NPASS Compound

Structure

CID162799 OpenBabel06191715532D 29 33 0 0 1 0 0 0 0 0999 V2000 5.0355 0.6763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6048 -1.1187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5824 -1.2475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6234 3.6996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8537 3.2553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0509 0.6222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4964 1.5020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8114 2.3428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 2.8112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8115 1.4059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1909 0.4197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0449 2.4689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4549 -0.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8547 -0.1625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8116 2.3426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4349 2.3424 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0170 1.0692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 0.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5242 2.0708 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4348 1.4055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8115 1.4057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6231 0.9368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6230 -0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2052 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6233 2.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5118 1.4479 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4210 2.4809 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.0551 -1.7273 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 7 2 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 7 26 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 15 1 0 0 0 0 10 18 2 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 28 3 0 0 0 0 14 24 1 0 0 0 0 15 21 2 0 0 0 0 15 25 1 0 0 0 0 16 12 1 1 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 20 2 0 0 0 0 17 26 1 0 0 0 0 18 21 1 0 0 0 0 18 29 1 0 0 0 0 19 26 1 1 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 21 22 1 0 0 0 0 22 23 2 0 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 26 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.19
Volume:	428.946
LogP:	6.385
LogD:	4.756
LogS:	-7.58
# Rotatable Bonds:	1
TPSA:	39.58
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.414
Synthetic Accessibility Score:	4.941
Fsp3:	0.423
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.694
MDCK Permeability:	1.6535892427782528e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.659
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	101.86807250976562%
Volume Distribution (VD):	3.272
Pgp-substrate:	0.9252634644508362%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.73
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.634
CYP2C9-inhibitor:	0.968
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.895
CYP2D6-substrate:	0.642
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.907

ADMET: Excretion

Clearance (CL):	2.412
Half-life (T1/2):	0.048

ADMET: Toxicity

hERG Blockers:	0.441
Human Hepatotoxicity (H-HT):	0.497
Drug-inuced Liver Injury (DILI):	0.226
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.616
Carcinogencity:	0.393
Eye Corrosion:	0.009
Eye Irritation:	0.358
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC162799

Natural Product ID:	NPC162799
*Common Name:**	Ambiguine G Nitrile
IUPAC Name:	n.a.
Synonyms:	Ambiguine G Nitrile
Standard InCHIKey:	HFHQOKOLRORURO-KGVVXCLESA-N
Standard InCHI:	InChI=1S/C26H27ClN2/c1-7-26(6)17-11-14(13-28)24(2,3)23-22-20(17)16(12-19(26)27)25(4,5)15-9-8-10-18(29-23)21(15)22/h7-11,16,19,29H,1,12H2,2-6H3/t16-,19+,26+/m0/s1
SMILES:	C=C[C@]1(C)C2=C3[C@H](C[C@H]1Cl)C(C)(C)c1cccc4c1c3c(C(C)(C)C(=C2)C#N)[nH]4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2205090
PubChem CID:	10834980
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO14060	Fischerella ambigua	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15787461]
NPO12573	Hypericum annulatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17260692]
NPO14060	Fischerella ambigua	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19371071]
NPO420	Eucheuma muricatum	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15556	Vernonia guineensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12573	Hypericum annulatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO420	Eucheuma muricatum	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9797	Aconitum toxicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17468	Hortia brasiliensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15556	Vernonia guineensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14019	Paraphaeosphaeria sporulosa	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO420	Eucheuma muricatum	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13801	Artemisia chamaemelifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14060	Fischerella ambigua	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12573	Hypericum annulatum	Species	Hypericaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	53700.0	nM	PMID[551644]

☑ 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 NPC162799 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	1075
0.1-0.2	7663
0.2-0.3	23099
0.3-0.4	6023
0.4-0.5	2458
0.5-0.6	1507
0.6-0.7	720
0.7-0.8	146
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9007	High Similarity	NPC477134
0.8408	Intermediate Similarity	NPC33421
0.8375	Intermediate Similarity	NPC286427
0.821	Intermediate Similarity	NPC41257
0.8182	Intermediate Similarity	NPC312092
0.8079	Intermediate Similarity	NPC475450
0.8013	Intermediate Similarity	NPC475428
0.7956	Intermediate Similarity	NPC476175
0.7947	Intermediate Similarity	NPC473587
0.7908	Intermediate Similarity	NPC473930
0.7881	Intermediate Similarity	NPC473762
0.7879	Intermediate Similarity	NPC206819
0.7879	Intermediate Similarity	NPC56765
0.7879	Intermediate Similarity	NPC318065
0.7867	Intermediate Similarity	NPC250361
0.7843	Intermediate Similarity	NPC179365
0.7785	Intermediate Similarity	NPC2949
0.7778	Intermediate Similarity	NPC22079
0.7758	Intermediate Similarity	NPC184476
0.7736	Intermediate Similarity	NPC473868
0.7736	Intermediate Similarity	NPC63157
0.7718	Intermediate Similarity	NPC41174
0.7716	Intermediate Similarity	NPC21605
0.7673	Intermediate Similarity	NPC59084
0.764	Intermediate Similarity	NPC242556
0.7619	Intermediate Similarity	NPC215584
0.7619	Intermediate Similarity	NPC44773
0.7584	Intermediate Similarity	NPC476319
0.758	Intermediate Similarity	NPC198988
0.7562	Intermediate Similarity	NPC230002
0.7562	Intermediate Similarity	NPC279081
0.7561	Intermediate Similarity	NPC124005
0.7532	Intermediate Similarity	NPC325252
0.7529	Intermediate Similarity	NPC90723
0.7526	Intermediate Similarity	NPC61637
0.75	Intermediate Similarity	NPC88097
0.75	Intermediate Similarity	NPC154293
0.7486	Intermediate Similarity	NPC288785
0.7457	Intermediate Similarity	NPC194411
0.7455	Intermediate Similarity	NPC37548
0.7453	Intermediate Similarity	NPC469783
0.7453	Intermediate Similarity	NPC469784
0.7453	Intermediate Similarity	NPC469779
0.7453	Intermediate Similarity	NPC469761
0.7453	Intermediate Similarity	NPC469780
0.7453	Intermediate Similarity	NPC469768
0.7453	Intermediate Similarity	NPC469767
0.7427	Intermediate Similarity	NPC472587
0.7421	Intermediate Similarity	NPC218268
0.741	Intermediate Similarity	NPC53947
0.7407	Intermediate Similarity	NPC469766
0.7391	Intermediate Similarity	NPC73767
0.7381	Intermediate Similarity	NPC38736
0.7375	Intermediate Similarity	NPC84911
0.7374	Intermediate Similarity	NPC19679
0.7356	Intermediate Similarity	NPC280548
0.7349	Intermediate Similarity	NPC2272
0.7349	Intermediate Similarity	NPC187951
0.7346	Intermediate Similarity	NPC115611
0.7346	Intermediate Similarity	NPC284635
0.7337	Intermediate Similarity	NPC316359
0.7337	Intermediate Similarity	NPC314058
0.7337	Intermediate Similarity	NPC315617
0.7337	Intermediate Similarity	NPC316018
0.7333	Intermediate Similarity	NPC129042
0.733	Intermediate Similarity	NPC275305
0.733	Intermediate Similarity	NPC37423
0.7312	Intermediate Similarity	NPC29886
0.7312	Intermediate Similarity	NPC261195
0.7312	Intermediate Similarity	NPC96102
0.7303	Intermediate Similarity	NPC176199
0.7303	Intermediate Similarity	NPC215795
0.7284	Intermediate Similarity	NPC110126
0.7278	Intermediate Similarity	NPC471458
0.7278	Intermediate Similarity	NPC470507
0.7273	Intermediate Similarity	NPC97525
0.7267	Intermediate Similarity	NPC150259
0.7267	Intermediate Similarity	NPC105127
0.7263	Intermediate Similarity	NPC314919
0.7251	Intermediate Similarity	NPC474880
0.7251	Intermediate Similarity	NPC221786
0.7251	Intermediate Similarity	NPC475990
0.7247	Intermediate Similarity	NPC68354
0.7247	Intermediate Similarity	NPC151939
0.7235	Intermediate Similarity	NPC51054
0.7235	Intermediate Similarity	NPC285469
0.7229	Intermediate Similarity	NPC288838
0.7219	Intermediate Similarity	NPC200743
0.7209	Intermediate Similarity	NPC473320
0.7209	Intermediate Similarity	NPC229173
0.72	Intermediate Similarity	NPC201700
0.7193	Intermediate Similarity	NPC216643
0.7193	Intermediate Similarity	NPC299594
0.7169	Intermediate Similarity	NPC204141
0.7169	Intermediate Similarity	NPC314372
0.7169	Intermediate Similarity	NPC470440
0.7168	Intermediate Similarity	NPC16667
0.7161	Intermediate Similarity	NPC122718
0.716	Intermediate Similarity	NPC125746
0.716	Intermediate Similarity	NPC470233
0.7152	Intermediate Similarity	NPC190296
0.7152	Intermediate Similarity	NPC81561
0.7151	Intermediate Similarity	NPC6436
0.7135	Intermediate Similarity	NPC477135
0.7128	Intermediate Similarity	NPC205403
0.7127	Intermediate Similarity	NPC192270
0.7126	Intermediate Similarity	NPC271734
0.7118	Intermediate Similarity	NPC325903
0.7111	Intermediate Similarity	NPC6093
0.7105	Intermediate Similarity	NPC54102
0.7105	Intermediate Similarity	NPC162689
0.7101	Intermediate Similarity	NPC105818
0.7101	Intermediate Similarity	NPC24678
0.7086	Intermediate Similarity	NPC148140
0.7083	Intermediate Similarity	NPC179787
0.7083	Intermediate Similarity	NPC201380
0.7076	Intermediate Similarity	NPC207726
0.7073	Intermediate Similarity	NPC104483
0.7072	Intermediate Similarity	NPC300688
0.7072	Intermediate Similarity	NPC198339
0.7063	Intermediate Similarity	NPC82295
0.7056	Intermediate Similarity	NPC293472
0.7048	Intermediate Similarity	NPC20144
0.7041	Intermediate Similarity	NPC321911
0.7039	Intermediate Similarity	NPC189812
0.7039	Intermediate Similarity	NPC329688
0.7033	Intermediate Similarity	NPC302191
0.7029	Intermediate Similarity	NPC271797
0.7029	Intermediate Similarity	NPC21174
0.7024	Intermediate Similarity	NPC63545
0.7024	Intermediate Similarity	NPC143872
0.7022	Intermediate Similarity	NPC6982
0.7018	Intermediate Similarity	NPC469763
0.7018	Intermediate Similarity	NPC469765
0.7018	Intermediate Similarity	NPC25008
0.7018	Intermediate Similarity	NPC469786
0.7018	Intermediate Similarity	NPC73952
0.7018	Intermediate Similarity	NPC469760
0.7018	Intermediate Similarity	NPC259644
0.7013	Intermediate Similarity	NPC215519
0.7	Intermediate Similarity	NPC148592
0.6989	Remote Similarity	NPC71132
0.6982	Remote Similarity	NPC469811
0.6982	Remote Similarity	NPC471957
0.6977	Remote Similarity	NPC212376
0.6977	Remote Similarity	NPC75540
0.6977	Remote Similarity	NPC211572
0.6977	Remote Similarity	NPC70922
0.6977	Remote Similarity	NPC80597
0.6966	Remote Similarity	NPC474897
0.6964	Remote Similarity	NPC159856
0.6957	Remote Similarity	NPC165201
0.6954	Remote Similarity	NPC135141
0.6954	Remote Similarity	NPC67056
0.6954	Remote Similarity	NPC92796
0.6952	Remote Similarity	NPC95783
0.6942	Remote Similarity	NPC112547
0.6923	Remote Similarity	NPC213468
0.6919	Remote Similarity	NPC200214
0.6909	Remote Similarity	NPC169433
0.6895	Remote Similarity	NPC85066
0.6895	Remote Similarity	NPC181502
0.6889	Remote Similarity	NPC34508
0.6884	Remote Similarity	NPC204303
0.6882	Remote Similarity	NPC99428
0.6879	Remote Similarity	NPC476297
0.6879	Remote Similarity	NPC476219
0.6878	Remote Similarity	NPC47190
0.686	Remote Similarity	NPC470823
0.6857	Remote Similarity	NPC474791
0.6854	Remote Similarity	NPC470509
0.6854	Remote Similarity	NPC474561
0.6854	Remote Similarity	NPC49954
0.6848	Remote Similarity	NPC470677
0.6848	Remote Similarity	NPC251722
0.6848	Remote Similarity	NPC314102
0.6845	Remote Similarity	NPC119700
0.6839	Remote Similarity	NPC476464
0.6839	Remote Similarity	NPC469785
0.6836	Remote Similarity	NPC317105
0.6821	Remote Similarity	NPC141926
0.6816	Remote Similarity	NPC317430
0.6816	Remote Similarity	NPC63751
0.6813	Remote Similarity	NPC280852
0.6809	Remote Similarity	NPC34271
0.68	Remote Similarity	NPC236711
0.68	Remote Similarity	NPC76982
0.68	Remote Similarity	NPC469762
0.6798	Remote Similarity	NPC470508
0.6796	Remote Similarity	NPC472123
0.6782	Remote Similarity	NPC34844
0.678	Remote Similarity	NPC470203
0.6774	Remote Similarity	NPC472294
0.6772	Remote Similarity	NPC206967
0.6772	Remote Similarity	NPC329858
0.6766	Remote Similarity	NPC32002
0.6766	Remote Similarity	NPC315348
0.6763	Remote Similarity	NPC216713
0.676	Remote Similarity	NPC109447
0.676	Remote Similarity	NPC160105

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 NPC162799 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	481
0.1-0.2	741
0.2-0.3	1313
0.3-0.4	2414
0.4-0.5	2628
0.5-0.6	1295
0.6-0.7	247
0.7-0.8	30
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8205	Intermediate Similarity	NPD5254	Discontinued
0.8095	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1262	Discovery
0.7738	Intermediate Similarity	NPD3323	Discontinued
0.758	Intermediate Similarity	NPD4880	Discontinued
0.7514	Intermediate Similarity	NPD3610	Approved
0.7514	Intermediate Similarity	NPD3609	Approved
0.7471	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4463	Approved
0.741	Intermediate Similarity	NPD4462	Approved
0.741	Intermediate Similarity	NPD2172	Phase 1
0.7407	Intermediate Similarity	NPD1722	Approved
0.7391	Intermediate Similarity	NPD786	Approved
0.7362	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3100	Discontinued
0.7349	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD4181	Approved
0.7333	Intermediate Similarity	NPD1683	Approved
0.7312	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3385	Approved
0.7288	Intermediate Similarity	NPD4075	Phase 2
0.7247	Intermediate Similarity	NPD3505	Approved
0.7247	Intermediate Similarity	NPD3506	Approved
0.7232	Intermediate Similarity	NPD4128	Approved
0.7207	Intermediate Similarity	NPD4079	Approved
0.7207	Intermediate Similarity	NPD4076	Approved
0.72	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD680	Discontinued
0.716	Intermediate Similarity	NPD6554	Approved
0.716	Intermediate Similarity	NPD45	Approved
0.7152	Intermediate Similarity	NPD3654	Approved
0.7126	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2837	Discontinued
0.7102	Intermediate Similarity	NPD5021	Discontinued
0.7069	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5315	Discontinued
0.7065	Intermediate Similarity	NPD6217	Discontinued
0.7063	Intermediate Similarity	NPD1251	Discontinued
0.7044	Intermediate Similarity	NPD947	Approved
0.7041	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2150	Discontinued
0.7027	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3339	Approved
0.6995	Remote Similarity	NPD3318	Approved
0.6995	Remote Similarity	NPD3320	Approved
0.6995	Remote Similarity	NPD3319	Phase 1
0.6936	Remote Similarity	NPD2580	Discontinued
0.6935	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3961	Discontinued
0.6915	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2641	Approved
0.691	Remote Similarity	NPD2640	Approved
0.6901	Remote Similarity	NPD3833	Phase 3
0.6901	Remote Similarity	NPD3835	Phase 3
0.6898	Remote Similarity	NPD1534	Approved
0.6897	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1254	Approved
0.689	Remote Similarity	NPD1256	Approved
0.689	Remote Similarity	NPD1255	Approved
0.689	Remote Similarity	NPD1253	Approved
0.6879	Remote Similarity	NPD2165	Phase 1
0.6872	Remote Similarity	NPD1325	Approved
0.6872	Remote Similarity	NPD1326	Approved
0.6868	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6133	Discontinued
0.6857	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD1248	Discontinued
0.6839	Remote Similarity	NPD3113	Approved
0.6839	Remote Similarity	NPD3115	Approved
0.6839	Remote Similarity	NPD3114	Approved
0.6839	Remote Similarity	NPD3112	Approved
0.6818	Remote Similarity	NPD1403	Approved
0.6818	Remote Similarity	NPD1404	Approved
0.6816	Remote Similarity	NPD4640	Approved
0.6816	Remote Similarity	NPD4639	Approved
0.6816	Remote Similarity	NPD4638	Approved
0.6816	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1592	Phase 3
0.6784	Remote Similarity	NPD4547	Phase 3
0.6771	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7455	Approved
0.6766	Remote Similarity	NPD7454	Approved
0.6766	Remote Similarity	NPD2072	Approved
0.6766	Remote Similarity	NPD2074	Approved
0.6766	Remote Similarity	NPD2073	Approved
0.6766	Remote Similarity	NPD2075	Approved
0.676	Remote Similarity	NPD2642	Approved
0.676	Remote Similarity	NPD2639	Approved
0.6755	Remote Similarity	NPD8431	Approved
0.6746	Remote Similarity	NPD4047	Discontinued
0.6743	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6664	Approved
0.6722	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5473	Discontinued
0.6702	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3476	Approved
0.6687	Remote Similarity	NPD3475	Approved
0.6685	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4499	Approved
0.6667	Remote Similarity	NPD4028	Approved
0.6667	Remote Similarity	NPD5065	Approved
0.6667	Remote Similarity	NPD4029	Approved
0.6667	Remote Similarity	NPD4030	Approved
0.6667	Remote Similarity	NPD3944	Approved
0.6667	Remote Similarity	NPD3942	Approved
0.6649	Remote Similarity	NPD8386	Phase 2
0.6648	Remote Similarity	NPD6828	Phase 2
0.6648	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3852	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD702	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6497	Approved
0.6608	Remote Similarity	NPD4509	Discontinued
0.6608	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD2118	Approved
0.6605	Remote Similarity	NPD2119	Approved
0.6591	Remote Similarity	NPD977	Approved
0.6591	Remote Similarity	NPD976	Approved
0.6591	Remote Similarity	NPD975	Approved
0.6588	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD1895	Discontinued
0.6568	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7185	Discontinued
0.6552	Remote Similarity	NPD2430	Phase 2
0.655	Remote Similarity	NPD2006	Phase 2
0.6543	Remote Similarity	NPD5105	Approved
0.6543	Remote Similarity	NPD5106	Approved
0.6524	Remote Similarity	NPD6595	Phase 3
0.6517	Remote Similarity	NPD4326	Phase 2
0.6505	Remote Similarity	NPD2144	Approved
0.6503	Remote Similarity	NPD5436	Phase 1
0.65	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3038	Discontinued
0.6486	Remote Similarity	NPD3799	Suspended
0.6474	Remote Similarity	NPD1227	Phase 2
0.6471	Remote Similarity	NPD6448	Phase 1
0.6467	Remote Similarity	NPD3116	Approved
0.6467	Remote Similarity	NPD3117	Approved
0.6462	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4511	Phase 1
0.6421	Remote Similarity	NPD5892	Approved
0.6406	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7394	Phase 2
0.6406	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6285	Phase 2
0.6402	Remote Similarity	NPD991	Phase 2
0.6402	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD1561	Phase 2
0.6398	Remote Similarity	NPD5787	Discontinued
0.6393	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5913	Phase 3
0.6392	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD6158	Phase 2
0.6384	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD2882	Phase 1
0.6383	Remote Similarity	NPD5730	Phase 2
0.6383	Remote Similarity	NPD40	Phase 2
0.6382	Remote Similarity	NPD6479	Discontinued
0.6378	Remote Similarity	NPD7618	Phase 3
0.6378	Remote Similarity	NPD7619	Phase 3
0.6378	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5140	Approved
0.6374	Remote Similarity	NPD3583	Phase 2
0.6374	Remote Similarity	NPD5138	Approved
0.6373	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4441	Phase 2
0.6368	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD2920	Discontinued
0.6368	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4332	Phase 3
0.6359	Remote Similarity	NPD4922	Phase 2
0.6358	Remote Similarity	NPD2938	Approved
0.6358	Remote Similarity	NPD2940	Approved
0.6358	Remote Similarity	NPD990	Approved
0.6358	Remote Similarity	NPD993	Approved
0.634	Remote Similarity	NPD6281	Approved
0.6332	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD4973	Approved
0.6319	Remote Similarity	NPD1685	Approved
0.6319	Remote Similarity	NPD1684	Approved
0.6318	Remote Similarity	NPD6975	Discontinued
0.6316	Remote Similarity	NPD1707	Approved
0.6316	Remote Similarity	NPD1708	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