NPASS Compound

Structure

NPC474880 OpenBabel07101718282D 33 39 0 0 1 0 0 0 0 0999 V2000 3.6720 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5955 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1888 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5768 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0078 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1943 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2701 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4041 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -2.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8060 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0132 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2701 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.6065 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4041 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5380 -2.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6120 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 20 2 0 0 0 0 8 21 2 0 0 0 0 9 24 2 0 0 0 0 10 25 2 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 30 1 0 0 0 0 14 33 1 0 0 0 0 16 19 1 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 17 33 1 0 0 0 0 18 2 1 1 0 0 0 18 19 1 0 0 0 0 19 15 1 6 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 21 23 1 0 0 0 0 21 25 1 0 0 0 0 22 28 2 0 0 0 0 23 29 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 15 1 1 0 0 0 26 28 1 0 0 0 0 26 30 1 0 0 0 0 27 29 1 0 0 0 0 27 33 1 1 0 0 0 28 31 1 0 0 0 0 29 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.29
Volume:	475.777
LogP:	5.059
LogD:	4.553
LogS:	-3.882
# Rotatable Bonds:	3
TPSA:	43.09
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.508
Synthetic Accessibility Score:	4.383
Fsp3:	0.517
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.453
MDCK Permeability:	5.186270755075384e-06
Pgp-inhibitor:	0.908
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.949
30% Bioavailability (F30%):	0.093

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.848
Plasma Protein Binding (PPB):	91.51909637451172%
Volume Distribution (VD):	2.904
Pgp-substrate:	4.911076068878174%

ADMET: Metabolism

CYP1A2-inhibitor:	0.116
CYP1A2-substrate:	0.783
CYP2C19-inhibitor:	0.389
CYP2C19-substrate:	0.807
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.103
CYP2D6-inhibitor:	0.977
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.452
CYP3A4-substrate:	0.893

ADMET: Excretion

Clearance (CL):	3.892
Half-life (T1/2):	0.136

ADMET: Toxicity

hERG Blockers:	0.966
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.762
AMES Toxicity:	0.633
Rat Oral Acute Toxicity:	0.889
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.197
Carcinogencity:	0.116
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC474880

Natural Product ID:	NPC474880
*Common Name:**	Ochrolifuanine E
IUPAC Name:	(2S,3R,12bR)-3-ethyl-2-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-1,2,3,4,6,7,7a,12,12a,12b-decahydroindolo[2,3-a]quinolizine
Synonyms:	Ochrolifuanine E
Standard InCHIKey:	WPRCHZNIQPXBQO-QTZZMGCWSA-N
Standard InCHI:	InChI=1S/C29H36N4/c1-2-18-17-33-14-12-23-21-8-4-6-10-25(21)32-29(23)27(33)16-19(18)15-26-28-22(11-13-30-26)20-7-3-5-9-24(20)31-28/h3-10,18-19,23,26-27,29-32H,2,11-17H2,1H3/t18-,19-,23?,26-,27+,29?/m0/s1
SMILES:	CCC1CN2CCC3C(C2CC1CC4C5=C(CCN4)C6=CC=CC=C6N5)NC7=CC=CC=C37
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486025
PubChem CID:	44559859
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO26262	Strychnos potatorum	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398531]
NPO26262	Strychnos potatorum	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
Others	6

Activity Type	# Activity
Cell Line	1
Organism	6
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	5700.0	nM	PMID[482796]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	702.0	nM	PMID[482796]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	276.0	nM	PMID[482796]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	1490.0	nM	PMID[482796]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1900.0	nM	PMID[482796]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	2420.0	nM	PMID[482796]
NPT2	Others	Unspecified		Ratio IC50	=	3.0	n.a.	PMID[482796]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	6760.0	nM	PMID[482796]
NPT2	Others	Unspecified		Ratio IC50	=	8.12	n.a.	PMID[482796]
NPT2	Others	Unspecified		Ratio IC50	=	20.7	n.a.	PMID[482796]

☑ 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 NPC474880 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	860
0.1-0.2	7660
0.2-0.3	22016
0.3-0.4	6075
0.4-0.5	2598
0.5-0.6	1840
0.6-0.7	1144
0.7-0.8	417
0.8-0.85	68
0.85-0.9	12
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC221786
0.9797	High Similarity	NPC229173
0.973	High Similarity	NPC475990
0.9416	High Similarity	NPC474897
0.9057	High Similarity	NPC280852
0.8973	High Similarity	NPC88097
0.8767	High Similarity	NPC325252
0.8699	High Similarity	NPC198988
0.8684	High Similarity	NPC21605
0.8614	High Similarity	NPC472294
0.86	High Similarity	NPC473868
0.86	High Similarity	NPC63157
0.8533	High Similarity	NPC59084
0.8452	Intermediate Similarity	NPC33421
0.8452	Intermediate Similarity	NPC53947
0.8431	Intermediate Similarity	NPC204141
0.8411	Intermediate Similarity	NPC115611
0.8411	Intermediate Similarity	NPC2949
0.8389	Intermediate Similarity	NPC218268
0.8354	Intermediate Similarity	NPC472123
0.8323	Intermediate Similarity	NPC271797
0.8323	Intermediate Similarity	NPC21174
0.8301	Intermediate Similarity	NPC20144
0.8291	Intermediate Similarity	NPC476219
0.828	Intermediate Similarity	NPC470233
0.8258	Intermediate Similarity	NPC288838
0.825	Intermediate Similarity	NPC56765
0.8243	Intermediate Similarity	NPC475450
0.8242	Intermediate Similarity	NPC161861
0.8228	Intermediate Similarity	NPC325903
0.821	Intermediate Similarity	NPC317105
0.8194	Intermediate Similarity	NPC470440
0.8187	Intermediate Similarity	NPC216643
0.8176	Intermediate Similarity	NPC22079
0.8176	Intermediate Similarity	NPC475428
0.817	Intermediate Similarity	NPC469767
0.817	Intermediate Similarity	NPC469784
0.817	Intermediate Similarity	NPC469768
0.817	Intermediate Similarity	NPC469783
0.817	Intermediate Similarity	NPC469761
0.817	Intermediate Similarity	NPC469780
0.817	Intermediate Similarity	NPC469779
0.8153	Intermediate Similarity	NPC321911
0.8151	Intermediate Similarity	NPC250361
0.8117	Intermediate Similarity	NPC469766
0.8108	Intermediate Similarity	NPC473587
0.8105	Intermediate Similarity	NPC73767
0.8089	Intermediate Similarity	NPC201380
0.8089	Intermediate Similarity	NPC179787
0.8089	Intermediate Similarity	NPC469811
0.8067	Intermediate Similarity	NPC473930
0.8061	Intermediate Similarity	NPC317430
0.8052	Intermediate Similarity	NPC284635
0.8041	Intermediate Similarity	NPC473762
0.8025	Intermediate Similarity	NPC63545
0.8025	Intermediate Similarity	NPC318065
0.8025	Intermediate Similarity	NPC206819
0.8	Intermediate Similarity	NPC179365
0.7987	Intermediate Similarity	NPC110126
0.7987	Intermediate Similarity	NPC40070
0.7974	Intermediate Similarity	NPC84911
0.795	Intermediate Similarity	NPC476297
0.7943	Intermediate Similarity	NPC231536
0.7927	Intermediate Similarity	NPC470203
0.7914	Intermediate Similarity	NPC92796
0.7914	Intermediate Similarity	NPC41257
0.7914	Intermediate Similarity	NPC135141
0.7908	Intermediate Similarity	NPC96102
0.7908	Intermediate Similarity	NPC261195
0.7908	Intermediate Similarity	NPC29886
0.7907	Intermediate Similarity	NPC139291
0.7907	Intermediate Similarity	NPC472108
0.7907	Intermediate Similarity	NPC470205
0.7877	Intermediate Similarity	NPC41174
0.7866	Intermediate Similarity	NPC255229
0.7866	Intermediate Similarity	NPC470204
0.7866	Intermediate Similarity	NPC122141
0.7866	Intermediate Similarity	NPC81229
0.7862	Intermediate Similarity	NPC477134
0.7857	Intermediate Similarity	NPC105127
0.7857	Intermediate Similarity	NPC125746
0.7853	Intermediate Similarity	NPC286427
0.7841	Intermediate Similarity	NPC469501
0.7841	Intermediate Similarity	NPC469470
0.7838	Intermediate Similarity	NPC87755
0.7818	Intermediate Similarity	NPC194881
0.7771	Intermediate Similarity	NPC90723
0.7771	Intermediate Similarity	NPC247987
0.7764	Intermediate Similarity	NPC105818
0.7764	Intermediate Similarity	NPC24678
0.7758	Intermediate Similarity	NPC44773
0.7758	Intermediate Similarity	NPC215584
0.7756	Intermediate Similarity	NPC312092
0.7754	Intermediate Similarity	NPC126066
0.7754	Intermediate Similarity	NPC475422
0.7751	Intermediate Similarity	NPC201634
0.7744	Intermediate Similarity	NPC236711
0.7742	Intermediate Similarity	NPC251722
0.7742	Intermediate Similarity	NPC314102
0.7736	Intermediate Similarity	NPC314372
0.7725	Intermediate Similarity	NPC2165
0.7725	Intermediate Similarity	NPC195507
0.7722	Intermediate Similarity	NPC190296
0.7719	Intermediate Similarity	NPC474958
0.7707	Intermediate Similarity	NPC279081
0.7706	Intermediate Similarity	NPC477611
0.7702	Intermediate Similarity	NPC2272
0.7702	Intermediate Similarity	NPC37548
0.7701	Intermediate Similarity	NPC472109
0.7701	Intermediate Similarity	NPC472110
0.7701	Intermediate Similarity	NPC476116
0.7692	Intermediate Similarity	NPC194411
0.7688	Intermediate Similarity	NPC143872
0.7674	Intermediate Similarity	NPC59269
0.767	Intermediate Similarity	NPC135601
0.767	Intermediate Similarity	NPC17273
0.767	Intermediate Similarity	NPC141612
0.7669	Intermediate Similarity	NPC73952
0.7669	Intermediate Similarity	NPC469760
0.7669	Intermediate Similarity	NPC25008
0.7669	Intermediate Similarity	NPC469765
0.7669	Intermediate Similarity	NPC259644
0.7669	Intermediate Similarity	NPC469786
0.7669	Intermediate Similarity	NPC469763
0.7661	Intermediate Similarity	NPC189812
0.7661	Intermediate Similarity	NPC329688
0.7647	Intermediate Similarity	NPC82295
0.7644	Intermediate Similarity	NPC183407
0.7643	Intermediate Similarity	NPC104483
0.7622	Intermediate Similarity	NPC70922
0.7622	Intermediate Similarity	NPC80597
0.7622	Intermediate Similarity	NPC212376
0.7622	Intermediate Similarity	NPC75540
0.7622	Intermediate Similarity	NPC211572
0.7614	Intermediate Similarity	NPC308931
0.7614	Intermediate Similarity	NPC15102
0.7614	Intermediate Similarity	NPC99939
0.7603	Intermediate Similarity	NPC162689
0.7603	Intermediate Similarity	NPC54102
0.7595	Intermediate Similarity	NPC230002
0.7574	Intermediate Similarity	NPC160105
0.7571	Intermediate Similarity	NPC94752
0.7562	Intermediate Similarity	NPC242556
0.7561	Intermediate Similarity	NPC200214
0.7558	Intermediate Similarity	NPC37423
0.7558	Intermediate Similarity	NPC275305
0.7544	Intermediate Similarity	NPC82331
0.7542	Intermediate Similarity	NPC472112
0.7541	Intermediate Similarity	NPC265576
0.7534	Intermediate Similarity	NPC81561
0.7533	Intermediate Similarity	NPC122718
0.7531	Intermediate Similarity	NPC471957
0.7531	Intermediate Similarity	NPC470111
0.753	Intermediate Similarity	NPC167635
0.753	Intermediate Similarity	NPC193740
0.7529	Intermediate Similarity	NPC63751
0.7516	Intermediate Similarity	NPC159856
0.7515	Intermediate Similarity	NPC470507
0.7515	Intermediate Similarity	NPC38736
0.7514	Intermediate Similarity	NPC133003
0.75	Intermediate Similarity	NPC475915
0.75	Intermediate Similarity	NPC477065
0.7486	Intermediate Similarity	NPC187827
0.7486	Intermediate Similarity	NPC63199
0.7486	Intermediate Similarity	NPC314919
0.7486	Intermediate Similarity	NPC196251
0.7486	Intermediate Similarity	NPC16659
0.7486	Intermediate Similarity	NPC111602
0.7486	Intermediate Similarity	NPC91179
0.7486	Intermediate Similarity	NPC175474
0.7486	Intermediate Similarity	NPC213629
0.7486	Intermediate Similarity	NPC472105
0.7486	Intermediate Similarity	NPC102338
0.7485	Intermediate Similarity	NPC187951
0.7471	Intermediate Similarity	NPC49954
0.7471	Intermediate Similarity	NPC474561
0.7471	Intermediate Similarity	NPC68354
0.747	Intermediate Similarity	NPC285469
0.747	Intermediate Similarity	NPC469785
0.7466	Intermediate Similarity	NPC148140
0.7459	Intermediate Similarity	NPC316359
0.7459	Intermediate Similarity	NPC315617
0.7459	Intermediate Similarity	NPC472113
0.7457	Intermediate Similarity	NPC471579
0.7446	Intermediate Similarity	NPC52557
0.7429	Intermediate Similarity	NPC215795
0.7429	Intermediate Similarity	NPC176199
0.7429	Intermediate Similarity	NPC265710
0.7427	Intermediate Similarity	NPC201700
0.7425	Intermediate Similarity	NPC469762
0.7423	Intermediate Similarity	NPC476041
0.7423	Intermediate Similarity	NPC304926
0.7414	Intermediate Similarity	NPC472122
0.7414	Intermediate Similarity	NPC24594
0.7412	Intermediate Similarity	NPC274229
0.741	Intermediate Similarity	NPC34844
0.7407	Intermediate Similarity	NPC166492
0.7407	Intermediate Similarity	NPC473362
0.7405	Intermediate Similarity	NPC150259
0.7401	Intermediate Similarity	NPC472104

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 NPC474880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	644
0.2-0.3	1165
0.3-0.4	1778
0.4-0.5	2285
0.5-0.6	1941
0.6-0.7	781
0.7-0.8	167
0.8-0.85	17
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8792	High Similarity	NPD4637	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1683	Approved
0.8323	Intermediate Similarity	NPD3323	Discontinued
0.8272	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD3385	Approved
0.8247	Intermediate Similarity	NPD5254	Discontinued
0.8235	Intermediate Similarity	NPD1722	Approved
0.8228	Intermediate Similarity	NPD2837	Discontinued
0.8153	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD786	Approved
0.8072	Intermediate Similarity	NPD6828	Phase 2
0.8072	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4181	Approved
0.7987	Intermediate Similarity	NPD4462	Approved
0.7987	Intermediate Similarity	NPD2172	Phase 1
0.7987	Intermediate Similarity	NPD4463	Approved
0.7952	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD3100	Discontinued
0.7917	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3610	Approved
0.7857	Intermediate Similarity	NPD1262	Discovery
0.7857	Intermediate Similarity	NPD3609	Approved
0.7816	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4128	Approved
0.7755	Intermediate Similarity	NPD5787	Discontinued
0.775	Intermediate Similarity	NPD4547	Phase 3
0.7748	Intermediate Similarity	NPD3654	Approved
0.7742	Intermediate Similarity	NPD45	Approved
0.7742	Intermediate Similarity	NPD6554	Approved
0.7711	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1253	Approved
0.7677	Intermediate Similarity	NPD1256	Approved
0.7677	Intermediate Similarity	NPD1255	Approved
0.7677	Intermediate Similarity	NPD1254	Approved
0.7674	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7111	Discontinued
0.7661	Intermediate Similarity	NPD5065	Approved
0.7633	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD2640	Approved
0.7633	Intermediate Similarity	NPD2641	Approved
0.7622	Intermediate Similarity	NPD6285	Phase 2
0.7619	Intermediate Similarity	NPD4811	Discontinued
0.7613	Intermediate Similarity	NPD4880	Discontinued
0.761	Intermediate Similarity	NPD4047	Discontinued
0.7586	Intermediate Similarity	NPD5473	Discontinued
0.7586	Intermediate Similarity	NPD6595	Phase 3
0.7578	Intermediate Similarity	NPD7469	Discontinued
0.7576	Intermediate Similarity	NPD2150	Discontinued
0.7574	Intermediate Similarity	NPD2639	Approved
0.7574	Intermediate Similarity	NPD2642	Approved
0.7571	Intermediate Similarity	NPD6217	Discontinued
0.7528	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD3961	Discontinued
0.7527	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD947	Approved
0.7514	Intermediate Similarity	NPD4075	Phase 2
0.75	Intermediate Similarity	NPD5105	Approved
0.75	Intermediate Similarity	NPD5106	Approved
0.7486	Intermediate Similarity	NPD5962	Phase 2
0.7485	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7618	Phase 3
0.7473	Intermediate Similarity	NPD7619	Phase 3
0.7471	Intermediate Similarity	NPD3505	Approved
0.7471	Intermediate Similarity	NPD3506	Approved
0.7469	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3835	Phase 3
0.7439	Intermediate Similarity	NPD3833	Phase 3
0.7432	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4076	Approved
0.7429	Intermediate Similarity	NPD4079	Approved
0.7427	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6771	Discontinued
0.7396	Intermediate Similarity	NPD5315	Discontinued
0.7391	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2119	Approved
0.7386	Intermediate Similarity	NPD2118	Approved
0.7384	Intermediate Similarity	NPD5436	Phase 1
0.7384	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2580	Discontinued
0.7365	Intermediate Similarity	NPD2927	Phase 3
0.736	Intermediate Similarity	NPD7564	Discontinued
0.7355	Intermediate Similarity	NPD3476	Approved
0.7355	Intermediate Similarity	NPD3475	Approved
0.7346	Intermediate Similarity	NPD4509	Discontinued
0.7345	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD1895	Discontinued
0.7337	Intermediate Similarity	NPD1404	Approved
0.7337	Intermediate Similarity	NPD1403	Approved
0.7333	Intermediate Similarity	NPD8431	Approved
0.733	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5021	Discontinued
0.7326	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3942	Approved
0.7325	Intermediate Similarity	NPD3944	Approved
0.7321	Intermediate Similarity	NPD4326	Phase 2
0.7308	Intermediate Similarity	NPD1251	Discontinued
0.7305	Intermediate Similarity	NPD975	Approved
0.7305	Intermediate Similarity	NPD976	Approved
0.7305	Intermediate Similarity	NPD977	Approved
0.7303	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7216	Approved
0.7299	Intermediate Similarity	NPD7217	Approved
0.7293	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD2882	Phase 1
0.7284	Intermediate Similarity	NPD2006	Phase 2
0.7283	Intermediate Similarity	NPD1326	Approved
0.7283	Intermediate Similarity	NPD1325	Approved
0.7273	Intermediate Similarity	NPD4601	Approved
0.7273	Intermediate Similarity	NPD2430	Phase 2
0.7273	Intermediate Similarity	NPD991	Phase 2
0.7273	Intermediate Similarity	NPD4600	Approved
0.7273	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5140	Approved
0.7251	Intermediate Similarity	NPD5138	Approved
0.7247	Intermediate Similarity	NPD1707	Approved
0.7247	Intermediate Similarity	NPD1708	Approved
0.7238	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5730	Phase 2
0.7232	Intermediate Similarity	NPD40	Phase 2
0.7232	Intermediate Similarity	NPD8386	Phase 2
0.7225	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5104	Approved
0.7215	Intermediate Similarity	NPD4028	Approved
0.7215	Intermediate Similarity	NPD4029	Approved
0.7215	Intermediate Similarity	NPD4030	Approved
0.7213	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2915	Discontinued
0.7207	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD2880	Discontinued
0.7204	Intermediate Similarity	NPD6664	Approved
0.7197	Intermediate Similarity	NPD803	Phase 1
0.7196	Intermediate Similarity	NPD3015	Discontinued
0.7186	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6158	Phase 2
0.7181	Intermediate Similarity	NPD4500	Approved
0.7181	Intermediate Similarity	NPD4501	Approved
0.7176	Intermediate Similarity	NPD5418	Discontinued
0.7175	Intermediate Similarity	NPD2144	Approved
0.716	Intermediate Similarity	NPD3115	Approved
0.716	Intermediate Similarity	NPD3112	Approved
0.716	Intermediate Similarity	NPD3113	Approved
0.716	Intermediate Similarity	NPD3114	Approved
0.7151	Intermediate Similarity	NPD3038	Discontinued
0.7151	Intermediate Similarity	NPD7867	Phase 1
0.7143	Intermediate Similarity	NPD7394	Phase 2
0.7143	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD715	Phase 3
0.7134	Intermediate Similarity	NPD5671	Approved
0.7128	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3348	Phase 2
0.7118	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1313	Approved
0.711	Intermediate Similarity	NPD1002	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2165	Phase 1
0.7099	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD2793	Discontinued
0.7088	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7722	Suspended
0.7081	Intermediate Similarity	NPD4615	Phase 2
0.7074	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4499	Approved
0.7062	Intermediate Similarity	NPD3799	Suspended
0.7059	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD8322	Phase 2
0.7039	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6044	Discontinued
0.7018	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD4441	Phase 2
0.7017	Intermediate Similarity	NPD3318	Approved
0.7017	Intermediate Similarity	NPD3320	Approved
0.7017	Intermediate Similarity	NPD3319	Phase 1
0.7012	Intermediate Similarity	NPD1592	Phase 3
0.7011	Intermediate Similarity	NPD509	Phase 3
0.7005	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7481	Approved
0.7	Intermediate Similarity	NPD7480	Approved
0.6995	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7271	Approved
0.6995	Remote Similarity	NPD7957	Phase 1
0.6995	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7823	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