NPASS Compound

Structure

CID114257 OpenBabel06191715472D 42 46 0 0 1 0 0 0 0 0999 V2000 -6.7808 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -6.3617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -5.3830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 -6.8511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6284 -2.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7808 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 -4.8936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9332 -6.3617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6284 -3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -0.4894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9332 -2.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9332 -5.3830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7808 -3.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9332 -3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 -3.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -1.4681 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2380 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7808 -4.8936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9574 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8476 -1.4681 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8476 -0.4894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5428 -0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7808 -6.8511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4760 -3.9149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -2.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -3.4255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -1.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6284 -5.3830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 -1.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 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 9 1 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 30 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 10 31 2 0 0 0 0 11 19 2 0 0 0 0 11 23 1 0 0 0 0 12 19 1 0 0 0 0 12 32 1 0 0 0 0 13 21 2 0 0 0 0 13 33 1 0 0 0 0 14 20 1 0 0 0 0 14 34 1 0 0 0 0 15 18 2 0 0 0 0 15 41 1 0 0 0 0 16 8 1 6 0 0 0 16 24 1 0 0 0 0 16 42 1 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 25 2 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 23 35 2 0 0 0 0 24 27 1 0 0 0 0 24 36 1 1 0 0 0 25 37 1 0 0 0 0 26 38 2 0 0 0 0 27 28 1 0 0 0 0 27 39 1 6 0 0 0 28 29 1 0 0 0 0 28 40 1 1 0 0 0 29 41 1 6 0 0 0 29 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.14
Volume:	549.993
LogP:	3.06
LogD:	1.377
LogS:	-5.597
# Rotatable Bonds:	5
TPSA:	231.51
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.151
Synthetic Accessibility Score:	4.349
Fsp3:	0.276
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.475
MDCK Permeability:	5.621944183076266e-06
Pgp-inhibitor:	0.892
Pgp-substrate:	0.068
Human Intestinal Absorption (HIA):	0.871
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	98.74958038330078%
Volume Distribution (VD):	0.496
Pgp-substrate:	1.5229289531707764%

ADMET: Metabolism

CYP1A2-inhibitor:	0.284
CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.307
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	3.114
Half-life (T1/2):	0.081

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.859
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.174
Carcinogencity:	0.193
Eye Corrosion:	0.003
Eye Irritation:	0.68
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC114257

Natural Product ID:	NPC114257
*Common Name:**	Bulbineloneside D
IUPAC Name:	1-[3-acetyl-2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-4,5-dihydroxy-2-methylanthracene-9,10-dione
Synonyms:	Bulbineloneside D
Standard InCHIKey:	AOJYFODHRHWWEN-GQUXZSRASA-N
Standard InCHI:	InChI=1S/C29H26O13/c1-9-6-13(33)21-22(23(35)11-4-3-5-12(32)19(11)26(21)38)17(9)20-14(34)7-15(18(10(2)31)25(20)37)41-29-28(40)27(39)24(36)16(8-30)42-29/h3-7,16,24,27-30,32-34,36-37,39-40H,8H2,1-2H3/t16-,24-,27+,28-,29-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(O)c(c(c2C(=O)C)O)c2c(C)cc(c3c2C(=O)c2cccc(c2C3=O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447622
PubChem CID:	10008440
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO6812	Bulbine frutescens	Species	Xanthorrhoeaceae	Eukaryota	n.a.	root	n.a.	PMID[12193014]
NPO19263	Bulbinella floribunda	Species	Asphodelaceae	Eukaryota	roots	n.a.	n.a.	PMID[12828488]
NPO6812	Bulbine frutescens	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19263	Bulbinella floribunda	Species	Asphodelaceae	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	7

Activity Type	# Activity
Cell Line	2
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	IC50	>	120.0	ug.mL-1	PMID[570533]
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	90.0	ug.mL-1	PMID[570534]
NPT27	Others	Unspecified		IC50	>	120.0	ug.mL-1	PMID[570533]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.41	ug.mL-1	PMID[570534]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.43	ug.mL-1	PMID[570534]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	6.8	ug.mL-1	PMID[570534]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	0.7	ug.mL-1	PMID[570534]

☑ 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 NPC114257 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	430
0.1-0.2	1651
0.2-0.3	3478
0.3-0.4	8452
0.4-0.5	9360
0.5-0.6	4693
0.6-0.7	5197
0.7-0.8	5741
0.8-0.85	2609
0.85-0.9	984
0.9-0.95	82
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC299149
1.0	High Similarity	NPC277710
1.0	High Similarity	NPC153578
0.9763	High Similarity	NPC87583
0.9759	High Similarity	NPC475246
0.9758	High Similarity	NPC85368
0.9699	High Similarity	NPC3718
0.9697	High Similarity	NPC30432
0.9697	High Similarity	NPC76128
0.9697	High Similarity	NPC111536
0.9697	High Similarity	NPC271385
0.9697	High Similarity	NPC5029
0.9641	High Similarity	NPC46958
0.9591	High Similarity	NPC105591
0.9586	High Similarity	NPC475161
0.9586	High Similarity	NPC477860
0.9581	High Similarity	NPC68381
0.9576	High Similarity	NPC222455
0.9524	High Similarity	NPC475233
0.9521	High Similarity	NPC203751
0.9458	High Similarity	NPC259905
0.9455	High Similarity	NPC178851
0.9412	High Similarity	NPC212290
0.9408	High Similarity	NPC289876
0.9408	High Similarity	NPC102053
0.9405	High Similarity	NPC98776
0.9405	High Similarity	NPC213052
0.9401	High Similarity	NPC298778
0.9357	High Similarity	NPC315221
0.9349	High Similarity	NPC146803
0.9302	High Similarity	NPC475662
0.9302	High Similarity	NPC473717
0.9302	High Similarity	NPC313452
0.9302	High Similarity	NPC473631
0.9302	High Similarity	NPC293227
0.9298	High Similarity	NPC58538
0.929	High Similarity	NPC472054
0.929	High Similarity	NPC199357
0.9277	High Similarity	NPC478022
0.9277	High Similarity	NPC478020
0.9273	High Similarity	NPC146837
0.9273	High Similarity	NPC278329
0.9273	High Similarity	NPC101116
0.9273	High Similarity	NPC212099
0.9273	High Similarity	NPC216752
0.9244	High Similarity	NPC85316
0.9244	High Similarity	NPC197357
0.9235	High Similarity	NPC63105
0.9235	High Similarity	NPC470454
0.9235	High Similarity	NPC199533
0.9235	High Similarity	NPC470667
0.9235	High Similarity	NPC474345
0.9235	High Similarity	NPC186800
0.9205	High Similarity	NPC264302
0.92	High Similarity	NPC205721
0.9195	High Similarity	NPC475352
0.9195	High Similarity	NPC473686
0.9195	High Similarity	NPC229817
0.9195	High Similarity	NPC475220
0.9195	High Similarity	NPC221140
0.9186	High Similarity	NPC245059
0.9186	High Similarity	NPC84494
0.9162	High Similarity	NPC178281
0.9138	High Similarity	NPC231254
0.9138	High Similarity	NPC292706
0.9138	High Similarity	NPC224557
0.9133	High Similarity	NPC164047
0.9133	High Similarity	NPC470453
0.9133	High Similarity	NPC470448
0.9133	High Similarity	NPC470452
0.9112	High Similarity	NPC473202
0.9091	High Similarity	NPC324736
0.9086	High Similarity	NPC241847
0.9064	High Similarity	NPC168789
0.9059	High Similarity	NPC76047
0.9059	High Similarity	NPC478021
0.9053	High Similarity	NPC105414
0.9053	High Similarity	NPC472058
0.9053	High Similarity	NPC63470
0.9053	High Similarity	NPC324522
0.9053	High Similarity	NPC470341
0.9053	High Similarity	NPC234497
0.9042	High Similarity	NPC44947
0.904	High Similarity	NPC314672
0.9036	High Similarity	NPC472320
0.9034	High Similarity	NPC65489
0.903	High Similarity	NPC23817
0.9006	High Similarity	NPC294501
0.9	High Similarity	NPC470207
0.9	High Similarity	NPC470206
0.8994	High Similarity	NPC178173
0.8994	High Similarity	NPC477835
0.8988	High Similarity	NPC124155
0.8988	High Similarity	NPC257566
0.8983	High Similarity	NPC473618
0.8982	High Similarity	NPC18380
0.8982	High Similarity	NPC47923
0.8982	High Similarity	NPC303913
0.8976	High Similarity	NPC73511
0.8971	High Similarity	NPC132111
0.897	High Similarity	NPC78492
0.897	High Similarity	NPC208152
0.8953	High Similarity	NPC470336
0.8953	High Similarity	NPC154986
0.8953	High Similarity	NPC470335
0.8947	High Similarity	NPC78734
0.8947	High Similarity	NPC150767
0.8939	High Similarity	NPC314459
0.8939	High Similarity	NPC470199
0.8935	High Similarity	NPC469664
0.8929	High Similarity	NPC472876
0.8929	High Similarity	NPC187934
0.8929	High Similarity	NPC190450
0.8929	High Similarity	NPC259834
0.8929	High Similarity	NPC15374
0.8929	High Similarity	NPC131745
0.8929	High Similarity	NPC97637
0.8927	High Similarity	NPC179947
0.8922	High Similarity	NPC184326
0.8922	High Similarity	NPC271479
0.8922	High Similarity	NPC292863
0.8916	High Similarity	NPC156457
0.8916	High Similarity	NPC258035
0.8916	High Similarity	NPC313163
0.8916	High Similarity	NPC161749
0.8916	High Similarity	NPC197896
0.8914	High Similarity	NPC208797
0.8914	High Similarity	NPC53680
0.8909	High Similarity	NPC66508
0.8909	High Similarity	NPC226656
0.8909	High Similarity	NPC99233
0.8908	High Similarity	NPC472387
0.8908	High Similarity	NPC470334
0.8908	High Similarity	NPC267549
0.8908	High Similarity	NPC47191
0.8895	High Similarity	NPC477836
0.8895	High Similarity	NPC4200
0.8895	High Similarity	NPC67134
0.8895	High Similarity	NPC260263
0.8895	High Similarity	NPC47140
0.8895	High Similarity	NPC256760
0.8889	High Similarity	NPC300307
0.8889	High Similarity	NPC53252
0.8889	High Similarity	NPC229687
0.8889	High Similarity	NPC246274
0.8882	High Similarity	NPC70441
0.8876	High Similarity	NPC278419
0.8876	High Similarity	NPC66087
0.8876	High Similarity	NPC183672
0.8876	High Similarity	NPC290160
0.8876	High Similarity	NPC179198
0.887	High Similarity	NPC111490
0.887	High Similarity	NPC261623
0.8869	High Similarity	NPC477629
0.8869	High Similarity	NPC210961
0.8869	High Similarity	NPC195685
0.8869	High Similarity	NPC472994
0.8869	High Similarity	NPC270675
0.8869	High Similarity	NPC477628
0.8869	High Similarity	NPC73148
0.8869	High Similarity	NPC137232
0.8864	High Similarity	NPC478001
0.8864	High Similarity	NPC321916
0.8862	High Similarity	NPC308265
0.8862	High Similarity	NPC51760
0.8862	High Similarity	NPC195167
0.8855	High Similarity	NPC170475
0.8855	High Similarity	NPC261866
0.8855	High Similarity	NPC206378
0.8855	High Similarity	NPC45165
0.8851	High Similarity	NPC66820
0.8851	High Similarity	NPC170018
0.8851	High Similarity	NPC76112
0.8851	High Similarity	NPC312630
0.8851	High Similarity	NPC67629
0.8851	High Similarity	NPC324220
0.8851	High Similarity	NPC92403
0.8851	High Similarity	NPC79736
0.8848	High Similarity	NPC106625
0.8844	High Similarity	NPC175230
0.8844	High Similarity	NPC208668
0.8844	High Similarity	NPC88560
0.8844	High Similarity	NPC172033
0.8844	High Similarity	NPC472993
0.884	High Similarity	NPC470200
0.884	High Similarity	NPC470197
0.884	High Similarity	NPC470194
0.884	High Similarity	NPC282474
0.884	High Similarity	NPC470193
0.884	High Similarity	NPC470195
0.884	High Similarity	NPC316274
0.884	High Similarity	NPC470198
0.884	High Similarity	NPC470196
0.8837	High Similarity	NPC105511
0.8837	High Similarity	NPC313304
0.8837	High Similarity	NPC231194
0.8837	High Similarity	NPC52598
0.8837	High Similarity	NPC287884
0.8837	High Similarity	NPC204937
0.8837	High Similarity	NPC241874

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 NPC114257 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	921
0.2-0.3	1757
0.3-0.4	2661
0.4-0.5	1889
0.5-0.6	978
0.6-0.7	356
0.7-0.8	136
0.8-0.85	44
0.85-0.9	23
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8982	High Similarity	NPD6959	Discontinued
0.8953	High Similarity	NPD6559	Discontinued
0.8927	High Similarity	NPD7879	Clinical (unspecified phase)
0.8916	High Similarity	NPD4381	Clinical (unspecified phase)
0.8851	High Similarity	NPD8313	Approved
0.8851	High Similarity	NPD8312	Approved
0.8779	High Similarity	NPD7804	Clinical (unspecified phase)
0.8728	High Similarity	NPD7074	Phase 3
0.8671	High Similarity	NPD7054	Approved
0.8621	High Similarity	NPD7472	Approved
0.8617	High Similarity	NPD8151	Discontinued
0.8613	High Similarity	NPD3818	Discontinued
0.8596	High Similarity	NPD6232	Discontinued
0.8587	High Similarity	NPD6776	Approved
0.8587	High Similarity	NPD6777	Approved
0.8587	High Similarity	NPD6779	Approved
0.8587	High Similarity	NPD6778	Approved
0.8587	High Similarity	NPD6780	Approved
0.8587	High Similarity	NPD6782	Approved
0.8587	High Similarity	NPD6781	Approved
0.8571	High Similarity	NPD6797	Phase 2
0.8563	High Similarity	NPD5844	Phase 1
0.8555	High Similarity	NPD7473	Discontinued
0.8554	High Similarity	NPD4380	Phase 2
0.8523	High Similarity	NPD7251	Discontinued
0.8497	Intermediate Similarity	NPD6166	Phase 2
0.8497	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8475	Intermediate Similarity	NPD7808	Phase 3
0.8449	Intermediate Similarity	NPD7435	Discontinued
0.8404	Intermediate Similarity	NPD7870	Phase 2
0.8404	Intermediate Similarity	NPD7871	Phase 2
0.8402	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD7819	Suspended
0.8398	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8371	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD7075	Discontinued
0.8353	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8351	Intermediate Similarity	NPD7698	Approved
0.8351	Intermediate Similarity	NPD7696	Phase 3
0.8351	Intermediate Similarity	NPD7697	Approved
0.8315	Intermediate Similarity	NPD6535	Approved
0.8315	Intermediate Similarity	NPD6534	Approved
0.8304	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD3751	Discontinued
0.8284	Intermediate Similarity	NPD7411	Suspended
0.8272	Intermediate Similarity	NPD7701	Phase 2
0.8238	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8238	Intermediate Similarity	NPD7783	Phase 2
0.8235	Intermediate Similarity	NPD1934	Approved
0.8201	Intermediate Similarity	NPD6823	Phase 2
0.8187	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7874	Approved
0.8187	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7699	Phase 2
0.8182	Intermediate Similarity	NPD7700	Phase 2
0.8171	Intermediate Similarity	NPD3787	Discontinued
0.8156	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7801	Approved
0.8144	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6801	Discontinued
0.8092	Intermediate Similarity	NPD7768	Phase 2
0.8084	Intermediate Similarity	NPD7390	Discontinued
0.8081	Intermediate Similarity	NPD8455	Phase 2
0.8065	Intermediate Similarity	NPD6213	Phase 3
0.8065	Intermediate Similarity	NPD6212	Phase 3
0.8065	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD3226	Approved
0.8057	Intermediate Similarity	NPD5494	Approved
0.8046	Intermediate Similarity	NPD3749	Approved
0.8036	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD8320	Phase 1
0.8021	Intermediate Similarity	NPD8319	Approved
0.8	Intermediate Similarity	NPD1549	Phase 2
0.7989	Intermediate Similarity	NPD7228	Approved
0.7977	Intermediate Similarity	NPD2801	Approved
0.7939	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD5402	Approved
0.7929	Intermediate Similarity	NPD2533	Approved
0.7929	Intermediate Similarity	NPD2532	Approved
0.7929	Intermediate Similarity	NPD2534	Approved
0.7907	Intermediate Similarity	NPD6599	Discontinued
0.7886	Intermediate Similarity	NPD3882	Suspended
0.7874	Intermediate Similarity	NPD1465	Phase 2
0.7871	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7458	Discontinued
0.7829	Intermediate Similarity	NPD3817	Phase 2
0.7818	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD37	Approved
0.7809	Intermediate Similarity	NPD7199	Phase 2
0.7797	Intermediate Similarity	NPD6234	Discontinued
0.7796	Intermediate Similarity	NPD8150	Discontinued
0.7784	Intermediate Similarity	NPD4967	Phase 2
0.7784	Intermediate Similarity	NPD4965	Approved
0.7784	Intermediate Similarity	NPD4966	Approved
0.7771	Intermediate Similarity	NPD2796	Approved
0.7765	Intermediate Similarity	NPD1511	Approved
0.7765	Intermediate Similarity	NPD6799	Approved
0.7733	Intermediate Similarity	NPD5403	Approved
0.7725	Intermediate Similarity	NPD2346	Discontinued
0.7711	Intermediate Similarity	NPD1510	Phase 2
0.7704	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1607	Approved
0.7692	Intermediate Similarity	NPD3750	Approved
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7674	Intermediate Similarity	NPD1512	Approved
0.7665	Intermediate Similarity	NPD7584	Approved
0.7647	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7240	Approved
0.7616	Intermediate Similarity	NPD5401	Approved
0.7616	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8059	Phase 3
0.7588	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1240	Approved
0.7574	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5408	Approved
0.756	Intermediate Similarity	NPD5405	Approved
0.756	Intermediate Similarity	NPD5404	Approved
0.756	Intermediate Similarity	NPD5406	Approved
0.7527	Intermediate Similarity	NPD3926	Phase 2
0.7514	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7003	Approved
0.7474	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD5710	Approved
0.7473	Intermediate Similarity	NPD5953	Discontinued
0.7473	Intermediate Similarity	NPD5711	Approved
0.7456	Intermediate Similarity	NPD1551	Phase 2
0.7456	Intermediate Similarity	NPD2935	Discontinued
0.7433	Intermediate Similarity	NPD7685	Pre-registration
0.7429	Intermediate Similarity	NPD920	Approved
0.7427	Intermediate Similarity	NPD2800	Approved
0.7427	Intermediate Similarity	NPD6674	Discontinued
0.7421	Intermediate Similarity	NPD8434	Phase 2
0.7412	Intermediate Similarity	NPD2344	Approved
0.7405	Intermediate Similarity	NPD7177	Discontinued
0.7396	Intermediate Similarity	NPD3748	Approved
0.7386	Intermediate Similarity	NPD1653	Approved
0.7377	Intermediate Similarity	NPD7229	Phase 3
0.736	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6100	Approved
0.7353	Intermediate Similarity	NPD6099	Approved
0.7349	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD1247	Approved
0.7314	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD8285	Discontinued
0.7308	Intermediate Similarity	NPD919	Approved
0.7294	Intermediate Similarity	NPD2799	Discontinued
0.7289	Intermediate Similarity	NPD4625	Phase 3
0.7283	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7585	Approved
0.7273	Intermediate Similarity	NPD6273	Approved
0.7273	Intermediate Similarity	NPD7286	Phase 2
0.7257	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7680	Approved
0.7241	Intermediate Similarity	NPD2309	Approved
0.7233	Intermediate Similarity	NPD7930	Approved
0.7229	Intermediate Similarity	NPD4908	Phase 1
0.7228	Intermediate Similarity	NPD7583	Approved
0.7225	Intermediate Similarity	NPD1243	Approved
0.7222	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4363	Phase 3
0.7194	Intermediate Similarity	NPD4360	Phase 2
0.7165	Intermediate Similarity	NPD4287	Approved
0.716	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1613	Approved
0.716	Intermediate Similarity	NPD943	Approved
0.7152	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7097	Phase 1
0.7128	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7266	Discontinued
0.7076	Intermediate Similarity	NPD6651	Approved
0.7045	Intermediate Similarity	NPD6190	Approved
0.7043	Intermediate Similarity	NPD8127	Discontinued
0.7042	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8366	Approved
0.7018	Intermediate Similarity	NPD1933	Approved
0.7018	Intermediate Similarity	NPD230	Phase 1
0.7011	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7999	Approved
0.7006	Intermediate Similarity	NPD2798	Approved
0.6995	Remote Similarity	NPD5761	Phase 2
0.6995	Remote Similarity	NPD5760	Phase 2
0.6994	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4060	Phase 1
0.6954	Remote Similarity	NPD2438	Suspended
0.6941	Remote Similarity	NPD3764	Approved
0.6941	Remote Similarity	NPD6798	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