NPASS Compound

Structure

NPC205403 OpenBabel07101718192D 30 34 0 0 1 0 0 0 0 0999 V2000 2.0834 1.3811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4121 1.2240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1344 0.6705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1713 -2.2739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8933 -1.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5560 0.6395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6224 -1.7047 0.0000 C 0 5 0 0 0 0 0 0 0 0 0 0 1.1775 1.4670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5973 -1.5812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4713 -0.6800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8799 -2.1410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3191 0.9670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2236 1.0796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2121 -0.1596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6278 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0364 -1.7996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5695 0.4724 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3834 -0.7987 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9103 -0.8984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0143 -0.7398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4134 -1.5430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2939 0.3217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0526 -1.3717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6501 0.7255 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6391 0.1713 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9613 -1.0794 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -0.2183 -2.1980 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1878 -1.0363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9082 1.5771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 27 3 0 0 0 0 8 24 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 28 1 0 0 0 0 17 22 1 0 0 0 0 17 26 1 1 0 0 0 18 23 1 0 0 0 0 18 29 1 1 0 0 0 19 20 1 0 0 0 0 20 21 2 0 0 0 0 20 26 1 0 0 0 0 21 23 1 0 0 0 0 21 28 1 0 0 0 0 24 25 1 6 0 0 0 25 26 1 1 0 0 0 25 27 1 0 0 0 0 26 30 1 1 0 0 0 M CHG 2 7 -1 27 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.25
Volume:	436.589
LogP:	4.128
LogD:	3.605
LogS:	-5.592
# Rotatable Bonds:	1
TPSA:	60.61
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.465
Synthetic Accessibility Score:	5.259
Fsp3:	0.577
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:	-5.032
MDCK Permeability:	1.7521288100397214e-05
Pgp-inhibitor:	0.903
Pgp-substrate:	0.313
Human Intestinal Absorption (HIA):	0.772
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963
Plasma Protein Binding (PPB):	93.21090698242188%
Volume Distribution (VD):	1.744
Pgp-substrate:	4.891219139099121%

ADMET: Metabolism

CYP1A2-inhibitor:	0.175
CYP1A2-substrate:	0.733
CYP2C19-inhibitor:	0.33
CYP2C19-substrate:	0.62
CYP2C9-inhibitor:	0.636
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.73
CYP2D6-substrate:	0.216
CYP3A4-inhibitor:	0.853
CYP3A4-substrate:	0.853

ADMET: Excretion

Clearance (CL):	3.875
Half-life (T1/2):	0.152

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.22
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.867
Carcinogencity:	0.762
Eye Corrosion:	0.012
Eye Irritation:	0.936
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC205403

Natural Product ID:	NPC205403
*Common Name:**	Ambiguine N Isonitrile
IUPAC Name:	n.a.
Synonyms:	Ambiguine N Isonitrile
Standard InCHIKey:	KAXIDSYNDHUROH-OWINPNOJSA-N
Standard InCHI:	InChI=1S/C26H32N2O2/c1-8-24(6)13-12-17-22(2,3)15-10-9-11-16-19(15)20-21(28-16)23(4,5)18(29)14-25(24,27-7)26(17,20)30/h8-11,17-18,28-30H,1,12-14H2,2-6H3/t17-,18-,24+,25+,26-/m1/s1
SMILES:	C=C[C@@]1(C)CC[C@H]2[C@@]3([C@]1([N+]#[C-])C[C@@H](O)C(c1c3c3c(C2(C)C)cccc3[nH]1)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL564329
PubChem CID:	44139370
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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]
NPO14060	Fischerella ambigua	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19371071]
NPO14060	Fischerella ambigua	Species	Hapalosiphonaceae	Bacteria	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	1
MIC	5

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	118400.0	nM	PMID[489126]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	27100.0	nM	PMID[489126]
NPT1550	Organism	Bacillus anthracis	Bacillus anthracis	MIC	=	30900.0	nM	PMID[489126]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5500.0	nM	PMID[489126]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	48800.0	nM	PMID[489126]
NPT20	Organism	Candida albicans	Candida albicans	MIC	<	1000.0	nM	PMID[489126]

☑ 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 NPC205403 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	389
0.1-0.2	1554
0.2-0.3	6447
0.3-0.4	18880
0.4-0.5	10512
0.5-0.6	2915
0.6-0.7	1658
0.7-0.8	322
0.8-0.85	14
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9368	High Similarity	NPC476319
0.9297	High Similarity	NPC61637
0.9081	High Similarity	NPC477135
0.8763	High Similarity	NPC476175
0.8603	High Similarity	NPC198339
0.8453	Intermediate Similarity	NPC302191
0.8362	Intermediate Similarity	NPC154293
0.8324	Intermediate Similarity	NPC97525
0.8284	Intermediate Similarity	NPC112547
0.8207	Intermediate Similarity	NPC19679
0.8177	Intermediate Similarity	NPC32200
0.8138	Intermediate Similarity	NPC206967
0.8128	Intermediate Similarity	NPC119700
0.8122	Intermediate Similarity	NPC34508
0.8098	Intermediate Similarity	NPC300688
0.8085	Intermediate Similarity	NPC34271
0.8065	Intermediate Similarity	NPC165201
0.8043	Intermediate Similarity	NPC270009
0.8031	Intermediate Similarity	NPC473747
0.8021	Intermediate Similarity	NPC231342
0.7946	Intermediate Similarity	NPC6093
0.7946	Intermediate Similarity	NPC472443
0.7914	Intermediate Similarity	NPC472444
0.7892	Intermediate Similarity	NPC151939
0.7892	Intermediate Similarity	NPC293472
0.7876	Intermediate Similarity	NPC181502
0.7876	Intermediate Similarity	NPC85066
0.7861	Intermediate Similarity	NPC192270
0.7857	Intermediate Similarity	NPC475151
0.7853	Intermediate Similarity	NPC469497
0.7853	Intermediate Similarity	NPC106833
0.7822	Intermediate Similarity	NPC250129
0.7809	Intermediate Similarity	NPC184476
0.7801	Intermediate Similarity	NPC128751
0.7784	Intermediate Similarity	NPC472586
0.7772	Intermediate Similarity	NPC475165
0.776	Intermediate Similarity	NPC95783
0.773	Intermediate Similarity	NPC313791
0.7718	Intermediate Similarity	NPC314552
0.7717	Intermediate Similarity	NPC280548
0.7708	Intermediate Similarity	NPC46413
0.7708	Intermediate Similarity	NPC246700
0.7707	Intermediate Similarity	NPC160527
0.7707	Intermediate Similarity	NPC473650
0.7707	Intermediate Similarity	NPC471284
0.7704	Intermediate Similarity	NPC153042
0.7696	Intermediate Similarity	NPC99428
0.7696	Intermediate Similarity	NPC235900
0.7672	Intermediate Similarity	NPC314394
0.767	Intermediate Similarity	NPC477134
0.7663	Intermediate Similarity	NPC201700
0.7654	Intermediate Similarity	NPC470507
0.7621	Intermediate Similarity	NPC97388
0.7608	Intermediate Similarity	NPC61813
0.7608	Intermediate Similarity	NPC470874
0.76	Intermediate Similarity	NPC242556
0.76	Intermediate Similarity	NPC123019
0.7598	Intermediate Similarity	NPC234999
0.7596	Intermediate Similarity	NPC472587
0.7594	Intermediate Similarity	NPC329688
0.7594	Intermediate Similarity	NPC189812
0.7581	Intermediate Similarity	NPC126492
0.7574	Intermediate Similarity	NPC187456
0.7573	Intermediate Similarity	NPC473547
0.7566	Intermediate Similarity	NPC176199
0.7566	Intermediate Similarity	NPC215795
0.756	Intermediate Similarity	NPC475476
0.756	Intermediate Similarity	NPC242446
0.7556	Intermediate Similarity	NPC471458
0.7548	Intermediate Similarity	NPC96131
0.7528	Intermediate Similarity	NPC37548
0.7528	Intermediate Similarity	NPC124005
0.7524	Intermediate Similarity	NPC475778
0.7514	Intermediate Similarity	NPC285469
0.7514	Intermediate Similarity	NPC141353
0.7513	Intermediate Similarity	NPC68354
0.75	Intermediate Similarity	NPC102423
0.75	Intermediate Similarity	NPC190007
0.7488	Intermediate Similarity	NPC476106
0.7488	Intermediate Similarity	NPC18661
0.7486	Intermediate Similarity	NPC473320
0.7477	Intermediate Similarity	NPC470873
0.7461	Intermediate Similarity	NPC94943
0.746	Intermediate Similarity	NPC288785
0.7459	Intermediate Similarity	NPC38736
0.7459	Intermediate Similarity	NPC470508
0.7451	Intermediate Similarity	NPC193777
0.7446	Intermediate Similarity	NPC16667
0.743	Intermediate Similarity	NPC475424
0.743	Intermediate Similarity	NPC187951
0.743	Intermediate Similarity	NPC79107
0.7427	Intermediate Similarity	NPC475422
0.7424	Intermediate Similarity	NPC195314
0.7416	Intermediate Similarity	NPC129042
0.7416	Intermediate Similarity	NPC203614
0.7416	Intermediate Similarity	NPC204491
0.7413	Intermediate Similarity	NPC249040
0.7407	Intermediate Similarity	NPC37423
0.7407	Intermediate Similarity	NPC471634
0.7407	Intermediate Similarity	NPC473806
0.7407	Intermediate Similarity	NPC275305
0.7405	Intermediate Similarity	NPC311276
0.7395	Intermediate Similarity	NPC249342
0.7391	Intermediate Similarity	NPC131718
0.7383	Intermediate Similarity	NPC141428
0.7382	Intermediate Similarity	NPC88363
0.738	Intermediate Similarity	NPC317430
0.7363	Intermediate Similarity	NPC207726
0.7358	Intermediate Similarity	NPC472108
0.7358	Intermediate Similarity	NPC212535
0.7358	Intermediate Similarity	NPC139291
0.7356	Intermediate Similarity	NPC48353
0.7354	Intermediate Similarity	NPC474409
0.7353	Intermediate Similarity	NPC470500
0.7337	Intermediate Similarity	NPC67056
0.733	Intermediate Similarity	NPC87755
0.732	Intermediate Similarity	NPC472294
0.7315	Intermediate Similarity	NPC57690
0.7315	Intermediate Similarity	NPC470126
0.7312	Intermediate Similarity	NPC476118
0.7312	Intermediate Similarity	NPC40779
0.7309	Intermediate Similarity	NPC470843
0.7309	Intermediate Similarity	NPC94541
0.7308	Intermediate Similarity	NPC204303
0.7304	Intermediate Similarity	NPC98715
0.7302	Intermediate Similarity	NPC158129
0.7295	Intermediate Similarity	NPC284102
0.7294	Intermediate Similarity	NPC282033
0.7293	Intermediate Similarity	NPC33421
0.7292	Intermediate Similarity	NPC72980
0.7291	Intermediate Similarity	NPC300183
0.7283	Intermediate Similarity	NPC469762
0.7282	Intermediate Similarity	NPC473189
0.7281	Intermediate Similarity	NPC253580
0.7277	Intermediate Similarity	NPC128823
0.7268	Intermediate Similarity	NPC48938
0.7264	Intermediate Similarity	NPC243834
0.7264	Intermediate Similarity	NPC70956
0.7264	Intermediate Similarity	NPC229332
0.7263	Intermediate Similarity	NPC472123
0.725	Intermediate Similarity	NPC133366
0.7249	Intermediate Similarity	NPC126481
0.7249	Intermediate Similarity	NPC194411
0.7246	Intermediate Similarity	NPC127677
0.7246	Intermediate Similarity	NPC258062
0.7243	Intermediate Similarity	NPC41257
0.7238	Intermediate Similarity	NPC478074
0.7236	Intermediate Similarity	NPC99666
0.7228	Intermediate Similarity	NPC469785
0.7225	Intermediate Similarity	NPC9894
0.7215	Intermediate Similarity	NPC477531
0.7211	Intermediate Similarity	NPC6982
0.7206	Intermediate Similarity	NPC267423
0.7202	Intermediate Similarity	NPC252251
0.72	Intermediate Similarity	NPC474177
0.7198	Intermediate Similarity	NPC46225
0.7198	Intermediate Similarity	NPC225821
0.719	Intermediate Similarity	NPC87856
0.719	Intermediate Similarity	NPC473180
0.719	Intermediate Similarity	NPC294620
0.719	Intermediate Similarity	NPC151976
0.7189	Intermediate Similarity	NPC286427
0.7189	Intermediate Similarity	NPC299594
0.7183	Intermediate Similarity	NPC469594
0.7178	Intermediate Similarity	NPC232130
0.7177	Intermediate Similarity	NPC5145
0.7177	Intermediate Similarity	NPC199667
0.7175	Intermediate Similarity	NPC312092
0.7173	Intermediate Similarity	NPC314603
0.7171	Intermediate Similarity	NPC475112
0.7171	Intermediate Similarity	NPC475085
0.7171	Intermediate Similarity	NPC291535
0.717	Intermediate Similarity	NPC469928
0.717	Intermediate Similarity	NPC132211
0.717	Intermediate Similarity	NPC251936
0.7169	Intermediate Similarity	NPC209174
0.7163	Intermediate Similarity	NPC475910
0.7157	Intermediate Similarity	NPC313985
0.7157	Intermediate Similarity	NPC49196
0.7157	Intermediate Similarity	NPC195461
0.7157	Intermediate Similarity	NPC79129
0.7157	Intermediate Similarity	NPC249150
0.7157	Intermediate Similarity	NPC81654
0.7156	Intermediate Similarity	NPC267965
0.715	Intermediate Similarity	NPC326575
0.7143	Intermediate Similarity	NPC49954
0.7143	Intermediate Similarity	NPC474561
0.7143	Intermediate Similarity	NPC50503
0.7143	Intermediate Similarity	NPC235885
0.7143	Intermediate Similarity	NPC102008
0.7143	Intermediate Similarity	NPC313884
0.7143	Intermediate Similarity	NPC98371
0.7143	Intermediate Similarity	NPC160105
0.7136	Intermediate Similarity	NPC223427
0.7136	Intermediate Similarity	NPC293151
0.7129	Intermediate Similarity	NPC201697
0.7129	Intermediate Similarity	NPC473181
0.7128	Intermediate Similarity	NPC159319
0.7128	Intermediate Similarity	NPC162799
0.7128	Intermediate Similarity	NPC271734

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 NPC205403 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	557
0.2-0.3	654
0.3-0.4	1683
0.4-0.5	3171
0.5-0.6	2217
0.6-0.7	559
0.7-0.8	75
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
0.7718	Intermediate Similarity	NPD5164	Discontinued
0.765	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1326	Approved
0.7622	Intermediate Similarity	NPD1325	Approved
0.7566	Intermediate Similarity	NPD4076	Approved
0.7566	Intermediate Similarity	NPD4079	Approved
0.7561	Intermediate Similarity	NPD5936	Approved
0.7561	Intermediate Similarity	NPD5939	Approved
0.7538	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD5913	Phase 3
0.7538	Intermediate Similarity	NPD2177	Approved
0.7538	Intermediate Similarity	NPD2176	Approved
0.7538	Intermediate Similarity	NPD2175	Phase 3
0.7513	Intermediate Similarity	NPD3505	Approved
0.7513	Intermediate Similarity	NPD3506	Approved
0.746	Intermediate Similarity	NPD2381	Approved
0.746	Intermediate Similarity	NPD2380	Approved
0.746	Intermediate Similarity	NPD2382	Approved
0.7448	Intermediate Similarity	NPD5596	Phase 2
0.7433	Intermediate Similarity	NPD7474	Suspended
0.7386	Intermediate Similarity	NPD1592	Phase 3
0.738	Intermediate Similarity	NPD5021	Discontinued
0.7379	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4511	Phase 1
0.7354	Intermediate Similarity	NPD7418	Discontinued
0.735	Intermediate Similarity	NPD5003	Discontinued
0.7348	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD6158	Phase 2
0.7316	Intermediate Similarity	NPD5065	Approved
0.7312	Intermediate Similarity	NPD5138	Approved
0.7312	Intermediate Similarity	NPD5140	Approved
0.7296	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4463	Approved
0.7293	Intermediate Similarity	NPD4462	Approved
0.7282	Intermediate Similarity	NPD6290	Phase 2
0.7273	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7948	Phase 1
0.7258	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD3525	Discontinued
0.7246	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4502	Phase 2
0.722	Intermediate Similarity	NPD2920	Discontinued
0.7208	Intermediate Similarity	NPD8431	Approved
0.7196	Intermediate Similarity	NPD4640	Approved
0.7196	Intermediate Similarity	NPD4639	Approved
0.7196	Intermediate Similarity	NPD4638	Approved
0.7189	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6975	Discontinued
0.7165	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2882	Phase 1
0.7157	Intermediate Similarity	NPD4600	Approved
0.7157	Intermediate Similarity	NPD4601	Approved
0.7156	Intermediate Similarity	NPD6978	Phase 2
0.7156	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7957	Phase 1
0.7143	Intermediate Similarity	NPD53	Approved
0.7143	Intermediate Similarity	NPD7777	Approved
0.7143	Intermediate Similarity	NPD7778	Approved
0.7143	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6281	Approved
0.7135	Intermediate Similarity	NPD6492	Phase 2
0.7114	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5254	Discontinued
0.7109	Intermediate Similarity	NPD8093	Discontinued
0.7105	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6595	Phase 3
0.7075	Intermediate Similarity	NPD8094	Discontinued
0.7074	Intermediate Similarity	NPD1684	Approved
0.7074	Intermediate Similarity	NPD1685	Approved
0.707	Intermediate Similarity	NPD6455	Phase 3
0.7068	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3003	Approved
0.705	Intermediate Similarity	NPD2565	Phase 2
0.705	Intermediate Similarity	NPD2564	Approved
0.7044	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6145	Phase 1
0.7037	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2383	Phase 1
0.7026	Intermediate Similarity	NPD8386	Phase 2
0.7024	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2844	Phase 3
0.7	Intermediate Similarity	NPD2916	Discontinued
0.6981	Remote Similarity	NPD5066	Phase 2
0.6981	Remote Similarity	NPD5067	Phase 2
0.6981	Remote Similarity	NPD6220	Phase 3
0.6976	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6159	Phase 2
0.697	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD4499	Approved
0.6963	Remote Similarity	NPD5903	Approved
0.6963	Remote Similarity	NPD5902	Approved
0.6954	Remote Similarity	NPD7867	Phase 1
0.6952	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD8395	Approved
0.6942	Remote Similarity	NPD8396	Approved
0.6939	Remote Similarity	NPD3417	Phase 1
0.692	Remote Similarity	NPD7558	Phase 2
0.6915	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7452	Approved
0.6872	Remote Similarity	NPD7453	Approved
0.6869	Remote Similarity	NPD3330	Phase 1
0.6868	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1038	Approved
0.686	Remote Similarity	NPD1768	Approved
0.6859	Remote Similarity	NPD3323	Discontinued
0.6851	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6376	Discontinued
0.6837	Remote Similarity	NPD5100	Phase 3
0.6818	Remote Similarity	NPD6995	Phase 1
0.6818	Remote Similarity	NPD6452	Discontinued
0.6814	Remote Similarity	NPD3404	Approved
0.6806	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4181	Approved
0.6802	Remote Similarity	NPD2144	Approved
0.68	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7222	Phase 2
0.6789	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6985	Discontinued
0.6788	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3038	Discontinued
0.6782	Remote Similarity	NPD4948	Discontinued
0.6782	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD1262	Discovery
0.6774	Remote Similarity	NPD5612	Discontinued
0.6766	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5658	Approved
0.6758	Remote Similarity	NPD7194	Discontinued
0.675	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6590	Discontinued
0.6745	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7470	Discontinued
0.6741	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3833	Phase 3
0.6738	Remote Similarity	NPD3835	Phase 3
0.6735	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD43	Approved
0.6735	Remote Similarity	NPD6182	Approved
0.6734	Remote Similarity	NPD5899	Approved
0.6734	Remote Similarity	NPD5897	Approved
0.6734	Remote Similarity	NPD5898	Approved
0.673	Remote Similarity	NPD6176	Phase 1
0.6712	Remote Similarity	NPD7878	Phase 2
0.6702	Remote Similarity	NPD5255	Approved
0.6701	Remote Similarity	NPD4128	Approved
0.67	Remote Similarity	NPD3961	Discontinued
0.6699	Remote Similarity	NPD802	Phase 2
0.6699	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5901	Discontinued
0.6698	Remote Similarity	NPD4037	Approved
0.6698	Remote Similarity	NPD4036	Approved
0.6698	Remote Similarity	NPD32	Approved
0.6698	Remote Similarity	NPD4034	Approved
0.6698	Remote Similarity	NPD31	Approved
0.6698	Remote Similarity	NPD4035	Approved
0.6698	Remote Similarity	NPD4122	Approved
0.6698	Remote Similarity	NPD4038	Approved
0.6698	Remote Similarity	NPD4039	Approved
0.6698	Remote Similarity	NPD4033	Approved
0.6684	Remote Similarity	NPD6026	Approved
0.6683	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6227	Discontinued
0.6682	Remote Similarity	NPD7671	Approved
0.6682	Remote Similarity	NPD7276	Approved
0.6682	Remote Similarity	NPD7672	Approved
0.6682	Remote Similarity	NPD7277	Approved
0.6667	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5530	Phase 1
0.6667	Remote Similarity	NPD4075	Phase 2
0.6667	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4880	Discontinued
0.6667	Remote Similarity	NPD2092	Phase 2
0.6667	Remote Similarity	NPD2094	Phase 2
0.6667	Remote Similarity	NPD484	Approved
0.6667	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1534	Approved
0.6667	Remote Similarity	NPD2095	Phase 2
0.6652	Remote Similarity	NPD7603	Discontinued
0.6651	Remote Similarity	NPD8072	Approved
0.6651	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2727	Phase 2
0.6651	Remote Similarity	NPD7946	Pre-registration

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