NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	488.35
Volume:	529.252
LogP:	5.53
LogD:	5.328
LogS:	-4.86
# Rotatable Bonds:	7
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.39
Synthetic Accessibility Score:	4.979
Fsp3:	0.867
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:	-4.766
MDCK Permeability:	3.7189412978477776e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.079
20% Bioavailability (F20%):	0.925
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.485
Plasma Protein Binding (PPB):	82.31981658935547%
Volume Distribution (VD):	0.84
Pgp-substrate:	1.3718900680541992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.523
CYP2C19-inhibitor:	0.101
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.905
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	2.666
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.303
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.528
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.839
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.626
Carcinogencity:	0.029
Eye Corrosion:	0.005
Eye Irritation:	0.038
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC477053

Natural Product ID:	NPC477053
*Common Name:**	Echrebsteroid C
IUPAC Name:	[(E,2R,3R,6R)-6-[(3S,5R,8S,9S,10R,13R,14S,17R)-3,5-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,3-dimethylhept-4-enyl] acetate
Synonyms:
Standard InCHIKey:	KTFQTQFVKTUBKY-KPLCCLTCSA-N
Standard InCHI:	InChI=1S/C30H48O5/c1-18(20(3)17-35-21(4)31)7-8-19(2)24-9-10-25-23-15-27(33)30(34)16-22(32)11-14-29(30,6)26(23)12-13-28(24,25)5/h7-8,18-20,22-26,32,34H,9-17H2,1-6H3/b8-7+/t18-,19-,20+,22+,23+,24-,25+,26+,28-,29-,30+/m1/s1
SMILES:	C[C@@H](COC(=O)C)[C@H](C)/C=C/[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC(=O)[C@@]4([C@@]3(CC[C@@H](C4)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90680710
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*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
NPO33679	Echinogorgia rebekka	Species	Paramuriceidae	Eukaryota	n.a.	the coral reef of Weizhou Island in the South China Sea, China	2010-APR	PMID[24882250]

☑ 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	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	IC50	=	190	nM	PMID[24882250]
NPT2	Others	Unspecified		TC50	=	24.4	nM	PMID[24882250]

☑ 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 NPC477053 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	196
0.1-0.2	1225
0.2-0.3	4760
0.3-0.4	10340
0.4-0.5	11100
0.5-0.6	5901
0.6-0.7	5309
0.7-0.8	3605
0.8-0.85	245
0.85-0.9	7
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477052
1.0	High Similarity	NPC477051
0.9894	High Similarity	NPC477054
0.9167	High Similarity	NPC191565
0.9167	High Similarity	NPC119036
0.9091	High Similarity	NPC29705
0.9053	High Similarity	NPC279974
0.899	High Similarity	NPC222153
0.883	High Similarity	NPC46758
0.875	High Similarity	NPC209662
0.8627	High Similarity	NPC196528
0.8617	High Similarity	NPC193360
0.8614	High Similarity	NPC249187
0.8614	High Similarity	NPC247957
0.86	High Similarity	NPC118964
0.8586	High Similarity	NPC474724
0.8586	High Similarity	NPC477854
0.8571	High Similarity	NPC471903
0.8544	High Similarity	NPC131665
0.8544	High Similarity	NPC263729
0.8544	High Similarity	NPC255387
0.8529	High Similarity	NPC471293
0.8529	High Similarity	NPC201763
0.8526	High Similarity	NPC475921
0.8526	High Similarity	NPC474704
0.8515	High Similarity	NPC22388
0.8491	Intermediate Similarity	NPC280782
0.8485	Intermediate Similarity	NPC108078
0.8462	Intermediate Similarity	NPC472218
0.8462	Intermediate Similarity	NPC472219
0.8462	Intermediate Similarity	NPC163216
0.8462	Intermediate Similarity	NPC472217
0.8462	Intermediate Similarity	NPC94529
0.8454	Intermediate Similarity	NPC107674
0.8454	Intermediate Similarity	NPC141497
0.8454	Intermediate Similarity	NPC170220
0.8454	Intermediate Similarity	NPC470224
0.8447	Intermediate Similarity	NPC257353
0.844	Intermediate Similarity	NPC146786
0.8438	Intermediate Similarity	NPC471896
0.8431	Intermediate Similarity	NPC312900
0.84	Intermediate Similarity	NPC28864
0.84	Intermediate Similarity	NPC20479
0.84	Intermediate Similarity	NPC477653
0.84	Intermediate Similarity	NPC38296
0.84	Intermediate Similarity	NPC98837
0.84	Intermediate Similarity	NPC162459
0.84	Intermediate Similarity	NPC38471
0.8384	Intermediate Similarity	NPC477853
0.8384	Intermediate Similarity	NPC327788
0.8384	Intermediate Similarity	NPC49371
0.8381	Intermediate Similarity	NPC472216
0.8381	Intermediate Similarity	NPC5475
0.8381	Intermediate Similarity	NPC173905
0.8381	Intermediate Similarity	NPC257082
0.8381	Intermediate Similarity	NPC284828
0.8381	Intermediate Similarity	NPC285298
0.8367	Intermediate Similarity	NPC159410
0.8367	Intermediate Similarity	NPC245972
0.8367	Intermediate Similarity	NPC196485
0.8365	Intermediate Similarity	NPC44063
0.8365	Intermediate Similarity	NPC59530
0.8351	Intermediate Similarity	NPC198054
0.8351	Intermediate Similarity	NPC212301
0.8351	Intermediate Similarity	NPC86266
0.8351	Intermediate Similarity	NPC110657
0.8351	Intermediate Similarity	NPC297265
0.835	Intermediate Similarity	NPC47281
0.835	Intermediate Similarity	NPC72255
0.8333	Intermediate Similarity	NPC474245
0.8333	Intermediate Similarity	NPC271980
0.8333	Intermediate Similarity	NPC193934
0.8318	Intermediate Similarity	NPC71348
0.8317	Intermediate Similarity	NPC293866
0.8317	Intermediate Similarity	NPC167974
0.8316	Intermediate Similarity	NPC142361
0.8316	Intermediate Similarity	NPC474684
0.83	Intermediate Similarity	NPC476878
0.83	Intermediate Similarity	NPC476879
0.83	Intermediate Similarity	NPC10864
0.83	Intermediate Similarity	NPC253586
0.8283	Intermediate Similarity	NPC84383
0.8283	Intermediate Similarity	NPC98639
0.8283	Intermediate Similarity	NPC469599
0.8269	Intermediate Similarity	NPC28791
0.8269	Intermediate Similarity	NPC231530
0.8269	Intermediate Similarity	NPC50535
0.8269	Intermediate Similarity	NPC278628
0.8269	Intermediate Similarity	NPC472655
0.8265	Intermediate Similarity	NPC244356
0.8265	Intermediate Similarity	NPC294263
0.8265	Intermediate Similarity	NPC224060
0.8265	Intermediate Similarity	NPC470375
0.8265	Intermediate Similarity	NPC470376
0.8252	Intermediate Similarity	NPC478057
0.8252	Intermediate Similarity	NPC36688
0.8252	Intermediate Similarity	NPC140723
0.8252	Intermediate Similarity	NPC191892
0.8252	Intermediate Similarity	NPC112009
0.8247	Intermediate Similarity	NPC175628
0.8247	Intermediate Similarity	NPC148414
0.8247	Intermediate Similarity	NPC111585
0.8235	Intermediate Similarity	NPC289670
0.8235	Intermediate Similarity	NPC253886
0.8235	Intermediate Similarity	NPC46848
0.8235	Intermediate Similarity	NPC235142
0.8235	Intermediate Similarity	NPC121218
0.8229	Intermediate Similarity	NPC474719
0.8218	Intermediate Similarity	NPC16911
0.8218	Intermediate Similarity	NPC78427
0.8218	Intermediate Similarity	NPC114274
0.8218	Intermediate Similarity	NPC89099
0.8211	Intermediate Similarity	NPC73038
0.8208	Intermediate Similarity	NPC2766
0.82	Intermediate Similarity	NPC200054
0.82	Intermediate Similarity	NPC471153
0.82	Intermediate Similarity	NPC29410
0.82	Intermediate Similarity	NPC62516
0.82	Intermediate Similarity	NPC157113
0.819	Intermediate Similarity	NPC251824
0.819	Intermediate Similarity	NPC201908
0.819	Intermediate Similarity	NPC176949
0.819	Intermediate Similarity	NPC64844
0.819	Intermediate Similarity	NPC42847
0.819	Intermediate Similarity	NPC86852
0.8182	Intermediate Similarity	NPC159365
0.8182	Intermediate Similarity	NPC47853
0.8182	Intermediate Similarity	NPC49670
0.8173	Intermediate Similarity	NPC160843
0.8163	Intermediate Similarity	NPC154101
0.8163	Intermediate Similarity	NPC26888
0.8163	Intermediate Similarity	NPC474525
0.8163	Intermediate Similarity	NPC475708
0.8163	Intermediate Similarity	NPC189520
0.8155	Intermediate Similarity	NPC170615
0.8155	Intermediate Similarity	NPC275990
0.8155	Intermediate Similarity	NPC88203
0.8155	Intermediate Similarity	NPC76866
0.8155	Intermediate Similarity	NPC148628
0.8155	Intermediate Similarity	NPC246736
0.8155	Intermediate Similarity	NPC286519
0.8155	Intermediate Similarity	NPC214946
0.8155	Intermediate Similarity	NPC476081
0.8155	Intermediate Similarity	NPC304832
0.8144	Intermediate Similarity	NPC128496
0.8144	Intermediate Similarity	NPC474889
0.8137	Intermediate Similarity	NPC327431
0.8137	Intermediate Similarity	NPC94906
0.8137	Intermediate Similarity	NPC15390
0.8137	Intermediate Similarity	NPC287676
0.8137	Intermediate Similarity	NPC83709
0.8137	Intermediate Similarity	NPC108371
0.8137	Intermediate Similarity	NPC477655
0.8125	Intermediate Similarity	NPC269360
0.8125	Intermediate Similarity	NPC159046
0.8125	Intermediate Similarity	NPC233836
0.8125	Intermediate Similarity	NPC264005
0.8125	Intermediate Similarity	NPC187376
0.8125	Intermediate Similarity	NPC33768
0.8119	Intermediate Similarity	NPC57416
0.8119	Intermediate Similarity	NPC107243
0.8113	Intermediate Similarity	NPC258323
0.81	Intermediate Similarity	NPC469329
0.81	Intermediate Similarity	NPC88310
0.81	Intermediate Similarity	NPC272617
0.81	Intermediate Similarity	NPC271195
0.81	Intermediate Similarity	NPC30677
0.81	Intermediate Similarity	NPC263135
0.81	Intermediate Similarity	NPC180557
0.81	Intermediate Similarity	NPC37787
0.81	Intermediate Similarity	NPC288906
0.81	Intermediate Similarity	NPC473415
0.81	Intermediate Similarity	NPC69548
0.81	Intermediate Similarity	NPC474727
0.81	Intermediate Similarity	NPC83693
0.81	Intermediate Similarity	NPC210214
0.81	Intermediate Similarity	NPC184848
0.8095	Intermediate Similarity	NPC166607
0.8095	Intermediate Similarity	NPC475494
0.8091	Intermediate Similarity	NPC270958
0.8091	Intermediate Similarity	NPC148458
0.8085	Intermediate Similarity	NPC471037
0.8081	Intermediate Similarity	NPC473690
0.8081	Intermediate Similarity	NPC118490
0.8081	Intermediate Similarity	NPC86368
0.8081	Intermediate Similarity	NPC474436
0.8081	Intermediate Similarity	NPC63118
0.8081	Intermediate Similarity	NPC477855
0.8081	Intermediate Similarity	NPC287118
0.8081	Intermediate Similarity	NPC471902
0.8081	Intermediate Similarity	NPC12722
0.8081	Intermediate Similarity	NPC49776
0.8077	Intermediate Similarity	NPC180204
0.8077	Intermediate Similarity	NPC120321
0.8073	Intermediate Similarity	NPC202889
0.8061	Intermediate Similarity	NPC291028
0.8061	Intermediate Similarity	NPC46441
0.8061	Intermediate Similarity	NPC10274
0.8061	Intermediate Similarity	NPC232202
0.8061	Intermediate Similarity	NPC469400

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 NPC477053 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1502
0.2-0.3	3966
0.3-0.4	2296
0.4-0.5	702
0.5-0.6	192
0.6-0.7	147
0.7-0.8	147
0.8-0.85	34
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD6881	Approved
0.8462	Intermediate Similarity	NPD6899	Approved
0.8447	Intermediate Similarity	NPD6402	Approved
0.8447	Intermediate Similarity	NPD5739	Approved
0.8447	Intermediate Similarity	NPD7128	Approved
0.8447	Intermediate Similarity	NPD6675	Approved
0.8396	Intermediate Similarity	NPD6649	Approved
0.8396	Intermediate Similarity	NPD6650	Approved
0.8381	Intermediate Similarity	NPD6372	Approved
0.8381	Intermediate Similarity	NPD6373	Approved
0.8365	Intermediate Similarity	NPD5697	Approved
0.8302	Intermediate Similarity	NPD6883	Approved
0.8302	Intermediate Similarity	NPD7102	Approved
0.8302	Intermediate Similarity	NPD7290	Approved
0.83	Intermediate Similarity	NPD6084	Phase 2
0.83	Intermediate Similarity	NPD6083	Phase 2
0.8286	Intermediate Similarity	NPD7320	Approved
0.8265	Intermediate Similarity	NPD6399	Phase 3
0.8224	Intermediate Similarity	NPD8130	Phase 1
0.8224	Intermediate Similarity	NPD6869	Approved
0.8224	Intermediate Similarity	NPD6617	Approved
0.8224	Intermediate Similarity	NPD6847	Approved
0.8208	Intermediate Similarity	NPD6013	Approved
0.8208	Intermediate Similarity	NPD6012	Approved
0.8208	Intermediate Similarity	NPD6014	Approved
0.819	Intermediate Similarity	NPD5701	Approved
0.8148	Intermediate Similarity	NPD8297	Approved
0.8148	Intermediate Similarity	NPD6882	Approved
0.8113	Intermediate Similarity	NPD6011	Approved
0.8039	Intermediate Similarity	NPD7638	Approved
0.8039	Intermediate Similarity	NPD5696	Approved
0.798	Intermediate Similarity	NPD8035	Phase 2
0.798	Intermediate Similarity	NPD8034	Phase 2
0.7961	Intermediate Similarity	NPD5285	Approved
0.7961	Intermediate Similarity	NPD7640	Approved
0.7961	Intermediate Similarity	NPD5286	Approved
0.7961	Intermediate Similarity	NPD7639	Approved
0.7961	Intermediate Similarity	NPD4696	Approved
0.7941	Intermediate Similarity	NPD4755	Approved
0.7921	Intermediate Similarity	NPD5695	Phase 3
0.7917	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD4632	Approved
0.789	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5737	Approved
0.7857	Intermediate Similarity	NPD6672	Approved
0.7843	Intermediate Similarity	NPD4697	Phase 3
0.7843	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD5222	Approved
0.7843	Intermediate Similarity	NPD5221	Approved
0.7835	Intermediate Similarity	NPD3618	Phase 1
0.7822	Intermediate Similarity	NPD7748	Approved
0.7812	Intermediate Similarity	NPD4786	Approved
0.781	Intermediate Similarity	NPD5225	Approved
0.781	Intermediate Similarity	NPD5226	Approved
0.781	Intermediate Similarity	NPD5224	Approved
0.781	Intermediate Similarity	NPD5211	Phase 2
0.781	Intermediate Similarity	NPD4633	Approved
0.7807	Intermediate Similarity	NPD6319	Approved
0.78	Intermediate Similarity	NPD7515	Phase 2
0.78	Intermediate Similarity	NPD6079	Approved
0.7788	Intermediate Similarity	NPD4700	Approved
0.7778	Intermediate Similarity	NPD4753	Phase 2
0.7778	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5328	Approved
0.7767	Intermediate Similarity	NPD7902	Approved
0.7767	Intermediate Similarity	NPD5173	Approved
0.7745	Intermediate Similarity	NPD4629	Approved
0.7745	Intermediate Similarity	NPD5210	Approved
0.7742	Intermediate Similarity	NPD6115	Approved
0.7742	Intermediate Similarity	NPD6697	Approved
0.7742	Intermediate Similarity	NPD6114	Approved
0.7742	Intermediate Similarity	NPD6118	Approved
0.7736	Intermediate Similarity	NPD5174	Approved
0.7736	Intermediate Similarity	NPD5175	Approved
0.7719	Intermediate Similarity	NPD7100	Approved
0.7719	Intermediate Similarity	NPD7101	Approved
0.7714	Intermediate Similarity	NPD5223	Approved
0.7699	Intermediate Similarity	NPD7115	Discovery
0.7699	Intermediate Similarity	NPD6009	Approved
0.7692	Intermediate Similarity	NPD7492	Approved
0.7664	Intermediate Similarity	NPD5141	Approved
0.7653	Intermediate Similarity	NPD6098	Approved
0.7652	Intermediate Similarity	NPD6054	Approved
0.7647	Intermediate Similarity	NPD7736	Approved
0.7636	Intermediate Similarity	NPD4634	Approved
0.7632	Intermediate Similarity	NPD6335	Approved
0.7627	Intermediate Similarity	NPD6616	Approved
0.7611	Intermediate Similarity	NPD6868	Approved
0.7611	Intermediate Similarity	NPD6274	Approved
0.7607	Intermediate Similarity	NPD7604	Phase 2
0.7604	Intermediate Similarity	NPD3667	Approved
0.76	Intermediate Similarity	NPD6080	Approved
0.76	Intermediate Similarity	NPD6904	Approved
0.76	Intermediate Similarity	NPD6673	Approved
0.7593	Intermediate Similarity	NPD6008	Approved
0.7586	Intermediate Similarity	NPD5983	Phase 2
0.7579	Intermediate Similarity	NPD7525	Registered
0.7573	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7078	Approved
0.7549	Intermediate Similarity	NPD4202	Approved
0.7544	Intermediate Similarity	NPD6317	Approved
0.7527	Intermediate Similarity	NPD6117	Approved
0.7521	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD6336	Discontinued
0.7478	Intermediate Similarity	NPD6314	Approved
0.7478	Intermediate Similarity	NPD6313	Approved
0.7476	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7900	Approved
0.7475	Intermediate Similarity	NPD7146	Approved
0.7475	Intermediate Similarity	NPD7521	Approved
0.7475	Intermediate Similarity	NPD7334	Approved
0.7475	Intermediate Similarity	NPD6409	Approved
0.7475	Intermediate Similarity	NPD6684	Approved
0.7475	Intermediate Similarity	NPD5330	Approved
0.7455	Intermediate Similarity	NPD4730	Approved
0.7455	Intermediate Similarity	NPD4729	Approved
0.7451	Intermediate Similarity	NPD7637	Suspended
0.7447	Intermediate Similarity	NPD6116	Phase 1
0.7436	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6016	Approved
0.7436	Intermediate Similarity	NPD6909	Approved
0.7436	Intermediate Similarity	NPD6015	Approved
0.7436	Intermediate Similarity	NPD6908	Approved
0.7431	Intermediate Similarity	NPD4768	Approved
0.7431	Intermediate Similarity	NPD4767	Approved
0.7417	Intermediate Similarity	NPD8293	Discontinued
0.7407	Intermediate Similarity	NPD4754	Approved
0.7374	Intermediate Similarity	NPD5329	Approved
0.7373	Intermediate Similarity	NPD5988	Approved
0.7327	Intermediate Similarity	NPD6903	Approved
0.7321	Intermediate Similarity	NPD5247	Approved
0.7321	Intermediate Similarity	NPD5249	Phase 3
0.7321	Intermediate Similarity	NPD5250	Approved
0.7321	Intermediate Similarity	NPD5248	Approved
0.7321	Intermediate Similarity	NPD5251	Approved
0.7315	Intermediate Similarity	NPD7632	Discontinued
0.7312	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5279	Phase 3
0.7297	Intermediate Similarity	NPD5128	Approved
0.7282	Intermediate Similarity	NPD5281	Approved
0.7282	Intermediate Similarity	NPD5694	Approved
0.7282	Intermediate Similarity	NPD5284	Approved
0.7282	Intermediate Similarity	NPD5693	Phase 1
0.7282	Intermediate Similarity	NPD6050	Approved
0.7273	Intermediate Similarity	NPD3665	Phase 1
0.7273	Intermediate Similarity	NPD3133	Approved
0.7273	Intermediate Similarity	NPD3666	Approved
0.7273	Intermediate Similarity	NPD4197	Approved
0.7257	Intermediate Similarity	NPD5215	Approved
0.7257	Intermediate Similarity	NPD5216	Approved
0.7257	Intermediate Similarity	NPD5217	Approved
0.7207	Intermediate Similarity	NPD6412	Phase 2
0.719	Intermediate Similarity	NPD7507	Approved
0.7188	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5692	Phase 3
0.7172	Intermediate Similarity	NPD4788	Approved
0.7172	Intermediate Similarity	NPD6695	Phase 3
0.7168	Intermediate Similarity	NPD5169	Approved
0.7168	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5135	Approved
0.7167	Intermediate Similarity	NPD8328	Phase 3
0.7154	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD5369	Approved
0.7143	Intermediate Similarity	NPD5168	Approved
0.7143	Intermediate Similarity	NPD6001	Approved
0.7129	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5690	Phase 2
0.7115	Intermediate Similarity	NPD6411	Approved
0.7105	Intermediate Similarity	NPD5127	Approved
0.71	Intermediate Similarity	NPD3668	Phase 3
0.71	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4223	Phase 3
0.7071	Intermediate Similarity	NPD6435	Approved
0.7071	Intermediate Similarity	NPD4221	Approved
0.7059	Intermediate Similarity	NPD3573	Approved
0.7053	Intermediate Similarity	NPD3703	Phase 2
0.7034	Intermediate Similarity	NPD7327	Approved
0.7034	Intermediate Similarity	NPD7328	Approved
0.7019	Intermediate Similarity	NPD5207	Approved
0.7018	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6921	Approved
0.699	Remote Similarity	NPD5208	Approved
0.6989	Remote Similarity	NPD4789	Approved
0.6983	Remote Similarity	NPD8133	Approved
0.6975	Remote Similarity	NPD7516	Approved
0.6961	Remote Similarity	NPD5280	Approved
0.6961	Remote Similarity	NPD4694	Approved
0.6949	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7645	Phase 2
0.6935	Remote Similarity	NPD6033	Approved
0.6923	Remote Similarity	NPD5167	Approved
0.6923	Remote Similarity	NPD6101	Approved
0.6923	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7285	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