NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.09
Volume:	262.82
LogP:	2.32
LogD:	2.173
LogS:	-3.618
# Rotatable Bonds:	2
TPSA:	74.43
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.545
Synthetic Accessibility Score:	2.781
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.011
MDCK Permeability:	7.599007403769065e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.076
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.101
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.838
Plasma Protein Binding (PPB):	93.13732147216797%
Volume Distribution (VD):	1.53
Pgp-substrate:	8.901151657104492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.731
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.486
CYP2C9-substrate:	0.6
CYP2D6-inhibitor:	0.834
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.931
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	9.725
Half-life (T1/2):	0.752

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.896
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.755
Rat Oral Acute Toxicity:	0.917
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.769
Carcinogencity:	0.022
Eye Corrosion:	0.004
Eye Irritation:	0.674
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC116555

Natural Product ID:	NPC116555
*Common Name:**	Des-N-Methylxestomanzamine A
IUPAC Name:	1H-imidazol-5-yl(9H-pyrido[3,4-b]indol-1-yl)methanone
Synonyms:
Standard InCHIKey:	LDAYUUNBNSTTAQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10N4O/c20-15(12-7-16-8-18-12)14-13-10(5-6-17-14)9-3-1-2-4-11(9)19-13/h1-8,19H,(H,16,18)
SMILES:	O=C(c1nccc2c1[nH]c1c2cccc1)c1cnc[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462028
PubChem CID:	11821407
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
NPO32531	sponge sp.	Species	n.a.	n.a.	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape, Manado Bay, Indonesia	2011-MAR	PMID[12828469]

☑ 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
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	35.0	ug.mL-1	PMID[541487]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	>	50.0	ug.mL-1	PMID[541487]

☑ 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 NPC116555 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	938
0.1-0.2	11483
0.2-0.3	19262
0.3-0.4	6023
0.4-0.5	1686
0.5-0.6	1951
0.6-0.7	1085
0.7-0.8	233
0.8-0.85	25
0.85-0.9	7
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9381	High Similarity	NPC267811
0.8883	High Similarity	NPC326422
0.8792	High Similarity	NPC267078
0.8792	High Similarity	NPC935
0.875	High Similarity	NPC474357
0.8744	High Similarity	NPC470323
0.8649	High Similarity	NPC191415
0.8571	High Similarity	NPC317701
0.8404	Intermediate Similarity	NPC102755
0.8387	Intermediate Similarity	NPC284775
0.8146	Intermediate Similarity	NPC470702
0.8146	Intermediate Similarity	NPC473218
0.8142	Intermediate Similarity	NPC74619
0.8112	Intermediate Similarity	NPC304203
0.8107	Intermediate Similarity	NPC470703
0.8103	Intermediate Similarity	NPC476460
0.8019	Intermediate Similarity	NPC282247
0.8018	Intermediate Similarity	NPC63109
0.8	Intermediate Similarity	NPC473380
0.8	Intermediate Similarity	NPC237414
0.8	Intermediate Similarity	NPC240088
0.7959	Intermediate Similarity	NPC324091
0.7958	Intermediate Similarity	NPC265710
0.7947	Intermediate Similarity	NPC151635
0.7917	Intermediate Similarity	NPC16659
0.79	Intermediate Similarity	NPC167710
0.7892	Intermediate Similarity	NPC470204
0.7887	Intermediate Similarity	NPC477003
0.7849	Intermediate Similarity	NPC470203
0.7842	Intermediate Similarity	NPC252572
0.7767	Intermediate Similarity	NPC229893
0.7761	Intermediate Similarity	NPC102592
0.7761	Intermediate Similarity	NPC79356
0.7704	Intermediate Similarity	NPC21429
0.7701	Intermediate Similarity	NPC122141
0.7672	Intermediate Similarity	NPC42372
0.7626	Intermediate Similarity	NPC17273
0.7626	Intermediate Similarity	NPC135601
0.7626	Intermediate Similarity	NPC141612
0.7619	Intermediate Similarity	NPC317105
0.7586	Intermediate Similarity	NPC128244
0.7583	Intermediate Similarity	NPC77101
0.7576	Intermediate Similarity	NPC133003
0.7576	Intermediate Similarity	NPC308931
0.7576	Intermediate Similarity	NPC99939
0.757	Intermediate Similarity	NPC27041
0.7566	Intermediate Similarity	NPC171393
0.7566	Intermediate Similarity	NPC295452
0.7547	Intermediate Similarity	NPC471194
0.7547	Intermediate Similarity	NPC471193
0.7545	Intermediate Similarity	NPC156003
0.7526	Intermediate Similarity	NPC293216
0.7526	Intermediate Similarity	NPC317054
0.7524	Intermediate Similarity	NPC266249
0.7523	Intermediate Similarity	NPC207686
0.7512	Intermediate Similarity	NPC474389
0.75	Intermediate Similarity	NPC469811
0.7488	Intermediate Similarity	NPC188821
0.7488	Intermediate Similarity	NPC474180
0.7476	Intermediate Similarity	NPC81535
0.746	Intermediate Similarity	NPC474492
0.7459	Intermediate Similarity	NPC321911
0.7453	Intermediate Similarity	NPC123839
0.7446	Intermediate Similarity	NPC63545
0.7438	Intermediate Similarity	NPC216550
0.7433	Intermediate Similarity	NPC325903
0.7432	Intermediate Similarity	NPC69843
0.7418	Intermediate Similarity	NPC72956
0.7405	Intermediate Similarity	NPC201380
0.7405	Intermediate Similarity	NPC179787
0.7391	Intermediate Similarity	NPC477004
0.7389	Intermediate Similarity	NPC235685
0.7387	Intermediate Similarity	NPC117027
0.7383	Intermediate Similarity	NPC6865
0.7383	Intermediate Similarity	NPC153980
0.7382	Intermediate Similarity	NPC225018
0.7374	Intermediate Similarity	NPC88110
0.7371	Intermediate Similarity	NPC471943
0.7357	Intermediate Similarity	NPC101350
0.735	Intermediate Similarity	NPC467063
0.7344	Intermediate Similarity	NPC478184
0.7337	Intermediate Similarity	NPC470677
0.7337	Intermediate Similarity	NPC307191
0.7336	Intermediate Similarity	NPC54981
0.733	Intermediate Similarity	NPC470680
0.733	Intermediate Similarity	NPC100104
0.7313	Intermediate Similarity	NPC476341
0.7306	Intermediate Similarity	NPC115232
0.73	Intermediate Similarity	NPC470205
0.7286	Intermediate Similarity	NPC73994
0.7281	Intermediate Similarity	NPC471192
0.7277	Intermediate Similarity	NPC62749
0.7277	Intermediate Similarity	NPC476527
0.7258	Intermediate Similarity	NPC288838
0.7258	Intermediate Similarity	NPC143872
0.7255	Intermediate Similarity	NPC154339
0.7225	Intermediate Similarity	NPC236711
0.7222	Intermediate Similarity	NPC118940
0.7222	Intermediate Similarity	NPC280852
0.7212	Intermediate Similarity	NPC227582
0.7207	Intermediate Similarity	NPC122436
0.7206	Intermediate Similarity	NPC473666
0.7206	Intermediate Similarity	NPC321708
0.7206	Intermediate Similarity	NPC103119
0.7204	Intermediate Similarity	NPC204141
0.7196	Intermediate Similarity	NPC71238
0.7188	Intermediate Similarity	NPC293487
0.7188	Intermediate Similarity	NPC135141
0.7188	Intermediate Similarity	NPC92796
0.7186	Intermediate Similarity	NPC157583
0.7186	Intermediate Similarity	NPC237188
0.7184	Intermediate Similarity	NPC272458
0.7179	Intermediate Similarity	NPC56233
0.7179	Intermediate Similarity	NPC49217
0.7178	Intermediate Similarity	NPC110158
0.7177	Intermediate Similarity	NPC474916
0.7165	Intermediate Similarity	NPC265100
0.715	Intermediate Similarity	NPC267343
0.7143	Intermediate Similarity	NPC153123
0.7143	Intermediate Similarity	NPC220797
0.7143	Intermediate Similarity	NPC471655
0.7143	Intermediate Similarity	NPC201266
0.7143	Intermediate Similarity	NPC474318
0.7143	Intermediate Similarity	NPC475914
0.7143	Intermediate Similarity	NPC74413
0.7143	Intermediate Similarity	NPC268744
0.7143	Intermediate Similarity	NPC53947
0.7137	Intermediate Similarity	NPC200553
0.7137	Intermediate Similarity	NPC279189
0.7136	Intermediate Similarity	NPC473376
0.7128	Intermediate Similarity	NPC233380
0.7123	Intermediate Similarity	NPC322064
0.7115	Intermediate Similarity	NPC202812
0.7113	Intermediate Similarity	NPC242116
0.7112	Intermediate Similarity	NPC467188
0.7109	Intermediate Similarity	NPC77241
0.7109	Intermediate Similarity	NPC13456
0.7109	Intermediate Similarity	NPC269203
0.7109	Intermediate Similarity	NPC166209
0.7109	Intermediate Similarity	NPC252338
0.7101	Intermediate Similarity	NPC47190
0.71	Intermediate Similarity	NPC83774
0.7098	Intermediate Similarity	NPC80681
0.7098	Intermediate Similarity	NPC300238
0.7097	Intermediate Similarity	NPC82370
0.7094	Intermediate Similarity	NPC108011
0.709	Intermediate Similarity	NPC282531
0.7085	Intermediate Similarity	NPC469529
0.7081	Intermediate Similarity	NPC115611
0.7077	Intermediate Similarity	NPC274981
0.7077	Intermediate Similarity	NPC478182
0.7075	Intermediate Similarity	NPC469308
0.7074	Intermediate Similarity	NPC174489
0.7073	Intermediate Similarity	NPC17059
0.7073	Intermediate Similarity	NPC278434
0.7068	Intermediate Similarity	NPC251391
0.7065	Intermediate Similarity	NPC11126
0.7056	Intermediate Similarity	NPC70949
0.7056	Intermediate Similarity	NPC132539
0.7054	Intermediate Similarity	NPC130570
0.7053	Intermediate Similarity	NPC138370
0.7048	Intermediate Similarity	NPC475286
0.7048	Intermediate Similarity	NPC174281
0.7047	Intermediate Similarity	NPC216643
0.7045	Intermediate Similarity	NPC470731
0.7045	Intermediate Similarity	NPC470732
0.7043	Intermediate Similarity	NPC162002
0.7042	Intermediate Similarity	NPC260900
0.7037	Intermediate Similarity	NPC114209
0.7035	Intermediate Similarity	NPC161861
0.7031	Intermediate Similarity	NPC476219
0.7031	Intermediate Similarity	NPC476297
0.703	Intermediate Similarity	NPC61011
0.703	Intermediate Similarity	NPC477042
0.7026	Intermediate Similarity	NPC478185
0.7026	Intermediate Similarity	NPC214106
0.7014	Intermediate Similarity	NPC131887
0.7014	Intermediate Similarity	NPC67288
0.7013	Intermediate Similarity	NPC26641
0.7011	Intermediate Similarity	NPC105127
0.7005	Intermediate Similarity	NPC190296
0.7005	Intermediate Similarity	NPC478183
0.7005	Intermediate Similarity	NPC114637
0.6996	Remote Similarity	NPC323969
0.6996	Remote Similarity	NPC276657
0.699	Remote Similarity	NPC21174
0.699	Remote Similarity	NPC271797
0.6986	Remote Similarity	NPC471603
0.6986	Remote Similarity	NPC477413
0.6982	Remote Similarity	NPC475736
0.6981	Remote Similarity	NPC19696
0.6981	Remote Similarity	NPC136957
0.6968	Remote Similarity	NPC36405
0.6966	Remote Similarity	NPC39092
0.6963	Remote Similarity	NPC473878
0.6963	Remote Similarity	NPC57398
0.6962	Remote Similarity	NPC91868
0.6962	Remote Similarity	NPC63971
0.6957	Remote Similarity	NPC96102
0.6955	Remote Similarity	NPC54744

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 NPC116555 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	434
0.1-0.2	818
0.2-0.3	1244
0.3-0.4	2338
0.4-0.5	1720
0.5-0.6	1609
0.6-0.7	852
0.7-0.8	121
0.8-0.85	10
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9062	High Similarity	NPD2008	Discontinued
0.8883	High Similarity	NPD2411	Approved
0.8872	High Similarity	NPD2442	Approved
0.8872	High Similarity	NPD2443	Approved
0.8731	High Similarity	NPD1600	Suspended
0.8636	High Similarity	NPD2408	Discontinued
0.8629	High Similarity	NPD1506	Discontinued
0.8586	High Similarity	NPD460	Discontinued
0.835	Intermediate Similarity	NPD3905	Phase 3
0.8333	Intermediate Similarity	NPD2879	Approved
0.8333	Intermediate Similarity	NPD2881	Approved
0.8265	Intermediate Similarity	NPD2880	Discontinued
0.8158	Intermediate Similarity	NPD1895	Discontinued
0.804	Intermediate Similarity	NPD1982	Phase 1
0.8038	Intermediate Similarity	NPD6470	Phase 3
0.801	Intermediate Similarity	NPD4863	Approved
0.801	Intermediate Similarity	NPD1658	Discontinued
0.79	Intermediate Similarity	NPD5446	Phase 2
0.7884	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD5198	Approved
0.783	Intermediate Similarity	NPD5199	Approved
0.7826	Intermediate Similarity	NPD2295	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD1952	Discontinued
0.77	Intermediate Similarity	NPD3430	Approved
0.77	Intermediate Similarity	NPD3431	Approved
0.7696	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6165	Phase 2
0.7661	Intermediate Similarity	NPD6164	Phase 2
0.7644	Intermediate Similarity	NPD3839	Phase 2
0.7644	Intermediate Similarity	NPD3840	Phase 2
0.7633	Intermediate Similarity	NPD7209	Approved
0.7633	Intermediate Similarity	NPD7207	Approved
0.7633	Intermediate Similarity	NPD7208	Approved
0.7633	Intermediate Similarity	NPD4299	Phase 1
0.763	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7585	Intermediate Similarity	NPD2364	Suspended
0.7573	Intermediate Similarity	NPD6837	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5854	Approved
0.7548	Intermediate Similarity	NPD6229	Phase 2
0.7547	Intermediate Similarity	NPD7657	Approved
0.7547	Intermediate Similarity	NPD7656	Approved
0.7546	Intermediate Similarity	NPD6210	Phase 3
0.7538	Intermediate Similarity	NPD2793	Discontinued
0.7523	Intermediate Similarity	NPD2412	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2333	Discontinued
0.7489	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD5643	Phase 2
0.7465	Intermediate Similarity	NPD6579	Phase 2
0.7463	Intermediate Similarity	NPD5016	Approved
0.7462	Intermediate Similarity	NPD5962	Phase 2
0.7455	Intermediate Similarity	NPD5887	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5855	Phase 3
0.7451	Intermediate Similarity	NPD5853	Phase 3
0.745	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4922	Phase 2
0.7438	Intermediate Similarity	NPD1896	Approved
0.7424	Intermediate Similarity	NPD1708	Approved
0.7424	Intermediate Similarity	NPD1707	Approved
0.7407	Intermediate Similarity	NPD8256	Approved
0.7407	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8257	Approved
0.7396	Intermediate Similarity	NPD1313	Approved
0.7395	Intermediate Similarity	NPD4395	Phase 1
0.7387	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD5415	Approved
0.7374	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD4541	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD4854	Phase 3
0.735	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2363	Discontinued
0.7346	Intermediate Similarity	NPD6271	Approved
0.7346	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6986	Phase 1
0.734	Intermediate Similarity	NPD5686	Approved
0.734	Intermediate Similarity	NPD5685	Approved
0.733	Intermediate Similarity	NPD1871	Approved
0.733	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD7445	Phase 1
0.7304	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6715	Discontinued
0.7282	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8641	Approved
0.7282	Intermediate Similarity	NPD7406	Phase 2
0.7277	Intermediate Similarity	NPD4940	Approved
0.7277	Intermediate Similarity	NPD6459	Phase 2
0.7277	Intermediate Similarity	NPD4902	Discontinued
0.7268	Intermediate Similarity	NPD4615	Phase 2
0.7264	Intermediate Similarity	NPD5491	Phase 3
0.7264	Intermediate Similarity	NPD5489	Phase 1
0.7241	Intermediate Similarity	NPD4988	Discontinued
0.7241	Intermediate Similarity	NPD3246	Discontinued
0.724	Intermediate Similarity	NPD5001	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7888	Approved
0.7232	Intermediate Similarity	NPD7887	Approved
0.723	Intermediate Similarity	NPD6328	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5827	Discontinued
0.7217	Intermediate Similarity	NPD4446	Approved
0.7204	Intermediate Similarity	NPD6268	Phase 1
0.7204	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1015	Phase 2
0.7202	Intermediate Similarity	NPD1016	Phase 2
0.72	Intermediate Similarity	NPD2481	Approved
0.72	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2479	Phase 3
0.7196	Intermediate Similarity	NPD6520	Phase 3
0.7196	Intermediate Similarity	NPD2509	Approved
0.7196	Intermediate Similarity	NPD2510	Approved
0.7196	Intermediate Similarity	NPD6521	Phase 3
0.7186	Intermediate Similarity	NPD3041	Approved
0.7179	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6469	Phase 3
0.7177	Intermediate Similarity	NPD6468	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD465	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5017	Discontinued
0.715	Intermediate Similarity	NPD3432	Approved
0.715	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6465	Phase 2
0.7149	Intermediate Similarity	NPD8159	Discontinued
0.7137	Intermediate Similarity	NPD7172	Approved
0.7137	Intermediate Similarity	NPD7173	Approved
0.7136	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4051	Discontinued
0.713	Intermediate Similarity	NPD5072	Discontinued
0.7129	Intermediate Similarity	NPD3830	Phase 1
0.7129	Intermediate Similarity	NPD6664	Approved
0.7129	Intermediate Similarity	NPD5462	Discontinued
0.7128	Intermediate Similarity	NPD509	Phase 3
0.7128	Intermediate Similarity	NPD1333	Phase 3
0.7124	Intermediate Similarity	NPD3959	Phase 2
0.7124	Intermediate Similarity	NPD3962	Phase 2
0.7115	Intermediate Similarity	NPD7618	Phase 3
0.7115	Intermediate Similarity	NPD7619	Phase 3
0.7114	Intermediate Similarity	NPD5473	Discontinued
0.7114	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6721	Phase 1
0.7108	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7106	Intermediate Similarity	NPD4558	Phase 2
0.7097	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7564	Discontinued
0.7092	Intermediate Similarity	NPD2392	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2813	Phase 3
0.7091	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3811	Discontinued
0.7083	Intermediate Similarity	NPD7704	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2927	Phase 3
0.7082	Intermediate Similarity	NPD5985	Phase 2
0.7081	Intermediate Similarity	NPD3362	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4848	Phase 1
0.7075	Intermediate Similarity	NPD3891	Phase 2
0.7075	Intermediate Similarity	NPD4318	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3890	Phase 2
0.7074	Intermediate Similarity	NPD6970	Phase 2
0.7073	Intermediate Similarity	NPD2770	Discontinued
0.707	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2445	Approved
0.7067	Intermediate Similarity	NPD2446	Approved
0.7065	Intermediate Similarity	NPD1327	Discontinued
0.7064	Intermediate Similarity	NPD7164	Discontinued
0.7062	Intermediate Similarity	NPD2405	Phase 3
0.7061	Intermediate Similarity	NPD3786	Phase 3
0.7061	Intermediate Similarity	NPD3960	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD1343	Approved
0.7056	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7661	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD1722	Approved
0.7039	Intermediate Similarity	NPD7175	Phase 1
0.7039	Intermediate Similarity	NPD1250	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1037	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7415	Suspended
0.703	Intermediate Similarity	NPD5508	Phase 1
0.7028	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5642	Approved
0.7024	Intermediate Similarity	NPD2591	Phase 2
0.7023	Intermediate Similarity	NPD7568	Phase 1
0.7018	Intermediate Similarity	NPD8316	Phase 2
0.7018	Intermediate Similarity	NPD8317	Phase 2
0.7018	Intermediate Similarity	NPD3265	Phase 1
0.7015	Intermediate Similarity	NPD4181	Approved
0.7014	Intermediate Similarity	NPD1591	Approved
0.7014	Intermediate Similarity	NPD5465	Phase 2
0.7009	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD1215	Discontinued
0.7005	Intermediate Similarity	NPD3860	Discontinued

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