NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	580.34
Volume:	603.47
LogP:	4.104
LogD:	3.069
LogS:	-3.741
# Rotatable Bonds:	1
TPSA:	84.85
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	9
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.335
Synthetic Accessibility Score:	7.434
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
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:	-5.351
MDCK Permeability:	1.8533510228735395e-05
Pgp-inhibitor:	0.932
Pgp-substrate:	0.966
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.33

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.721
Plasma Protein Binding (PPB):	91.05945587158203%
Volume Distribution (VD):	3.182
Pgp-substrate:	6.527639389038086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.783
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.729
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.149
CYP2D6-inhibitor:	0.947
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	7.299
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.921
Human Hepatotoxicity (H-HT):	0.983
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.304
Rat Oral Acute Toxicity:	0.709
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.931
Carcinogencity:	0.371
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC476492

Natural Product ID:	NPC476492
*Common Name:**	(1R,2R,4R,7R,8S,12R,13S,16Z)-25-(9H-pyrido[3,4-b]indol-1-yl)-28-oxa-11,22-diazahexacyclo[11.11.2.12,22.14,8.02,12.04,11]octacosa-16,25-diene-7,13-diol
IUPAC Name:	(1R,2R,4R,7R,8S,12R,13S,16Z)-25-(9H-pyrido[3,4-b]indol-1-yl)-28-oxa-11,22-diazahexacyclo[11.11.2.12,22.14,8.02,12.04,11]octacosa-16,25-diene-7,13-diol
Synonyms:
Standard InCHIKey:	BKEROKGINJVXMS-WKFOMSDBSA-N
Standard InCHI:	InChI=1S/C36H44N4O3/c41-29-11-16-36-22-34-23-39-18-8-4-2-1-3-7-15-35(42,33(34)40(36)20-14-30(29)43-36)21-26(27(34)13-19-39)31-32-25(12-17-37-31)24-9-5-6-10-28(24)38-32/h1,3,5-6,9-10,12,17,21,27,29-30,33,38,41-42H,2,4,7-8,11,13-16,18-20,22-23H2/b3-1-/t27-,29+,30-,33+,34-,35-,36+/m0/s1
SMILES:	C1CCN2CC[C@H]3C(=C[C@@](CC/C=C\C1)([C@H]4[C@]3(C2)C[C@]56N4CC[C@H](O5)[C@@H](CC6)O)O)C7=NC=CC8=C7NC9=CC=CC=C89
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90683390
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
NPO33663	Acanthostrongylophora ingens	Species	Petrosiidae	Eukaryota	n.a.	Indonesia	n.a.	PMID[24902064]
NPO33663	Acanthostrongylophora ingens	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27933894]

☑ 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	2
Others	1

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	16000	nM	PMID[24902064]
NPT2	Others	Unspecified		IC50	=	340	nM	PMID[24902064]
NPT2	Others	Unspecified		Inhibition	=	91	%	PMID[24902064]

☑ 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 NPC476492 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	475
0.1-0.2	1928
0.2-0.3	10227
0.3-0.4	21395
0.4-0.5	4416
0.5-0.6	2294
0.6-0.7	1661
0.7-0.8	278
0.8-0.85	14
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9272	High Similarity	NPC471506
0.922	High Similarity	NPC471564
0.9095	High Similarity	NPC476493
0.8824	High Similarity	NPC473362
0.8824	High Similarity	NPC166492
0.8619	High Similarity	NPC250835
0.8614	High Similarity	NPC265576
0.8604	High Similarity	NPC81175
0.8578	High Similarity	NPC472027
0.8571	High Similarity	NPC473757
0.8498	Intermediate Similarity	NPC473310
0.8413	Intermediate Similarity	NPC475288
0.8273	Intermediate Similarity	NPC475258
0.8273	Intermediate Similarity	NPC6215
0.8255	Intermediate Similarity	NPC475422
0.8233	Intermediate Similarity	NPC251936
0.8227	Intermediate Similarity	NPC909
0.8227	Intermediate Similarity	NPC475338
0.816	Intermediate Similarity	NPC87755
0.8108	Intermediate Similarity	NPC476491
0.8095	Intermediate Similarity	NPC471891
0.808	Intermediate Similarity	NPC476451
0.7948	Intermediate Similarity	NPC41679
0.7917	Intermediate Similarity	NPC126066
0.789	Intermediate Similarity	NPC475602
0.7882	Intermediate Similarity	NPC472108
0.7882	Intermediate Similarity	NPC139291
0.7857	Intermediate Similarity	NPC232130
0.7783	Intermediate Similarity	NPC476041
0.7783	Intermediate Similarity	NPC304926
0.7768	Intermediate Similarity	NPC473312
0.7742	Intermediate Similarity	NPC314957
0.774	Intermediate Similarity	NPC469501
0.774	Intermediate Similarity	NPC469470
0.7734	Intermediate Similarity	NPC133261
0.7707	Intermediate Similarity	NPC472109
0.7707	Intermediate Similarity	NPC472110
0.7696	Intermediate Similarity	NPC472105
0.7696	Intermediate Similarity	NPC187827
0.7682	Intermediate Similarity	NPC477861
0.7633	Intermediate Similarity	NPC62510
0.7624	Intermediate Similarity	NPC472123
0.7621	Intermediate Similarity	NPC98371
0.7621	Intermediate Similarity	NPC48938
0.7621	Intermediate Similarity	NPC313884
0.7598	Intermediate Similarity	NPC253580
0.7594	Intermediate Similarity	NPC133366
0.7591	Intermediate Similarity	NPC5145
0.7573	Intermediate Similarity	NPC314394
0.7571	Intermediate Similarity	NPC95783
0.7555	Intermediate Similarity	NPC470126
0.7549	Intermediate Similarity	NPC24594
0.7549	Intermediate Similarity	NPC472122
0.7548	Intermediate Similarity	NPC15102
0.7547	Intermediate Similarity	NPC474177
0.7523	Intermediate Similarity	NPC470500
0.7522	Intermediate Similarity	NPC33949
0.7522	Intermediate Similarity	NPC314954
0.7512	Intermediate Similarity	NPC326575
0.7512	Intermediate Similarity	NPC155143
0.7479	Intermediate Similarity	NPC295228
0.7465	Intermediate Similarity	NPC475506
0.7463	Intermediate Similarity	NPC280852
0.7463	Intermediate Similarity	NPC150048
0.7463	Intermediate Similarity	NPC203754
0.7454	Intermediate Similarity	NPC100321
0.7452	Intermediate Similarity	NPC472444
0.7434	Intermediate Similarity	NPC469594
0.7431	Intermediate Similarity	NPC193761
0.7427	Intermediate Similarity	NPC59269
0.7425	Intermediate Similarity	NPC469554
0.7416	Intermediate Similarity	NPC472294
0.7411	Intermediate Similarity	NPC234078
0.7411	Intermediate Similarity	NPC221100
0.7407	Intermediate Similarity	NPC473640
0.7403	Intermediate Similarity	NPC110151
0.7389	Intermediate Similarity	NPC317430
0.7368	Intermediate Similarity	NPC19679
0.7368	Intermediate Similarity	NPC472104
0.7366	Intermediate Similarity	NPC151976
0.7366	Intermediate Similarity	NPC314603
0.7364	Intermediate Similarity	NPC475070
0.7358	Intermediate Similarity	NPC65215
0.7358	Intermediate Similarity	NPC173028
0.7357	Intermediate Similarity	NPC477714
0.7357	Intermediate Similarity	NPC281049
0.7344	Intermediate Similarity	NPC107836
0.7343	Intermediate Similarity	NPC151939
0.7342	Intermediate Similarity	NPC127677
0.7339	Intermediate Similarity	NPC249040
0.7333	Intermediate Similarity	NPC469592
0.7333	Intermediate Similarity	NPC471080
0.733	Intermediate Similarity	NPC329688
0.733	Intermediate Similarity	NPC189812
0.7315	Intermediate Similarity	NPC231342
0.7313	Intermediate Similarity	NPC477715
0.7311	Intermediate Similarity	NPC204565
0.7311	Intermediate Similarity	NPC317030
0.7309	Intermediate Similarity	NPC478158
0.7308	Intermediate Similarity	NPC472443
0.7304	Intermediate Similarity	NPC201700
0.7299	Intermediate Similarity	NPC188387
0.7299	Intermediate Similarity	NPC163421
0.7297	Intermediate Similarity	NPC46225
0.7289	Intermediate Similarity	NPC75634
0.7285	Intermediate Similarity	NPC470505
0.7277	Intermediate Similarity	NPC101543
0.7277	Intermediate Similarity	NPC213629
0.7277	Intermediate Similarity	NPC46413
0.7273	Intermediate Similarity	NPC476874
0.7273	Intermediate Similarity	NPC300688
0.7269	Intermediate Similarity	NPC204491
0.7269	Intermediate Similarity	NPC183407
0.7264	Intermediate Similarity	NPC474707
0.7261	Intermediate Similarity	NPC310118
0.7257	Intermediate Similarity	NPC229348
0.7255	Intermediate Similarity	NPC160105
0.7253	Intermediate Similarity	NPC57690
0.7251	Intermediate Similarity	NPC284678
0.7249	Intermediate Similarity	NPC52254
0.7248	Intermediate Similarity	NPC52557
0.7246	Intermediate Similarity	NPC70155
0.7244	Intermediate Similarity	NPC320968
0.7241	Intermediate Similarity	NPC141428
0.7241	Intermediate Similarity	NPC40779
0.724	Intermediate Similarity	NPC98715
0.7238	Intermediate Similarity	NPC233936
0.7232	Intermediate Similarity	NPC271862
0.7232	Intermediate Similarity	NPC223791
0.7232	Intermediate Similarity	NPC162860
0.7232	Intermediate Similarity	NPC107077
0.7229	Intermediate Similarity	NPC162748
0.7227	Intermediate Similarity	NPC300183
0.7225	Intermediate Similarity	NPC141377
0.7225	Intermediate Similarity	NPC478157
0.7225	Intermediate Similarity	NPC270009
0.722	Intermediate Similarity	NPC63751
0.7215	Intermediate Similarity	NPC32200
0.7212	Intermediate Similarity	NPC87856
0.7203	Intermediate Similarity	NPC89987
0.7202	Intermediate Similarity	NPC229332
0.7193	Intermediate Similarity	NPC132211
0.7191	Intermediate Similarity	NPC477175
0.7191	Intermediate Similarity	NPC470730
0.7188	Intermediate Similarity	NPC258062
0.7181	Intermediate Similarity	NPC267965
0.7174	Intermediate Similarity	NPC193267
0.7174	Intermediate Similarity	NPC213530
0.7171	Intermediate Similarity	NPC49954
0.7171	Intermediate Similarity	NPC474561
0.7171	Intermediate Similarity	NPC54988
0.7169	Intermediate Similarity	NPC149708
0.7163	Intermediate Similarity	NPC472586
0.7161	Intermediate Similarity	NPC475969
0.7161	Intermediate Similarity	NPC475859
0.7157	Intermediate Similarity	NPC311276
0.7157	Intermediate Similarity	NPC476446
0.7157	Intermediate Similarity	NPC78375
0.7157	Intermediate Similarity	NPC469813
0.7156	Intermediate Similarity	NPC476116
0.7155	Intermediate Similarity	NPC155444
0.715	Intermediate Similarity	NPC119700
0.7149	Intermediate Similarity	NPC191382
0.7149	Intermediate Similarity	NPC56109
0.7143	Intermediate Similarity	NPC225821
0.7143	Intermediate Similarity	NPC176199
0.7143	Intermediate Similarity	NPC81229
0.7143	Intermediate Similarity	NPC54420
0.7143	Intermediate Similarity	NPC255229
0.7143	Intermediate Similarity	NPC215795
0.7136	Intermediate Similarity	NPC293917
0.7131	Intermediate Similarity	NPC165743
0.713	Intermediate Similarity	NPC174788
0.7129	Intermediate Similarity	NPC469762
0.7124	Intermediate Similarity	NPC64216
0.712	Intermediate Similarity	NPC472846
0.7119	Intermediate Similarity	NPC326363
0.7118	Intermediate Similarity	NPC476114
0.7118	Intermediate Similarity	NPC203614
0.7115	Intermediate Similarity	NPC34508
0.7112	Intermediate Similarity	NPC2395
0.7104	Intermediate Similarity	NPC49196
0.7104	Intermediate Similarity	NPC81654
0.7104	Intermediate Similarity	NPC106771
0.7104	Intermediate Similarity	NPC205254
0.7104	Intermediate Similarity	NPC470497
0.7104	Intermediate Similarity	NPC79129
0.7104	Intermediate Similarity	NPC303820
0.7104	Intermediate Similarity	NPC195461
0.7104	Intermediate Similarity	NPC23420
0.7104	Intermediate Similarity	NPC249150
0.7104	Intermediate Similarity	NPC313985
0.7103	Intermediate Similarity	NPC62749
0.7098	Intermediate Similarity	NPC238457
0.7095	Intermediate Similarity	NPC472207
0.7095	Intermediate Similarity	NPC68354
0.7091	Intermediate Similarity	NPC470499
0.7091	Intermediate Similarity	NPC171317
0.7091	Intermediate Similarity	NPC50503
0.7089	Intermediate Similarity	NPC165201

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 NPC476492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	557
0.2-0.3	832
0.3-0.4	2133
0.4-0.5	2780
0.5-0.6	1917
0.6-0.7	648
0.7-0.8	58
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7633	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6978	Phase 2
0.7621	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD7824	Approved
0.7478	Intermediate Similarity	NPD7731	Approved
0.7478	Intermediate Similarity	NPD7730	Approved
0.7468	Intermediate Similarity	NPD7790	Approved
0.7468	Intermediate Similarity	NPD7951	Approved
0.7468	Intermediate Similarity	NPD7952	Approved
0.7468	Intermediate Similarity	NPD7950	Approved
0.7468	Intermediate Similarity	NPD7789	Approved
0.7468	Intermediate Similarity	NPD7791	Approved
0.7468	Intermediate Similarity	NPD7953	Approved
0.7467	Intermediate Similarity	NPD7271	Approved
0.744	Intermediate Similarity	NPD6595	Phase 3
0.7421	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD3330	Phase 1
0.7344	Intermediate Similarity	NPD8250	Phase 2
0.7343	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7957	Phase 1
0.7319	Intermediate Similarity	NPD7558	Phase 2
0.7318	Intermediate Similarity	NPD4886	Phase 2
0.7301	Intermediate Similarity	NPD7073	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6455	Phase 3
0.7246	Intermediate Similarity	NPD5065	Approved
0.723	Intermediate Similarity	NPD8431	Approved
0.7217	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8321	Discontinued
0.7196	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8408	Discontinued
0.715	Intermediate Similarity	NPD8020	Approved
0.715	Intermediate Similarity	NPD8021	Approved
0.7149	Intermediate Similarity	NPD7780	Approved
0.7149	Intermediate Similarity	NPD7781	Approved
0.7143	Intermediate Similarity	NPD4076	Approved
0.7143	Intermediate Similarity	NPD7502	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4079	Approved
0.7137	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD8289	Discontinued
0.7136	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD4601	Approved
0.7104	Intermediate Similarity	NPD4600	Approved
0.71	Intermediate Similarity	NPD3402	Phase 1
0.7095	Intermediate Similarity	NPD3506	Approved
0.7095	Intermediate Similarity	NPD3505	Approved
0.7093	Intermediate Similarity	NPD7470	Discontinued
0.7087	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4034	Approved
0.7054	Intermediate Similarity	NPD4033	Approved
0.7054	Intermediate Similarity	NPD4122	Approved
0.7054	Intermediate Similarity	NPD4035	Approved
0.7054	Intermediate Similarity	NPD8272	Phase 2
0.7054	Intermediate Similarity	NPD4038	Approved
0.7054	Intermediate Similarity	NPD4039	Approved
0.7054	Intermediate Similarity	NPD32	Approved
0.7054	Intermediate Similarity	NPD4036	Approved
0.7054	Intermediate Similarity	NPD31	Approved
0.7054	Intermediate Similarity	NPD4037	Approved
0.7053	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7948	Phase 1
0.7045	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5596	Phase 2
0.7035	Intermediate Similarity	NPD7665	Phase 2
0.7035	Intermediate Similarity	NPD7666	Phase 3
0.7028	Intermediate Similarity	NPD8442	Discontinued
0.7028	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2144	Approved
0.7005	Intermediate Similarity	NPD8063	Discontinued
0.7004	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3038	Discontinued
0.6991	Remote Similarity	NPD8322	Phase 2
0.6987	Remote Similarity	NPD8093	Discontinued
0.698	Remote Similarity	NPD7921	Approved
0.6978	Remote Similarity	NPD5426	Phase 3
0.6963	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD4602	Approved
0.6951	Remote Similarity	NPD4500	Approved
0.6951	Remote Similarity	NPD4501	Approved
0.6948	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7001	Phase 3
0.6941	Remote Similarity	NPD3404	Approved
0.694	Remote Similarity	NPD8325	Phase 3
0.694	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.694	Remote Similarity	NPD8326	Phase 3
0.6937	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD8123	Approved
0.6934	Remote Similarity	NPD8122	Approved
0.6933	Remote Similarity	NPD8072	Approved
0.6912	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3961	Discontinued
0.6906	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD3082	Discontinued
0.6897	Remote Similarity	NPD3389	Approved
0.6897	Remote Similarity	NPD5612	Discontinued
0.6897	Remote Similarity	NPD3394	Approved
0.6897	Remote Similarity	NPD3393	Approved
0.689	Remote Similarity	NPD5862	Discovery
0.6889	Remote Similarity	NPD8073	Approved
0.6887	Remote Similarity	NPD2381	Approved
0.6887	Remote Similarity	NPD2382	Approved
0.6887	Remote Similarity	NPD2380	Approved
0.688	Remote Similarity	NPD7194	Discontinued
0.6878	Remote Similarity	NPD7944	Discontinued
0.6867	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4181	Approved
0.6853	Remote Similarity	NPD8370	Discontinued
0.6849	Remote Similarity	NPD7674	Phase 3
0.6849	Remote Similarity	NPD7675	Phase 3
0.6849	Remote Similarity	NPD6352	Phase 2
0.6849	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6281	Approved
0.6842	Remote Similarity	NPD1392	Approved
0.6838	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8374	Phase 3
0.6833	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8115	Approved
0.6828	Remote Similarity	NPD8114	Approved
0.6828	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7112	Discontinued
0.6822	Remote Similarity	NPD8386	Phase 2
0.682	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5913	Phase 3
0.6818	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6992	Phase 2
0.6815	Remote Similarity	NPD8375	Approved
0.6814	Remote Similarity	NPD5486	Discontinued
0.6814	Remote Similarity	NPD2837	Discontinued
0.6812	Remote Similarity	NPD4612	Discontinued
0.681	Remote Similarity	NPD4640	Approved
0.681	Remote Similarity	NPD4639	Approved
0.681	Remote Similarity	NPD4638	Approved
0.681	Remote Similarity	NPD8094	Discontinued
0.6806	Remote Similarity	NPD2092	Phase 2
0.6806	Remote Similarity	NPD2095	Phase 2
0.6806	Remote Similarity	NPD2094	Phase 2
0.6802	Remote Similarity	NPD7619	Phase 3
0.6802	Remote Similarity	NPD7618	Phase 3
0.6797	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7181	Phase 3
0.6777	Remote Similarity	NPD8119	Discontinued
0.6774	Remote Similarity	NPD4957	Phase 2
0.6774	Remote Similarity	NPD2091	Phase 2
0.6774	Remote Similarity	NPD2096	Phase 2
0.677	Remote Similarity	NPD8629	Discontinued
0.6766	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5255	Approved
0.676	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD8246	Approved
0.6759	Remote Similarity	NPD7867	Phase 1
0.6759	Remote Similarity	NPD8247	Approved
0.6756	Remote Similarity	NPD6999	Discontinued
0.6756	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD3013	Phase 3
0.6753	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7726	Phase 1
0.675	Remote Similarity	NPD6165	Phase 2
0.675	Remote Similarity	NPD6164	Phase 2
0.6746	Remote Similarity	NPD3323	Discontinued
0.6739	Remote Similarity	NPD2509	Approved
0.6739	Remote Similarity	NPD2357	Approved
0.6739	Remote Similarity	NPD2510	Approved
0.6737	Remote Similarity	NPD534	Phase 2
0.6737	Remote Similarity	NPD537	Phase 2
0.6734	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD3003	Approved
0.6725	Remote Similarity	NPD5458	Discontinued
0.6724	Remote Similarity	NPD5066	Phase 2
0.6724	Remote Similarity	NPD5067	Phase 2
0.6721	Remote Similarity	NPD8329	Phase 3
0.6712	Remote Similarity	NPD706	Phase 1
0.6709	Remote Similarity	NPD7188	Phase 3
0.6708	Remote Similarity	NPD7603	Discontinued
0.6705	Remote Similarity	NPD6456	Discontinued
0.6698	Remote Similarity	NPD1325	Approved
0.6698	Remote Similarity	NPD1326	Approved
0.6697	Remote Similarity	NPD6178	Phase 3
0.6696	Remote Similarity	NPD7818	Clinical (unspecified phase)

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