NPASS Compound

Structure

NPC16197 OpenBabel07101718302D 37 38 0 0 0 0 0 0 0 0999 V2000 6.7506 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9067 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0629 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0629 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0629 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9067 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 -2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0629 -0.9744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 2.4359 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 15 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 36 1 0 0 0 0 8 37 1 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 12 1 0 0 0 0 10 15 2 0 0 0 0 11 18 1 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 16 22 1 0 0 0 0 16 30 2 0 0 0 0 17 23 1 0 0 0 0 17 31 2 0 0 0 0 18 24 1 0 0 0 0 18 28 2 0 0 0 0 19 25 1 0 0 0 0 19 29 2 0 0 0 0 20 26 2 0 0 0 0 20 28 1 0 0 0 0 21 27 2 0 0 0 0 21 29 1 0 0 0 0 22 24 2 0 0 0 0 22 26 1 0 0 0 0 23 25 2 0 0 0 0 23 27 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 28 36 1 0 0 0 0 29 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.24
Volume:	536.984
LogP:	7.155
LogD:	2.63
LogS:	-3.39
# Rotatable Bonds:	10
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.241
Synthetic Accessibility Score:	3.315
Fsp3:	0.379
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.368
MDCK Permeability:	1.1071552762587089e-05
Pgp-inhibitor:	0.793
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.4
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	89.88729095458984%
Volume Distribution (VD):	0.645
Pgp-substrate:	11.19440746307373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.81
CYP2C19-inhibitor:	0.619
CYP2C19-substrate:	0.231
CYP2C9-inhibitor:	0.715
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	6.609
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.782
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.201
Maximum Recommended Daily Dose:	0.046
Skin Sensitization:	0.93
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.811
Respiratory Toxicity:	0.262

Download Data

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

Natural Product: NPC16197

Natural Product ID:	NPC16197
*Common Name:**	Mallotojaponin C
IUPAC Name:	1-[3-[[3-acetyl-2,4-dihydroxy-6-methoxy-5-(3-methylbut-2-enyl)phenyl]methyl]-2,6-dihydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]ethanone
Synonyms:	Mallotojaponin C
Standard InCHIKey:	SQDDGCHCPZMCOU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C29H36O8/c1-14(2)9-11-18-24(32)22(16(5)30)26(34)20(28(18)36-7)13-21-27(35)23(17(6)31)25(33)19(29(21)37-8)12-10-15(3)4/h9-10,32-35H,11-13H2,1-8H3
SMILES:	COc1c(Cc2c(OC)c(CC=C(C)C)c(c(c2O)C(=O)C)O)c(O)c(c(c1CC=C(C)C)O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337125
PubChem CID:	71658103
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO32759	mallotus oppositifolius	Species	Euphorbiaceae	Eukaryota	n.a.	Madagascar Dry Forest	n.a.	PMID[23286240]

☑ 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
LD50	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1300.0	nM	PMID[506598]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC100	=	39.0	uM	PMID[506598]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	70.0	nM	PMID[506598]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3600.0	nM	PMID[506598]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	LD50	=	0.81	uM	PMID[506598]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	LD50	=	0.8	uM	PMID[506598]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	140.0	nM	PMID[506598]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	=	750.0	nM	PMID[506599]

☑ 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 NPC16197 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	327
0.1-0.2	1468
0.2-0.3	3741
0.3-0.4	9921
0.4-0.5	9203
0.5-0.6	4382
0.6-0.7	6327
0.7-0.8	5127
0.8-0.85	1326
0.85-0.9	625
0.9-0.95	236
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC15834
0.9921	High Similarity	NPC215875
0.9764	High Similarity	NPC279566
0.9695	High Similarity	NPC322301
0.9695	High Similarity	NPC255801
0.9685	High Similarity	NPC186628
0.9615	High Similarity	NPC103842
0.9542	High Similarity	NPC156092
0.9542	High Similarity	NPC13575
0.947	High Similarity	NPC249606
0.947	High Similarity	NPC477243
0.947	High Similarity	NPC66349
0.947	High Similarity	NPC25287
0.947	High Similarity	NPC186838
0.947	High Similarity	NPC150399
0.947	High Similarity	NPC98115
0.947	High Similarity	NPC477244
0.947	High Similarity	NPC12165
0.947	High Similarity	NPC1486
0.947	High Similarity	NPC477242
0.947	High Similarity	NPC168105
0.947	High Similarity	NPC41461
0.947	High Similarity	NPC274109
0.9407	High Similarity	NPC476508
0.9398	High Similarity	NPC317119
0.9398	High Similarity	NPC472419
0.9398	High Similarity	NPC153979
0.9394	High Similarity	NPC131039
0.9389	High Similarity	NPC20560
0.9389	High Similarity	NPC28753
0.9389	High Similarity	NPC204960
0.9389	High Similarity	NPC82225
0.9389	High Similarity	NPC144051
0.9389	High Similarity	NPC18877
0.9389	High Similarity	NPC159623
0.9389	High Similarity	NPC294593
0.9328	High Similarity	NPC272844
0.9328	High Similarity	NPC254168
0.9328	High Similarity	NPC477056
0.9328	High Similarity	NPC471620
0.9328	High Similarity	NPC21350
0.9328	High Similarity	NPC243528
0.9328	High Similarity	NPC248995
0.9328	High Similarity	NPC251681
0.9328	High Similarity	NPC477055
0.9318	High Similarity	NPC286336
0.9313	High Similarity	NPC285054
0.9259	High Similarity	NPC53181
0.9259	High Similarity	NPC217186
0.9259	High Similarity	NPC470211
0.9259	High Similarity	NPC240305
0.9259	High Similarity	NPC283429
0.9259	High Similarity	NPC472366
0.9259	High Similarity	NPC477956
0.9248	High Similarity	NPC101752
0.9242	High Similarity	NPC312318
0.9242	High Similarity	NPC472365
0.9242	High Similarity	NPC337373
0.9242	High Similarity	NPC242294
0.9242	High Similarity	NPC192304
0.9242	High Similarity	NPC175098
0.9242	High Similarity	NPC56031
0.9242	High Similarity	NPC27643
0.9242	High Similarity	NPC263670
0.9242	High Similarity	NPC188646
0.9242	High Similarity	NPC139813
0.9237	High Similarity	NPC186097
0.9237	High Similarity	NPC475009
0.9237	High Similarity	NPC475008
0.9231	High Similarity	NPC84772
0.9203	High Similarity	NPC194949
0.9203	High Similarity	NPC328623
0.9203	High Similarity	NPC282957
0.9197	High Similarity	NPC297600
0.9191	High Similarity	NPC213659
0.9191	High Similarity	NPC144118
0.9191	High Similarity	NPC80962
0.9191	High Similarity	NPC241100
0.9191	High Similarity	NPC326109
0.9191	High Similarity	NPC259166
0.9191	High Similarity	NPC11056
0.9191	High Similarity	NPC204985
0.9191	High Similarity	NPC172250
0.9191	High Similarity	NPC159275
0.9191	High Similarity	NPC48624
0.9191	High Similarity	NPC215311
0.9191	High Similarity	NPC253822
0.9191	High Similarity	NPC219917
0.9179	High Similarity	NPC174999
0.9167	High Similarity	NPC87231
0.9167	High Similarity	NPC129132
0.9167	High Similarity	NPC212631
0.9167	High Similarity	NPC257756
0.9167	High Similarity	NPC103105
0.9167	High Similarity	NPC205468
0.916	High Similarity	NPC250057
0.916	High Similarity	NPC324482
0.9154	High Similarity	NPC230818
0.913	High Similarity	NPC185276
0.9124	High Similarity	NPC470089
0.9124	High Similarity	NPC258630
0.9124	High Similarity	NPC469404
0.9124	High Similarity	NPC110969
0.9124	High Similarity	NPC321980
0.9124	High Similarity	NPC55832
0.9124	High Similarity	NPC470087
0.9124	High Similarity	NPC279650
0.9124	High Similarity	NPC268204
0.9124	High Similarity	NPC156190
0.9124	High Similarity	NPC248372
0.9124	High Similarity	NPC110038
0.9124	High Similarity	NPC26051
0.9124	High Similarity	NPC17170
0.9124	High Similarity	NPC166689
0.9124	High Similarity	NPC282300
0.9124	High Similarity	NPC52789
0.9124	High Similarity	NPC96408
0.9124	High Similarity	NPC26238
0.9118	High Similarity	NPC18260
0.9118	High Similarity	NPC78913
0.9118	High Similarity	NPC55018
0.9118	High Similarity	NPC295384
0.9118	High Similarity	NPC301217
0.9118	High Similarity	NPC303633
0.9118	High Similarity	NPC96565
0.9118	High Similarity	NPC216978
0.9118	High Similarity	NPC220062
0.9091	High Similarity	NPC164236
0.9091	High Similarity	NPC313618
0.9091	High Similarity	NPC27490
0.9091	High Similarity	NPC66384
0.9091	High Similarity	NPC64359
0.9091	High Similarity	NPC262359
0.9091	High Similarity	NPC112192
0.9091	High Similarity	NPC308037
0.9091	High Similarity	NPC309717
0.9091	High Similarity	NPC189106
0.9091	High Similarity	NPC128348
0.9065	High Similarity	NPC235217
0.9065	High Similarity	NPC473014
0.9065	High Similarity	NPC197252
0.9065	High Similarity	NPC236766
0.9058	High Similarity	NPC324134
0.9058	High Similarity	NPC296917
0.9058	High Similarity	NPC64915
0.9058	High Similarity	NPC40833
0.9058	High Similarity	NPC78
0.9058	High Similarity	NPC166934
0.9058	High Similarity	NPC161506
0.9058	High Similarity	NPC166482
0.9058	High Similarity	NPC37496
0.9058	High Similarity	NPC1089
0.9058	High Similarity	NPC148757
0.9058	High Similarity	NPC227579
0.9058	High Similarity	NPC76338
0.9058	High Similarity	NPC325346
0.9058	High Similarity	NPC220998
0.9058	High Similarity	NPC76372
0.9058	High Similarity	NPC11561
0.9058	High Similarity	NPC32739
0.9058	High Similarity	NPC265040
0.9058	High Similarity	NPC177354
0.9058	High Similarity	NPC10937
0.9058	High Similarity	NPC266725
0.9058	High Similarity	NPC194432
0.9058	High Similarity	NPC324436
0.9058	High Similarity	NPC223500
0.9058	High Similarity	NPC66515
0.9058	High Similarity	NPC226636
0.9058	High Similarity	NPC328164
0.9058	High Similarity	NPC182852
0.9058	High Similarity	NPC228504
0.9058	High Similarity	NPC306829
0.9058	High Similarity	NPC167624
0.9058	High Similarity	NPC107572
0.9058	High Similarity	NPC125855
0.9051	High Similarity	NPC150522
0.9051	High Similarity	NPC261227
0.9051	High Similarity	NPC69769
0.9051	High Similarity	NPC101366
0.9051	High Similarity	NPC172986
0.9051	High Similarity	NPC471587
0.9051	High Similarity	NPC265178
0.9051	High Similarity	NPC270883
0.9044	High Similarity	NPC470083
0.9044	High Similarity	NPC219584
0.9044	High Similarity	NPC124269
0.9044	High Similarity	NPC201395
0.9044	High Similarity	NPC472368
0.9044	High Similarity	NPC131130
0.9037	High Similarity	NPC476333
0.9037	High Similarity	NPC156910
0.9037	High Similarity	NPC473391
0.9037	High Similarity	NPC472364
0.9037	High Similarity	NPC213603
0.9037	High Similarity	NPC24394
0.9037	High Similarity	NPC472367
0.903	High Similarity	NPC164136
0.903	High Similarity	NPC125920
0.9008	High Similarity	NPC69235

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 NPC16197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	996
0.2-0.3	1635
0.3-0.4	2734
0.4-0.5	1902
0.5-0.6	1117
0.6-0.7	330
0.7-0.8	99
0.8-0.85	19
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9242	High Similarity	NPD6651	Approved
0.9091	High Similarity	NPD1240	Approved
0.8955	High Similarity	NPD1607	Approved
0.8929	High Similarity	NPD4378	Clinical (unspecified phase)
0.8929	High Similarity	NPD7410	Clinical (unspecified phase)
0.8824	High Similarity	NPD1510	Phase 2
0.8696	High Similarity	NPD1550	Clinical (unspecified phase)
0.8696	High Similarity	NPD1552	Clinical (unspecified phase)
0.8639	High Similarity	NPD8443	Clinical (unspecified phase)
0.8633	High Similarity	NPD1549	Phase 2
0.8621	High Similarity	NPD4380	Phase 2
0.8571	High Similarity	NPD2800	Approved
0.8562	High Similarity	NPD7411	Suspended
0.8523	High Similarity	NPD7075	Discontinued
0.8446	Intermediate Similarity	NPD7819	Suspended
0.8446	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD2532	Approved
0.8403	Intermediate Similarity	NPD2534	Approved
0.8403	Intermediate Similarity	NPD2533	Approved
0.8357	Intermediate Similarity	NPD2796	Approved
0.8322	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD6801	Discontinued
0.8239	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD2935	Discontinued
0.8207	Intermediate Similarity	NPD6799	Approved
0.8141	Intermediate Similarity	NPD7473	Discontinued
0.8133	Intermediate Similarity	NPD1934	Approved
0.8117	Intermediate Similarity	NPD6959	Discontinued
0.8116	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7768	Phase 2
0.8082	Intermediate Similarity	NPD1511	Approved
0.8079	Intermediate Similarity	NPD2801	Approved
0.8077	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6232	Discontinued
0.8056	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6599	Discontinued
0.7974	Intermediate Similarity	NPD3882	Suspended
0.7973	Intermediate Similarity	NPD1512	Approved
0.7931	Intermediate Similarity	NPD1243	Approved
0.7902	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD3750	Approved
0.7848	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6166	Phase 2
0.7848	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1551	Phase 2
0.7838	Intermediate Similarity	NPD7390	Discontinued
0.7826	Intermediate Similarity	NPD5953	Discontinued
0.7812	Intermediate Similarity	NPD7286	Phase 2
0.7808	Intermediate Similarity	NPD2654	Approved
0.7792	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD2799	Discontinued
0.7764	Intermediate Similarity	NPD7074	Phase 3
0.7746	Intermediate Similarity	NPD943	Approved
0.7722	Intermediate Similarity	NPD5710	Approved
0.7722	Intermediate Similarity	NPD5711	Approved
0.7714	Intermediate Similarity	NPD6832	Phase 2
0.7702	Intermediate Similarity	NPD7054	Approved
0.7692	Intermediate Similarity	NPD3749	Approved
0.7682	Intermediate Similarity	NPD5403	Approved
0.7682	Intermediate Similarity	NPD920	Approved
0.7671	Intermediate Similarity	NPD2344	Approved
0.7654	Intermediate Similarity	NPD7472	Approved
0.7651	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3818	Discontinued
0.7628	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD1203	Approved
0.7622	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2313	Discontinued
0.7603	Intermediate Similarity	NPD6099	Approved
0.7603	Intermediate Similarity	NPD6100	Approved
0.7595	Intermediate Similarity	NPD5494	Approved
0.7571	Intermediate Similarity	NPD2798	Approved
0.7561	Intermediate Similarity	NPD7251	Discontinued
0.7561	Intermediate Similarity	NPD6559	Discontinued
0.755	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD5401	Approved
0.7536	Intermediate Similarity	NPD3972	Approved
0.7534	Intermediate Similarity	NPD3748	Approved
0.7515	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3226	Approved
0.7467	Intermediate Similarity	NPD2309	Approved
0.7451	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD5124	Phase 1
0.7448	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD9717	Approved
0.7407	Intermediate Similarity	NPD9493	Approved
0.74	Intermediate Similarity	NPD4628	Phase 3
0.74	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3268	Approved
0.7355	Intermediate Similarity	NPD7458	Discontinued
0.7346	Intermediate Similarity	NPD3926	Phase 2
0.7343	Intermediate Similarity	NPD4908	Phase 1
0.7342	Intermediate Similarity	NPD5402	Approved
0.7338	Intermediate Similarity	NPD422	Phase 1
0.7338	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2346	Discontinued
0.7312	Intermediate Similarity	NPD919	Approved
0.7305	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD9545	Approved
0.7299	Intermediate Similarity	NPD1548	Phase 1
0.7299	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD5844	Phase 1
0.7261	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1164	Approved
0.7254	Intermediate Similarity	NPD2797	Approved
0.7248	Intermediate Similarity	NPD5404	Approved
0.7248	Intermediate Similarity	NPD5408	Approved
0.7248	Intermediate Similarity	NPD5405	Approved
0.7248	Intermediate Similarity	NPD5406	Approved
0.7229	Intermediate Similarity	NPD1729	Discontinued
0.7222	Intermediate Similarity	NPD1247	Approved
0.7214	Intermediate Similarity	NPD1610	Phase 2
0.7214	Intermediate Similarity	NPD1201	Approved
0.7211	Intermediate Similarity	NPD230	Phase 1
0.7186	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4360	Phase 2
0.7184	Intermediate Similarity	NPD4363	Phase 3
0.7171	Intermediate Similarity	NPD7003	Approved
0.717	Intermediate Similarity	NPD1465	Phase 2
0.7168	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7133	Intermediate Similarity	NPD1470	Approved
0.7079	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4308	Phase 3
0.7063	Intermediate Similarity	NPD3225	Approved
0.7063	Intermediate Similarity	NPD1876	Approved
0.7055	Intermediate Similarity	NPD4625	Phase 3
0.7055	Intermediate Similarity	NPD3027	Phase 3
0.7042	Intermediate Similarity	NPD1608	Approved
0.7041	Intermediate Similarity	NPD6104	Discontinued
0.7032	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD3266	Approved
0.7014	Intermediate Similarity	NPD3267	Approved
0.7007	Intermediate Similarity	NPD1296	Phase 2
0.7007	Intermediate Similarity	NPD3764	Approved
0.7	Intermediate Similarity	NPD1651	Approved
0.7	Intermediate Similarity	NPD37	Approved
0.6987	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1933	Approved
0.698	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7229	Phase 3
0.6966	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1283	Approved
0.6943	Remote Similarity	NPD5049	Phase 3
0.694	Remote Similarity	NPD7584	Approved
0.6937	Remote Similarity	NPD5889	Approved
0.6937	Remote Similarity	NPD5890	Approved
0.6934	Remote Similarity	NPD1241	Discontinued
0.6918	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2296	Approved
0.6914	Remote Similarity	NPD4288	Approved
0.6905	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3847	Discontinued
0.6892	Remote Similarity	NPD411	Approved
0.6892	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6798	Discontinued
0.689	Remote Similarity	NPD6234	Discontinued
0.6886	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2403	Approved
0.6879	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4749	Approved
0.6875	Remote Similarity	NPD6585	Discontinued
0.6875	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4966	Approved
0.6871	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4967	Phase 2
0.6871	Remote Similarity	NPD4965	Approved
0.687	Remote Similarity	NPD940	Approved
0.687	Remote Similarity	NPD846	Approved
0.6867	Remote Similarity	NPD6355	Discontinued
0.6867	Remote Similarity	NPD447	Suspended
0.6865	Remote Similarity	NPD8151	Discontinued
0.6863	Remote Similarity	NPD1471	Phase 3
0.686	Remote Similarity	NPD8312	Approved
0.686	Remote Similarity	NPD8313	Approved
0.6857	Remote Similarity	NPD4287	Approved
0.6849	Remote Similarity	NPD1019	Discontinued
0.6831	Remote Similarity	NPD4626	Approved
0.6831	Remote Similarity	NPD17	Approved
0.6815	Remote Similarity	NPD9266	Approved
0.6815	Remote Similarity	NPD74	Approved
0.6813	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1894	Discontinued
0.6807	Remote Similarity	NPD7199	Phase 2
0.6806	Remote Similarity	NPD1481	Phase 2
0.6803	Remote Similarity	NPD9494	Approved
0.6803	Remote Similarity	NPD3018	Phase 2
0.68	Remote Similarity	NPD1612	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