NPASS Compound

Structure

NPC186800 OpenBabel07101719252D 36 40 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 -6.0622 2.5000 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 -3.4641 0.0000 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 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 0.0000 4.0000 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 -3.4641 1.0000 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 -5.1962 1.0000 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 -1.7321 3.0000 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 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 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 2.5981 1.5000 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 -6.0622 1.5000 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 10 1 0 0 0 0 2 34 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 12 1 0 0 0 0 5 14 2 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 11 16 2 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 34 1 0 0 0 0 15 16 1 0 0 0 0 15 35 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 27 2 0 0 0 0 20 28 2 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 29 1 1 0 0 0 22 24 1 0 0 0 0 22 30 1 6 0 0 0 23 26 1 0 0 0 0 23 31 1 6 0 0 0 24 25 1 1 0 0 0 24 36 1 0 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 26 35 1 1 0 0 0 26 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.12
Volume:	474.371
LogP:	2.664
LogD:	1.67
LogS:	-4.946
# Rotatable Bonds:	4
TPSA:	159.82
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	3.919
Fsp3:	0.269
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.24
MDCK Permeability:	1.57515678438358e-05
Pgp-inhibitor:	0.094
Pgp-substrate:	0.05
Human Intestinal Absorption (HIA):	0.464
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	91.00067901611328%
Volume Distribution (VD):	0.544
Pgp-substrate:	3.193326950073242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.146
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.196
CYP2C9-substrate:	0.247
CYP2D6-inhibitor:	0.089
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.039

ADMET: Excretion

Clearance (CL):	1.463
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.887
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.1
Carcinogencity:	0.792
Eye Corrosion:	0.003
Eye Irritation:	0.089
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC186800

Natural Product ID:	NPC186800
*Common Name:**	Pseudonocardone B
IUPAC Name:	(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(8-methoxy-3-methyl-7,12-dioxobenzo[a]anthracen-1-yl)oxyoxane-2-carboxylic acid
Synonyms:	Pseudonocardone B
Standard InCHIKey:	AMWRMWBDZWNIIN-TYUWDEHNSA-N
Standard InCHI:	InChI=1S/C26H22O10/c1-10-8-11-6-7-13-18(20(28)12-4-3-5-14(34-2)17(12)19(13)27)16(11)15(9-10)35-26-23(31)21(29)22(30)24(36-26)25(32)33/h3-9,21-24,26,29-31H,1-2H3,(H,32,33)/t21-,22-,23+,24-,26+/m0/s1
SMILES:	Cc1cc2ccc3c(c2c(c1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O)C(=O)c1cccc(c1C3=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152475
PubChem CID:	71458437
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[459989]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	IC50	=	50000.0	nM	PMID[459989]
NPT1466	Organism	Escherichia coli K12	Escherichia coli K-12	MIC	>	50.0	ug.mL-1	PMID[459989]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	50.0	ug.mL-1	PMID[459989]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50.0	ug.mL-1	PMID[459989]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	50.0	ug.mL-1	PMID[459989]

☑ 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 NPC186800 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	391
0.1-0.2	1561
0.2-0.3	3310
0.3-0.4	7578
0.4-0.5	9963
0.5-0.6	5899
0.6-0.7	5948
0.7-0.8	6618
0.8-0.85	1220
0.85-0.9	183
0.9-0.95	24
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC470667
0.9474	High Similarity	NPC205721
0.9458	High Similarity	NPC85368
0.9458	High Similarity	NPC203751
0.9345	High Similarity	NPC102053
0.9345	High Similarity	NPC289876
0.9329	High Similarity	NPC178281
0.9235	High Similarity	NPC277710
0.9235	High Similarity	NPC299149
0.9235	High Similarity	NPC153578
0.9235	High Similarity	NPC114257
0.9235	High Similarity	NPC58538
0.9207	High Similarity	NPC101116
0.9207	High Similarity	NPC212099
0.9207	High Similarity	NPC146837
0.9207	High Similarity	NPC278329
0.9181	High Similarity	NPC197357
0.9181	High Similarity	NPC85316
0.9091	High Similarity	NPC187934
0.9091	High Similarity	NPC97637
0.9086	High Similarity	NPC314672
0.908	High Similarity	NPC105591
0.9075	High Similarity	NPC224557
0.9075	High Similarity	NPC292706
0.907	High Similarity	NPC475161
0.907	High Similarity	NPC477860
0.9059	High Similarity	NPC68381
0.9023	High Similarity	NPC87583
0.9006	High Similarity	NPC475246
0.9006	High Similarity	NPC76112
0.9006	High Similarity	NPC170018
0.9006	High Similarity	NPC66820
0.9006	High Similarity	NPC92403
0.9	High Similarity	NPC199357
0.8994	High Similarity	NPC52598
0.8988	High Similarity	NPC63470
0.8976	High Similarity	NPC216752
0.8953	High Similarity	NPC47191
0.8947	High Similarity	NPC3718
0.8941	High Similarity	NPC76128
0.8941	High Similarity	NPC30432
0.8941	High Similarity	NPC271385
0.8941	High Similarity	NPC5029
0.8941	High Similarity	NPC183441
0.8941	High Similarity	NPC111536
0.8922	High Similarity	NPC17432
0.8895	High Similarity	NPC46958
0.8882	High Similarity	NPC478021
0.8882	High Similarity	NPC298778
0.8869	High Similarity	NPC478020
0.8869	High Similarity	NPC478022
0.8851	High Similarity	NPC315221
0.8848	High Similarity	NPC206641
0.8848	High Similarity	NPC208651
0.8837	High Similarity	NPC146803
0.883	High Similarity	NPC294501
0.8824	High Similarity	NPC246274
0.8824	High Similarity	NPC222455
0.8807	High Similarity	NPC241847
0.88	High Similarity	NPC473631
0.88	High Similarity	NPC313452
0.88	High Similarity	NPC473717
0.88	High Similarity	NPC293227
0.88	High Similarity	NPC475662
0.8788	High Similarity	NPC148323
0.8788	High Similarity	NPC283480
0.8786	High Similarity	NPC176246
0.8786	High Similarity	NPC475233
0.8779	High Similarity	NPC472054
0.8728	High Similarity	NPC470454
0.8728	High Similarity	NPC223735
0.8728	High Similarity	NPC307754
0.8728	High Similarity	NPC474345
0.8728	High Similarity	NPC199533
0.8728	High Similarity	NPC63105
0.8727	High Similarity	NPC3449
0.8727	High Similarity	NPC82190
0.8727	High Similarity	NPC174599
0.8727	High Similarity	NPC192219
0.8721	High Similarity	NPC315619
0.8715	High Similarity	NPC264302
0.8713	High Similarity	NPC175477
0.8713	High Similarity	NPC259905
0.8706	High Similarity	NPC178851
0.8701	High Similarity	NPC229817
0.8701	High Similarity	NPC473686
0.8701	High Similarity	NPC475220
0.8701	High Similarity	NPC221140
0.8701	High Similarity	NPC475352
0.8686	High Similarity	NPC212290
0.8686	High Similarity	NPC245059
0.8686	High Similarity	NPC84494
0.8683	High Similarity	NPC53139
0.8674	High Similarity	NPC282474
0.8674	High Similarity	NPC470198
0.8674	High Similarity	NPC470193
0.8674	High Similarity	NPC470196
0.8674	High Similarity	NPC470200
0.8674	High Similarity	NPC470194
0.8674	High Similarity	NPC470197
0.8674	High Similarity	NPC316274
0.8674	High Similarity	NPC470195
0.8671	High Similarity	NPC98776
0.8671	High Similarity	NPC65118
0.8671	High Similarity	NPC213052
0.8667	High Similarity	NPC474622
0.8667	High Similarity	NPC205172
0.8667	High Similarity	NPC474621
0.8667	High Similarity	NPC209393
0.8647	High Similarity	NPC99216
0.8644	High Similarity	NPC75574
0.8644	High Similarity	NPC231254
0.8636	High Similarity	NPC164047
0.8636	High Similarity	NPC470448
0.8636	High Similarity	NPC470452
0.8636	High Similarity	NPC470453
0.8634	High Similarity	NPC131405
0.8631	High Similarity	NPC328093
0.8629	High Similarity	NPC35167
0.8613	High Similarity	NPC471922
0.8613	High Similarity	NPC129930
0.8613	High Similarity	NPC471920
0.8613	High Similarity	NPC471921
0.8613	High Similarity	NPC114550
0.8613	High Similarity	NPC292712
0.8613	High Similarity	NPC20114
0.8613	High Similarity	NPC312006
0.8613	High Similarity	NPC474075
0.8611	High Similarity	NPC48474
0.8606	High Similarity	NPC474533
0.8606	High Similarity	NPC474534
0.8605	High Similarity	NPC473202
0.8605	High Similarity	NPC191653
0.8588	High Similarity	NPC478001
0.858	High Similarity	NPC72783
0.8571	High Similarity	NPC232818
0.8571	High Similarity	NPC198893
0.8571	High Similarity	NPC61904
0.8571	High Similarity	NPC144097
0.8571	High Similarity	NPC314489
0.8564	High Similarity	NPC314459
0.8564	High Similarity	NPC470199
0.8563	High Similarity	NPC229051
0.8563	High Similarity	NPC470336
0.8563	High Similarity	NPC470438
0.8563	High Similarity	NPC154986
0.8563	High Similarity	NPC470335
0.8555	High Similarity	NPC313304
0.8555	High Similarity	NPC280385
0.8555	High Similarity	NPC76047
0.8555	High Similarity	NPC469344
0.8547	High Similarity	NPC65489
0.8547	High Similarity	NPC469521
0.8538	High Similarity	NPC129264
0.8538	High Similarity	NPC19240
0.8538	High Similarity	NPC139060
0.8538	High Similarity	NPC280923
0.8538	High Similarity	NPC470735
0.8538	High Similarity	NPC205824
0.8538	High Similarity	NPC329647
0.8538	High Similarity	NPC85751
0.8531	High Similarity	NPC208069
0.8529	High Similarity	NPC326278
0.8523	High Similarity	NPC217387
0.8523	High Similarity	NPC477895
0.8523	High Similarity	NPC217520
0.8523	High Similarity	NPC293626
0.8523	High Similarity	NPC113836
0.8523	High Similarity	NPC258044
0.8523	High Similarity	NPC477682
0.8523	High Similarity	NPC139571
0.8523	High Similarity	NPC253521
0.8523	High Similarity	NPC196127
0.8523	High Similarity	NPC477683
0.8523	High Similarity	NPC470334
0.8523	High Similarity	NPC267680
0.8523	High Similarity	NPC37668
0.8514	High Similarity	NPC34267
0.8514	High Similarity	NPC81042
0.8514	High Similarity	NPC214621
0.8514	High Similarity	NPC193377
0.8514	High Similarity	NPC70862
0.8514	High Similarity	NPC223426
0.8512	High Similarity	NPC177742
0.8506	High Similarity	NPC478002
0.8506	High Similarity	NPC217822
0.8506	High Similarity	NPC473113
0.8506	High Similarity	NPC221288
0.8506	High Similarity	NPC101399
0.8506	High Similarity	NPC11847
0.8497	Intermediate Similarity	NPC137460
0.8488	Intermediate Similarity	NPC477835
0.8483	Intermediate Similarity	NPC36138
0.8483	Intermediate Similarity	NPC97119
0.8483	Intermediate Similarity	NPC135831
0.8483	Intermediate Similarity	NPC476203
0.8483	Intermediate Similarity	NPC297503
0.848	Intermediate Similarity	NPC66087
0.848	Intermediate Similarity	NPC179198
0.848	Intermediate Similarity	NPC278419

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 NPC186800 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	908
0.2-0.3	1677
0.3-0.4	2625
0.4-0.5	2045
0.5-0.6	1014
0.6-0.7	352
0.7-0.8	130
0.8-0.85	49
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.908	High Similarity	NPD7879	Clinical (unspecified phase)
0.9006	High Similarity	NPD8312	Approved
0.9006	High Similarity	NPD8313	Approved
0.8587	High Similarity	NPD7435	Discontinued
0.8424	Intermediate Similarity	NPD6776	Approved
0.8424	Intermediate Similarity	NPD6778	Approved
0.8424	Intermediate Similarity	NPD6782	Approved
0.8424	Intermediate Similarity	NPD6779	Approved
0.8424	Intermediate Similarity	NPD6780	Approved
0.8424	Intermediate Similarity	NPD6781	Approved
0.8424	Intermediate Similarity	NPD6777	Approved
0.8391	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD6559	Discontinued
0.8333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8316	Intermediate Similarity	NPD7874	Approved
0.8316	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3226	Approved
0.8256	Intermediate Similarity	NPD6959	Discontinued
0.8245	Intermediate Similarity	NPD7870	Phase 2
0.8245	Intermediate Similarity	NPD7871	Phase 2
0.8229	Intermediate Similarity	NPD3751	Discontinued
0.8225	Intermediate Similarity	NPD8455	Phase 2
0.8225	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD3787	Discontinued
0.8202	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8192	Intermediate Similarity	NPD6797	Phase 2
0.8191	Intermediate Similarity	NPD7696	Phase 3
0.8191	Intermediate Similarity	NPD7697	Approved
0.8191	Intermediate Similarity	NPD7698	Approved
0.8187	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7075	Discontinued
0.8182	Intermediate Similarity	NPD5844	Phase 1
0.8168	Intermediate Similarity	NPD8151	Discontinued
0.8152	Intermediate Similarity	NPD6535	Approved
0.8152	Intermediate Similarity	NPD6534	Approved
0.8148	Intermediate Similarity	NPD8319	Approved
0.8148	Intermediate Similarity	NPD8320	Phase 1
0.8146	Intermediate Similarity	NPD7251	Discontinued
0.8118	Intermediate Similarity	NPD7819	Suspended
0.8115	Intermediate Similarity	NPD7701	Phase 2
0.8103	Intermediate Similarity	NPD6232	Discontinued
0.8101	Intermediate Similarity	NPD7808	Phase 3
0.8086	Intermediate Similarity	NPD2346	Discontinued
0.807	Intermediate Similarity	NPD5402	Approved
0.8068	Intermediate Similarity	NPD7473	Discontinued
0.8059	Intermediate Similarity	NPD6801	Discontinued
0.8034	Intermediate Similarity	NPD7074	Phase 3
0.8022	Intermediate Similarity	NPD8150	Discontinued
0.8021	Intermediate Similarity	NPD7699	Phase 2
0.8021	Intermediate Similarity	NPD7700	Phase 2
0.8011	Intermediate Similarity	NPD6166	Phase 2
0.8011	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD7801	Approved
0.799	Intermediate Similarity	NPD7783	Phase 2
0.799	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7054	Approved
0.7941	Intermediate Similarity	NPD6599	Discontinued
0.7933	Intermediate Similarity	NPD7472	Approved
0.7921	Intermediate Similarity	NPD3818	Discontinued
0.791	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD6213	Phase 3
0.7903	Intermediate Similarity	NPD6212	Phase 3
0.7895	Intermediate Similarity	NPD7411	Suspended
0.7889	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7458	Discontinued
0.787	Intermediate Similarity	NPD5403	Approved
0.7861	Intermediate Similarity	NPD3817	Phase 2
0.7857	Intermediate Similarity	NPD5401	Approved
0.7853	Intermediate Similarity	NPD6823	Phase 2
0.7836	Intermediate Similarity	NPD4380	Phase 2
0.7816	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6799	Approved
0.7751	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD4628	Phase 3
0.7701	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD8434	Phase 2
0.7624	Intermediate Similarity	NPD7177	Discontinued
0.7614	Intermediate Similarity	NPD7768	Phase 2
0.7584	Intermediate Similarity	NPD5494	Approved
0.7571	Intermediate Similarity	NPD3749	Approved
0.7551	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD1934	Approved
0.7542	Intermediate Similarity	NPD7199	Phase 2
0.7527	Intermediate Similarity	NPD7228	Approved
0.7515	Intermediate Similarity	NPD7003	Approved
0.7514	Intermediate Similarity	NPD3882	Suspended
0.7513	Intermediate Similarity	NPD8285	Discontinued
0.7485	Intermediate Similarity	NPD2313	Discontinued
0.7443	Intermediate Similarity	NPD37	Approved
0.7442	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD2534	Approved
0.7442	Intermediate Similarity	NPD2533	Approved
0.7442	Intermediate Similarity	NPD2532	Approved
0.7425	Intermediate Similarity	NPD2799	Discontinued
0.7416	Intermediate Similarity	NPD4965	Approved
0.7416	Intermediate Similarity	NPD4967	Phase 2
0.7416	Intermediate Similarity	NPD4966	Approved
0.7401	Intermediate Similarity	NPD1465	Phase 2
0.7399	Intermediate Similarity	NPD6273	Approved
0.7384	Intermediate Similarity	NPD7390	Discontinued
0.7381	Intermediate Similarity	NPD5406	Approved
0.7381	Intermediate Similarity	NPD5405	Approved
0.7381	Intermediate Similarity	NPD5404	Approved
0.7381	Intermediate Similarity	NPD5408	Approved
0.7378	Intermediate Similarity	NPD6798	Discontinued
0.7366	Intermediate Similarity	NPD7240	Approved
0.7366	Intermediate Similarity	NPD7685	Pre-registration
0.7356	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6674	Discontinued
0.7337	Intermediate Similarity	NPD7799	Discontinued
0.7337	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6234	Discontinued
0.7333	Intermediate Similarity	NPD919	Approved
0.732	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2801	Approved
0.7294	Intermediate Similarity	NPD1549	Phase 2
0.7286	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD8059	Phase 3
0.7283	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2796	Approved
0.7278	Intermediate Similarity	NPD2935	Discontinued
0.7268	Intermediate Similarity	NPD3926	Phase 2
0.7262	Intermediate Similarity	NPD7097	Phase 1
0.7246	Intermediate Similarity	NPD1933	Approved
0.7243	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5763	Approved
0.7235	Intermediate Similarity	NPD1471	Phase 3
0.7235	Intermediate Similarity	NPD5762	Approved
0.7235	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6233	Phase 2
0.7225	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3750	Approved
0.72	Intermediate Similarity	NPD1512	Approved
0.7186	Intermediate Similarity	NPD4060	Phase 1
0.7176	Intermediate Similarity	NPD1551	Phase 2
0.7168	Intermediate Similarity	NPD6190	Approved
0.7159	Intermediate Similarity	NPD920	Approved
0.7158	Intermediate Similarity	NPD8127	Discontinued
0.7158	Intermediate Similarity	NPD1247	Approved
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2344	Approved
0.7134	Intermediate Similarity	NPD2798	Approved
0.712	Intermediate Similarity	NPD7229	Phase 3
0.7118	Intermediate Similarity	NPD7033	Discontinued
0.7118	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3748	Approved
0.7114	Intermediate Similarity	NPD7999	Approved
0.7093	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7930	Approved
0.7086	Intermediate Similarity	NPD1511	Approved
0.7079	Intermediate Similarity	NPD7584	Approved
0.7076	Intermediate Similarity	NPD2438	Suspended
0.7073	Intermediate Similarity	NPD1470	Approved
0.7066	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6844	Discontinued
0.7052	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD447	Suspended
0.7041	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5953	Discontinued
0.7035	Intermediate Similarity	NPD7266	Discontinued
0.7027	Intermediate Similarity	NPD5710	Approved
0.7027	Intermediate Similarity	NPD5711	Approved
0.7018	Intermediate Similarity	NPD1510	Phase 2
0.7011	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1607	Approved
0.6994	Remote Similarity	NPD2897	Discontinued
0.6994	Remote Similarity	NPD1608	Approved
0.6982	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2309	Approved
0.6954	Remote Similarity	NPD1243	Approved
0.6952	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD1653	Approved
0.6919	Remote Similarity	NPD4308	Phase 3
0.6912	Remote Similarity	NPD7583	Approved
0.6911	Remote Similarity	NPD8368	Discontinued
0.6911	Remote Similarity	NPD6765	Approved
0.6911	Remote Similarity	NPD6764	Approved
0.691	Remote Similarity	NPD5049	Phase 3
0.6909	Remote Similarity	NPD1283	Approved
0.6905	Remote Similarity	NPD7095	Approved
0.6887	Remote Similarity	NPD8366	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