NPASS Compound

Structure

NPC108011 OpenBabel07101718302D 23 25 0 0 0 0 0 0 0 0999 V2000 -3.1646 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5714 -1.1226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5659 -1.2271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 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 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9671 -2.2452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -6.5549 -1.4362 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.3739 -3.1588 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 -1.8271 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9726 -2.1407 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 -0.3090 0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 7 1 0 0 0 0 3 13 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 21 1 0 0 0 0 8 20 2 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 12 15 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	375.07
Volume:	324.225
LogP:	1.765
LogD:	1.349
LogS:	-3.267
# Rotatable Bonds:	6
TPSA:	99.95
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.238
Synthetic Accessibility Score:	2.828
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.305
MDCK Permeability:	1.5266188711393625e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.854

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	92.4673080444336%
Volume Distribution (VD):	1.706
Pgp-substrate:	7.706210136413574%

ADMET: Metabolism

CYP1A2-inhibitor:	0.669
CYP1A2-substrate:	0.742
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.175
CYP2D6-inhibitor:	0.141
CYP2D6-substrate:	0.457
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	4.576
Half-life (T1/2):	0.52

ADMET: Toxicity

hERG Blockers:	0.487
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.326
AMES Toxicity:	0.682
Rat Oral Acute Toxicity:	0.397
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.098
Carcinogencity:	0.925
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.821

Download Data

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

Natural Product: NPC108011

Natural Product ID:	NPC108011
*Common Name:**	Opacaline B
IUPAC Name:	2-[4-(7-bromo-9-hydroxypyrido[3,4-b]indol-1-yl)butyl]guanidine
Synonyms:	Opacaline B
Standard InCHIKey:	IWEPNARAXMZDRC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H18BrN5O/c17-10-4-5-11-12-6-8-20-13(3-1-2-7-21-16(18)19)15(12)22(23)14(11)9-10/h4-6,8-9,23H,1-3,7H2,(H4,18,19,21)
SMILES:	C(CCNC(=N)N)Cc1c2c(ccn1)c1ccc(cc1n2O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1821996
PubChem CID:	54669780
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
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[21846091]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21846091]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26670413]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	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	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	120000.0	nM	PMID[522493]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	27000.0	nM	PMID[522493]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	107000.0	nM	PMID[522493]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	101000.0	nM	PMID[522493]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	4500.0	nM	PMID[522493]

☑ 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 NPC108011 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	1164
0.1-0.2	15189
0.2-0.3	17935
0.3-0.4	3697
0.4-0.5	2116
0.5-0.6	1600
0.6-0.7	763
0.7-0.8	201
0.8-0.85	24
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9518	High Similarity	NPC307191
0.8855	High Similarity	NPC274229
0.8824	High Similarity	NPC474958
0.8757	High Similarity	NPC82331
0.8735	High Similarity	NPC225018
0.8735	High Similarity	NPC470203
0.8683	High Similarity	NPC247987
0.8675	High Similarity	NPC470204
0.8631	High Similarity	NPC17751
0.8343	Intermediate Similarity	NPC122141
0.8297	Intermediate Similarity	NPC473342
0.8297	Intermediate Similarity	NPC477166
0.8297	Intermediate Similarity	NPC304187
0.8297	Intermediate Similarity	NPC477167
0.8287	Intermediate Similarity	NPC231536
0.8276	Intermediate Similarity	NPC477611
0.8266	Intermediate Similarity	NPC97343
0.8263	Intermediate Similarity	NPC141926
0.8242	Intermediate Similarity	NPC470111
0.8229	Intermediate Similarity	NPC280297
0.8198	Intermediate Similarity	NPC280864
0.8133	Intermediate Similarity	NPC469811
0.8084	Intermediate Similarity	NPC321911
0.8072	Intermediate Similarity	NPC63545
0.8054	Intermediate Similarity	NPC474180
0.8054	Intermediate Similarity	NPC188821
0.8047	Intermediate Similarity	NPC325903
0.8024	Intermediate Similarity	NPC201380
0.8024	Intermediate Similarity	NPC179787
0.8012	Intermediate Similarity	NPC236711
0.7921	Intermediate Similarity	NPC317054
0.7906	Intermediate Similarity	NPC473761
0.7904	Intermediate Similarity	NPC204141
0.7886	Intermediate Similarity	NPC2165
0.7884	Intermediate Similarity	NPC474389
0.787	Intermediate Similarity	NPC2272
0.7857	Intermediate Similarity	NPC143872
0.7842	Intermediate Similarity	NPC237414
0.7829	Intermediate Similarity	NPC149265
0.7791	Intermediate Similarity	NPC34844
0.7791	Intermediate Similarity	NPC476219
0.7791	Intermediate Similarity	NPC476297
0.7733	Intermediate Similarity	NPC232798
0.7727	Intermediate Similarity	NPC317105
0.7711	Intermediate Similarity	NPC316811
0.7708	Intermediate Similarity	NPC23420
0.7708	Intermediate Similarity	NPC106771
0.7708	Intermediate Similarity	NPC303820
0.7708	Intermediate Similarity	NPC205254
0.767	Intermediate Similarity	NPC253687
0.7668	Intermediate Similarity	NPC475935
0.7668	Intermediate Similarity	NPC52909
0.7668	Intermediate Similarity	NPC94211
0.7647	Intermediate Similarity	NPC316069
0.7574	Intermediate Similarity	NPC477114
0.7565	Intermediate Similarity	NPC153123
0.7565	Intermediate Similarity	NPC475914
0.7565	Intermediate Similarity	NPC201266
0.7565	Intermediate Similarity	NPC268744
0.7565	Intermediate Similarity	NPC220797
0.7565	Intermediate Similarity	NPC474318
0.756	Intermediate Similarity	NPC469767
0.756	Intermediate Similarity	NPC469784
0.756	Intermediate Similarity	NPC469768
0.756	Intermediate Similarity	NPC115611
0.756	Intermediate Similarity	NPC469779
0.756	Intermediate Similarity	NPC469761
0.756	Intermediate Similarity	NPC469783
0.756	Intermediate Similarity	NPC469780
0.7544	Intermediate Similarity	NPC288838
0.7542	Intermediate Similarity	NPC478183
0.753	Intermediate Similarity	NPC96102
0.7526	Intermediate Similarity	NPC13456
0.7526	Intermediate Similarity	NPC77241
0.7526	Intermediate Similarity	NPC166209
0.7526	Intermediate Similarity	NPC269203
0.7515	Intermediate Similarity	NPC469766
0.7514	Intermediate Similarity	NPC53947
0.75	Intermediate Similarity	NPC73767
0.75	Intermediate Similarity	NPC233050
0.75	Intermediate Similarity	NPC276540
0.7486	Intermediate Similarity	NPC195507
0.7486	Intermediate Similarity	NPC280852
0.7485	Intermediate Similarity	NPC314372
0.7485	Intermediate Similarity	NPC84911
0.7485	Intermediate Similarity	NPC105127
0.7471	Intermediate Similarity	NPC190296
0.7463	Intermediate Similarity	NPC470702
0.7463	Intermediate Similarity	NPC473218
0.7458	Intermediate Similarity	NPC92796
0.7458	Intermediate Similarity	NPC135141
0.7444	Intermediate Similarity	NPC49217
0.743	Intermediate Similarity	NPC478182
0.743	Intermediate Similarity	NPC478184
0.7426	Intermediate Similarity	NPC470703
0.7425	Intermediate Similarity	NPC261195
0.7425	Intermediate Similarity	NPC29886
0.7419	Intermediate Similarity	NPC275292
0.7419	Intermediate Similarity	NPC243381
0.7414	Intermediate Similarity	NPC40070
0.7414	Intermediate Similarity	NPC24678
0.7414	Intermediate Similarity	NPC105818
0.7396	Intermediate Similarity	NPC110126
0.7393	Intermediate Similarity	NPC470323
0.7391	Intermediate Similarity	NPC121903
0.7384	Intermediate Similarity	NPC159856
0.7381	Intermediate Similarity	NPC125746
0.7381	Intermediate Similarity	NPC156003
0.7374	Intermediate Similarity	NPC470505
0.7371	Intermediate Similarity	NPC470233
0.7366	Intermediate Similarity	NPC16659
0.736	Intermediate Similarity	NPC293487
0.7358	Intermediate Similarity	NPC267078
0.7358	Intermediate Similarity	NPC935
0.7353	Intermediate Similarity	NPC279081
0.7351	Intermediate Similarity	NPC473380
0.7351	Intermediate Similarity	NPC240088
0.7337	Intermediate Similarity	NPC471579
0.733	Intermediate Similarity	NPC25008
0.733	Intermediate Similarity	NPC469760
0.733	Intermediate Similarity	NPC469763
0.733	Intermediate Similarity	NPC73952
0.733	Intermediate Similarity	NPC469786
0.733	Intermediate Similarity	NPC469765
0.733	Intermediate Similarity	NPC259644
0.7324	Intermediate Similarity	NPC474357
0.7321	Intermediate Similarity	NPC325252
0.7312	Intermediate Similarity	NPC265710
0.7303	Intermediate Similarity	NPC216643
0.7299	Intermediate Similarity	NPC471957
0.7289	Intermediate Similarity	NPC82295
0.7288	Intermediate Similarity	NPC70922
0.7288	Intermediate Similarity	NPC80597
0.7288	Intermediate Similarity	NPC75540
0.7288	Intermediate Similarity	NPC211572
0.7288	Intermediate Similarity	NPC212376
0.7283	Intermediate Similarity	NPC288074
0.7282	Intermediate Similarity	NPC475736
0.7278	Intermediate Similarity	NPC251722
0.7278	Intermediate Similarity	NPC314102
0.7268	Intermediate Similarity	NPC32534
0.7263	Intermediate Similarity	NPC477591
0.7263	Intermediate Similarity	NPC56765
0.7263	Intermediate Similarity	NPC6436
0.7262	Intermediate Similarity	NPC198988
0.7251	Intermediate Similarity	NPC230002
0.7249	Intermediate Similarity	NPC110158
0.7247	Intermediate Similarity	NPC469785
0.7222	Intermediate Similarity	NPC44773
0.7222	Intermediate Similarity	NPC215584
0.7212	Intermediate Similarity	NPC474195
0.7208	Intermediate Similarity	NPC477004
0.7207	Intermediate Similarity	NPC469762
0.7206	Intermediate Similarity	NPC128084
0.7196	Intermediate Similarity	NPC48938
0.7193	Intermediate Similarity	NPC88097
0.7189	Intermediate Similarity	NPC64055
0.7182	Intermediate Similarity	NPC478185
0.7176	Intermediate Similarity	NPC150259
0.7175	Intermediate Similarity	NPC216713
0.7164	Intermediate Similarity	NPC476121
0.7158	Intermediate Similarity	NPC109447
0.7158	Intermediate Similarity	NPC56233
0.7156	Intermediate Similarity	NPC474196
0.7151	Intermediate Similarity	NPC284635
0.7143	Intermediate Similarity	NPC191415
0.7143	Intermediate Similarity	NPC90723
0.7135	Intermediate Similarity	NPC200214
0.712	Intermediate Similarity	NPC63751
0.7118	Intermediate Similarity	NPC218268
0.7117	Intermediate Similarity	NPC46358
0.7111	Intermediate Similarity	NPC286427
0.7105	Intermediate Similarity	NPC102755
0.7094	Intermediate Similarity	NPC116555
0.7087	Intermediate Similarity	NPC477610
0.7086	Intermediate Similarity	NPC285731
0.7083	Intermediate Similarity	NPC62749
0.7083	Intermediate Similarity	NPC101165
0.7081	Intermediate Similarity	NPC91895
0.7077	Intermediate Similarity	NPC324149
0.7074	Intermediate Similarity	NPC59269
0.7072	Intermediate Similarity	NPC318065
0.7072	Intermediate Similarity	NPC41257
0.7072	Intermediate Similarity	NPC206819
0.7071	Intermediate Similarity	NPC265576
0.7068	Intermediate Similarity	NPC284678
0.7065	Intermediate Similarity	NPC49954
0.7065	Intermediate Similarity	NPC474561
0.7065	Intermediate Similarity	NPC160105
0.7056	Intermediate Similarity	NPC51054
0.7052	Intermediate Similarity	NPC59084
0.7052	Intermediate Similarity	NPC2949
0.7049	Intermediate Similarity	NPC311276
0.7041	Intermediate Similarity	NPC88315
0.7033	Intermediate Similarity	NPC279918
0.7031	Intermediate Similarity	NPC15102
0.7011	Intermediate Similarity	NPC63157
0.7011	Intermediate Similarity	NPC473868
0.7006	Intermediate Similarity	NPC89490
0.6995	Remote Similarity	NPC475288

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 NPC108011 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	966
0.2-0.3	1160
0.3-0.4	2322
0.4-0.5	2004
0.5-0.6	1582
0.6-0.7	629
0.7-0.8	58
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.779	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD1722	Approved
0.7711	Intermediate Similarity	NPD2068	Approved
0.7711	Intermediate Similarity	NPD2069	Approved
0.7711	Intermediate Similarity	NPD2071	Approved
0.7711	Intermediate Similarity	NPD2070	Approved
0.7705	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD1895	Discontinued
0.7697	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD4181	Approved
0.7582	Intermediate Similarity	NPD2367	Phase 2
0.7558	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD438	Approved
0.7542	Intermediate Similarity	NPD439	Approved
0.754	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD2837	Discontinued
0.7527	Intermediate Similarity	NPD4128	Approved
0.7526	Intermediate Similarity	NPD4615	Phase 2
0.75	Intermediate Similarity	NPD786	Approved
0.7487	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1313	Approved
0.7471	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1993	Approved
0.7455	Intermediate Similarity	NPD1994	Approved
0.7455	Intermediate Similarity	NPD1995	Approved
0.7447	Intermediate Similarity	NPD4902	Discontinued
0.7418	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2333	Discontinued
0.7371	Intermediate Similarity	NPD3830	Phase 1
0.7356	Intermediate Similarity	NPD3100	Discontinued
0.7356	Intermediate Similarity	NPD1183	Approved
0.7351	Intermediate Similarity	NPD7111	Discontinued
0.7345	Intermediate Similarity	NPD2927	Phase 3
0.7345	Intermediate Similarity	NPD2150	Discontinued
0.7308	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4547	Phase 3
0.7273	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2006	Phase 2
0.7257	Intermediate Similarity	NPD2430	Phase 2
0.7238	Intermediate Similarity	NPD3323	Discontinued
0.7231	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD715	Phase 3
0.7216	Intermediate Similarity	NPD2172	Phase 1
0.7213	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD509	Phase 3
0.7198	Intermediate Similarity	NPD1333	Phase 3
0.7194	Intermediate Similarity	NPD2880	Discontinued
0.7191	Intermediate Similarity	NPD975	Approved
0.7191	Intermediate Similarity	NPD977	Approved
0.7191	Intermediate Similarity	NPD976	Approved
0.7182	Intermediate Similarity	NPD1015	Phase 2
0.7182	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD1016	Phase 2
0.7174	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6721	Phase 1
0.7173	Intermediate Similarity	NPD2793	Discontinued
0.7171	Intermediate Similarity	NPD4341	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD991	Phase 2
0.7151	Intermediate Similarity	NPD5065	Approved
0.7151	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1708	Approved
0.7143	Intermediate Similarity	NPD1707	Approved
0.7143	Intermediate Similarity	NPD1683	Approved
0.7135	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6828	Phase 2
0.7126	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3476	Approved
0.7126	Intermediate Similarity	NPD3475	Approved
0.712	Intermediate Similarity	NPD2641	Approved
0.712	Intermediate Similarity	NPD2640	Approved
0.7119	Intermediate Similarity	NPD971	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4462	Approved
0.7119	Intermediate Similarity	NPD4463	Approved
0.7112	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5462	Discontinued
0.7105	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD1661	Suspended
0.7101	Intermediate Similarity	NPD3385	Approved
0.709	Intermediate Similarity	NPD6595	Phase 3
0.709	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5962	Phase 2
0.7088	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD706	Phase 1
0.7081	Intermediate Similarity	NPD5436	Phase 1
0.7071	Intermediate Similarity	NPD6469	Phase 3
0.7071	Intermediate Similarity	NPD6468	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5892	Approved
0.7056	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2118	Approved
0.7048	Intermediate Similarity	NPD2119	Approved
0.7047	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7394	Phase 2
0.7039	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4872	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1002	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD2442	Approved
0.701	Intermediate Similarity	NPD2443	Approved
0.7005	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8026	Phase 1
0.6995	Remote Similarity	NPD7026	Phase 2
0.6995	Remote Similarity	NPD2591	Phase 2
0.6995	Remote Similarity	NPD2008	Discontinued
0.6989	Remote Similarity	NPD4024	Phase 3
0.6982	Remote Similarity	NPD803	Phase 1
0.6982	Remote Similarity	NPD809	Discontinued
0.6978	Remote Similarity	NPD5418	Discontinued
0.6977	Remote Similarity	NPD1262	Discovery
0.6974	Remote Similarity	NPD2818	Discontinued
0.6973	Remote Similarity	NPD1248	Discontinued
0.6973	Remote Similarity	NPD6794	Approved
0.6973	Remote Similarity	NPD1215	Discontinued
0.6971	Remote Similarity	NPD4047	Discontinued
0.6965	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2580	Discontinued
0.6954	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3609	Approved
0.6952	Remote Similarity	NPD3610	Approved
0.6947	Remote Similarity	NPD1327	Discontinued
0.6946	Remote Similarity	NPD1598	Discontinued
0.6944	Remote Similarity	NPD1917	Discontinued
0.6943	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1403	Approved
0.694	Remote Similarity	NPD1404	Approved
0.6931	Remote Similarity	NPD3015	Discontinued
0.6931	Remote Similarity	NPD2751	Phase 1
0.6927	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4612	Discontinued
0.6923	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4999	Phase 3
0.6919	Remote Similarity	NPD4998	Phase 3
0.6915	Remote Similarity	NPD6816	Phase 3
0.6915	Remote Similarity	NPD966	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD702	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2165	Phase 1
0.6904	Remote Similarity	NPD3431	Approved
0.6904	Remote Similarity	NPD3430	Approved
0.6901	Remote Similarity	NPD4030	Approved
0.6901	Remote Similarity	NPD4028	Approved
0.6901	Remote Similarity	NPD4029	Approved
0.6897	Remote Similarity	NPD2364	Suspended
0.6895	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2316	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2642	Approved
0.6882	Remote Similarity	NPD5611	Phase 2
0.6882	Remote Similarity	NPD2639	Approved
0.6881	Remote Similarity	NPD4142	Discontinued
0.6878	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3799	Suspended
0.6878	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2411	Approved
0.6868	Remote Similarity	NPD3114	Approved
0.6868	Remote Similarity	NPD3112	Approved
0.6868	Remote Similarity	NPD3113	Approved
0.6868	Remote Similarity	NPD3115	Approved
0.6864	Remote Similarity	NPD3654	Approved
0.686	Remote Similarity	NPD2141	Approved
0.686	Remote Similarity	NPD2142	Approved
0.686	Remote Similarity	NPD2140	Approved
0.6859	Remote Similarity	NPD40	Phase 2
0.6859	Remote Similarity	NPD1892	Phase 2
0.6859	Remote Similarity	NPD5730	Phase 2
0.6859	Remote Similarity	NPD1893	Phase 2
0.6856	Remote Similarity	NPD2868	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7469	Discontinued
0.6851	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6664	Approved
0.6845	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3348	Phase 2
0.6836	Remote Similarity	NPD5254	Discontinued
0.6834	Remote Similarity	NPD7619	Phase 3
0.6834	Remote Similarity	NPD7618	Phase 3
0.6833	Remote Similarity	NPD1030	Approved
0.6833	Remote Similarity	NPD1027	Approved
0.6833	Remote Similarity	NPD1029	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3889	Approved
0.6825	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5642	Approved
0.6821	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6285	Phase 2
0.6812	Remote Similarity	NPD2408	Discontinued
0.6806	Remote Similarity	NPD3505	Approved
0.6806	Remote Similarity	NPD3506	Approved
0.6804	Remote Similarity	NPD4957	Phase 2

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