	Discontinued
0.7772	Intermediate Similarity	NPD7584	Approved
0.7765	Intermediate Similarity	NPD7286	Phase 2
0.7765	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD5124	Phase 1
0.7763	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD8312	Approved
0.7746	Intermediate Similarity	NPD8313	Approved
0.7736	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2799	Discontinued
0.7727	Intermediate Similarity	NPD3748	Approved
0.7727	Intermediate Similarity	NPD7033	Discontinued
0.7722	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3751	Discontinued
0.7692	Intermediate Similarity	NPD2424	Discontinued
0.7683	Intermediate Similarity	NPD8455	Phase 2
0.7682	Intermediate Similarity	NPD2313	Discontinued
0.7679	Intermediate Similarity	NPD3787	Discontinued
0.7673	Intermediate Similarity	NPD7390	Discontinued
0.7671	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2344	Approved
0.7619	Intermediate Similarity	NPD1247	Approved
0.7613	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD919	Approved
0.76	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD943	Approved
0.7561	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1610	Phase 2
0.755	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3226	Approved
0.7541	Intermediate Similarity	NPD6781	Approved
0.7541	Intermediate Similarity	NPD6780	Approved
0.7541	Intermediate Similarity	NPD6782	Approved
0.7541	Intermediate Similarity	NPD6776	Approved
0.7541	Intermediate Similarity	NPD6778	Approved
0.7541	Intermediate Similarity	NPD6777	Approved
0.7541	Intermediate Similarity	NPD6779	Approved
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD8151	Discontinued
0.7471	Intermediate Similarity	NPD5710	Approved
0.7471	Intermediate Similarity	NPD5711	Approved
0.7471	Intermediate Similarity	NPD3823	Discontinued
0.7467	Intermediate Similarity	NPD1203	Approved
0.7451	Intermediate Similarity	NPD6798	Discontinued
0.7439	Intermediate Similarity	NPD7458	Discontinued
0.7439	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2309	Approved
0.7434	Intermediate Similarity	NPD6832	Phase 2
0.7427	Intermediate Similarity	NPD3926	Phase 2
0.7421	Intermediate Similarity	NPD7783	Phase 2
0.7421	Intermediate Similarity	NPD1652	Phase 2
0.7421	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7698	Approved
0.7419	Intermediate Similarity	NPD7696	Phase 3
0.7419	Intermediate Similarity	NPD7697	Approved
0.7419	Intermediate Similarity	NPD7435	Discontinued
0.7419	Intermediate Similarity	NPD230	Phase 1
0.7418	Intermediate Similarity	NPD4361	Phase 2
0.7418	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8434	Phase 2
0.7416	Intermediate Similarity	NPD8150	Discontinued
0.7399	Intermediate Similarity	NPD7228	Approved
0.7397	Intermediate Similarity	NPD1548	Phase 1
0.7386	Intermediate Similarity	NPD4625	Phase 3
0.7354	Intermediate Similarity	NPD7585	Approved
0.7354	Intermediate Similarity	NPD7701	Phase 2
0.7351	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3268	Approved
0.7338	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2654	Approved
0.731	Intermediate Similarity	NPD7199	Phase 2
0.7308	Intermediate Similarity	NPD6355	Discontinued
0.7308	Intermediate Similarity	NPD1933	Approved
0.7305	Intermediate Similarity	NPD6844	Discontinued
0.7305	Intermediate Similarity	NPD37	Approved
0.7303	Intermediate Similarity	NPD2798	Approved
0.7302	Intermediate Similarity	NPD7583	Approved
0.7301	Intermediate Similarity	NPD4662	Approved
0.7301	Intermediate Similarity	NPD4661	Approved
0.7294	Intermediate Similarity	NPD6234	Discontinued
0.729	Intermediate Similarity	NPD6233	Phase 2
0.7287	Intermediate Similarity	NPD7870	Phase 2
0.7287	Intermediate Similarity	NPD7871	Phase 2
0.7283	Intermediate Similarity	NPD2403	Approved
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD4966	Approved
0.7278	Intermediate Similarity	NPD4965	Approved
0.7273	Intermediate Similarity	NPD6823	Phase 2
0.7268	Intermediate Similarity	NPD6535	Approved
0.7268	Intermediate Similarity	NPD6534	Approved
0.7267	Intermediate Similarity	NPD9717	Approved
0.7263	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7699	Phase 2
0.7243	Intermediate Similarity	NPD7700	Phase 2
0.7237	Intermediate Similarity	NPD2797	Approved
0.7222	Intermediate Similarity	NPD6190	Approved
0.7219	Intermediate Similarity	NPD4749	Approved
0.7216	Intermediate Similarity	NPD1729	Discontinued
0.7215	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4536	Approved
0.7215	Intermediate Similarity	NPD4538	Approved
0.7205	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD422	Phase 1
0.7197	Intermediate Similarity	NPD447	Suspended
0.7197	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7874	Approved
0.7184	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3225	Approved
0.7169	Intermediate Similarity	NPD1653	Approved
0.7168	Intermediate Similarity	NPD7229	Phase 3
0.716	Intermediate Similarity	NPD5760	Phase 2
0.716	Intermediate Similarity	NPD5761	Phase 2
0.7152	Intermediate Similarity	NPD5049	Phase 3
0.715	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD2861	Phase 2

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