NPASS Compound

Structure

NPC474534 OpenBabel07101719132D 36 40 0 0 1 0 0 0 0 0999 V2000 -5.1962 -3.0000 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 1.7321 -3.0000 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 0.8660 -3.5000 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 3.4641 -2.0000 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 0.8660 -4.5000 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 -4.3301 -4.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 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 -0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 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 -0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 19 2 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 20 2 0 0 0 0 13 22 1 0 0 0 0 13 35 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 23 2 0 0 0 0 17 12 1 6 0 0 0 17 18 1 0 0 0 0 18 24 2 0 0 0 0 19 23 1 0 0 0 0 19 29 1 0 0 0 0 20 24 1 0 0 0 0 20 30 1 0 0 0 0 21 12 1 6 0 0 0 21 25 1 0 0 0 0 21 35 1 0 0 0 0 22 26 1 0 0 0 0 22 36 1 6 0 0 0 23 27 1 0 0 0 0 24 27 1 0 0 0 0 25 26 1 0 0 0 0 25 31 1 1 0 0 0 26 32 1 6 0 0 0 27 33 2 0 0 0 0 28 34 2 0 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.16
Volume:	491.383
LogP:	4.894
LogD:	3.005
LogS:	-3.914
# Rotatable Bonds:	5
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.217
Synthetic Accessibility Score:	4.008
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.69
MDCK Permeability:	5.815893928229343e-06
Pgp-inhibitor:	0.03
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.904
20% Bioavailability (F20%):	0.091
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	99.13050079345703%
Volume Distribution (VD):	0.383
Pgp-substrate:	1.8536441326141357%

ADMET: Metabolism

CYP1A2-inhibitor:	0.689
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.662
CYP2C9-substrate:	0.643
CYP2D6-inhibitor:	0.769
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.124
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	7.0
Half-life (T1/2):	0.753

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.074
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.72
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.094
Skin Sensitization:	0.947
Carcinogencity:	0.623
Eye Corrosion:	0.003
Eye Irritation:	0.912
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC474534

Natural Product ID:	NPC474534
*Common Name:**	Picramnioside H
IUPAC Name:	[(3R,4S,5S,6R)-6-[[(9R)-4,5-dihydroxy-2-methyl-10-oxo-9H-anthracen-9-yl]methyl]-4,5-dihydroxyoxan-3-yl] benzoate
Synonyms:	Picramnioside H
Standard InCHIKey:	HQLGEJWTJQYJJK-AHVPVAHRSA-N
Standard InCHI:	InChI=1S/C28H26O8/c1-14-10-18-17(16-8-5-9-19(29)23(16)27(33)24(18)20(30)11-14)12-21-25(31)26(32)22(13-35-21)36-28(34)15-6-3-2-4-7-15/h2-11,17,21-22,25-26,29-32H,12-13H2,1H3/t17-,21-,22-,25-,26-/m1/s1
SMILES:	Cc1cc(O)c2c(c1)[C@H](C[C@H]1OC[C@H]([C@H]([C@@H]1O)O)OC(=O)c1ccccc1)c1c(C2=O)c(O)ccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471183
PubChem CID:	44575608
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO1872	Picramnia latifolia	Species	Picramniaceae	Eukaryota	n.a.	Peru	n.a.	PMID[15043409]
NPO1872	Picramnia latifolia	Species	Picramniaceae	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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[456294]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[456294]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[456294]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[456294]

☑ 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 NPC474534 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	334
0.1-0.2	1214
0.2-0.3	2668
0.3-0.4	5799
0.4-0.5	10844
0.5-0.6	6644
0.6-0.7	6734
0.7-0.8	7917
0.8-0.85	463
0.85-0.9	62
0.9-0.95	14
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474533
0.9796	High Similarity	NPC474621
0.9796	High Similarity	NPC474622
0.9477	High Similarity	NPC97637
0.9477	High Similarity	NPC187934
0.9211	High Similarity	NPC82190
0.9211	High Similarity	NPC174599
0.9211	High Similarity	NPC192219
0.915	High Similarity	NPC148323
0.915	High Similarity	NPC283480
0.9122	High Similarity	NPC170055
0.9054	High Similarity	NPC218866
0.9054	High Similarity	NPC48130
0.9054	High Similarity	NPC84568
0.9054	High Similarity	NPC300684
0.9032	High Similarity	NPC53139
0.902	High Similarity	NPC205172
0.902	High Similarity	NPC209393
0.8968	High Similarity	NPC208651
0.8968	High Similarity	NPC206641
0.8933	High Similarity	NPC285122
0.8933	High Similarity	NPC147250
0.8868	High Similarity	NPC478020
0.8868	High Similarity	NPC178281
0.8868	High Similarity	NPC478022
0.8839	High Similarity	NPC266469
0.8839	High Similarity	NPC3449
0.88	High Similarity	NPC103910
0.8784	High Similarity	NPC225243
0.8782	High Similarity	NPC478027
0.878	High Similarity	NPC76112
0.878	High Similarity	NPC66820
0.878	High Similarity	NPC92403
0.878	High Similarity	NPC170018
0.875	High Similarity	NPC119767
0.8742	High Similarity	NPC278329
0.8742	High Similarity	NPC146837
0.872	High Similarity	NPC470667
0.8684	High Similarity	NPC120536
0.8659	High Similarity	NPC85368
0.8659	High Similarity	NPC203751
0.8654	High Similarity	NPC470408
0.8654	High Similarity	NPC182921
0.8654	High Similarity	NPC218870
0.8654	High Similarity	NPC474824
0.865	High Similarity	NPC478021
0.8625	High Similarity	NPC212099
0.8625	High Similarity	NPC101116
0.8609	High Similarity	NPC476473
0.8608	High Similarity	NPC317580
0.8606	High Similarity	NPC186800
0.8599	High Similarity	NPC66029
0.8598	High Similarity	NPC183441
0.8598	High Similarity	NPC294501
0.8581	High Similarity	NPC205766
0.8571	High Similarity	NPC106524
0.8571	High Similarity	NPC94781
0.8571	High Similarity	NPC290695
0.8554	High Similarity	NPC102053
0.8554	High Similarity	NPC289876
0.8553	High Similarity	NPC326084
0.8544	High Similarity	NPC471787
0.8544	High Similarity	NPC474861
0.8543	High Similarity	NPC474300
0.8528	High Similarity	NPC469521
0.8528	High Similarity	NPC107009
0.8528	High Similarity	NPC63470
0.8519	High Similarity	NPC71390
0.8516	High Similarity	NPC44378
0.8516	High Similarity	NPC280753
0.8506	High Similarity	NPC52161
0.8506	High Similarity	NPC162751
0.8506	High Similarity	NPC81835
0.8503	High Similarity	NPC472262
0.8503	High Similarity	NPC161964
0.8503	High Similarity	NPC287604
0.85	High Similarity	NPC475449
0.8491	Intermediate Similarity	NPC29552
0.8487	Intermediate Similarity	NPC21873
0.8481	Intermediate Similarity	NPC318270
0.8477	Intermediate Similarity	NPC130485
0.8471	Intermediate Similarity	NPC478220
0.8467	Intermediate Similarity	NPC86744
0.8467	Intermediate Similarity	NPC295339
0.8466	Intermediate Similarity	NPC477835
0.8462	Intermediate Similarity	NPC475662
0.8462	Intermediate Similarity	NPC475890
0.8462	Intermediate Similarity	NPC477914
0.8462	Intermediate Similarity	NPC293227
0.8462	Intermediate Similarity	NPC315520
0.8462	Intermediate Similarity	NPC473631
0.8462	Intermediate Similarity	NPC473717
0.8452	Intermediate Similarity	NPC299149
0.8452	Intermediate Similarity	NPC58538
0.8452	Intermediate Similarity	NPC114257
0.8452	Intermediate Similarity	NPC277710
0.8452	Intermediate Similarity	NPC153578
0.8447	Intermediate Similarity	NPC97812
0.8443	Intermediate Similarity	NPC176246
0.8442	Intermediate Similarity	NPC314437
0.8438	Intermediate Similarity	NPC314795
0.8434	Intermediate Similarity	NPC472054
0.8424	Intermediate Similarity	NPC313304
0.8424	Intermediate Similarity	NPC241874
0.8424	Intermediate Similarity	NPC298778
0.8421	Intermediate Similarity	NPC105591
0.8411	Intermediate Similarity	NPC220496
0.8411	Intermediate Similarity	NPC147542
0.8411	Intermediate Similarity	NPC37992
0.8411	Intermediate Similarity	NPC241349
0.8411	Intermediate Similarity	NPC327916
0.8411	Intermediate Similarity	NPC42262
0.8411	Intermediate Similarity	NPC32749
0.8405	Intermediate Similarity	NPC478026
0.8405	Intermediate Similarity	NPC471788
0.8402	Intermediate Similarity	NPC477860
0.8402	Intermediate Similarity	NPC85316
0.8402	Intermediate Similarity	NPC197357
0.8402	Intermediate Similarity	NPC475161
0.84	Intermediate Similarity	NPC61590
0.84	Intermediate Similarity	NPC197666
0.84	Intermediate Similarity	NPC126739
0.8397	Intermediate Similarity	NPC478219
0.8397	Intermediate Similarity	NPC477221
0.8397	Intermediate Similarity	NPC247219
0.8395	Intermediate Similarity	NPC216752
0.8395	Intermediate Similarity	NPC315772
0.8385	Intermediate Similarity	NPC208676
0.8385	Intermediate Similarity	NPC472055
0.8385	Intermediate Similarity	NPC130489
0.8383	Intermediate Similarity	NPC68381
0.8383	Intermediate Similarity	NPC474345
0.8373	Intermediate Similarity	NPC477836
0.8372	Intermediate Similarity	NPC205721
0.8366	Intermediate Similarity	NPC471682
0.8366	Intermediate Similarity	NPC471731
0.8365	Intermediate Similarity	NPC472807
0.8364	Intermediate Similarity	NPC246274
0.8364	Intermediate Similarity	NPC175477
0.8363	Intermediate Similarity	NPC229817
0.8363	Intermediate Similarity	NPC473686
0.8363	Intermediate Similarity	NPC221140
0.8363	Intermediate Similarity	NPC475352
0.8363	Intermediate Similarity	NPC475220
0.8355	Intermediate Similarity	NPC257003
0.8354	Intermediate Similarity	NPC257847
0.8354	Intermediate Similarity	NPC178173
0.8344	Intermediate Similarity	NPC256463
0.8344	Intermediate Similarity	NPC306835
0.8344	Intermediate Similarity	NPC476477
0.8344	Intermediate Similarity	NPC299405
0.8344	Intermediate Similarity	NPC111422
0.8344	Intermediate Similarity	NPC29771
0.8344	Intermediate Similarity	NPC471602
0.8344	Intermediate Similarity	NPC216312
0.8333	Intermediate Similarity	NPC324220
0.8333	Intermediate Similarity	NPC62272
0.8333	Intermediate Similarity	NPC475246
0.8333	Intermediate Similarity	NPC312630
0.8333	Intermediate Similarity	NPC245923
0.8333	Intermediate Similarity	NPC472261
0.8333	Intermediate Similarity	NPC18380
0.8323	Intermediate Similarity	NPC199357
0.8323	Intermediate Similarity	NPC324736
0.8323	Intermediate Similarity	NPC300540
0.8323	Intermediate Similarity	NPC470339
0.8323	Intermediate Similarity	NPC65118
0.8323	Intermediate Similarity	NPC470570
0.8322	Intermediate Similarity	NPC142027
0.8322	Intermediate Similarity	NPC27407
0.8313	Intermediate Similarity	NPC313299
0.8313	Intermediate Similarity	NPC478223
0.8313	Intermediate Similarity	NPC208152
0.8313	Intermediate Similarity	NPC78492
0.8312	Intermediate Similarity	NPC151607
0.8312	Intermediate Similarity	NPC477913
0.8312	Intermediate Similarity	NPC42540
0.8304	Intermediate Similarity	NPC292706
0.8304	Intermediate Similarity	NPC224557
0.8303	Intermediate Similarity	NPC472058
0.8303	Intermediate Similarity	NPC105414
0.8303	Intermediate Similarity	NPC324522
0.8303	Intermediate Similarity	NPC234497
0.8303	Intermediate Similarity	NPC470341
0.8303	Intermediate Similarity	NPC471295
0.8302	Intermediate Similarity	NPC478218
0.8301	Intermediate Similarity	NPC471733
0.8301	Intermediate Similarity	NPC257644
0.8301	Intermediate Similarity	NPC469520
0.8301	Intermediate Similarity	NPC85310
0.8291	Intermediate Similarity	NPC205918
0.8291	Intermediate Similarity	NPC477276
0.8291	Intermediate Similarity	NPC39819
0.8289	Intermediate Similarity	NPC168471
0.8289	Intermediate Similarity	NPC315578
0.8282	Intermediate Similarity	NPC473961
0.8282	Intermediate Similarity	NPC15374
0.828	Intermediate Similarity	NPC120171
0.828	Intermediate Similarity	NPC327962
0.8274	Intermediate Similarity	NPC223735

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 NPC474534 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	795
0.2-0.3	1461
0.3-0.4	2474
0.4-0.5	2264
0.5-0.6	1199
0.6-0.7	506
0.7-0.8	161
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.878	High Similarity	NPD8313	Approved
0.878	High Similarity	NPD8312	Approved
0.8512	High Similarity	NPD8150	Discontinued
0.8333	Intermediate Similarity	NPD5408	Approved
0.8333	Intermediate Similarity	NPD5406	Approved
0.8333	Intermediate Similarity	NPD5405	Approved
0.8333	Intermediate Similarity	NPD5404	Approved
0.8314	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6959	Discontinued
0.8198	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD3226	Approved
0.8158	Intermediate Similarity	NPD2346	Discontinued
0.8141	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7473	Discontinued
0.8113	Intermediate Similarity	NPD4380	Phase 2
0.8077	Intermediate Similarity	NPD7390	Discontinued
0.8061	Intermediate Similarity	NPD6232	Discontinued
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD7003	Approved
0.7963	Intermediate Similarity	NPD7819	Suspended
0.7927	Intermediate Similarity	NPD7075	Discontinued
0.7912	Intermediate Similarity	NPD8320	Phase 1
0.7912	Intermediate Similarity	NPD8319	Approved
0.791	Intermediate Similarity	NPD6534	Approved
0.791	Intermediate Similarity	NPD6535	Approved
0.7891	Intermediate Similarity	NPD1470	Approved
0.7862	Intermediate Similarity	NPD1201	Approved
0.7857	Intermediate Similarity	NPD7435	Discontinued
0.7857	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6166	Phase 2
0.7857	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2935	Discontinued
0.7853	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6212	Phase 3
0.7853	Intermediate Similarity	NPD6213	Phase 3
0.784	Intermediate Similarity	NPD7411	Suspended
0.7826	Intermediate Similarity	NPD7458	Discontinued
0.7805	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5402	Approved
0.779	Intermediate Similarity	NPD6779	Approved
0.779	Intermediate Similarity	NPD6780	Approved
0.779	Intermediate Similarity	NPD6776	Approved
0.779	Intermediate Similarity	NPD6781	Approved
0.779	Intermediate Similarity	NPD6777	Approved
0.779	Intermediate Similarity	NPD6778	Approved
0.779	Intermediate Similarity	NPD6782	Approved
0.7778	Intermediate Similarity	NPD7699	Phase 2
0.7778	Intermediate Similarity	NPD7700	Phase 2
0.7771	Intermediate Similarity	NPD8166	Discontinued
0.7758	Intermediate Similarity	NPD7768	Phase 2
0.7758	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD6823	Phase 2
0.7702	Intermediate Similarity	NPD5403	Approved
0.7688	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6801	Discontinued
0.7677	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD8151	Discontinued
0.764	Intermediate Similarity	NPD6273	Approved
0.7636	Intermediate Similarity	NPD8455	Phase 2
0.7632	Intermediate Similarity	NPD3764	Approved
0.763	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7871	Phase 2
0.7622	Intermediate Similarity	NPD7870	Phase 2
0.7616	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7874	Approved
0.7606	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2533	Approved
0.7578	Intermediate Similarity	NPD2534	Approved
0.7578	Intermediate Similarity	NPD2532	Approved
0.7578	Intermediate Similarity	NPD5401	Approved
0.7576	Intermediate Similarity	NPD1934	Approved
0.7572	Intermediate Similarity	NPD7074	Phase 3
0.7568	Intermediate Similarity	NPD7698	Approved
0.7568	Intermediate Similarity	NPD7696	Phase 3
0.7568	Intermediate Similarity	NPD7697	Approved
0.7566	Intermediate Similarity	NPD7008	Discontinued
0.7566	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7514	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD7701	Phase 2
0.7474	Intermediate Similarity	NPD7801	Approved
0.7471	Intermediate Similarity	NPD7472	Approved
0.7469	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7228	Approved
0.7457	Intermediate Similarity	NPD7177	Discontinued
0.7455	Intermediate Similarity	NPD6599	Discontinued
0.7438	Intermediate Similarity	NPD3750	Approved
0.7429	Intermediate Similarity	NPD6797	Phase 2
0.7421	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5494	Approved
0.7405	Intermediate Similarity	NPD2438	Suspended
0.7405	Intermediate Similarity	NPD1551	Phase 2
0.7396	Intermediate Similarity	NPD3749	Approved
0.7391	Intermediate Similarity	NPD6190	Approved
0.7386	Intermediate Similarity	NPD7251	Discontinued
0.7382	Intermediate Similarity	NPD7783	Phase 2
0.7382	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3817	Phase 2
0.7368	Intermediate Similarity	NPD2798	Approved
0.7368	Intermediate Similarity	NPD8127	Discontinued
0.7365	Intermediate Similarity	NPD37	Approved
0.7362	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7266	Discontinued
0.7356	Intermediate Similarity	NPD3818	Discontinued
0.7353	Intermediate Similarity	NPD6234	Discontinued
0.7346	Intermediate Similarity	NPD3300	Phase 2
0.7345	Intermediate Similarity	NPD7808	Phase 3
0.7345	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4967	Phase 2
0.7337	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4966	Approved
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD9493	Approved
0.7312	Intermediate Similarity	NPD1549	Phase 2
0.731	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4060	Phase 1
0.7302	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6799	Approved
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD6832	Phase 2
0.7257	Intermediate Similarity	NPD3751	Discontinued
0.725	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1283	Approved
0.7233	Intermediate Similarity	NPD1510	Phase 2
0.7225	Intermediate Similarity	NPD3787	Discontinued
0.7222	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1465	Phase 2
0.7219	Intermediate Similarity	NPD2801	Approved
0.7215	Intermediate Similarity	NPD1607	Approved
0.7197	Intermediate Similarity	NPD2979	Phase 3
0.719	Intermediate Similarity	NPD1203	Approved
0.719	Intermediate Similarity	NPD1164	Approved
0.7179	Intermediate Similarity	NPD6798	Discontinued
0.7166	Intermediate Similarity	NPD8285	Discontinued
0.7152	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD5763	Approved
0.7135	Intermediate Similarity	NPD3882	Suspended
0.7134	Intermediate Similarity	NPD7236	Approved
0.7134	Intermediate Similarity	NPD6663	Approved
0.7126	Intermediate Similarity	NPD5710	Approved
0.7126	Intermediate Similarity	NPD5711	Approved
0.7126	Intermediate Similarity	NPD7239	Suspended
0.7125	Intermediate Similarity	NPD3748	Approved
0.7125	Intermediate Similarity	NPD4308	Phase 3
0.7097	Intermediate Similarity	NPD5736	Approved
0.7095	Intermediate Similarity	NPD7240	Approved
0.7095	Intermediate Similarity	NPD7685	Pre-registration
0.7095	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1511	Approved
0.7089	Intermediate Similarity	NPD943	Approved
0.7089	Intermediate Similarity	NPD1240	Approved
0.7081	Intermediate Similarity	NPD2796	Approved
0.7078	Intermediate Similarity	NPD2797	Approved
0.7075	Intermediate Similarity	NPD5951	Approved
0.707	Intermediate Similarity	NPD3268	Approved
0.707	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD411	Approved
0.7069	Intermediate Similarity	NPD7199	Phase 2
0.7063	Intermediate Similarity	NPD7097	Phase 1
0.7062	Intermediate Similarity	NPD7799	Discontinued
0.7059	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6844	Discontinued
0.7055	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1933	Approved
0.7044	Intermediate Similarity	NPD6355	Discontinued
0.7044	Intermediate Similarity	NPD230	Phase 1
0.7039	Intermediate Similarity	NPD1281	Approved
0.7032	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6233	Phase 2
0.702	Intermediate Similarity	NPD5125	Phase 3
0.702	Intermediate Similarity	NPD4626	Approved
0.702	Intermediate Similarity	NPD5126	Approved
0.702	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7033	Discontinued
0.7006	Intermediate Similarity	NPD1512	Approved
0.7	Intermediate Similarity	NPD9545	Approved
0.6993	Remote Similarity	NPD9717	Approved
0.6988	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6099	Approved
0.6975	Remote Similarity	NPD6100	Approved
0.6964	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5028	Approved
0.6961	Remote Similarity	NPD5026	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