NPASS Compound

Structure

NPC475783 OpenBabel07101718302D 37 42 0 0 1 0 0 0 0 0999 V2000 -5.6950 0.2582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3006 1.9009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3967 2.5804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6434 0.4859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2490 2.1286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0910 3.4251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0663 1.7357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4142 -1.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7248 -1.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8930 2.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0236 0.9657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0910 1.7357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9204 1.4211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5695 -2.1157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4142 -0.6526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0663 3.4251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5540 2.5804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1575 1.6811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1639 2.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7248 -0.6526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1268 0.5103 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5695 -0.1650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6930 1.1075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9639 1.2229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3667 0.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0114 -0.2188 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6994 1.9121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3967 0.8910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8688 1.6488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5695 -3.0910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5540 4.2697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5293 2.5804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1208 1.5285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8144 3.3963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8430 -0.7284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7360 2.0647 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 4 1 0 0 0 0 1 11 2 0 0 0 0 2 5 2 0 0 0 0 2 11 1 0 0 0 0 3 6 2 0 0 0 0 3 12 1 0 0 0 0 4 13 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 14 1 0 0 0 0 9 20 2 0 0 0 0 10 18 2 0 0 0 0 10 19 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 22 2 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 31 1 0 0 0 0 17 32 1 0 0 0 0 18 23 1 0 0 0 0 18 33 1 0 0 0 0 19 27 2 0 0 0 0 19 34 1 0 0 0 0 20 22 1 0 0 0 0 20 37 1 0 0 0 0 21 11 1 1 0 0 0 21 23 1 0 0 0 0 21 26 1 0 0 0 0 22 25 1 0 0 0 0 23 24 2 0 0 0 0 24 25 1 0 0 0 0 24 27 1 0 0 0 0 25 28 2 0 0 0 0 26 35 1 6 0 0 0 27 36 1 0 0 0 0 28 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.11
Volume:	486.343
LogP:	3.921
LogD:	2.551
LogS:	-5.124
# Rotatable Bonds:	2
TPSA:	174.98
# H-Bond Aceptor:	9
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.124
Synthetic Accessibility Score:	3.884
Fsp3:	0.071
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.177
MDCK Permeability:	4.901877673546551e-06
Pgp-inhibitor:	0.027
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.884
20% Bioavailability (F20%):	0.963
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	95.64180755615234%
Volume Distribution (VD):	0.449
Pgp-substrate:	4.505913257598877%

ADMET: Metabolism

CYP1A2-inhibitor:	0.654
CYP1A2-substrate:	0.146
CYP2C19-inhibitor:	0.124
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.639
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.267
CYP3A4-inhibitor:	0.096
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	9.327
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.581
Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.553
Skin Sensitization:	0.921
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.905
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC475783

Natural Product ID:	NPC475783
*Common Name:**	Malibatol B
IUPAC Name:	n.a.
Synonyms:	3',4'-Dihydroxy Malibatol A; Malibatol B
Standard InCHIKey:	OTJUFGKCGUDJEI-LVXARBLLSA-N
Standard InCHI:	InChI=1S/C28H20O9/c29-13-4-1-11(2-5-13)21-23-18(33)10-19(34)27(36)24(23)25-22-15(26(21)35)8-14(30)9-20(22)37-28(25)12-3-6-16(31)17(32)7-12/h1-10,21,26,29-36H/t21-,26-/m0/s1
SMILES:	Oc1ccc(cc1)[C@@H]1[C@@H](O)c2cc(O)cc3c2c(c2c1c(O)cc(c2O)O)c(o3)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515460
PubChem CID:	44575509
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	Eukaryota	Barks	n.a.	n.a.	PMID[22209731]
NPO10046	Hopea malibato	Species	n.a.	n.a.	Leaves	n.a.	n.a.	PMID[9544565]
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	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	4

Activity Type	# Activity
Cell Line	1
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	=	21.0	ug.mL-1	PMID[558809]
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	IC50	=	143000.0	nM	PMID[558810]
NPT671	Individual Protein	Acidic alpha-glucosidase	Rattus norvegicus	IC50	=	262000.0	nM	PMID[558810]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	10000.0	nM	PMID[558810]

☑ 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 NPC475783 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	515
0.1-0.2	1919
0.2-0.3	4233
0.3-0.4	10514
0.4-0.5	7674
0.5-0.6	3892
0.6-0.7	5400
0.7-0.8	5454
0.8-0.85	2259
0.85-0.9	817
0.9-0.95	19
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9451	High Similarity	NPC474591
0.9286	High Similarity	NPC174700
0.9172	High Similarity	NPC28589
0.9172	High Similarity	NPC248593
0.9107	High Similarity	NPC50394
0.9086	High Similarity	NPC73929
0.9086	High Similarity	NPC47905
0.9086	High Similarity	NPC139683
0.9048	High Similarity	NPC277480
0.9042	High Similarity	NPC133065
0.9029	High Similarity	NPC304322
0.9006	High Similarity	NPC473834
0.8994	High Similarity	NPC247973
0.8988	High Similarity	NPC37183
0.8988	High Similarity	NPC39306
0.8982	High Similarity	NPC312056
0.8982	High Similarity	NPC3448
0.8982	High Similarity	NPC477239
0.8982	High Similarity	NPC84515
0.8953	High Similarity	NPC287243
0.8941	High Similarity	NPC247136
0.8935	High Similarity	NPC224851
0.8935	High Similarity	NPC171985
0.8935	High Similarity	NPC320741
0.8922	High Similarity	NPC188486
0.8916	High Similarity	NPC329091
0.8914	High Similarity	NPC150977
0.8895	High Similarity	NPC216842
0.8895	High Similarity	NPC476640
0.8895	High Similarity	NPC149846
0.8895	High Similarity	NPC82217
0.8895	High Similarity	NPC310794
0.8882	High Similarity	NPC14662
0.8882	High Similarity	NPC470704
0.8882	High Similarity	NPC243877
0.8876	High Similarity	NPC291110
0.8876	High Similarity	NPC259757
0.8857	High Similarity	NPC47883
0.8855	High Similarity	NPC185526
0.8851	High Similarity	NPC265380
0.8841	High Similarity	NPC125300
0.8837	High Similarity	NPC230619
0.8837	High Similarity	NPC472454
0.8837	High Similarity	NPC54098
0.8837	High Similarity	NPC257667
0.8837	High Similarity	NPC186847
0.8837	High Similarity	NPC307286
0.883	High Similarity	NPC53252
0.883	High Similarity	NPC107627
0.883	High Similarity	NPC300307
0.8817	High Similarity	NPC475985
0.8802	High Similarity	NPC16935
0.8802	High Similarity	NPC196879
0.8802	High Similarity	NPC154304
0.8802	High Similarity	NPC190487
0.88	High Similarity	NPC185275
0.88	High Similarity	NPC324742
0.8795	High Similarity	NPC137100
0.8793	High Similarity	NPC8127
0.8793	High Similarity	NPC49667
0.8779	High Similarity	NPC476641
0.8779	High Similarity	NPC102277
0.8779	High Similarity	NPC131866
0.8779	High Similarity	NPC279209
0.8765	High Similarity	NPC36320
0.8765	High Similarity	NPC45449
0.8765	High Similarity	NPC29411
0.8765	High Similarity	NPC473286
0.8765	High Similarity	NPC326520
0.8757	High Similarity	NPC477841
0.8757	High Similarity	NPC231254
0.8757	High Similarity	NPC219927
0.8757	High Similarity	NPC154527
0.875	High Similarity	NPC188967
0.8743	High Similarity	NPC297807
0.8743	High Similarity	NPC471789
0.8735	High Similarity	NPC67396
0.8728	High Similarity	NPC81332
0.8728	High Similarity	NPC262580
0.8728	High Similarity	NPC289396
0.8728	High Similarity	NPC212038
0.8728	High Similarity	NPC271848
0.8728	High Similarity	NPC4200
0.8727	High Similarity	NPC207624
0.8721	High Similarity	NPC188079
0.8713	High Similarity	NPC128293
0.8713	High Similarity	NPC272560
0.8713	High Similarity	NPC170245
0.8708	High Similarity	NPC261623
0.8708	High Similarity	NPC111490
0.8708	High Similarity	NPC226725
0.8708	High Similarity	NPC469650
0.8706	High Similarity	NPC473313
0.8706	High Similarity	NPC39305
0.8706	High Similarity	NPC272064
0.8706	High Similarity	NPC59295
0.8706	High Similarity	NPC38591
0.8706	High Similarity	NPC263092
0.8706	High Similarity	NPC1755
0.8706	High Similarity	NPC329669
0.8706	High Similarity	NPC476295
0.8706	High Similarity	NPC472278
0.8706	High Similarity	NPC1706
0.8698	High Similarity	NPC158188
0.8698	High Similarity	NPC96031
0.8698	High Similarity	NPC196179
0.8698	High Similarity	NPC228383
0.8698	High Similarity	NPC231758
0.8698	High Similarity	NPC142252
0.8698	High Similarity	NPC34089
0.8693	High Similarity	NPC183843
0.869	High Similarity	NPC172202
0.869	High Similarity	NPC284127
0.869	High Similarity	NPC476410
0.8686	High Similarity	NPC478050
0.8683	High Similarity	NPC24640
0.8683	High Similarity	NPC45131
0.8678	High Similarity	NPC65885
0.8678	High Similarity	NPC261471
0.8675	High Similarity	NPC89474
0.8667	High Similarity	NPC115324
0.8667	High Similarity	NPC23668
0.8667	High Similarity	NPC58668
0.8667	High Similarity	NPC193976
0.8667	High Similarity	NPC204515
0.8667	High Similarity	NPC106372
0.8663	High Similarity	NPC477154
0.8663	High Similarity	NPC295082
0.8663	High Similarity	NPC6588
0.8663	High Similarity	NPC86477
0.8663	High Similarity	NPC260266
0.8663	High Similarity	NPC117854
0.8659	High Similarity	NPC269625
0.8659	High Similarity	NPC248315
0.8659	High Similarity	NPC65489
0.8655	High Similarity	NPC477840
0.8655	High Similarity	NPC169471
0.8655	High Similarity	NPC38914
0.8647	High Similarity	NPC238995
0.8647	High Similarity	NPC472964
0.8647	High Similarity	NPC329760
0.8647	High Similarity	NPC220912
0.8647	High Similarity	NPC476247
0.8647	High Similarity	NPC272722
0.8647	High Similarity	NPC81679
0.8639	High Similarity	NPC321399
0.8639	High Similarity	NPC472902
0.8636	High Similarity	NPC246877
0.8636	High Similarity	NPC98546
0.8631	High Similarity	NPC222814
0.8631	High Similarity	NPC99597
0.8631	High Similarity	NPC162869
0.8631	High Similarity	NPC472914
0.8631	High Similarity	NPC474836
0.8631	High Similarity	NPC210084
0.8631	High Similarity	NPC475267
0.8631	High Similarity	NPC300727
0.8631	High Similarity	NPC472910
0.8631	High Similarity	NPC63454
0.8631	High Similarity	NPC129684
0.8631	High Similarity	NPC245758
0.8631	High Similarity	NPC156057
0.8631	High Similarity	NPC472913
0.8631	High Similarity	NPC96167
0.8631	High Similarity	NPC470402
0.8631	High Similarity	NPC472911
0.8631	High Similarity	NPC183851
0.8631	High Similarity	NPC299520
0.8631	High Similarity	NPC469584
0.8631	High Similarity	NPC241904
0.8631	High Similarity	NPC48208
0.8631	High Similarity	NPC181960
0.8631	High Similarity	NPC474208
0.8629	High Similarity	NPC227906
0.8629	High Similarity	NPC300657
0.8623	High Similarity	NPC148938
0.8623	High Similarity	NPC99199
0.8621	High Similarity	NPC247964
0.8621	High Similarity	NPC469506
0.8621	High Similarity	NPC121333
0.8614	High Similarity	NPC142308
0.8614	High Similarity	NPC474843
0.8613	High Similarity	NPC475212
0.8613	High Similarity	NPC202470
0.8613	High Similarity	NPC476279
0.8611	High Similarity	NPC477083
0.8611	High Similarity	NPC477081
0.8605	High Similarity	NPC173292
0.8605	High Similarity	NPC477517
0.8605	High Similarity	NPC53640
0.8605	High Similarity	NPC43065
0.8596	High Similarity	NPC124038
0.8596	High Similarity	NPC7483
0.8596	High Similarity	NPC273959
0.8596	High Similarity	NPC228209
0.8588	High Similarity	NPC87431
0.8588	High Similarity	NPC66618
0.8588	High Similarity	NPC45124
0.8588	High Similarity	NPC32694
0.8588	High Similarity	NPC305987

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 NPC475783 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	447
0.1-0.2	988
0.2-0.3	1854
0.3-0.4	2704
0.4-0.5	1790
0.5-0.6	896
0.6-0.7	314
0.7-0.8	118
0.8-0.85	28
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8555	High Similarity	NPD3818	Discontinued
0.8547	High Similarity	NPD6166	Phase 2
0.8547	High Similarity	NPD6168	Clinical (unspecified phase)
0.8547	High Similarity	NPD6167	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD2801	Approved
0.8421	Intermediate Similarity	NPD5494	Approved
0.8412	Intermediate Similarity	NPD3749	Approved
0.8409	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD1934	Approved
0.8372	Intermediate Similarity	NPD6959	Discontinued
0.8353	Intermediate Similarity	NPD3882	Suspended
0.8295	Intermediate Similarity	NPD5844	Phase 1
0.8242	Intermediate Similarity	NPD1511	Approved
0.8212	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7473	Discontinued
0.8166	Intermediate Similarity	NPD4380	Phase 2
0.8146	Intermediate Similarity	NPD7074	Phase 3
0.8144	Intermediate Similarity	NPD1512	Approved
0.8114	Intermediate Similarity	NPD6232	Discontinued
0.8092	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD7054	Approved
0.8081	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD6559	Discontinued
0.8045	Intermediate Similarity	NPD7472	Approved
0.8043	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7977	Intermediate Similarity	NPD5402	Approved
0.7966	Intermediate Similarity	NPD3926	Phase 2
0.7956	Intermediate Similarity	NPD7251	Discontinued
0.7939	Intermediate Similarity	NPD1549	Phase 2
0.7921	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7819	Suspended
0.7879	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD3817	Phase 2
0.787	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1247	Approved
0.7829	Intermediate Similarity	NPD7768	Phase 2
0.7814	Intermediate Similarity	NPD7808	Phase 3
0.7803	Intermediate Similarity	NPD7411	Suspended
0.7784	Intermediate Similarity	NPD7075	Discontinued
0.7772	Intermediate Similarity	NPD8312	Approved
0.7772	Intermediate Similarity	NPD8313	Approved
0.7765	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD1510	Phase 2
0.7753	Intermediate Similarity	NPD7199	Phase 2
0.7735	Intermediate Similarity	NPD3751	Discontinued
0.7711	Intermediate Similarity	NPD2796	Approved
0.7709	Intermediate Similarity	NPD3787	Discontinued
0.7688	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD2344	Approved
0.7661	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6801	Discontinued
0.764	Intermediate Similarity	NPD6234	Discontinued
0.7633	Intermediate Similarity	NPD3750	Approved
0.7622	Intermediate Similarity	NPD943	Approved
0.7614	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7390	Discontinued
0.7596	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD5403	Approved
0.7569	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD2532	Approved
0.7558	Intermediate Similarity	NPD2533	Approved
0.7558	Intermediate Similarity	NPD2534	Approved
0.7557	Intermediate Similarity	NPD37	Approved
0.7553	Intermediate Similarity	NPD8434	Phase 2
0.7545	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD919	Approved
0.7541	Intermediate Similarity	NPD7228	Approved
0.7528	Intermediate Similarity	NPD4967	Phase 2
0.7528	Intermediate Similarity	NPD4966	Approved
0.7528	Intermediate Similarity	NPD4965	Approved
0.7515	Intermediate Similarity	NPD1240	Approved
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6799	Approved
0.7485	Intermediate Similarity	NPD2309	Approved
0.7474	Intermediate Similarity	NPD4287	Approved
0.7471	Intermediate Similarity	NPD920	Approved
0.7471	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5401	Approved
0.7443	Intermediate Similarity	NPD6599	Discontinued
0.7425	Intermediate Similarity	NPD1607	Approved
0.741	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1613	Approved
0.7398	Intermediate Similarity	NPD6776	Approved
0.7398	Intermediate Similarity	NPD6777	Approved
0.7398	Intermediate Similarity	NPD6779	Approved
0.7398	Intermediate Similarity	NPD6780	Approved
0.7398	Intermediate Similarity	NPD6781	Approved
0.7398	Intermediate Similarity	NPD6778	Approved
0.7398	Intermediate Similarity	NPD6782	Approved
0.7386	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3226	Approved
0.7384	Intermediate Similarity	NPD6190	Approved
0.7368	Intermediate Similarity	NPD2800	Approved
0.7363	Intermediate Similarity	NPD8151	Discontinued
0.7341	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3748	Approved
0.7322	Intermediate Similarity	NPD7229	Phase 3
0.7294	Intermediate Similarity	NPD2935	Discontinued
0.7286	Intermediate Similarity	NPD7435	Discontinued
0.7277	Intermediate Similarity	NPD8150	Discontinued
0.7267	Intermediate Similarity	NPD1243	Approved
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD230	Phase 1
0.725	Intermediate Similarity	NPD7870	Phase 2
0.725	Intermediate Similarity	NPD7871	Phase 2
0.7249	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1653	Approved
0.7225	Intermediate Similarity	NPD4628	Phase 3
0.7222	Intermediate Similarity	NPD5760	Phase 2
0.7222	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5761	Phase 2
0.7206	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7783	Phase 2
0.72	Intermediate Similarity	NPD7698	Approved
0.72	Intermediate Similarity	NPD7696	Phase 3
0.72	Intermediate Similarity	NPD7697	Approved
0.7196	Intermediate Similarity	NPD7685	Pre-registration
0.7193	Intermediate Similarity	NPD5408	Approved
0.7193	Intermediate Similarity	NPD5404	Approved
0.7193	Intermediate Similarity	NPD1551	Phase 2
0.7193	Intermediate Similarity	NPD5406	Approved
0.7193	Intermediate Similarity	NPD5405	Approved
0.7169	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4908	Phase 1
0.715	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD6535	Approved
0.7135	Intermediate Similarity	NPD2799	Discontinued
0.7129	Intermediate Similarity	NPD4665	Approved
0.7129	Intermediate Similarity	NPD4111	Phase 1
0.7127	Intermediate Similarity	NPD8455	Phase 2
0.7126	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3027	Phase 3
0.7122	Intermediate Similarity	NPD7801	Approved
0.7119	Intermediate Similarity	NPD6273	Approved
0.7108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7240	Approved
0.7102	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6100	Approved
0.7093	Intermediate Similarity	NPD6099	Approved
0.7083	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3764	Approved
0.7081	Intermediate Similarity	NPD8127	Discontinued
0.7073	Intermediate Similarity	NPD7874	Approved
0.7073	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5953	Discontinued
0.7052	Intermediate Similarity	NPD2346	Discontinued
0.7052	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5710	Approved
0.7043	Intermediate Similarity	NPD5711	Approved
0.7035	Intermediate Similarity	NPD7700	Phase 2
0.7035	Intermediate Similarity	NPD7699	Phase 2
0.7006	Intermediate Similarity	NPD2861	Phase 2
0.6995	Remote Similarity	NPD2296	Approved
0.6984	Remote Similarity	NPD7177	Discontinued
0.6982	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7907	Approved
0.6978	Remote Similarity	NPD6844	Discontinued
0.697	Remote Similarity	NPD4360	Phase 2
0.697	Remote Similarity	NPD4363	Phase 3
0.6959	Remote Similarity	NPD447	Suspended
0.6954	Remote Similarity	NPD1471	Phase 3
0.6947	Remote Similarity	NPD7286	Phase 2
0.6946	Remote Similarity	NPD7680	Approved
0.6932	Remote Similarity	NPD7003	Approved
0.6919	Remote Similarity	NPD6651	Approved
0.6919	Remote Similarity	NPD6212	Phase 3
0.6919	Remote Similarity	NPD6213	Phase 3
0.6919	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1470	Approved
0.6885	Remote Similarity	NPD6279	Approved
0.6885	Remote Similarity	NPD6280	Approved
0.6882	Remote Similarity	NPD2313	Discontinued
0.6878	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6808	Phase 2
0.685	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.685	Remote Similarity	NPD4361	Phase 2
0.6848	Remote Similarity	NPD1610	Phase 2
0.6848	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7033	Discontinued
0.6839	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD8166	Discontinued
0.6836	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8319	Approved
0.6829	Remote Similarity	NPD8320	Phase 1
0.6822	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7458	Discontinued

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