NPASS Compound

Structure

NPC470134 OpenBabel07101718242D 29 32 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 1.7321 1.0000 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 -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 1.5000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 14 2 0 0 0 0 5 17 2 0 0 0 0 6 8 1 0 0 0 0 6 13 2 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 11 20 1 0 0 0 0 12 19 2 0 0 0 0 12 21 1 0 0 0 0 14 17 1 0 0 0 0 15 24 1 0 0 0 0 16 21 2 0 0 0 0 16 23 1 0 0 0 0 17 25 1 0 0 0 0 18 22 1 0 0 0 0 18 26 2 0 0 0 0 19 22 1 0 0 0 0 19 27 1 0 0 0 0 20 13 1 1 0 0 0 20 29 1 0 0 0 0 21 28 1 0 0 0 0 22 23 2 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.13
Volume:	398.515
LogP:	4.264
LogD:	3.407
LogS:	-3.97
# Rotatable Bonds:	4
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.618
Synthetic Accessibility Score:	3.032
Fsp3:	0.174
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:	-4.762
MDCK Permeability:	1.5167930541792884e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	98.28298950195312%
Volume Distribution (VD):	0.464
Pgp-substrate:	1.5623737573623657%

ADMET: Metabolism

CYP1A2-inhibitor:	0.492
CYP1A2-substrate:	0.778
CYP2C19-inhibitor:	0.95
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.911
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.829
CYP2D6-substrate:	0.807
CYP3A4-inhibitor:	0.654
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	13.823
Half-life (T1/2):	0.62

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.091
Rat Oral Acute Toxicity:	0.812
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.915
Carcinogencity:	0.619
Eye Corrosion:	0.003
Eye Irritation:	0.9
Respiratory Toxicity:	0.707

Download Data

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

Natural Product: NPC470134

Natural Product ID:	NPC470134
*Common Name:**	Epi-Methylphelligrin B
IUPAC Name:	(2S)-5-hydroxy-2-(4-hydroxyphenyl)-8-[(2-hydroxyphenyl)methyl]-7-methoxy-2,3-dihydrochromen-4-one
Synonyms:	Epi-Methylphelligrin B
Standard InCHIKey:	BOEWXOMRJRXFIU-FQEVSTJZSA-N
Standard InCHI:	InChI=1S/C23H20O6/c1-28-21-12-19(27)22-18(26)11-20(13-6-8-15(24)9-7-13)29-23(22)16(21)10-14-4-2-3-5-17(14)25/h2-9,12,20,24-25,27H,10-11H2,1H3/t20-/m0/s1
SMILES:	COC1=C(C2=C(C(=O)CC(O2)C3=CC=C(C=C3)O)C(=C1)O)CC4=CC=CC=C4O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1780033
PubChem CID:	53248707
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO32484	phellinus baumii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20708931]
NPO32484	phellinus baumii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21531558]
NPO32484	phellinus baumii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26077494]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	22460.0	nM	PMID[485171]

☑ 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 NPC470134 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	367
0.1-0.2	1589
0.2-0.3	3930
0.3-0.4	10581
0.4-0.5	7749
0.5-0.6	3725
0.6-0.7	5659
0.7-0.8	5025
0.8-0.85	2274
0.85-0.9	1080
0.9-0.95	553
0.95-1	165

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470133
1.0	High Similarity	NPC109183
1.0	High Similarity	NPC470131
1.0	High Similarity	NPC473078
1.0	High Similarity	NPC470132
0.9928	High Similarity	NPC470136
0.9928	High Similarity	NPC470135
0.9928	High Similarity	NPC39045
0.9857	High Similarity	NPC228779
0.9789	High Similarity	NPC3642
0.9784	High Similarity	NPC125855
0.9784	High Similarity	NPC107572
0.9784	High Similarity	NPC265040
0.9784	High Similarity	NPC227579
0.9784	High Similarity	NPC10937
0.9784	High Similarity	NPC324436
0.9784	High Similarity	NPC223500
0.9784	High Similarity	NPC40833
0.9784	High Similarity	NPC167624
0.9784	High Similarity	NPC1089
0.9784	High Similarity	NPC76372
0.9784	High Similarity	NPC161506
0.9784	High Similarity	NPC78
0.9784	High Similarity	NPC66515
0.9784	High Similarity	NPC166482
0.9784	High Similarity	NPC194432
0.9784	High Similarity	NPC32739
0.9784	High Similarity	NPC328164
0.9784	High Similarity	NPC64915
0.9784	High Similarity	NPC148757
0.9784	High Similarity	NPC324134
0.9784	High Similarity	NPC228504
0.9784	High Similarity	NPC220998
0.9784	High Similarity	NPC182852
0.9784	High Similarity	NPC296917
0.9784	High Similarity	NPC37496
0.9784	High Similarity	NPC166934
0.9784	High Similarity	NPC177354
0.9784	High Similarity	NPC76338
0.9784	High Similarity	NPC306829
0.9718	High Similarity	NPC122894
0.9716	High Similarity	NPC267375
0.9716	High Similarity	NPC301276
0.9716	High Similarity	NPC54577
0.9716	High Similarity	NPC214774
0.9716	High Similarity	NPC176229
0.9716	High Similarity	NPC312973
0.9716	High Similarity	NPC20488
0.9716	High Similarity	NPC195621
0.9716	High Similarity	NPC475052
0.9716	High Similarity	NPC83357
0.9716	High Similarity	NPC67805
0.9716	High Similarity	NPC246948
0.9716	High Similarity	NPC111786
0.9716	High Similarity	NPC88964
0.9716	High Similarity	NPC470647
0.9716	High Similarity	NPC142405
0.9714	High Similarity	NPC68104
0.9714	High Similarity	NPC164980
0.9714	High Similarity	NPC221432
0.9714	High Similarity	NPC91560
0.9714	High Similarity	NPC185276
0.9714	High Similarity	NPC75049
0.9714	High Similarity	NPC257097
0.9714	High Similarity	NPC107177
0.9714	High Similarity	NPC175504
0.9714	High Similarity	NPC149026
0.9714	High Similarity	NPC214166
0.9714	High Similarity	NPC77794
0.9714	High Similarity	NPC169591
0.9714	High Similarity	NPC316816
0.9714	High Similarity	NPC125894
0.9714	High Similarity	NPC278249
0.9714	High Similarity	NPC223812
0.9714	High Similarity	NPC85162
0.9714	High Similarity	NPC39329
0.9714	High Similarity	NPC143896
0.9714	High Similarity	NPC310130
0.9714	High Similarity	NPC478086
0.9714	High Similarity	NPC150408
0.9714	High Similarity	NPC81697
0.9712	High Similarity	NPC258630
0.9712	High Similarity	NPC324386
0.9712	High Similarity	NPC213322
0.9712	High Similarity	NPC17170
0.9712	High Similarity	NPC110038
0.9712	High Similarity	NPC156190
0.9712	High Similarity	NPC166689
0.9712	High Similarity	NPC4743
0.9712	High Similarity	NPC312391
0.9712	High Similarity	NPC96408
0.9712	High Similarity	NPC279650
0.9712	High Similarity	NPC248372
0.9653	High Similarity	NPC178484
0.9648	High Similarity	NPC296998
0.9648	High Similarity	NPC473077
0.9648	High Similarity	NPC283234
0.9648	High Similarity	NPC110303
0.9648	High Similarity	NPC23728
0.9645	High Similarity	NPC473013
0.9645	High Similarity	NPC197252
0.9645	High Similarity	NPC236766
0.9645	High Similarity	NPC235217
0.9645	High Similarity	NPC473014
0.9645	High Similarity	NPC209040
0.9645	High Similarity	NPC473015
0.9645	High Similarity	NPC131579
0.9645	High Similarity	NPC131568
0.9645	High Similarity	NPC319752
0.964	High Similarity	NPC110228
0.964	High Similarity	NPC188243
0.964	High Similarity	NPC6407
0.958	High Similarity	NPC160821
0.958	High Similarity	NPC132592
0.958	High Similarity	NPC161191
0.9577	High Similarity	NPC285630
0.9577	High Similarity	NPC127059
0.9577	High Similarity	NPC474161
0.9577	High Similarity	NPC472629
0.9577	High Similarity	NPC476088
0.9571	High Similarity	NPC14871
0.9571	High Similarity	NPC3188
0.9568	High Similarity	NPC265871
0.9568	High Similarity	NPC150648
0.9568	High Similarity	NPC310135
0.9568	High Similarity	NPC225153
0.9568	High Similarity	NPC20709
0.9568	High Similarity	NPC222342
0.9568	High Similarity	NPC140890
0.9568	High Similarity	NPC329203
0.9568	High Similarity	NPC274784
0.9517	High Similarity	NPC78835
0.9517	High Similarity	NPC309512
0.9517	High Similarity	NPC204561
0.9517	High Similarity	NPC148945
0.9517	High Similarity	NPC316960
0.9517	High Similarity	NPC317715
0.9514	High Similarity	NPC473016
0.951	High Similarity	NPC472627
0.951	High Similarity	NPC10990
0.951	High Similarity	NPC300988
0.9507	High Similarity	NPC271288
0.9507	High Similarity	NPC124780
0.9507	High Similarity	NPC87486
0.9507	High Similarity	NPC470890
0.9504	High Similarity	NPC147145
0.95	High Similarity	NPC129853
0.95	High Similarity	NPC76445
0.95	High Similarity	NPC69769
0.95	High Similarity	NPC284550
0.95	High Similarity	NPC159275
0.95	High Similarity	NPC241100
0.9496	High Similarity	NPC251681
0.9496	High Similarity	NPC243528
0.9452	High Similarity	NPC39154
0.9452	High Similarity	NPC208011
0.9452	High Similarity	NPC174086
0.9452	High Similarity	NPC115601
0.9452	High Similarity	NPC78324
0.9448	High Similarity	NPC472633
0.9444	High Similarity	NPC189087
0.9444	High Similarity	NPC321623
0.9441	High Similarity	NPC476153
0.9441	High Similarity	NPC187282
0.9441	High Similarity	NPC24136
0.9441	High Similarity	NPC215885
0.9441	High Similarity	NPC290133
0.9441	High Similarity	NPC2416
0.9437	High Similarity	NPC166138
0.9437	High Similarity	NPC106985
0.9437	High Similarity	NPC471621
0.9437	High Similarity	NPC38219
0.9437	High Similarity	NPC219915
0.9437	High Similarity	NPC18585
0.9433	High Similarity	NPC110969
0.9433	High Similarity	NPC26238
0.9433	High Similarity	NPC282300
0.9429	High Similarity	NPC220062
0.9429	High Similarity	NPC78913
0.9429	High Similarity	NPC53181
0.9429	High Similarity	NPC55018
0.9429	High Similarity	NPC216978
0.9429	High Similarity	NPC301217
0.9429	High Similarity	NPC303633
0.9429	High Similarity	NPC217186
0.9429	High Similarity	NPC18260
0.9429	High Similarity	NPC96565
0.9424	High Similarity	NPC287246
0.9424	High Similarity	NPC295261
0.9424	High Similarity	NPC259685
0.9424	High Similarity	NPC79943
0.9424	High Similarity	NPC107586
0.9424	High Similarity	NPC296490
0.9424	High Similarity	NPC32441
0.9424	High Similarity	NPC243083
0.9424	High Similarity	NPC13768
0.9424	High Similarity	NPC12296
0.9392	High Similarity	NPC208152
0.9392	High Similarity	NPC78492
0.9388	High Similarity	NPC20907

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 NPC470134 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	949
0.2-0.3	1490
0.3-0.4	2609
0.4-0.5	1898
0.5-0.6	1207
0.6-0.7	447
0.7-0.8	154
0.8-0.85	38
0.85-0.9	19
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9456	High Similarity	NPD8443	Clinical (unspecified phase)
0.9424	High Similarity	NPD1550	Clinical (unspecified phase)
0.9424	High Similarity	NPD1552	Clinical (unspecified phase)
0.9384	High Similarity	NPD7411	Suspended
0.9371	High Similarity	NPD7410	Clinical (unspecified phase)
0.9357	High Similarity	NPD1549	Phase 2
0.9236	High Similarity	NPD4378	Clinical (unspecified phase)
0.9128	High Similarity	NPD2393	Clinical (unspecified phase)
0.9054	High Similarity	NPD4380	Phase 2
0.8947	High Similarity	NPD7075	Discontinued
0.8944	High Similarity	NPD2796	Approved
0.8896	High Similarity	NPD6959	Discontinued
0.8874	High Similarity	NPD7096	Clinical (unspecified phase)
0.8873	High Similarity	NPD1510	Phase 2
0.8857	High Similarity	NPD1240	Approved
0.8846	High Similarity	NPD7852	Clinical (unspecified phase)
0.8808	High Similarity	NPD1934	Approved
0.8759	High Similarity	NPD7421	Clinical (unspecified phase)
0.8758	High Similarity	NPD7768	Phase 2
0.875	High Similarity	NPD7819	Suspended
0.8732	High Similarity	NPD1607	Approved
0.8726	High Similarity	NPD6166	Phase 2
0.8726	High Similarity	NPD6168	Clinical (unspecified phase)
0.8726	High Similarity	NPD6167	Clinical (unspecified phase)
0.8701	High Similarity	NPD4381	Clinical (unspecified phase)
0.8684	High Similarity	NPD6801	Discontinued
0.8562	High Similarity	NPD7804	Clinical (unspecified phase)
0.8523	High Similarity	NPD6799	Approved
0.8462	Intermediate Similarity	NPD3749	Approved
0.8451	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1511	Approved
0.8397	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD2801	Approved
0.8354	Intermediate Similarity	NPD5494	Approved
0.8322	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD3750	Approved
0.8312	Intermediate Similarity	NPD6599	Discontinued
0.831	Intermediate Similarity	NPD4908	Phase 1
0.8289	Intermediate Similarity	NPD1512	Approved
0.8282	Intermediate Similarity	NPD7074	Phase 3
0.828	Intermediate Similarity	NPD3882	Suspended
0.8255	Intermediate Similarity	NPD2800	Approved
0.8235	Intermediate Similarity	NPD5403	Approved
0.8221	Intermediate Similarity	NPD7054	Approved
0.8221	Intermediate Similarity	NPD5844	Phase 1
0.8219	Intermediate Similarity	NPD6651	Approved
0.8182	Intermediate Similarity	NPD6559	Discontinued
0.8176	Intermediate Similarity	NPD1551	Phase 2
0.8171	Intermediate Similarity	NPD7472	Approved
0.8137	Intermediate Similarity	NPD6232	Discontinued
0.8121	Intermediate Similarity	NPD6797	Phase 2
0.8105	Intermediate Similarity	NPD5401	Approved
0.8101	Intermediate Similarity	NPD3817	Phase 2
0.8098	Intermediate Similarity	NPD7473	Discontinued
0.8072	Intermediate Similarity	NPD7251	Discontinued
0.8071	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD2935	Discontinued
0.8049	Intermediate Similarity	NPD3818	Discontinued
0.8024	Intermediate Similarity	NPD7808	Phase 3
0.8024	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1243	Approved
0.8012	Intermediate Similarity	NPD5953	Discontinued
0.8	Intermediate Similarity	NPD7286	Phase 2
0.8	Intermediate Similarity	NPD920	Approved
0.8	Intermediate Similarity	NPD2344	Approved
0.7987	Intermediate Similarity	NPD2533	Approved
0.7987	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD3748	Approved
0.7987	Intermediate Similarity	NPD2532	Approved
0.7987	Intermediate Similarity	NPD2799	Discontinued
0.7974	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD7390	Discontinued
0.7917	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5124	Phase 1
0.7904	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5402	Approved
0.7874	Intermediate Similarity	NPD4363	Phase 3
0.7874	Intermediate Similarity	NPD4360	Phase 2
0.7871	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD7033	Discontinued
0.7847	Intermediate Similarity	NPD1203	Approved
0.7843	Intermediate Similarity	NPD4628	Phase 3
0.7843	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2313	Discontinued
0.7817	Intermediate Similarity	NPD1610	Phase 2
0.7815	Intermediate Similarity	NPD6100	Approved
0.7815	Intermediate Similarity	NPD6099	Approved
0.7808	Intermediate Similarity	NPD6832	Phase 2
0.7799	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2309	Approved
0.7786	Intermediate Similarity	NPD1548	Phase 1
0.7785	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3226	Approved
0.7703	Intermediate Similarity	NPD3268	Approved
0.7703	Intermediate Similarity	NPD6798	Discontinued
0.7647	Intermediate Similarity	NPD2346	Discontinued
0.7639	Intermediate Similarity	NPD9717	Approved
0.7622	Intermediate Similarity	NPD919	Approved
0.7613	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2797	Approved
0.76	Intermediate Similarity	NPD943	Approved
0.758	Intermediate Similarity	NPD7212	Phase 2
0.758	Intermediate Similarity	NPD7213	Phase 3
0.7569	Intermediate Similarity	NPD422	Phase 1
0.7562	Intermediate Similarity	NPD7458	Discontinued
0.7558	Intermediate Similarity	NPD8312	Approved
0.7558	Intermediate Similarity	NPD8313	Approved
0.7557	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2798	Approved
0.7548	Intermediate Similarity	NPD2654	Approved
0.7547	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD3926	Phase 2
0.7534	Intermediate Similarity	NPD3225	Approved
0.753	Intermediate Similarity	NPD1247	Approved
0.7529	Intermediate Similarity	NPD1729	Discontinued
0.7528	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4361	Phase 2
0.7517	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD7003	Approved
0.7485	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD8455	Phase 2
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7483	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD5889	Approved
0.7469	Intermediate Similarity	NPD5890	Approved
0.7468	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD5406	Approved
0.7468	Intermediate Similarity	NPD5404	Approved
0.7468	Intermediate Similarity	NPD5408	Approved
0.7443	Intermediate Similarity	NPD4287	Approved
0.7434	Intermediate Similarity	NPD1933	Approved
0.7423	Intermediate Similarity	NPD7577	Discontinued
0.7421	Intermediate Similarity	NPD7447	Phase 1
0.7417	Intermediate Similarity	NPD6233	Phase 2
0.7413	Intermediate Similarity	NPD9545	Approved
0.7412	Intermediate Similarity	NPD3751	Discontinued
0.7405	Intermediate Similarity	NPD7584	Approved
0.7403	Intermediate Similarity	NPD4308	Phase 3
0.7397	Intermediate Similarity	NPD3972	Approved
0.7381	Intermediate Similarity	NPD3787	Discontinued
0.7365	Intermediate Similarity	NPD3266	Approved
0.7365	Intermediate Similarity	NPD3267	Approved
0.7363	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3764	Approved
0.7345	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6104	Discontinued
0.7333	Intermediate Similarity	NPD4288	Approved
0.7333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1201	Approved
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.732	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6844	Discontinued
0.731	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7177	Discontinued
0.7308	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1241	Discontinued
0.7301	Intermediate Similarity	NPD6585	Discontinued
0.7294	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1608	Approved
0.7273	Intermediate Similarity	NPD9493	Approved
0.7268	Intermediate Similarity	NPD6777	Approved
0.7268	Intermediate Similarity	NPD6781	Approved
0.7268	Intermediate Similarity	NPD6779	Approved
0.7268	Intermediate Similarity	NPD6776	Approved
0.7268	Intermediate Similarity	NPD6778	Approved
0.7268	Intermediate Similarity	NPD6780	Approved
0.7268	Intermediate Similarity	NPD6782	Approved
0.7267	Intermediate Similarity	NPD2861	Phase 2
0.7267	Intermediate Similarity	NPD6273	Approved
0.7267	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2424	Discontinued
0.7248	Intermediate Similarity	NPD1470	Approved
0.7237	Intermediate Similarity	NPD1296	Phase 2
0.7237	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8151	Discontinued
0.723	Intermediate Similarity	NPD4749	Approved
0.7229	Intermediate Similarity	NPD2296	Approved
0.7215	Intermediate Similarity	NPD1652	Phase 2
0.7208	Intermediate Similarity	NPD230	Phase 1
0.7208	Intermediate Similarity	NPD6355	Discontinued
0.7205	Intermediate Similarity	NPD4662	Approved
0.7205	Intermediate Similarity	NPD4661	Approved
0.7204	Intermediate Similarity	NPD7870	Phase 2
0.7204	Intermediate Similarity	NPD7871	Phase 2
0.72	Intermediate Similarity	NPD1019	Discontinued
0.7188	Intermediate Similarity	NPD7440	Discontinued
0.7171	Intermediate Similarity	NPD3027	Phase 3
0.7169	Intermediate Similarity	NPD5761	Phase 2
0.7169	Intermediate Similarity	NPD5760	Phase 2
0.7158	Intermediate Similarity	NPD7782	Clinical (unspecified phase)

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