NPASS Compound

Structure

NPC205721 OpenBabel07101718242D 37 41 0 0 1 0 0 0 0 0999 V2000 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 3.4641 -0.0000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 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 5.1962 -2.0000 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 0.8660 -0.5000 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 35 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 13 2 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 12 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 23 1 0 0 0 0 10 14 2 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 35 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 27 2 0 0 0 0 18 28 2 0 0 0 0 19 23 2 0 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 30 1 1 0 0 0 21 24 1 0 0 0 0 21 31 1 6 0 0 0 22 26 1 0 0 0 0 22 32 1 6 0 0 0 23 36 1 0 0 0 0 24 25 1 1 0 0 0 24 37 1 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 36 1 1 0 0 0 26 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.12
Volume:	483.161
LogP:	2.44
LogD:	1.502
LogS:	-4.536
# Rotatable Bonds:	4
TPSA:	180.05
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.263
Synthetic Accessibility Score:	4.038
Fsp3:	0.269
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.237
MDCK Permeability:	9.425474672752898e-06
Pgp-inhibitor:	0.163
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.674
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	93.1323013305664%
Volume Distribution (VD):	0.5
Pgp-substrate:	3.7564809322357178%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.159
CYP2C9-substrate:	0.158
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.029

ADMET: Excretion

Clearance (CL):	1.189
Half-life (T1/2):	0.28

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.884
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.057
Carcinogencity:	0.542
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC205721

Natural Product ID:	NPC205721
*Common Name:**	Pseudonocardone C
IUPAC Name:	(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1-hydroxy-8-methoxy-3-methyl-7,12-dioxobenzo[a]anthracen-2-yl)oxyoxane-2-carboxylic acid
Synonyms:	Pseudonocardone C
Standard InCHIKey:	PFYZXYHKMIBQRL-SNYRDRRFSA-N
Standard InCHI:	InChI=1S/C26H22O11/c1-9-8-10-6-7-12-16(18(28)11-4-3-5-13(35-2)15(11)17(12)27)14(10)19(29)23(9)36-26-22(32)20(30)21(31)24(37-26)25(33)34/h3-8,20-22,24,26,29-32H,1-2H3,(H,33,34)/t20-,21-,22+,24-,26+/m0/s1
SMILES:	COc1cccc2c1C(=O)c1ccc3c(c1C2=O)c(O)c(c(c3)C)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152476
PubChem CID:	71460288
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003415] Angucyclines

*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
NPO32794	pseudonocardia sp.	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23025282]

☑ 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	2
MIC	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[459918]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	IC50	>	100000.0	nM	PMID[459918]
NPT1466	Organism	Escherichia coli K12	Escherichia coli K-12	MIC	>	50.0	ug.mL-1	PMID[459918]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	50.0	ug.mL-1	PMID[459918]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50.0	ug.mL-1	PMID[459918]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	50.0	ug.mL-1	PMID[459918]

☑ 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 NPC205721 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	419
0.1-0.2	1720
0.2-0.3	3620
0.3-0.4	8421
0.4-0.5	9285
0.5-0.6	4957
0.6-0.7	5802
0.7-0.8	6069
0.8-0.85	1663
0.85-0.9	698
0.9-0.95	41
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9486	High Similarity	NPC105591
0.9477	High Similarity	NPC47191
0.9474	High Similarity	NPC470667
0.9474	High Similarity	NPC186800
0.9415	High Similarity	NPC199357
0.92	High Similarity	NPC277710
0.92	High Similarity	NPC114257
0.92	High Similarity	NPC153578
0.92	High Similarity	NPC212290
0.92	High Similarity	NPC299149
0.9191	High Similarity	NPC85368
0.9191	High Similarity	NPC203751
0.9186	High Similarity	NPC52598
0.9162	High Similarity	NPC314672
0.9111	High Similarity	NPC264302
0.9086	High Similarity	NPC289876
0.9086	High Similarity	NPC102053
0.907	High Similarity	NPC469521
0.9064	High Similarity	NPC178281
0.9045	High Similarity	NPC231254
0.904	High Similarity	NPC475161
0.904	High Similarity	NPC477860
0.9034	High Similarity	NPC35167
0.9034	High Similarity	NPC217520
0.9034	High Similarity	NPC139571
0.9029	High Similarity	NPC193377
0.9029	High Similarity	NPC146803
0.9029	High Similarity	NPC68381
0.8994	High Similarity	NPC87583
0.8989	High Similarity	NPC476203
0.8989	High Similarity	NPC36138
0.8983	High Similarity	NPC58538
0.8977	High Similarity	NPC475246
0.8977	High Similarity	NPC144097
0.8977	High Similarity	NPC61904
0.896	High Similarity	NPC298847
0.895	High Similarity	NPC201814
0.8947	High Similarity	NPC146837
0.8947	High Similarity	NPC278329
0.8947	High Similarity	NPC101116
0.8947	High Similarity	NPC212099
0.8944	High Similarity	NPC65489
0.8939	High Similarity	NPC470416
0.8933	High Similarity	NPC197357
0.8933	High Similarity	NPC85316
0.8933	High Similarity	NPC315221
0.8927	High Similarity	NPC267680
0.8927	High Similarity	NPC217387
0.8927	High Similarity	NPC477895
0.8927	High Similarity	NPC253521
0.8927	High Similarity	NPC293626
0.8927	High Similarity	NPC37668
0.8927	High Similarity	NPC196127
0.8927	High Similarity	NPC267549
0.8927	High Similarity	NPC258044
0.8927	High Similarity	NPC113836
0.892	High Similarity	NPC223426
0.892	High Similarity	NPC34267
0.892	High Similarity	NPC214621
0.892	High Similarity	NPC81042
0.892	High Similarity	NPC3718
0.8914	High Similarity	NPC111536
0.8914	High Similarity	NPC271385
0.8914	High Similarity	NPC30432
0.8914	High Similarity	NPC76128
0.8914	High Similarity	NPC5029
0.8907	High Similarity	NPC314020
0.8889	High Similarity	NPC111490
0.8889	High Similarity	NPC474093
0.8889	High Similarity	NPC104910
0.8889	High Similarity	NPC261623
0.8883	High Similarity	NPC313452
0.8883	High Similarity	NPC97119
0.8883	High Similarity	NPC135831
0.8883	High Similarity	NPC297503
0.887	High Similarity	NPC46958
0.887	High Similarity	NPC67629
0.887	High Similarity	NPC79736
0.8864	High Similarity	NPC175230
0.8864	High Similarity	NPC4390
0.8864	High Similarity	NPC88560
0.8864	High Similarity	NPC316539
0.8864	High Similarity	NPC172033
0.8864	High Similarity	NPC472993
0.8857	High Similarity	NPC298778
0.8857	High Similarity	NPC204937
0.8857	High Similarity	NPC149011
0.884	High Similarity	NPC475179
0.884	High Similarity	NPC174486
0.8837	High Similarity	NPC187934
0.8837	High Similarity	NPC469472
0.8837	High Similarity	NPC97637
0.8833	High Similarity	NPC470713
0.8833	High Similarity	NPC25946
0.8833	High Similarity	NPC470720
0.8833	High Similarity	NPC292706
0.8833	High Similarity	NPC460984
0.8833	High Similarity	NPC21359
0.8833	High Similarity	NPC224557
0.8833	High Similarity	NPC470717
0.8827	High Similarity	NPC208797
0.8827	High Similarity	NPC53680
0.882	High Similarity	NPC476620
0.882	High Similarity	NPC168584
0.882	High Similarity	NPC472387
0.882	High Similarity	NPC476621
0.882	High Similarity	NPC476622
0.882	High Similarity	NPC476618
0.882	High Similarity	NPC476623
0.882	High Similarity	NPC476619
0.8814	High Similarity	NPC294629
0.8814	High Similarity	NPC473630
0.8814	High Similarity	NPC108202
0.8811	High Similarity	NPC3474
0.8807	High Similarity	NPC153755
0.8807	High Similarity	NPC294501
0.8807	High Similarity	NPC292712
0.8807	High Similarity	NPC471921
0.8807	High Similarity	NPC175107
0.8807	High Similarity	NPC114550
0.8807	High Similarity	NPC67134
0.8807	High Similarity	NPC129930
0.8807	High Similarity	NPC474075
0.8807	High Similarity	NPC190003
0.8807	High Similarity	NPC471920
0.8807	High Similarity	NPC47140
0.8807	High Similarity	NPC471922
0.8807	High Similarity	NPC312006
0.8807	High Similarity	NPC20114
0.88	High Similarity	NPC222455
0.8791	High Similarity	NPC473618
0.8791	High Similarity	NPC119094
0.8791	High Similarity	NPC173872
0.8786	High Similarity	NPC147596
0.8785	High Similarity	NPC295625
0.8785	High Similarity	NPC473554
0.8785	High Similarity	NPC470719
0.8785	High Similarity	NPC241847
0.8785	High Similarity	NPC469650
0.8778	High Similarity	NPC241781
0.8778	High Similarity	NPC470718
0.8778	High Similarity	NPC473631
0.8778	High Similarity	NPC156785
0.8778	High Similarity	NPC162394
0.8778	High Similarity	NPC475662
0.8778	High Similarity	NPC293227
0.8778	High Similarity	NPC473717
0.8771	High Similarity	NPC471030
0.8771	High Similarity	NPC244903
0.8771	High Similarity	NPC80956
0.8764	High Similarity	NPC472385
0.8764	High Similarity	NPC472991
0.8764	High Similarity	NPC198324
0.8764	High Similarity	NPC472384
0.8764	High Similarity	NPC66820
0.8764	High Similarity	NPC472723
0.8764	High Similarity	NPC472992
0.8764	High Similarity	NPC472380
0.8764	High Similarity	NPC154741
0.8764	High Similarity	NPC475054
0.8764	High Similarity	NPC170018
0.8764	High Similarity	NPC297574
0.8764	High Similarity	NPC296018
0.8764	High Similarity	NPC472382
0.8764	High Similarity	NPC76112
0.8764	High Similarity	NPC268533
0.8764	High Similarity	NPC475233
0.8764	High Similarity	NPC92403
0.8757	High Similarity	NPC472054
0.875	High Similarity	NPC206123
0.875	High Similarity	NPC155763
0.875	High Similarity	NPC235260
0.875	High Similarity	NPC20505
0.875	High Similarity	NPC116864
0.875	High Similarity	NPC244776
0.875	High Similarity	NPC478021
0.8743	High Similarity	NPC31208
0.8743	High Similarity	NPC93065
0.8743	High Similarity	NPC469652
0.8743	High Similarity	NPC472720
0.8743	High Similarity	NPC63470
0.8743	High Similarity	NPC116745
0.8743	High Similarity	NPC160543
0.8743	High Similarity	NPC472721
0.8743	High Similarity	NPC472724
0.8736	High Similarity	NPC30011
0.8736	High Similarity	NPC179947
0.8736	High Similarity	NPC260521
0.8736	High Similarity	NPC64755
0.8736	High Similarity	NPC478020
0.8736	High Similarity	NPC72554
0.8736	High Similarity	NPC478022
0.8736	High Similarity	NPC97817
0.8736	High Similarity	NPC469649
0.8729	High Similarity	NPC223860
0.8729	High Similarity	NPC249560
0.8729	High Similarity	NPC275977
0.8729	High Similarity	NPC148710
0.8728	High Similarity	NPC61594
0.8728	High Similarity	NPC56735

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 NPC205721 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	944
0.2-0.3	1867
0.3-0.4	2622
0.4-0.5	1868
0.5-0.6	926
0.6-0.7	375
0.7-0.8	127
0.8-0.85	30
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8944	High Similarity	NPD7879	Clinical (unspecified phase)
0.8833	High Similarity	NPD8397	Clinical (unspecified phase)
0.8764	High Similarity	NPD8313	Approved
0.8764	High Similarity	NPD8312	Approved
0.8708	High Similarity	NPD4338	Clinical (unspecified phase)
0.8596	High Similarity	NPD6797	Phase 2
0.8547	High Similarity	NPD7251	Discontinued
0.8539	High Similarity	NPD7074	Phase 3
0.8523	High Similarity	NPD6168	Clinical (unspecified phase)
0.8523	High Similarity	NPD6166	Phase 2
0.8523	High Similarity	NPD6167	Clinical (unspecified phase)
0.8514	High Similarity	NPD6232	Discontinued
0.85	High Similarity	NPD7808	Phase 3
0.8483	Intermediate Similarity	NPD7054	Approved
0.8483	Intermediate Similarity	NPD5844	Phase 1
0.8475	Intermediate Similarity	NPD7473	Discontinued
0.8474	Intermediate Similarity	NPD7435	Discontinued
0.8436	Intermediate Similarity	NPD7472	Approved
0.8427	Intermediate Similarity	NPD3818	Discontinued
0.838	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6559	Discontinued
0.8316	Intermediate Similarity	NPD6781	Approved
0.8316	Intermediate Similarity	NPD6777	Approved
0.8316	Intermediate Similarity	NPD6778	Approved
0.8316	Intermediate Similarity	NPD6782	Approved
0.8316	Intermediate Similarity	NPD6779	Approved
0.8316	Intermediate Similarity	NPD6776	Approved
0.8316	Intermediate Similarity	NPD6780	Approved
0.8287	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD8151	Discontinued
0.8249	Intermediate Similarity	NPD6959	Discontinued
0.8229	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7874	Approved
0.8182	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7075	Discontinued
0.8162	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7870	Phase 2
0.8144	Intermediate Similarity	NPD7871	Phase 2
0.8122	Intermediate Similarity	NPD3751	Discontinued
0.8114	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8093	Intermediate Similarity	NPD7698	Approved
0.8093	Intermediate Similarity	NPD7696	Phase 3
0.8093	Intermediate Similarity	NPD7697	Approved
0.8068	Intermediate Similarity	NPD3817	Phase 2
0.8057	Intermediate Similarity	NPD1934	Approved
0.8053	Intermediate Similarity	NPD6534	Approved
0.8053	Intermediate Similarity	NPD6535	Approved
0.8051	Intermediate Similarity	NPD8319	Approved
0.8051	Intermediate Similarity	NPD8320	Phase 1
0.8023	Intermediate Similarity	NPD3882	Suspended
0.8022	Intermediate Similarity	NPD7228	Approved
0.802	Intermediate Similarity	NPD7701	Phase 2
0.8011	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD8455	Phase 2
0.8	Intermediate Similarity	NPD3787	Discontinued
0.799	Intermediate Similarity	NPD7783	Phase 2
0.799	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD3226	Approved
0.7955	Intermediate Similarity	NPD6801	Discontinued
0.7927	Intermediate Similarity	NPD7700	Phase 2
0.7927	Intermediate Similarity	NPD7699	Phase 2
0.7926	Intermediate Similarity	NPD8150	Discontinued
0.7912	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD1465	Phase 2
0.791	Intermediate Similarity	NPD7819	Suspended
0.7902	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD7801	Approved
0.7857	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7685	Pre-registration
0.7841	Intermediate Similarity	NPD4380	Phase 2
0.7833	Intermediate Similarity	NPD6234	Discontinued
0.7809	Intermediate Similarity	NPD2801	Approved
0.7797	Intermediate Similarity	NPD7411	Suspended
0.779	Intermediate Similarity	NPD5494	Approved
0.7784	Intermediate Similarity	NPD7458	Discontinued
0.7766	Intermediate Similarity	NPD6823	Phase 2
0.7765	Intermediate Similarity	NPD5402	Approved
0.7753	Intermediate Similarity	NPD37	Approved
0.7747	Intermediate Similarity	NPD7199	Phase 2
0.774	Intermediate Similarity	NPD6599	Discontinued
0.7722	Intermediate Similarity	NPD4965	Approved
0.7722	Intermediate Similarity	NPD4967	Phase 2
0.7722	Intermediate Similarity	NPD4966	Approved
0.772	Intermediate Similarity	NPD6212	Phase 3
0.772	Intermediate Similarity	NPD6213	Phase 3
0.772	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD2346	Discontinued
0.7657	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD4628	Phase 3
0.7624	Intermediate Similarity	NPD7768	Phase 2
0.7614	Intermediate Similarity	NPD1512	Approved
0.76	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6799	Approved
0.7586	Intermediate Similarity	NPD6190	Approved
0.7582	Intermediate Similarity	NPD3749	Approved
0.7572	Intermediate Similarity	NPD6674	Discontinued
0.7572	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5403	Approved
0.7566	Intermediate Similarity	NPD7240	Approved
0.7557	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD8434	Phase 2
0.7541	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD1511	Approved
0.7475	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD3926	Phase 2
0.7458	Intermediate Similarity	NPD2533	Approved
0.7458	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD2534	Approved
0.7458	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5401	Approved
0.7458	Intermediate Similarity	NPD2532	Approved
0.7457	Intermediate Similarity	NPD7266	Discontinued
0.743	Intermediate Similarity	NPD1653	Approved
0.7429	Intermediate Similarity	NPD7003	Approved
0.7401	Intermediate Similarity	NPD7390	Discontinued
0.7399	Intermediate Similarity	NPD5405	Approved
0.7399	Intermediate Similarity	NPD5408	Approved
0.7399	Intermediate Similarity	NPD5406	Approved
0.7399	Intermediate Similarity	NPD5404	Approved
0.7366	Intermediate Similarity	NPD8127	Discontinued
0.7366	Intermediate Similarity	NPD1247	Approved
0.7354	Intermediate Similarity	NPD7177	Discontinued
0.7337	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD1549	Phase 2
0.7299	Intermediate Similarity	NPD2935	Discontinued
0.7291	Intermediate Similarity	NPD7680	Approved
0.7267	Intermediate Similarity	NPD1933	Approved
0.7264	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2799	Discontinued
0.7232	Intermediate Similarity	NPD3750	Approved
0.7222	Intermediate Similarity	NPD8059	Phase 3
0.7222	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6273	Approved
0.7209	Intermediate Similarity	NPD4060	Phase 1
0.7193	Intermediate Similarity	NPD6798	Discontinued
0.7178	Intermediate Similarity	NPD8285	Discontinued
0.7168	Intermediate Similarity	NPD447	Suspended
0.7159	Intermediate Similarity	NPD2344	Approved
0.7143	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8166	Discontinued
0.7119	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7930	Approved
0.7102	Intermediate Similarity	NPD2796	Approved
0.7101	Intermediate Similarity	NPD7584	Approved
0.7093	Intermediate Similarity	NPD2313	Discontinued
0.7086	Intermediate Similarity	NPD7097	Phase 1
0.7083	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7799	Discontinued
0.7062	Intermediate Similarity	NPD5953	Discontinued
0.7053	Intermediate Similarity	NPD5710	Approved
0.7053	Intermediate Similarity	NPD5711	Approved
0.7052	Intermediate Similarity	NPD6233	Phase 2
0.7045	Intermediate Similarity	NPD1510	Phase 2
0.7029	Intermediate Similarity	NPD1607	Approved
0.7026	Intermediate Similarity	NPD7039	Approved
0.7026	Intermediate Similarity	NPD7038	Approved
0.7024	Intermediate Similarity	NPD2494	Approved
0.7024	Intermediate Similarity	NPD2493	Approved
0.7006	Intermediate Similarity	NPD1551	Phase 2
0.7	Intermediate Similarity	NPD2309	Approved
0.6995	Remote Similarity	NPD920	Approved
0.6991	Remote Similarity	NPD7907	Approved
0.6984	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD230	Phase 1
0.6971	Remote Similarity	NPD7999	Approved
0.6971	Remote Similarity	NPD6355	Discontinued
0.6966	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1471	Phase 3
0.6963	Remote Similarity	NPD7229	Phase 3
0.6949	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3748	Approved
0.6942	Remote Similarity	NPD3450	Approved
0.6942	Remote Similarity	NPD3452	Approved
0.6923	Remote Similarity	NPD4582	Approved
0.6923	Remote Similarity	NPD4583	Approved
0.6919	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD2488	Approved
0.6915	Remote Similarity	NPD2490	Approved
0.6914	Remote Similarity	NPD1613	Approved
0.6914	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1240	Approved
0.6914	Remote Similarity	NPD943	Approved
0.6912	Remote Similarity	NPD8366	Approved
0.691	Remote Similarity	NPD2438	Suspended
0.6908	Remote Similarity	NPD3057	Approved
0.6905	Remote Similarity	NPD7585	Approved
0.6901	Remote Similarity	NPD1470	Approved
0.6898	Remote Similarity	NPD4665	Approved
0.6898	Remote Similarity	NPD4111	Phase 1
0.6897	Remote Similarity	NPD3764	Approved
0.6889	Remote Similarity	NPD5698	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