NPASS Compound

Structure

NPC150123 OpenBabel07101719122D 29 32 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 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 1.0000 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 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 2 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 -3.4641 1.0000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 1 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 2 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 1.7321 3.0000 0.0000 C 0 0 1 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 -4.3301 1.5000 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 -3.0000 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 4.0000 0.0000 O 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 2 10 2 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 7 16 2 0 0 0 0 8 15 1 0 0 0 0 8 17 1 0 0 0 0 9 1 1 1 0 0 0 9 20 1 0 0 0 0 9 28 1 0 0 0 0 10 16 1 0 0 0 0 11 22 1 0 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 19 2 0 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 14 25 2 0 0 0 0 15 20 1 0 0 0 0 15 26 1 6 0 0 0 16 29 1 0 0 0 0 17 19 1 1 0 0 0 17 28 1 0 0 0 0 18 21 2 0 0 0 0 19 21 1 0 0 0 0 20 27 1 1 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.12
Volume:	386.776
LogP:	3.202
LogD:	1.335
LogS:	-4.045
# Rotatable Bonds:	2
TPSA:	140.59
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.441
Synthetic Accessibility Score:	3.971
Fsp3:	0.286
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:	-5.845
MDCK Permeability:	5.030079137213761e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.292
20% Bioavailability (F20%):	0.839
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	96.5836410522461%
Volume Distribution (VD):	0.725
Pgp-substrate:	6.473367691040039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.802
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.686
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.418
CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	0.172
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	4.752
Half-life (T1/2):	0.717

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.601
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.788
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.897
Carcinogencity:	0.387
Eye Corrosion:	0.003
Eye Irritation:	0.407
Respiratory Toxicity:	0.296

Download Data

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

Natural Product: NPC150123

Natural Product ID:	NPC150123
*Common Name:**	8-C-Beta-D-Boivinopyranosylapigenin
IUPAC Name:	8-[(2R,4S,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	BZHMTPJDQAFTNF-MXKBHJLWSA-N
Standard InCHI:	InChI=1S/C21H20O8/c1-9-20(27)15(26)8-17(28-9)19-13(24)6-12(23)18-14(25)7-16(29-21(18)19)10-2-4-11(22)5-3-10/h2-7,9,15,17,20,22-24,26-27H,8H2,1H3/t9-,15+,17-,20+/m1/s1
SMILES:	C[C@@H]1[C@@H]([C@H](C[C@H](c2c(cc(c3c(=O)cc(c4ccc(cc4)O)oc23)O)O)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011651
PubChem CID:	57332513
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001737] Flavonoid C-glycosides [CHEMONTID:0003535] Flavonoid 8-C-glycosides

*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
NPO32718	chrysopogon aciculatis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22272829]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	74980.0	nM	PMID[494128]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	11960.0	nM	PMID[494128]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	10000.0	nM	PMID[494128]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	2580.0	nM	PMID[494128]

☑ 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 NPC150123 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	398
0.1-0.2	1576
0.2-0.3	3456
0.3-0.4	8989
0.4-0.5	9768
0.5-0.6	3855
0.6-0.7	5468
0.7-0.8	4618
0.8-0.85	2102
0.85-0.9	2115
0.9-0.95	335
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC244583
1.0	High Similarity	NPC161881
1.0	High Similarity	NPC56232
1.0	High Similarity	NPC10807
0.9931	High Similarity	NPC209846
0.9931	High Similarity	NPC289774
0.9931	High Similarity	NPC328740
0.9931	High Similarity	NPC477897
0.9864	High Similarity	NPC304745
0.9864	High Similarity	NPC111341
0.9796	High Similarity	NPC7989
0.9796	High Similarity	NPC326592
0.9796	High Similarity	NPC472583
0.9796	High Similarity	NPC112701
0.9796	High Similarity	NPC223701
0.9796	High Similarity	NPC109594
0.9796	High Similarity	NPC268193
0.973	High Similarity	NPC470681
0.973	High Similarity	NPC207809
0.973	High Similarity	NPC217706
0.973	High Similarity	NPC304207
0.973	High Similarity	NPC259710
0.973	High Similarity	NPC48579
0.9728	High Similarity	NPC475790
0.9726	High Similarity	NPC124478
0.9726	High Similarity	NPC177308
0.9724	High Similarity	NPC10097
0.9662	High Similarity	NPC248793
0.9662	High Similarity	NPC180301
0.9662	High Similarity	NPC469405
0.966	High Similarity	NPC244577
0.966	High Similarity	NPC319910
0.966	High Similarity	NPC474023
0.966	High Similarity	NPC262038
0.966	High Similarity	NPC472422
0.966	High Similarity	NPC474021
0.966	High Similarity	NPC471677
0.966	High Similarity	NPC262039
0.966	High Similarity	NPC472420
0.966	High Similarity	NPC263384
0.966	High Similarity	NPC278476
0.966	High Similarity	NPC254412
0.966	High Similarity	NPC471676
0.9658	High Similarity	NPC139966
0.9658	High Similarity	NPC307052
0.9658	High Similarity	NPC89442
0.9597	High Similarity	NPC477958
0.9595	High Similarity	NPC243171
0.9595	High Similarity	NPC138288
0.9595	High Similarity	NPC171651
0.9595	High Similarity	NPC35567
0.9595	High Similarity	NPC216035
0.9595	High Similarity	NPC217149
0.9592	High Similarity	NPC105136
0.9586	High Similarity	NPC472629
0.9539	High Similarity	NPC26326
0.9536	High Similarity	NPC117418
0.9536	High Similarity	NPC53545
0.9533	High Similarity	NPC78492
0.9533	High Similarity	NPC215917
0.9533	High Similarity	NPC208152
0.9533	High Similarity	NPC10754
0.9533	High Similarity	NPC20530
0.953	High Similarity	NPC236756
0.953	High Similarity	NPC244250
0.953	High Similarity	NPC293286
0.953	High Similarity	NPC20907
0.953	High Similarity	NPC311579
0.9527	High Similarity	NPC472636
0.9527	High Similarity	NPC471675
0.9524	High Similarity	NPC5173
0.9524	High Similarity	NPC472628
0.9521	High Similarity	NPC472627
0.9521	High Similarity	NPC85773
0.9521	High Similarity	NPC473077
0.9521	High Similarity	NPC296998
0.9517	High Similarity	NPC470890
0.9517	High Similarity	NPC124780
0.9517	High Similarity	NPC224714
0.9517	High Similarity	NPC87486
0.9477	High Similarity	NPC131745
0.9477	High Similarity	NPC44947
0.9474	High Similarity	NPC475784
0.9467	High Similarity	NPC477530
0.9467	High Similarity	NPC476169
0.9463	High Similarity	NPC476238
0.9463	High Similarity	NPC327269
0.9463	High Similarity	NPC285623
0.9463	High Similarity	NPC31627
0.9463	High Similarity	NPC473996
0.9459	High Similarity	NPC472633
0.9452	High Similarity	NPC214774
0.9452	High Similarity	NPC67805
0.9452	High Similarity	NPC267375
0.9452	High Similarity	NPC88964
0.9452	High Similarity	NPC312973
0.9452	High Similarity	NPC470647
0.9452	High Similarity	NPC111786
0.9452	High Similarity	NPC301276
0.9452	High Similarity	NPC474302
0.9452	High Similarity	NPC54577
0.9452	High Similarity	NPC195621
0.9452	High Similarity	NPC475052
0.9452	High Similarity	NPC246948
0.9452	High Similarity	NPC83357
0.9452	High Similarity	NPC142405
0.9452	High Similarity	NPC20488
0.9452	High Similarity	NPC176229
0.9416	High Similarity	NPC66087
0.9416	High Similarity	NPC183672
0.9416	High Similarity	NPC278419
0.9416	High Similarity	NPC257566
0.9416	High Similarity	NPC124155
0.9416	High Similarity	NPC179198
0.9412	High Similarity	NPC474038
0.9412	High Similarity	NPC142252
0.9412	High Similarity	NPC47923
0.9412	High Similarity	NPC289771
0.9408	High Similarity	NPC123544
0.9408	High Similarity	NPC73511
0.9404	High Similarity	NPC471787
0.94	High Similarity	NPC88983
0.9396	High Similarity	NPC472423
0.9396	High Similarity	NPC474772
0.9396	High Similarity	NPC472580
0.9396	High Similarity	NPC474744
0.9388	High Similarity	NPC23728
0.9388	High Similarity	NPC44721
0.9388	High Similarity	NPC176869
0.9388	High Similarity	NPC222298
0.9388	High Similarity	NPC51070
0.9388	High Similarity	NPC283234
0.9388	High Similarity	NPC470670
0.9388	High Similarity	NPC3779
0.9388	High Similarity	NPC40086
0.9388	High Similarity	NPC476182
0.9388	High Similarity	NPC122828
0.9388	High Similarity	NPC473133
0.9388	High Similarity	NPC110303
0.9388	High Similarity	NPC211466
0.9388	High Similarity	NPC47388
0.9388	High Similarity	NPC91902
0.9384	High Similarity	NPC319752
0.9379	High Similarity	NPC166934
0.9379	High Similarity	NPC220998
0.9379	High Similarity	NPC37496
0.9379	High Similarity	NPC64915
0.9379	High Similarity	NPC107572
0.9379	High Similarity	NPC227579
0.9379	High Similarity	NPC10937
0.9379	High Similarity	NPC40833
0.9379	High Similarity	NPC223500
0.9379	High Similarity	NPC76338
0.9379	High Similarity	NPC177354
0.9379	High Similarity	NPC1089
0.9379	High Similarity	NPC265040
0.9379	High Similarity	NPC194432
0.9379	High Similarity	NPC78
0.9379	High Similarity	NPC166482
0.9379	High Similarity	NPC76372
0.9379	High Similarity	NPC324436
0.9379	High Similarity	NPC161506
0.9379	High Similarity	NPC32739
0.9379	High Similarity	NPC66515
0.9379	High Similarity	NPC328164
0.9379	High Similarity	NPC306829
0.9379	High Similarity	NPC167624
0.9379	High Similarity	NPC148757
0.9379	High Similarity	NPC125855
0.9379	High Similarity	NPC296917
0.9379	High Similarity	NPC228504
0.9379	High Similarity	NPC324134
0.9379	High Similarity	NPC182852
0.9351	High Similarity	NPC259834
0.9346	High Similarity	NPC192686
0.9346	High Similarity	NPC118256
0.9346	High Similarity	NPC471976
0.9346	High Similarity	NPC472320
0.9346	High Similarity	NPC119209
0.9342	High Similarity	NPC313163
0.9342	High Similarity	NPC156457
0.9342	High Similarity	NPC284820
0.9342	High Similarity	NPC23817
0.9342	High Similarity	NPC472598
0.9342	High Similarity	NPC474055
0.9342	High Similarity	NPC258035
0.9342	High Similarity	NPC473272
0.9342	High Similarity	NPC197896
0.9342	High Similarity	NPC161749
0.9338	High Similarity	NPC95090
0.9338	High Similarity	NPC27408
0.9338	High Similarity	NPC321779
0.9338	High Similarity	NPC470603
0.9338	High Similarity	NPC470605
0.9338	High Similarity	NPC470604
0.9333	High Similarity	NPC256141
0.9333	High Similarity	NPC210597
0.9333	High Similarity	NPC477957
0.9329	High Similarity	NPC472421
0.9329	High Similarity	NPC29777

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 NPC150123 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	854
0.2-0.3	1624
0.3-0.4	2591
0.4-0.5	2012
0.5-0.6	1110
0.6-0.7	385
0.7-0.8	145
0.8-0.85	32
0.85-0.9	29
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9726	High Similarity	NPD4380	Phase 2
0.9342	High Similarity	NPD4381	Clinical (unspecified phase)
0.9272	High Similarity	NPD2393	Clinical (unspecified phase)
0.9252	High Similarity	NPD4378	Clinical (unspecified phase)
0.9216	High Similarity	NPD7075	Discontinued
0.9177	High Similarity	NPD7804	Clinical (unspecified phase)
0.9085	High Similarity	NPD8443	Clinical (unspecified phase)
0.9079	High Similarity	NPD1934	Approved
0.9079	High Similarity	NPD6801	Discontinued
0.9034	High Similarity	NPD1552	Clinical (unspecified phase)
0.9034	High Similarity	NPD1550	Clinical (unspecified phase)
0.902	High Similarity	NPD7096	Clinical (unspecified phase)
0.8993	High Similarity	NPD7410	Clinical (unspecified phase)
0.8987	High Similarity	NPD6166	Phase 2
0.8987	High Similarity	NPD6168	Clinical (unspecified phase)
0.8987	High Similarity	NPD6167	Clinical (unspecified phase)
0.8973	High Similarity	NPD1549	Phase 2
0.8889	High Similarity	NPD7411	Suspended
0.8836	High Similarity	NPD2796	Approved
0.882	High Similarity	NPD7054	Approved
0.8774	High Similarity	NPD2801	Approved
0.8767	High Similarity	NPD1510	Phase 2
0.8765	High Similarity	NPD7074	Phase 3
0.8765	High Similarity	NPD7472	Approved
0.8712	High Similarity	NPD6797	Phase 2
0.8679	High Similarity	NPD6959	Discontinued
0.8675	High Similarity	NPD1511	Approved
0.8659	High Similarity	NPD7251	Discontinued
0.8654	High Similarity	NPD7819	Suspended
0.8642	High Similarity	NPD3818	Discontinued
0.8627	High Similarity	NPD5403	Approved
0.8606	High Similarity	NPD7808	Phase 3
0.8599	High Similarity	NPD3817	Phase 2
0.8562	High Similarity	NPD1512	Approved
0.8553	High Similarity	NPD6799	Approved
0.8545	High Similarity	NPD6559	Discontinued
0.8544	High Similarity	NPD4868	Clinical (unspecified phase)
0.8519	High Similarity	NPD7852	Clinical (unspecified phase)
0.85	High Similarity	NPD5494	Approved
0.8497	Intermediate Similarity	NPD5401	Approved
0.8494	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1240	Approved
0.8481	Intermediate Similarity	NPD5402	Approved
0.8428	Intermediate Similarity	NPD3882	Suspended
0.8378	Intermediate Similarity	NPD1607	Approved
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8313	Intermediate Similarity	NPD7768	Phase 2
0.8253	Intermediate Similarity	NPD5844	Phase 1
0.8235	Intermediate Similarity	NPD3750	Approved
0.8171	Intermediate Similarity	NPD6232	Discontinued
0.817	Intermediate Similarity	NPD2800	Approved
0.817	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7473	Discontinued
0.8117	Intermediate Similarity	NPD4628	Phase 3
0.8059	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD920	Approved
0.8037	Intermediate Similarity	NPD3749	Approved
0.8023	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6651	Approved
0.8011	Intermediate Similarity	NPD4363	Phase 3
0.8011	Intermediate Similarity	NPD4360	Phase 2
0.7987	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2935	Discontinued
0.7974	Intermediate Similarity	NPD1551	Phase 2
0.7941	Intermediate Similarity	NPD5953	Discontinued
0.7935	Intermediate Similarity	NPD1243	Approved
0.7923	Intermediate Similarity	NPD7584	Approved
0.7911	Intermediate Similarity	NPD2533	Approved
0.7911	Intermediate Similarity	NPD2534	Approved
0.7911	Intermediate Similarity	NPD2532	Approved
0.7911	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD3748	Approved
0.7898	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1613	Approved
0.7867	Intermediate Similarity	NPD2313	Discontinued
0.7853	Intermediate Similarity	NPD1465	Phase 2
0.7852	Intermediate Similarity	NPD4908	Phase 1
0.7829	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5124	Phase 1
0.7824	Intermediate Similarity	NPD7286	Phase 2
0.7803	Intermediate Similarity	NPD8313	Approved
0.7803	Intermediate Similarity	NPD8312	Approved
0.7792	Intermediate Similarity	NPD2799	Discontinued
0.7792	Intermediate Similarity	NPD7033	Discontinued
0.7784	Intermediate Similarity	NPD1247	Approved
0.7771	Intermediate Similarity	NPD919	Approved
0.7744	Intermediate Similarity	NPD8455	Phase 2
0.774	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7390	Discontinued
0.7716	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD2344	Approved
0.7661	Intermediate Similarity	NPD3751	Discontinued
0.7647	Intermediate Similarity	NPD943	Approved
0.7643	Intermediate Similarity	NPD2424	Discontinued
0.7633	Intermediate Similarity	NPD3787	Discontinued
0.7628	Intermediate Similarity	NPD6099	Approved
0.7628	Intermediate Similarity	NPD6100	Approved
0.7622	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7616	Intermediate Similarity	NPD6832	Phase 2
0.7616	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6781	Approved
0.7596	Intermediate Similarity	NPD6776	Approved
0.7596	Intermediate Similarity	NPD6778	Approved
0.7596	Intermediate Similarity	NPD6777	Approved
0.7596	Intermediate Similarity	NPD6779	Approved
0.7596	Intermediate Similarity	NPD6782	Approved
0.7596	Intermediate Similarity	NPD6780	Approved
0.7595	Intermediate Similarity	NPD1652	Phase 2
0.7588	Intermediate Similarity	NPD3926	Phase 2
0.7586	Intermediate Similarity	NPD1548	Phase 1
0.758	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4361	Phase 2
0.7566	Intermediate Similarity	NPD3027	Phase 3
0.7564	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1203	Approved
0.7516	Intermediate Similarity	NPD6798	Discontinued
0.7516	Intermediate Similarity	NPD3268	Approved
0.75	Intermediate Similarity	NPD7585	Approved
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2798	Approved
0.7473	Intermediate Similarity	NPD7435	Discontinued
0.7472	Intermediate Similarity	NPD8150	Discontinued
0.7472	Intermediate Similarity	NPD8434	Phase 2
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.747	Intermediate Similarity	NPD6844	Discontinued
0.746	Intermediate Similarity	NPD8151	Discontinued
0.7447	Intermediate Similarity	NPD7583	Approved
0.7442	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1653	Approved
0.7438	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3823	Discontinued
0.7427	Intermediate Similarity	NPD5711	Approved
0.7427	Intermediate Similarity	NPD5710	Approved
0.7417	Intermediate Similarity	NPD2797	Approved
0.7383	Intermediate Similarity	NPD422	Phase 1
0.7382	Intermediate Similarity	NPD7783	Phase 2
0.7382	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7697	Approved
0.738	Intermediate Similarity	NPD7696	Phase 3
0.738	Intermediate Similarity	NPD7698	Approved
0.7372	Intermediate Similarity	NPD6355	Discontinued
0.7372	Intermediate Similarity	NPD1933	Approved
0.7372	Intermediate Similarity	NPD230	Phase 1
0.7365	Intermediate Similarity	NPD37	Approved
0.7362	Intermediate Similarity	NPD4662	Approved
0.7362	Intermediate Similarity	NPD4661	Approved
0.7356	Intermediate Similarity	NPD7228	Approved
0.7355	Intermediate Similarity	NPD6233	Phase 2
0.7353	Intermediate Similarity	NPD6234	Discontinued
0.7351	Intermediate Similarity	NPD3225	Approved
0.7342	Intermediate Similarity	NPD4308	Phase 3
0.734	Intermediate Similarity	NPD7871	Phase 2
0.734	Intermediate Similarity	NPD7870	Phase 2
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7337	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4967	Phase 2
0.7337	Intermediate Similarity	NPD4966	Approved
0.7333	Intermediate Similarity	NPD9717	Approved
0.7326	Intermediate Similarity	NPD6823	Phase 2
0.7322	Intermediate Similarity	NPD6534	Approved
0.7322	Intermediate Similarity	NPD6535	Approved
0.7318	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7701	Phase 2
0.7305	Intermediate Similarity	NPD5889	Approved
0.7305	Intermediate Similarity	NPD5890	Approved
0.7288	Intermediate Similarity	NPD7685	Pre-registration
0.7284	Intermediate Similarity	NPD6190	Approved
0.7283	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4538	Approved
0.7278	Intermediate Similarity	NPD4536	Approved
0.7278	Intermediate Similarity	NPD4288	Approved
0.7278	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1729	Discontinued
0.7267	Intermediate Similarity	NPD2654	Approved
0.7267	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD447	Suspended
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7874	Approved
0.724	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7229	Phase 3
0.7208	Intermediate Similarity	NPD2861	Phase 2
0.7204	Intermediate Similarity	NPD7699	Phase 2
0.7204	Intermediate Similarity	NPD7700	Phase 2
0.7202	Intermediate Similarity	NPD7801	Approved
0.7197	Intermediate Similarity	NPD4060	Phase 1

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