NPASS Compound

Structure

NPC472876 OpenBabel07101718312D 42 46 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -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 -4.3301 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 -4.3301 -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 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 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 -3.4641 2.0000 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 -5.1962 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.3301 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 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 -3.4641 -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 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 6 1 0 0 0 0 1 15 2 0 0 0 0 2 7 2 0 0 0 0 2 15 1 0 0 0 0 3 10 2 0 0 0 0 3 15 1 0 0 0 0 4 8 1 0 0 0 0 4 16 2 0 0 0 0 5 9 2 0 0 0 0 5 16 1 0 0 0 0 6 17 2 0 0 0 0 7 17 1 0 0 0 0 8 18 2 0 0 0 0 9 18 1 0 0 0 0 10 25 1 0 0 0 0 11 19 2 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 12 23 2 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 39 1 0 0 0 0 16 21 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 26 1 0 0 0 0 20 34 2 0 0 0 0 21 40 1 0 0 0 0 22 26 2 0 0 0 0 22 40 1 0 0 0 0 23 26 1 0 0 0 0 23 41 1 0 0 0 0 24 14 1 1 0 0 0 24 27 1 0 0 0 0 24 42 1 0 0 0 0 25 35 2 0 0 0 0 25 39 1 0 0 0 0 27 28 1 0 0 0 0 27 36 1 6 0 0 0 28 29 1 0 0 0 0 28 37 1 1 0 0 0 29 30 1 0 0 0 0 29 38 1 6 0 0 0 30 41 1 1 0 0 0 30 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.16
Volume:	558.499
LogP:	2.421
LogD:	2.271
LogS:	-4.486
# Rotatable Bonds:	8
TPSA:	192.44
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.176
Synthetic Accessibility Score:	4.279
Fsp3:	0.267
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.355
MDCK Permeability:	1.5711668311269023e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.115
Human Intestinal Absorption (HIA):	0.576
20% Bioavailability (F20%):	0.573
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	98.0602035522461%
Volume Distribution (VD):	0.521
Pgp-substrate:	1.627741813659668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.17
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.623
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.894
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.837
CYP2D6-substrate:	0.59
CYP3A4-inhibitor:	0.744
CYP3A4-substrate:	0.126

ADMET: Excretion

Clearance (CL):	7.402
Half-life (T1/2):	0.731

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.138
Drug-inuced Liver Injury (DILI):	0.817
AMES Toxicity:	0.586
Rat Oral Acute Toxicity:	0.362
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.954
Carcinogencity:	0.468
Eye Corrosion:	0.003
Eye Irritation:	0.139
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC472876

Natural Product ID:	NPC472876
*Common Name:**	XPMNRCHLRQPMTQ-XTKHIGPMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XPMNRCHLRQPMTQ-XTKHIGPMSA-N
Standard InCHI:	InChI=1S/C30H28O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-27(36)28(37)29(38)30(42-24)41-23-12-19(33)11-22-26(23)20(34)13-21(40-22)16-4-8-18(32)9-5-16/h1-12,21,24,27-33,36-38H,13-14H2/b10-3+/t21?,24-,27-,28+,29-,30-/m1/s1
SMILES:	C1C(OC2=C(C1=O)C(=CC(=C2)O)OC3C(C(C(C(O3)COC(=O)C=CC4=CC=C(C=C4)O)O)O)O)C5=CC=C(C=C5)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593483
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003679] Flavonoid 5-O-p-coumaroyl 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
NPO15254	Macropidia fuliginosa	Species	Haemodoraceae	Eukaryota	n.a.	Australian	n.a.	PMID[26151487]
NPO15254	Macropidia fuliginosa	Species	Haemodoraceae	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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	1.0	mm	PMID[480889]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	10.0	mm	PMID[480889]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	IZ	=	1.0	mm	PMID[480889]

☑ 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 NPC472876 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	381
0.1-0.2	1541
0.2-0.3	3707
0.3-0.4	8241
0.4-0.5	9849
0.5-0.6	4587
0.6-0.7	5501
0.7-0.8	5780
0.8-0.85	2027
0.85-0.9	839
0.9-0.95	212
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC477628
0.9805	High Similarity	NPC210961
0.9805	High Similarity	NPC477629
0.9805	High Similarity	NPC270675
0.9805	High Similarity	NPC195685
0.9805	High Similarity	NPC472994
0.9679	High Similarity	NPC80068
0.9673	High Similarity	NPC170475
0.9618	High Similarity	NPC129264
0.9618	High Similarity	NPC139060
0.9618	High Similarity	NPC205824
0.9618	High Similarity	NPC19240
0.9618	High Similarity	NPC85751
0.961	High Similarity	NPC43638
0.9608	High Similarity	NPC97052
0.9608	High Similarity	NPC72649
0.9608	High Similarity	NPC169248
0.9608	High Similarity	NPC26195
0.9608	High Similarity	NPC39351
0.9563	High Similarity	NPC47140
0.9563	High Similarity	NPC67134
0.9557	High Similarity	NPC89809
0.9557	High Similarity	NPC473278
0.9557	High Similarity	NPC260504
0.9551	High Similarity	NPC303913
0.9551	High Similarity	NPC101636
0.9545	High Similarity	NPC127406
0.9545	High Similarity	NPC206378
0.95	High Similarity	NPC164704
0.95	High Similarity	NPC470712
0.95	High Similarity	NPC76047
0.949	High Similarity	NPC298171
0.9487	High Similarity	NPC271479
0.9487	High Similarity	NPC246469
0.9487	High Similarity	NPC200708
0.9487	High Similarity	NPC142860
0.9487	High Similarity	NPC97285
0.9487	High Similarity	NPC472320
0.9487	High Similarity	NPC271270
0.9484	High Similarity	NPC44931
0.9484	High Similarity	NPC473512
0.9484	High Similarity	NPC313163
0.9484	High Similarity	NPC161749
0.9484	High Similarity	NPC197896
0.9484	High Similarity	NPC258035
0.9484	High Similarity	NPC129827
0.9484	High Similarity	NPC65003
0.9484	High Similarity	NPC156457
0.9481	High Similarity	NPC99233
0.9477	High Similarity	NPC121001
0.9477	High Similarity	NPC88484
0.9477	High Similarity	NPC259767
0.9477	High Similarity	NPC259182
0.9441	High Similarity	NPC470715
0.9441	High Similarity	NPC474522
0.9441	High Similarity	NPC470714
0.9441	High Similarity	NPC470716
0.9427	High Similarity	NPC470125
0.9427	High Similarity	NPC47923
0.9423	High Similarity	NPC43761
0.9423	High Similarity	NPC138811
0.9423	High Similarity	NPC22062
0.9423	High Similarity	NPC73511
0.9423	High Similarity	NPC308265
0.9423	High Similarity	NPC473634
0.9416	High Similarity	NPC106625
0.9416	High Similarity	NPC83283
0.9416	High Similarity	NPC29763
0.9416	High Similarity	NPC39360
0.9416	High Similarity	NPC143851
0.9416	High Similarity	NPC210003
0.9379	High Similarity	NPC188815
0.9379	High Similarity	NPC96605
0.9379	High Similarity	NPC218161
0.9379	High Similarity	NPC469344
0.9379	High Similarity	NPC280642
0.9367	High Similarity	NPC190450
0.9367	High Similarity	NPC44947
0.9363	High Similarity	NPC304741
0.9363	High Similarity	NPC136761
0.9363	High Similarity	NPC470405
0.9363	High Similarity	NPC187379
0.9363	High Similarity	NPC473623
0.9363	High Similarity	NPC471079
0.9363	High Similarity	NPC153342
0.9359	High Similarity	NPC23817
0.9355	High Similarity	NPC95090
0.9355	High Similarity	NPC27408
0.9329	High Similarity	NPC476622
0.9329	High Similarity	NPC476620
0.9329	High Similarity	NPC476623
0.9329	High Similarity	NPC472387
0.9329	High Similarity	NPC476618
0.9329	High Similarity	NPC476619
0.9329	High Similarity	NPC476621
0.9321	High Similarity	NPC11847
0.9321	High Similarity	NPC221288
0.9321	High Similarity	NPC101399
0.9321	High Similarity	NPC217822
0.9313	High Similarity	NPC64425
0.9313	High Similarity	NPC262222
0.9313	High Similarity	NPC68592
0.9313	High Similarity	NPC298666
0.9308	High Similarity	NPC257566
0.9308	High Similarity	NPC124155
0.9304	High Similarity	NPC215710
0.9304	High Similarity	NPC163242
0.9304	High Similarity	NPC216496
0.9304	High Similarity	NPC116458
0.9304	High Similarity	NPC64305
0.9304	High Similarity	NPC276377
0.9304	High Similarity	NPC173582
0.9304	High Similarity	NPC181465
0.9304	High Similarity	NPC224530
0.9304	High Similarity	NPC135846
0.9304	High Similarity	NPC48093
0.9304	High Similarity	NPC170052
0.9304	High Similarity	NPC85707
0.9304	High Similarity	NPC159579
0.9304	High Similarity	NPC249281
0.9304	High Similarity	NPC246943
0.9304	High Similarity	NPC259957
0.9304	High Similarity	NPC476215
0.9304	High Similarity	NPC473438
0.9304	High Similarity	NPC297987
0.9304	High Similarity	NPC129217
0.9304	High Similarity	NPC139320
0.9304	High Similarity	NPC265885
0.9304	High Similarity	NPC282169
0.9304	High Similarity	NPC253788
0.9295	High Similarity	NPC295613
0.9295	High Similarity	NPC265480
0.9295	High Similarity	NPC203500
0.9295	High Similarity	NPC149368
0.9295	High Similarity	NPC473657
0.9295	High Similarity	NPC323593
0.9295	High Similarity	NPC45165
0.9295	High Similarity	NPC307938
0.9268	High Similarity	NPC231787
0.9264	High Similarity	NPC472993
0.9259	High Similarity	NPC149011
0.9259	High Similarity	NPC199079
0.9259	High Similarity	NPC210808
0.9259	High Similarity	NPC204937
0.9245	High Similarity	NPC240306
0.9245	High Similarity	NPC475382
0.9245	High Similarity	NPC27942
0.9245	High Similarity	NPC259834
0.9236	High Similarity	NPC122809
0.9236	High Similarity	NPC197304
0.9236	High Similarity	NPC108831
0.9236	High Similarity	NPC135391
0.9236	High Similarity	NPC78263
0.9236	High Similarity	NPC77672
0.9236	High Similarity	NPC54802
0.9236	High Similarity	NPC6985
0.9236	High Similarity	NPC182634
0.9236	High Similarity	NPC60966
0.9236	High Similarity	NPC133671
0.9221	High Similarity	NPC213723
0.9217	High Similarity	NPC469371
0.9207	High Similarity	NPC34267
0.9207	High Similarity	NPC223426
0.9207	High Similarity	NPC81042
0.9207	High Similarity	NPC214621
0.9202	High Similarity	NPC288152
0.9202	High Similarity	NPC9002
0.9202	High Similarity	NPC257011
0.9202	High Similarity	NPC137871
0.9193	High Similarity	NPC70441
0.9187	High Similarity	NPC29830
0.9187	High Similarity	NPC311850
0.9187	High Similarity	NPC121290
0.9187	High Similarity	NPC121703
0.9187	High Similarity	NPC473644
0.9182	High Similarity	NPC97812
0.9177	High Similarity	NPC41121
0.9177	High Similarity	NPC111929
0.9177	High Similarity	NPC320283
0.9177	High Similarity	NPC472459
0.9177	High Similarity	NPC104677
0.9172	High Similarity	NPC471787
0.9172	High Similarity	NPC261866
0.9152	High Similarity	NPC472991
0.9152	High Similarity	NPC472992
0.9152	High Similarity	NPC61904
0.9152	High Similarity	NPC144097
0.915	High Similarity	NPC302989
0.9146	High Similarity	NPC175230
0.9146	High Similarity	NPC172033
0.9146	High Similarity	NPC168789
0.9146	High Similarity	NPC88560
0.9141	High Similarity	NPC138990
0.9141	High Similarity	NPC175429
0.9141	High Similarity	NPC92815
0.9141	High Similarity	NPC231194
0.9141	High Similarity	NPC209550
0.9141	High Similarity	NPC51326
0.9141	High Similarity	NPC277532
0.9136	High Similarity	NPC45400

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 NPC472876 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	871
0.2-0.3	1767
0.3-0.4	2624
0.4-0.5	1956
0.5-0.6	1058
0.6-0.7	338
0.7-0.8	148
0.8-0.85	35
0.85-0.9	13
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9484	High Similarity	NPD4381	Clinical (unspecified phase)
0.908	High Similarity	NPD7804	Clinical (unspecified phase)
0.9024	High Similarity	NPD7074	Phase 3
0.8963	High Similarity	NPD7054	Approved
0.8909	High Similarity	NPD7472	Approved
0.8855	High Similarity	NPD6797	Phase 2
0.8854	High Similarity	NPD4380	Phase 2
0.8802	High Similarity	NPD7251	Discontinued
0.8797	High Similarity	NPD7411	Suspended
0.8788	High Similarity	NPD3818	Discontinued
0.878	High Similarity	NPD6168	Clinical (unspecified phase)
0.878	High Similarity	NPD6167	Clinical (unspecified phase)
0.878	High Similarity	NPD6166	Phase 2
0.8758	High Similarity	NPD7075	Discontinued
0.875	High Similarity	NPD4338	Clinical (unspecified phase)
0.875	High Similarity	NPD7808	Phase 3
0.8696	High Similarity	NPD4868	Clinical (unspecified phase)
0.869	High Similarity	NPD6559	Discontinued
0.8627	High Similarity	NPD1549	Phase 2
0.8625	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD7096	Clinical (unspecified phase)
0.8562	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD1552	Clinical (unspecified phase)
0.8544	High Similarity	NPD5403	Approved
0.8521	High Similarity	NPD7993	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD8312	Approved
0.848	Intermediate Similarity	NPD8313	Approved
0.8471	Intermediate Similarity	NPD6799	Approved
0.8443	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD5401	Approved
0.8405	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD8455	Phase 2
0.8293	Intermediate Similarity	NPD5402	Approved
0.8272	Intermediate Similarity	NPD6599	Discontinued
0.8263	Intermediate Similarity	NPD6959	Discontinued
0.8249	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7819	Suspended
0.8194	Intermediate Similarity	NPD1510	Phase 2
0.8193	Intermediate Similarity	NPD3749	Approved
0.8187	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3817	Phase 2
0.8141	Intermediate Similarity	NPD2796	Approved
0.8133	Intermediate Similarity	NPD7768	Phase 2
0.8101	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD5844	Phase 1
0.8052	Intermediate Similarity	NPD1240	Approved
0.805	Intermediate Similarity	NPD3750	Approved
0.8012	Intermediate Similarity	NPD1511	Approved
0.8012	Intermediate Similarity	NPD2801	Approved
0.7979	Intermediate Similarity	NPD8151	Discontinued
0.7975	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1607	Approved
0.7937	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD4628	Phase 3
0.7919	Intermediate Similarity	NPD3751	Discontinued
0.7917	Intermediate Similarity	NPD3882	Suspended
0.7914	Intermediate Similarity	NPD1512	Approved
0.7911	Intermediate Similarity	NPD1551	Phase 2
0.7904	Intermediate Similarity	NPD1465	Phase 2
0.7895	Intermediate Similarity	NPD6232	Discontinued
0.7882	Intermediate Similarity	NPD5494	Approved
0.7869	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7473	Discontinued
0.7836	Intermediate Similarity	NPD7199	Phase 2
0.7818	Intermediate Similarity	NPD1653	Approved
0.7816	Intermediate Similarity	NPD7228	Approved
0.7807	Intermediate Similarity	NPD7435	Discontinued
0.7806	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD7783	Phase 2
0.7801	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3787	Discontinued
0.7778	Intermediate Similarity	NPD7584	Approved
0.7771	Intermediate Similarity	NPD7458	Discontinued
0.7742	Intermediate Similarity	NPD6780	Approved
0.7742	Intermediate Similarity	NPD6782	Approved
0.7742	Intermediate Similarity	NPD6778	Approved
0.7742	Intermediate Similarity	NPD6781	Approved
0.7742	Intermediate Similarity	NPD6777	Approved
0.7742	Intermediate Similarity	NPD6776	Approved
0.7742	Intermediate Similarity	NPD6779	Approved
0.7736	Intermediate Similarity	NPD3748	Approved
0.7735	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1933	Approved
0.7644	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7698	Approved
0.7619	Intermediate Similarity	NPD7697	Approved
0.7619	Intermediate Similarity	NPD7696	Phase 3
0.7597	Intermediate Similarity	NPD1203	Approved
0.7593	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5953	Discontinued
0.758	Intermediate Similarity	NPD6798	Discontinued
0.7579	Intermediate Similarity	NPD7871	Phase 2
0.7579	Intermediate Similarity	NPD7870	Phase 2
0.7578	Intermediate Similarity	NPD2935	Discontinued
0.7576	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7286	Phase 2
0.7565	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD7874	Approved
0.7564	Intermediate Similarity	NPD6832	Phase 2
0.7552	Intermediate Similarity	NPD7585	Approved
0.7552	Intermediate Similarity	NPD7701	Phase 2
0.7545	Intermediate Similarity	NPD920	Approved
0.7542	Intermediate Similarity	NPD7685	Pre-registration
0.7531	Intermediate Similarity	NPD7266	Discontinued
0.753	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD37	Approved
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7515	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD7583	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD4965	Approved
0.7487	Intermediate Similarity	NPD8320	Phase 1
0.7487	Intermediate Similarity	NPD8319	Approved
0.7474	Intermediate Similarity	NPD6823	Phase 2
0.7473	Intermediate Similarity	NPD6535	Approved
0.7473	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6534	Approved
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.7456	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3226	Approved
0.7452	Intermediate Similarity	NPD4908	Phase 1
0.7451	Intermediate Similarity	NPD1091	Approved
0.7451	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7699	Phase 2
0.7447	Intermediate Similarity	NPD7700	Phase 2
0.7444	Intermediate Similarity	NPD7240	Approved
0.7439	Intermediate Similarity	NPD1243	Approved
0.7425	Intermediate Similarity	NPD2532	Approved
0.7425	Intermediate Similarity	NPD2534	Approved
0.7425	Intermediate Similarity	NPD2533	Approved
0.7421	Intermediate Similarity	NPD6233	Phase 2
0.7407	Intermediate Similarity	NPD2799	Discontinued
0.7375	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1613	Approved
0.7358	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6190	Approved
0.7347	Intermediate Similarity	NPD7801	Approved
0.7346	Intermediate Similarity	NPD7097	Phase 1
0.7337	Intermediate Similarity	NPD8150	Discontinued
0.7333	Intermediate Similarity	NPD2800	Approved
0.7333	Intermediate Similarity	NPD1652	Phase 2
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2344	Approved
0.7314	Intermediate Similarity	NPD919	Approved
0.7303	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD9717	Approved
0.7284	Intermediate Similarity	NPD6651	Approved
0.7277	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD943	Approved
0.7267	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7390	Discontinued
0.7258	Intermediate Similarity	NPD4287	Approved
0.725	Intermediate Similarity	NPD3268	Approved
0.7247	Intermediate Similarity	NPD3926	Phase 2
0.7243	Intermediate Similarity	NPD8434	Phase 2
0.7234	Intermediate Similarity	NPD6213	Phase 3
0.7234	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6212	Phase 3
0.7222	Intermediate Similarity	NPD230	Phase 1
0.7215	Intermediate Similarity	NPD2798	Approved
0.7213	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2346	Discontinued
0.7197	Intermediate Similarity	NPD3225	Approved
0.7196	Intermediate Similarity	NPD4363	Phase 3
0.7196	Intermediate Similarity	NPD4360	Phase 2
0.7186	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD2309	Approved
0.7125	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6355	Discontinued
0.7117	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD447	Suspended
0.7115	Intermediate Similarity	NPD422	Phase 1
0.7115	Intermediate Similarity	NPD1610	Phase 2
0.7101	Intermediate Similarity	NPD7440	Discontinued
0.7091	Intermediate Similarity	NPD4308	Phase 3
0.7083	Intermediate Similarity	NPD7003	Approved
0.7078	Intermediate Similarity	NPD9545	Approved
0.7078	Intermediate Similarity	NPD1548	Phase 1
0.7077	Intermediate Similarity	NPD7680	Approved
0.7063	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6099	Approved
0.7048	Intermediate Similarity	NPD5406	Approved
0.7048	Intermediate Similarity	NPD6100	Approved
0.7048	Intermediate Similarity	NPD5405	Approved
0.7048	Intermediate Similarity	NPD5404	Approved
0.7048	Intermediate Similarity	NPD5408	Approved
0.7047	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3887	Approved
0.7041	Intermediate Similarity	NPD2354	Approved
0.7039	Intermediate Similarity	NPD1247	Approved

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