NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	648.08
Volume:	557.798
LogP:	4.863
LogD:	2.621
LogS:	-3.758
# Rotatable Bonds:	8
TPSA:	145.66
# H-Bond Aceptor:	7
# H-Bond Donor:	10
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.108
Synthetic Accessibility Score:	4.121
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.843
MDCK Permeability:	1.75E-06
Pgp-inhibitor:	0.907
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.714
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.142

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	96.11%
Volume Distribution (VD):	1.392
Pgp-substrate:	1.29%

ADMET: Metabolism

CYP1A2-inhibitor:	0.694
CYP1A2-substrate:	0.913
CYP2C19-inhibitor:	0.825
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.764
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.949
CYP2D6-substrate:	0.938
CYP3A4-inhibitor:	0.527
CYP3A4-substrate:	0.615

ADMET: Excretion

Clearance (CL):	3.229
Half-life (T1/2):	0.425

ADMET: Toxicity

hERG Blockers:	0.892
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.662
AMES Toxicity:	0.188
Rat Oral Acute Toxicity:	0.379
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.77
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.885

Download Data

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

Natural Product: NPC477608

Natural Product ID:	NPC477608
*Common Name:**	(+/-)-gelliusine C
IUPAC Name:	2,4-bis[2-amino-1-(6-bromo-1H-indol-3-yl)ethyl]-3-(2-aminoethyl)-1H-indol-5-ol
Synonyms:	(+/-)-Gelliusine C
Standard InCHIKey:	KJQYELPBSPDCOH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H30Br2N6O/c31-15-1-3-17-22(13-36-25(17)9-15)20(11-34)29-27(39)6-5-24-28(29)19(7-8-33)30(38-24)21(12-35)23-14-37-26-10-16(32)2-4-18(23)26/h1-6,9-10,13-14,20-21,36-39H,7-8,11-12,33-35H2
SMILES:	C1=CC2=C(C=C1Br)NC=C2C(CN)C3=C(C=CC4=C3C(=C(N4)C(CN)C5=CNC6=C5C=CC(=C6)Br)CCN)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10055034
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000183] Tryptamines and derivatives [CHEMONTID:0001637] Serotonins

*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
NPO33565	Orina sp.	Species	n.a.	n.a.	n.a.	New Caledonian, stations DW 114-115, at a depth of 255-285 m	n.a.	PMID[7595591]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	2000	nM	PMID[7595591]

☑ 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 NPC477608 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	872
0.1-0.2	7220
0.2-0.3	11018
0.3-0.4	15888
0.4-0.5	3899
0.5-0.6	2361
0.6-0.7	1232
0.7-0.8	185
0.8-0.85	18
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC477607
0.9554	High Similarity	NPC477609
0.9356	High Similarity	NPC477610
0.8382	Intermediate Similarity	NPC222018
0.8182	Intermediate Similarity	NPC475935
0.8182	Intermediate Similarity	NPC52909
0.8182	Intermediate Similarity	NPC94211
0.8164	Intermediate Similarity	NPC77555
0.8146	Intermediate Similarity	NPC99666
0.814	Intermediate Similarity	NPC128084
0.8134	Intermediate Similarity	NPC106771
0.8134	Intermediate Similarity	NPC205254
0.8134	Intermediate Similarity	NPC23420
0.8134	Intermediate Similarity	NPC303820
0.81	Intermediate Similarity	NPC167908
0.8093	Intermediate Similarity	NPC475746
0.8073	Intermediate Similarity	NPC304926
0.8073	Intermediate Similarity	NPC476041
0.8066	Intermediate Similarity	NPC475070
0.802	Intermediate Similarity	NPC220765
0.799	Intermediate Similarity	NPC171171
0.7982	Intermediate Similarity	NPC245348
0.798	Intermediate Similarity	NPC204717
0.7946	Intermediate Similarity	NPC60006
0.7944	Intermediate Similarity	NPC476121
0.7942	Intermediate Similarity	NPC117980
0.7941	Intermediate Similarity	NPC314002
0.7937	Intermediate Similarity	NPC211416
0.7926	Intermediate Similarity	NPC246518
0.7826	Intermediate Similarity	NPC246700
0.7826	Intermediate Similarity	NPC128751
0.7822	Intermediate Similarity	NPC184964
0.7798	Intermediate Similarity	NPC5145
0.7788	Intermediate Similarity	NPC106833
0.7788	Intermediate Similarity	NPC469497
0.7778	Intermediate Similarity	NPC130570
0.7778	Intermediate Similarity	NPC476124
0.7748	Intermediate Similarity	NPC477114
0.7703	Intermediate Similarity	NPC142901
0.7682	Intermediate Similarity	NPC208284
0.7675	Intermediate Similarity	NPC6215
0.7673	Intermediate Similarity	NPC477611
0.7671	Intermediate Similarity	NPC80596
0.7671	Intermediate Similarity	NPC476116
0.7653	Intermediate Similarity	NPC156704
0.7642	Intermediate Similarity	NPC253580
0.763	Intermediate Similarity	NPC324149
0.7608	Intermediate Similarity	NPC46580
0.7606	Intermediate Similarity	NPC242209
0.7598	Intermediate Similarity	NPC470126
0.757	Intermediate Similarity	NPC153042
0.7566	Intermediate Similarity	NPC276657
0.7564	Intermediate Similarity	NPC15801
0.7555	Intermediate Similarity	NPC214980
0.7543	Intermediate Similarity	NPC63031
0.7512	Intermediate Similarity	NPC307963
0.7512	Intermediate Similarity	NPC15102
0.75	Intermediate Similarity	NPC470549
0.75	Intermediate Similarity	NPC470501
0.75	Intermediate Similarity	NPC477861
0.7479	Intermediate Similarity	NPC97902
0.7479	Intermediate Similarity	NPC325976
0.7478	Intermediate Similarity	NPC264285
0.7468	Intermediate Similarity	NPC207686
0.7468	Intermediate Similarity	NPC81175
0.7467	Intermediate Similarity	NPC170114
0.7467	Intermediate Similarity	NPC183407
0.7465	Intermediate Similarity	NPC45459
0.7465	Intermediate Similarity	NPC213308
0.7465	Intermediate Similarity	NPC315491
0.7458	Intermediate Similarity	NPC11408
0.7456	Intermediate Similarity	NPC470502
0.7455	Intermediate Similarity	NPC266931
0.7453	Intermediate Similarity	NPC76748
0.7445	Intermediate Similarity	NPC255110
0.7442	Intermediate Similarity	NPC251090
0.744	Intermediate Similarity	NPC88363
0.7418	Intermediate Similarity	NPC92111
0.7411	Intermediate Similarity	NPC294620
0.7406	Intermediate Similarity	NPC296527
0.7406	Intermediate Similarity	NPC32771
0.7395	Intermediate Similarity	NPC217554
0.7395	Intermediate Similarity	NPC326634
0.7391	Intermediate Similarity	NPC470503
0.7391	Intermediate Similarity	NPC59269
0.7384	Intermediate Similarity	NPC41679
0.7383	Intermediate Similarity	NPC477166
0.7383	Intermediate Similarity	NPC477167
0.7383	Intermediate Similarity	NPC473342
0.7383	Intermediate Similarity	NPC304187
0.7373	Intermediate Similarity	NPC192315
0.735	Intermediate Similarity	NPC476451
0.7339	Intermediate Similarity	NPC476167
0.733	Intermediate Similarity	NPC474409
0.733	Intermediate Similarity	NPC470505
0.7323	Intermediate Similarity	NPC77101
0.7318	Intermediate Similarity	NPC473761
0.7314	Intermediate Similarity	NPC471891
0.7308	Intermediate Similarity	NPC96890
0.7308	Intermediate Similarity	NPC326363
0.7306	Intermediate Similarity	NPC249040
0.7306	Intermediate Similarity	NPC176538
0.7303	Intermediate Similarity	NPC284141
0.73	Intermediate Similarity	NPC295228
0.7292	Intermediate Similarity	NPC39092
0.7292	Intermediate Similarity	NPC201831
0.7292	Intermediate Similarity	NPC17487
0.7273	Intermediate Similarity	NPC16352
0.7269	Intermediate Similarity	NPC329541
0.7269	Intermediate Similarity	NPC106937
0.7265	Intermediate Similarity	NPC88008
0.7265	Intermediate Similarity	NPC193777
0.7265	Intermediate Similarity	NPC252251
0.7261	Intermediate Similarity	NPC477109
0.7261	Intermediate Similarity	NPC477107
0.7261	Intermediate Similarity	NPC477108
0.7257	Intermediate Similarity	NPC207020
0.7252	Intermediate Similarity	NPC470500
0.7244	Intermediate Similarity	NPC11464
0.724	Intermediate Similarity	NPC476073
0.7235	Intermediate Similarity	NPC195314
0.7234	Intermediate Similarity	NPC209174
0.7228	Intermediate Similarity	NPC135141
0.7228	Intermediate Similarity	NPC92796
0.7225	Intermediate Similarity	NPC478074
0.722	Intermediate Similarity	NPC477113
0.7217	Intermediate Similarity	NPC213530
0.7217	Intermediate Similarity	NPC193267
0.7209	Intermediate Similarity	NPC95783
0.7209	Intermediate Similarity	NPC231536
0.7208	Intermediate Similarity	NPC37152
0.7207	Intermediate Similarity	NPC223427
0.7203	Intermediate Similarity	NPC477531
0.7202	Intermediate Similarity	NPC178858
0.7198	Intermediate Similarity	NPC162748
0.7192	Intermediate Similarity	NPC131718
0.7189	Intermediate Similarity	NPC216369
0.7185	Intermediate Similarity	NPC245055
0.7183	Intermediate Similarity	NPC94943
0.7181	Intermediate Similarity	NPC316981
0.7181	Intermediate Similarity	NPC48353
0.7178	Intermediate Similarity	NPC216643
0.7175	Intermediate Similarity	NPC285558
0.7162	Intermediate Similarity	NPC74969
0.7162	Intermediate Similarity	NPC211813
0.7156	Intermediate Similarity	NPC477111
0.7149	Intermediate Similarity	NPC171393
0.7149	Intermediate Similarity	NPC295452
0.7149	Intermediate Similarity	NPC473185
0.7143	Intermediate Similarity	NPC292958
0.7137	Intermediate Similarity	NPC82370
0.7137	Intermediate Similarity	NPC9894
0.7136	Intermediate Similarity	NPC190007
0.7136	Intermediate Similarity	NPC131887
0.713	Intermediate Similarity	NPC475774
0.7119	Intermediate Similarity	NPC156003
0.7112	Intermediate Similarity	NPC132642
0.7109	Intermediate Similarity	NPC72980
0.7105	Intermediate Similarity	NPC219087
0.7101	Intermediate Similarity	NPC63751
0.7101	Intermediate Similarity	NPC200553
0.7101	Intermediate Similarity	NPC279189
0.7089	Intermediate Similarity	NPC212535
0.7087	Intermediate Similarity	NPC477110
0.7083	Intermediate Similarity	NPC162002
0.7082	Intermediate Similarity	NPC310118
0.7081	Intermediate Similarity	NPC313791
0.708	Intermediate Similarity	NPC171787
0.708	Intermediate Similarity	NPC476465
0.7078	Intermediate Similarity	NPC276517
0.7078	Intermediate Similarity	NPC473312
0.7072	Intermediate Similarity	NPC13456
0.7072	Intermediate Similarity	NPC77241
0.7072	Intermediate Similarity	NPC269203
0.7072	Intermediate Similarity	NPC166209
0.7056	Intermediate Similarity	NPC471536
0.7056	Intermediate Similarity	NPC153400
0.7051	Intermediate Similarity	NPC280272
0.7045	Intermediate Similarity	NPC13880
0.7042	Intermediate Similarity	NPC174489
0.7039	Intermediate Similarity	NPC102423
0.7034	Intermediate Similarity	NPC227908
0.7031	Intermediate Similarity	NPC94157
0.7031	Intermediate Similarity	NPC473180
0.7029	Intermediate Similarity	NPC469554
0.7029	Intermediate Similarity	NPC101543
0.7027	Intermediate Similarity	NPC201266
0.7027	Intermediate Similarity	NPC268744
0.7027	Intermediate Similarity	NPC153123
0.7027	Intermediate Similarity	NPC475914
0.7027	Intermediate Similarity	NPC220797
0.7027	Intermediate Similarity	NPC474318
0.702	Intermediate Similarity	NPC470504
0.7018	Intermediate Similarity	NPC167860
0.7018	Intermediate Similarity	NPC123976
0.7014	Intermediate Similarity	NPC474958
0.7014	Intermediate Similarity	NPC227582
0.7013	Intermediate Similarity	NPC469928
0.7012	Intermediate Similarity	NPC477549
0.7009	Intermediate Similarity	NPC193761

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 NPC477608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	735
0.2-0.3	856
0.3-0.4	2185
0.4-0.5	2711
0.5-0.6	1754
0.6-0.7	480
0.7-0.8	26
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8195	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD7948	Phase 1
0.7746	Intermediate Similarity	NPD8396	Approved
0.7746	Intermediate Similarity	NPD8395	Approved
0.7545	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD1038	Approved
0.7512	Intermediate Similarity	NPD4511	Phase 1
0.7512	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5612	Discontinued
0.7465	Intermediate Similarity	NPD484	Approved
0.743	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5065	Approved
0.7362	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6975	Discontinued
0.7308	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD802	Phase 2
0.7264	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6595	Phase 3
0.7238	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3931	Approved
0.7162	Intermediate Similarity	NPD3928	Approved
0.7104	Intermediate Similarity	NPD3825	Phase 3
0.7104	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2189	Approved
0.708	Intermediate Similarity	NPD2187	Approved
0.7071	Intermediate Similarity	NPD7558	Phase 2
0.7037	Intermediate Similarity	NPD8431	Approved
0.7034	Intermediate Similarity	NPD7603	Discontinued
0.7027	Intermediate Similarity	NPD3814	Phase 1
0.7022	Intermediate Similarity	NPD5426	Phase 3
0.7013	Intermediate Similarity	NPD7112	Discontinued
0.7	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1325	Approved
0.6986	Remote Similarity	NPD3404	Approved
0.6986	Remote Similarity	NPD1326	Approved
0.6966	Remote Similarity	NPD6242	Discontinued
0.696	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3330	Phase 1
0.6957	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4795	Phase 2
0.693	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.693	Remote Similarity	NPD2916	Discontinued
0.6926	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.692	Remote Similarity	NPD4890	Phase 2
0.6916	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4886	Phase 2
0.6886	Remote Similarity	NPD7453	Approved
0.6886	Remote Similarity	NPD7452	Approved
0.6886	Remote Similarity	NPD7222	Phase 2
0.6875	Remote Similarity	NPD2176	Approved
0.6875	Remote Similarity	NPD2175	Phase 3
0.6875	Remote Similarity	NPD2177	Approved
0.6856	Remote Similarity	NPD7672	Approved
0.6856	Remote Similarity	NPD7671	Approved
0.6844	Remote Similarity	NPD1740	Approved
0.6844	Remote Similarity	NPD1739	Approved
0.6842	Remote Similarity	NPD5530	Phase 1
0.684	Remote Similarity	NPD5067	Phase 2
0.684	Remote Similarity	NPD5939	Approved
0.684	Remote Similarity	NPD5936	Approved
0.684	Remote Similarity	NPD5066	Phase 2
0.6833	Remote Similarity	NPD5559	Phase 2
0.6828	Remote Similarity	NPD6991	Approved
0.6826	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6531	Approved
0.6824	Remote Similarity	NPD6530	Approved
0.6812	Remote Similarity	NPD6290	Phase 2
0.6812	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1392	Approved
0.6809	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6999	Discontinued
0.6798	Remote Similarity	NPD5901	Discontinued
0.6792	Remote Similarity	NPD4845	Discontinued
0.6791	Remote Similarity	NPD4079	Approved
0.6791	Remote Similarity	NPD4076	Approved
0.6783	Remote Similarity	NPD5658	Approved
0.6783	Remote Similarity	NPD8284	Discontinued
0.6781	Remote Similarity	NPD8094	Discontinued
0.6776	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3003	Approved
0.6767	Remote Similarity	NPD7470	Discontinued
0.6766	Remote Similarity	NPD5164	Discontinued
0.6752	Remote Similarity	NPD5903	Approved
0.6752	Remote Similarity	NPD5902	Approved
0.6744	Remote Similarity	NPD3506	Approved
0.6744	Remote Similarity	NPD3505	Approved
0.6738	Remote Similarity	NPD8093	Discontinued
0.6737	Remote Similarity	NPD2021	Discontinued
0.6736	Remote Similarity	NPD7567	Approved
0.6732	Remote Similarity	NPD8442	Discontinued
0.6724	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3013	Phase 3
0.6723	Remote Similarity	NPD2763	Phase 2
0.6721	Remote Similarity	NPD6494	Phase 2
0.6716	Remote Similarity	NPD8349	Phase 1
0.6714	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2615	Phase 3
0.6709	Remote Similarity	NPD2616	Phase 3
0.6708	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8403	Phase 1
0.6695	Remote Similarity	NPD4502	Phase 2
0.6694	Remote Similarity	NPD7555	Discontinued
0.6693	Remote Similarity	NPD8358	Approved
0.6681	Remote Similarity	NPD4044	Discontinued
0.668	Remote Similarity	NPD5050	Approved
0.668	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6159	Phase 2
0.6667	Remote Similarity	NPD7392	Phase 2
0.6667	Remote Similarity	NPD6281	Approved
0.6667	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD6978	Phase 2
0.6653	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4039	Approved
0.6652	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD32	Approved
0.6652	Remote Similarity	NPD4038	Approved
0.6652	Remote Similarity	NPD4034	Approved
0.6652	Remote Similarity	NPD4037	Approved
0.6652	Remote Similarity	NPD4033	Approved
0.6652	Remote Similarity	NPD4122	Approved
0.6652	Remote Similarity	NPD4035	Approved
0.6652	Remote Similarity	NPD4036	Approved
0.6652	Remote Similarity	NPD31	Approved
0.6651	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.664	Remote Similarity	NPD4344	Clinical (unspecified phase)
0.664	Remote Similarity	NPD4343	Phase 1
0.6639	Remote Similarity	NPD3763	Approved
0.6639	Remote Similarity	NPD7271	Approved
0.6639	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7665	Phase 2
0.6638	Remote Similarity	NPD7666	Phase 3
0.6636	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD3323	Discontinued
0.6627	Remote Similarity	NPD3872	Phase 3
0.6625	Remote Similarity	NPD7221	Approved
0.6625	Remote Similarity	NPD7219	Approved
0.662	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3746	Discontinued
0.661	Remote Similarity	NPD4358	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3924	Approved
0.6607	Remote Similarity	NPD3922	Approved
0.6607	Remote Similarity	NPD3921	Approved
0.6607	Remote Similarity	NPD3923	Approved
0.66	Remote Similarity	NPD5051	Phase 1
0.6595	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4181	Approved
0.6588	Remote Similarity	NPD1685	Approved
0.6588	Remote Similarity	NPD1684	Approved
0.6585	Remote Similarity	NPD7951	Approved
0.6585	Remote Similarity	NPD7789	Approved
0.6585	Remote Similarity	NPD7950	Approved
0.6585	Remote Similarity	NPD7790	Approved
0.6585	Remote Similarity	NPD7791	Approved
0.6585	Remote Similarity	NPD7952	Approved
0.6585	Remote Similarity	NPD7953	Approved
0.6584	Remote Similarity	NPD7730	Approved
0.6584	Remote Similarity	NPD7731	Approved
0.6578	Remote Similarity	NPD9695	Approved
0.6577	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2383	Phase 1
0.6574	Remote Similarity	NPD4128	Approved
0.6574	Remote Similarity	NPD9690	Approved
0.657	Remote Similarity	NPD6158	Phase 2
0.657	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3402	Phase 1
0.6569	Remote Similarity	NPD7194	Discontinued
0.6564	Remote Similarity	NPD2952	Discontinued
0.6557	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3233	Phase 2
0.6556	Remote Similarity	NPD3234	Phase 3
0.6555	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7001	Phase 3
0.6552	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7957	Phase 1
0.6549	Remote Similarity	NPD4418	Discontinued
0.6548	Remote Similarity	NPD6230	Discontinued
0.6548	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2095	Phase 2
0.6545	Remote Similarity	NPD2092	Phase 2
0.6545	Remote Similarity	NPD2094	Phase 2
0.6544	Remote Similarity	NPD4075	Phase 2
0.6543	Remote Similarity	NPD7051	Phase 3
0.6543	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD2781	Approved
0.654	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.654	Remote Similarity	NPD9705	Discontinued
0.654	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.654	Remote Similarity	NPD112	Approved
0.6532	Remote Similarity	NPD5891	Approved
0.6531	Remote Similarity	NPD8512	Phase 3

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