NPASS Compound

Structure

NPC83357 OpenBabel07101719252D 32 35 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 7.7942 -2.5000 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 6.0622 -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 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 1 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 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 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 7.7942 -1.5000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 30 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 16 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 26 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 15 30 1 0 0 0 0 16 19 2 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 28 2 0 0 0 0 21 16 1 1 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 22 25 2 0 0 0 0 23 29 1 0 0 0 0 24 32 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.19
Volume:	453.039
LogP:	6.787
LogD:	4.304
LogS:	-2.595
# Rotatable Bonds:	4
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.615
Synthetic Accessibility Score:	3.655
Fsp3:	0.346
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:	-4.727
MDCK Permeability:	1.6286947357002646e-05
Pgp-inhibitor:	0.792
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	97.19780731201172%
Volume Distribution (VD):	0.656
Pgp-substrate:	6.128369331359863%

ADMET: Metabolism

CYP1A2-inhibitor:	0.368
CYP1A2-substrate:	0.824
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.582
CYP2C9-inhibitor:	0.939
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.87
CYP2D6-substrate:	0.727
CYP3A4-inhibitor:	0.727
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	7.225
Half-life (T1/2):	0.068

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.903
Carcinogencity:	0.686
Eye Corrosion:	0.003
Eye Irritation:	0.206
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC83357

Natural Product ID:	NPC83357
*Common Name:**	Khonklonginol H
IUPAC Name:	(8S)-5-hydroxy-8-(2-hydroxy-4-methoxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)-7,8-dihydropyrano[3,2-g]chromen-6-one
Synonyms:	khonklonginol H
Standard InCHIKey:	DODLFMXUTHHGIM-NRFANRHFSA-N
Standard InCHI:	InChI=1S/C26H28O6/c1-14(2)6-8-18-24-17(10-11-26(3,4)32-24)23(29)22-20(28)13-21(31-25(18)22)16-9-7-15(30-5)12-19(16)27/h6-7,9-12,21,27,29H,8,13H2,1-5H3/t21-/m0/s1
SMILES:	CC(=CCc1c2c(C=CC(C)(C)O2)c(c2C(=O)C[C@@H](c3ccc(cc3O)OC)Oc12)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557097
PubChem CID:	44179862
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-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
NPO12525	Eriosema chinense	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[19555123]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24054487]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24412339]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12525	Eriosema chinense	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	5
Ki	2
MIC	1

Activity Type	# Activity
Cell Line	3
Individual Protein	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	5.4	ug.mL-1	PMID[509162]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	3.3	ug.mL-1	PMID[509162]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	6.4	ug.mL-1	PMID[509162]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	8150.0	nM	PMID[509163]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	20400.0	nM	PMID[509163]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	2070.0	nM	PMID[509163]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	4960.0	nM	PMID[509163]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	25.0	ug.mL-1	PMID[509162]

☑ 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 NPC83357 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	365
0.1-0.2	1528
0.2-0.3	3760
0.3-0.4	10265
0.4-0.5	8249
0.5-0.6	3647
0.6-0.7	5884
0.7-0.8	5288
0.8-0.85	2042
0.85-0.9	1029
0.9-0.95	460
0.95-1	180

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC312973
1.0	High Similarity	NPC267375
1.0	High Similarity	NPC214774
1.0	High Similarity	NPC67805
1.0	High Similarity	NPC195621
1.0	High Similarity	NPC301276
1.0	High Similarity	NPC142405
1.0	High Similarity	NPC20488
1.0	High Similarity	NPC176229
1.0	High Similarity	NPC470647
1.0	High Similarity	NPC54577
1.0	High Similarity	NPC246948
1.0	High Similarity	NPC111786
1.0	High Similarity	NPC475052
1.0	High Similarity	NPC88964
0.9929	High Similarity	NPC23728
0.9929	High Similarity	NPC283234
0.9929	High Similarity	NPC296998
0.9929	High Similarity	NPC110303
0.9929	High Similarity	NPC473077
0.9858	High Similarity	NPC160821
0.9858	High Similarity	NPC161191
0.9858	High Similarity	NPC132592
0.9856	High Similarity	NPC214166
0.9856	High Similarity	NPC316816
0.9856	High Similarity	NPC478086
0.9786	High Similarity	NPC209040
0.9786	High Similarity	NPC131579
0.9786	High Similarity	NPC319752
0.9786	High Similarity	NPC131568
0.9784	High Similarity	NPC125855
0.9784	High Similarity	NPC107572
0.9784	High Similarity	NPC166482
0.9784	High Similarity	NPC220998
0.9784	High Similarity	NPC265040
0.9784	High Similarity	NPC227579
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	NPC10937
0.9784	High Similarity	NPC76372
0.9784	High Similarity	NPC161506
0.9784	High Similarity	NPC78
0.9784	High Similarity	NPC66515
0.9784	High Similarity	NPC194432
0.9784	High Similarity	NPC32739
0.9784	High Similarity	NPC328164
0.9784	High Similarity	NPC148757
0.9784	High Similarity	NPC324134
0.9784	High Similarity	NPC228504
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	NPC64915
0.9784	High Similarity	NPC306829
0.9784	High Similarity	NPC76338
0.972	High Similarity	NPC472633
0.9718	High Similarity	NPC189087
0.9718	High Similarity	NPC321623
0.9716	High Similarity	NPC470132
0.9716	High Similarity	NPC470131
0.9716	High Similarity	NPC470134
0.9716	High Similarity	NPC109183
0.9716	High Similarity	NPC127059
0.9716	High Similarity	NPC285630
0.9716	High Similarity	NPC470133
0.9716	High Similarity	NPC474161
0.9716	High Similarity	NPC476088
0.9716	High Similarity	NPC473078
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	NPC149026
0.9714	High Similarity	NPC257097
0.9714	High Similarity	NPC107177
0.9714	High Similarity	NPC77794
0.9714	High Similarity	NPC169591
0.9714	High Similarity	NPC143896
0.9714	High Similarity	NPC125894
0.9714	High Similarity	NPC278249
0.9714	High Similarity	NPC219915
0.9714	High Similarity	NPC223812
0.9714	High Similarity	NPC175504
0.9714	High Similarity	NPC85162
0.9714	High Similarity	NPC39329
0.9714	High Similarity	NPC310130
0.9714	High Similarity	NPC150408
0.9714	High Similarity	NPC38219
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
0.965	High Similarity	NPC164205
0.965	High Similarity	NPC473016
0.965	High Similarity	NPC104236
0.965	High Similarity	NPC5173
0.9648	High Similarity	NPC104406
0.9648	High Similarity	NPC79469
0.9648	High Similarity	NPC472627
0.9648	High Similarity	NPC201731
0.9648	High Similarity	NPC97716
0.9648	High Similarity	NPC237635
0.9648	High Similarity	NPC24673
0.9645	High Similarity	NPC473013
0.9645	High Similarity	NPC197252
0.9645	High Similarity	NPC473014
0.9645	High Similarity	NPC473015
0.9645	High Similarity	NPC470136
0.9645	High Similarity	NPC470135
0.9645	High Similarity	NPC235217
0.9645	High Similarity	NPC39045
0.9645	High Similarity	NPC236766
0.9643	High Similarity	NPC226636
0.9643	High Similarity	NPC293852
0.9643	High Similarity	NPC214236
0.9643	High Similarity	NPC147145
0.9643	High Similarity	NPC299080
0.9643	High Similarity	NPC78803
0.9643	High Similarity	NPC62840
0.9643	High Similarity	NPC59739
0.9643	High Similarity	NPC11561
0.9643	High Similarity	NPC217083
0.964	High Similarity	NPC6407
0.964	High Similarity	NPC150522
0.964	High Similarity	NPC159275
0.964	High Similarity	NPC110228
0.964	High Similarity	NPC241100
0.964	High Similarity	NPC188243
0.9583	High Similarity	NPC471115
0.9583	High Similarity	NPC29777
0.958	High Similarity	NPC266572
0.958	High Similarity	NPC296869
0.958	High Similarity	NPC6511
0.9577	High Similarity	NPC472629
0.9577	High Similarity	NPC228779
0.9574	High Similarity	NPC106985
0.9574	High Similarity	NPC166138
0.9574	High Similarity	NPC18585
0.9571	High Similarity	NPC205006
0.9571	High Similarity	NPC103362
0.9571	High Similarity	NPC156590
0.9571	High Similarity	NPC118840
0.9571	High Similarity	NPC110969
0.9571	High Similarity	NPC64908
0.9571	High Similarity	NPC282300
0.9571	High Similarity	NPC3188
0.9571	High Similarity	NPC147688
0.9568	High Similarity	NPC265871
0.9568	High Similarity	NPC150648
0.9568	High Similarity	NPC216978
0.9568	High Similarity	NPC310135
0.9568	High Similarity	NPC23257
0.9568	High Similarity	NPC55018
0.9568	High Similarity	NPC301217
0.9568	High Similarity	NPC303633
0.9568	High Similarity	NPC140890
0.9568	High Similarity	NPC18260
0.9568	High Similarity	NPC78913
0.9568	High Similarity	NPC217186
0.9568	High Similarity	NPC53181
0.9568	High Similarity	NPC220062
0.9568	High Similarity	NPC225153
0.9568	High Similarity	NPC20709
0.9568	High Similarity	NPC96565
0.9568	High Similarity	NPC222342
0.9568	High Similarity	NPC329203
0.9568	High Similarity	NPC274784
0.9521	High Similarity	NPC7989
0.9521	High Similarity	NPC223701
0.9521	High Similarity	NPC472583
0.9521	High Similarity	NPC236756
0.9521	High Similarity	NPC311579
0.9514	High Similarity	NPC3642
0.9514	High Similarity	NPC472628
0.9514	High Similarity	NPC19238
0.951	High Similarity	NPC300988
0.951	High Similarity	NPC10990
0.9507	High Similarity	NPC271288
0.9507	High Similarity	NPC124780
0.9507	High Similarity	NPC224714
0.9507	High Similarity	NPC311741
0.9507	High Similarity	NPC87486
0.9507	High Similarity	NPC234629
0.9507	High Similarity	NPC470890

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 NPC83357 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	932
0.2-0.3	1514
0.3-0.4	2573
0.4-0.5	1960
0.5-0.6	1182
0.6-0.7	454
0.7-0.8	162
0.8-0.85	30
0.85-0.9	13
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9424	High Similarity	NPD1550	Clinical (unspecified phase)
0.9424	High Similarity	NPD1552	Clinical (unspecified phase)
0.9371	High Similarity	NPD7410	Clinical (unspecified phase)
0.9371	High Similarity	NPD4378	Clinical (unspecified phase)
0.9357	High Similarity	NPD1549	Phase 2
0.9195	High Similarity	NPD8443	Clinical (unspecified phase)
0.9184	High Similarity	NPD4380	Phase 2
0.9128	High Similarity	NPD2393	Clinical (unspecified phase)
0.9122	High Similarity	NPD7411	Suspended
0.9078	High Similarity	NPD2796	Approved
0.9007	High Similarity	NPD1510	Phase 2
0.8947	High Similarity	NPD7075	Discontinued
0.8874	High Similarity	NPD7096	Clinical (unspecified phase)
0.8857	High Similarity	NPD1240	Approved
0.8824	High Similarity	NPD4381	Clinical (unspecified phase)
0.8808	High Similarity	NPD1934	Approved
0.8808	High Similarity	NPD6801	Discontinued
0.875	High Similarity	NPD7819	Suspended
0.8732	High Similarity	NPD1607	Approved
0.8679	High Similarity	NPD7804	Clinical (unspecified phase)
0.8654	High Similarity	NPD6959	Discontinued
0.8608	High Similarity	NPD7852	Clinical (unspecified phase)
0.8523	High Similarity	NPD1511	Approved
0.8523	High Similarity	NPD6799	Approved
0.8516	High Similarity	NPD7768	Phase 2
0.8506	High Similarity	NPD2801	Approved
0.8503	High Similarity	NPD7421	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD6166	Phase 2
0.8491	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD3750	Approved
0.8411	Intermediate Similarity	NPD1512	Approved
0.8355	Intermediate Similarity	NPD5403	Approved
0.8354	Intermediate Similarity	NPD5494	Approved
0.8344	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD7054	Approved
0.8322	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD6599	Discontinued
0.8282	Intermediate Similarity	NPD7472	Approved
0.8282	Intermediate Similarity	NPD7074	Phase 3
0.828	Intermediate Similarity	NPD3882	Suspended
0.8255	Intermediate Similarity	NPD2800	Approved
0.8232	Intermediate Similarity	NPD6797	Phase 2
0.8224	Intermediate Similarity	NPD5401	Approved
0.8219	Intermediate Similarity	NPD6651	Approved
0.8217	Intermediate Similarity	NPD3817	Phase 2
0.8194	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7251	Discontinued
0.8176	Intermediate Similarity	NPD1551	Phase 2
0.8165	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD3818	Discontinued
0.8151	Intermediate Similarity	NPD5124	Phase 1
0.8151	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7808	Phase 3
0.8133	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1243	Approved
0.8117	Intermediate Similarity	NPD920	Approved
0.8108	Intermediate Similarity	NPD7033	Discontinued
0.8108	Intermediate Similarity	NPD3748	Approved
0.8092	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6559	Discontinued
0.8071	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD4908	Phase 1
0.8054	Intermediate Similarity	NPD2935	Discontinued
0.8024	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5953	Discontinued
0.8	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD7286	Phase 2
0.7987	Intermediate Similarity	NPD2533	Approved
0.7987	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2799	Discontinued
0.7987	Intermediate Similarity	NPD2532	Approved
0.7987	Intermediate Similarity	NPD5402	Approved
0.7977	Intermediate Similarity	NPD4360	Phase 2
0.7977	Intermediate Similarity	NPD4363	Phase 3
0.7961	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD2313	Discontinued
0.7933	Intermediate Similarity	NPD6100	Approved
0.7933	Intermediate Similarity	NPD6099	Approved
0.7914	Intermediate Similarity	NPD1548	Phase 1
0.7914	Intermediate Similarity	NPD6232	Discontinued
0.7881	Intermediate Similarity	NPD2344	Approved
0.7879	Intermediate Similarity	NPD7473	Discontinued
0.7847	Intermediate Similarity	NPD1203	Approved
0.7843	Intermediate Similarity	NPD4628	Phase 3
0.7823	Intermediate Similarity	NPD3268	Approved
0.7817	Intermediate Similarity	NPD1610	Phase 2
0.7808	Intermediate Similarity	NPD6832	Phase 2
0.7799	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD919	Approved
0.7727	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD2797	Approved
0.7692	Intermediate Similarity	NPD422	Phase 1
0.7692	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7390	Discontinued
0.7677	Intermediate Similarity	NPD2309	Approved
0.7673	Intermediate Similarity	NPD3226	Approved
0.7671	Intermediate Similarity	NPD2798	Approved
0.7655	Intermediate Similarity	NPD3225	Approved
0.7647	Intermediate Similarity	NPD2346	Discontinued
0.7643	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD9717	Approved
0.7636	Intermediate Similarity	NPD1247	Approved
0.7635	Intermediate Similarity	NPD4625	Phase 3
0.7632	Intermediate Similarity	NPD4308	Phase 3
0.7627	Intermediate Similarity	NPD4361	Phase 2
0.7627	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD943	Approved
0.7596	Intermediate Similarity	NPD7584	Approved
0.7578	Intermediate Similarity	NPD5889	Approved
0.7578	Intermediate Similarity	NPD5890	Approved
0.7562	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2654	Approved
0.7529	Intermediate Similarity	NPD1729	Discontinued
0.7516	Intermediate Similarity	NPD6585	Discontinued
0.7485	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7483	Intermediate Similarity	NPD3266	Approved
0.7483	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD3267	Approved
0.7483	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7213	Phase 3
0.7468	Intermediate Similarity	NPD7212	Phase 2
0.7467	Intermediate Similarity	NPD6798	Discontinued
0.7453	Intermediate Similarity	NPD7458	Discontinued
0.744	Intermediate Similarity	NPD3926	Phase 2
0.7439	Intermediate Similarity	NPD4288	Approved
0.7434	Intermediate Similarity	NPD1933	Approved
0.7423	Intermediate Similarity	NPD6844	Discontinued
0.7413	Intermediate Similarity	NPD9545	Approved
0.7412	Intermediate Similarity	NPD3751	Discontinued
0.7397	Intermediate Similarity	NPD3972	Approved
0.7396	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3787	Discontinued
0.7372	Intermediate Similarity	NPD2424	Discontinued
0.7368	Intermediate Similarity	NPD4307	Phase 2
0.7363	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8312	Approved
0.7356	Intermediate Similarity	NPD8313	Approved
0.7351	Intermediate Similarity	NPD1296	Phase 2
0.7351	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4749	Approved
0.7345	Intermediate Similarity	NPD4287	Approved
0.7341	Intermediate Similarity	NPD6104	Discontinued
0.7333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1652	Phase 2
0.732	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7577	Discontinued
0.7312	Intermediate Similarity	NPD7447	Phase 1
0.731	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1241	Discontinued
0.7279	Intermediate Similarity	NPD1608	Approved
0.7278	Intermediate Similarity	NPD7003	Approved
0.7278	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD9493	Approved
0.7273	Intermediate Similarity	NPD8455	Phase 2
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	NPD1530	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5404	Approved
0.7244	Intermediate Similarity	NPD5406	Approved
0.7244	Intermediate Similarity	NPD5408	Approved
0.7244	Intermediate Similarity	NPD5405	Approved
0.7237	Intermediate Similarity	NPD3764	Approved
0.7233	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3887	Approved
0.7211	Intermediate Similarity	NPD1201	Approved
0.7209	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6355	Discontinued
0.7208	Intermediate Similarity	NPD230	Phase 1
0.7205	Intermediate Similarity	NPD4662	Approved
0.7205	Intermediate Similarity	NPD4661	Approved
0.72	Intermediate Similarity	NPD1019	Discontinued
0.7197	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6233	Phase 2
0.7184	Intermediate Similarity	NPD3823	Discontinued
0.7181	Intermediate Similarity	NPD7585	Approved
0.7171	Intermediate Similarity	NPD3027	Phase 3
0.7169	Intermediate Similarity	NPD5761	Phase 2
0.7169	Intermediate Similarity	NPD5760	Phase 2
0.716	Intermediate Similarity	NPD6273	Approved
0.716	Intermediate Similarity	NPD5049	Phase 3
0.7151	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7697	Approved
0.7151	Intermediate Similarity	NPD7435	Discontinued
0.7151	Intermediate Similarity	NPD7698	Approved
0.7151	Intermediate Similarity	NPD7696	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data