NPASS Compound

Structure

NPC471525 OpenBabel07101719122D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.5995 -2.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1600 -1.6739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3452 4.2517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3596 2.6372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8762 -0.5516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7289 3.3507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7540 3.5732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9972 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 1.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5107 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7540 -0.9207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5107 -0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1628 -1.5992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7790 3.3507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7289 -0.6982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7790 -0.6982 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5633 0.8262 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9446 0.8262 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9446 1.8262 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9972 -0.0747 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3452 -1.5992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8106 1.3262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 14 2 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 16 20 1 1 0 0 0 16 21 1 0 0 0 0 17 20 1 6 0 0 0 17 23 1 0 0 0 0 18 19 1 6 0 0 0 18 22 1 0 0 0 0 19 4 1 6 0 0 0 19 22 1 0 0 0 0 20 5 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	349.905
LogP:	4.149
LogD:	3.736
LogS:	-2.772
# Rotatable Bonds:	1
TPSA:	45.29
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	5.158
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.491
MDCK Permeability:	2.7438249162514694e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.106
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.883
30% Bioavailability (F30%):	0.834

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.674
Plasma Protein Binding (PPB):	87.98155975341797%
Volume Distribution (VD):	1.819
Pgp-substrate:	4.938452243804932%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.106
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.322
CYP3A4-inhibitor:	0.558
CYP3A4-substrate:	0.419

ADMET: Excretion

Clearance (CL):	12.014
Half-life (T1/2):	0.399

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.484
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.675
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.726
Carcinogencity:	0.713
Eye Corrosion:	0.04
Eye Irritation:	0.04
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC471525

Natural Product ID:	NPC471525
*Common Name:**	Gibberosene C
IUPAC Name:	n.a.
Synonyms:	gibberosene C
Standard InCHIKey:	AIAZQWPYYSEAAV-CPERAUHSSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-13(2)15-11-16(21)20(5)17(23-20)9-8-14(3)7-6-10-19(4)18(12-15)22-19/h7,12-13,16-18,21H,6,8-11H2,1-5H3/b14-7+,15-12-/t16-,17-,18-,19-,20-/m0/s1
SMILES:	CC1=CCCC2(C(O2)C=C(CC(C3(C(O3)CC1)C)O)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254750
PubChem CID:	44448198
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921403]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[16124762]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16989519]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17917291]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[18198839]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561904]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[501092]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[501092]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[501092]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[501092]

☑ 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 NPC471525 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	211
0.1-0.2	1951
0.2-0.3	6687
0.3-0.4	18135
0.4-0.5	9720
0.5-0.6	5055
0.6-0.7	851
0.7-0.8	76
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8732	High Similarity	NPC129630
0.8667	High Similarity	NPC477089
0.8571	High Similarity	NPC474894
0.8333	Intermediate Similarity	NPC239373
0.8333	Intermediate Similarity	NPC246621
0.8333	Intermediate Similarity	NPC329989
0.8312	Intermediate Similarity	NPC476701
0.8289	Intermediate Similarity	NPC476703
0.8243	Intermediate Similarity	NPC476709
0.8194	Intermediate Similarity	NPC272961
0.8194	Intermediate Similarity	NPC305698
0.8158	Intermediate Similarity	NPC236228
0.8158	Intermediate Similarity	NPC170148
0.8158	Intermediate Similarity	NPC256720
0.8133	Intermediate Similarity	NPC190859
0.8077	Intermediate Similarity	NPC471537
0.8056	Intermediate Similarity	NPC259299
0.7975	Intermediate Similarity	NPC474592
0.7922	Intermediate Similarity	NPC271070
0.7922	Intermediate Similarity	NPC301525
0.7901	Intermediate Similarity	NPC231601
0.7848	Intermediate Similarity	NPC233295
0.7838	Intermediate Similarity	NPC101622
0.7838	Intermediate Similarity	NPC304690
0.7838	Intermediate Similarity	NPC472947
0.7838	Intermediate Similarity	NPC74722
0.7826	Intermediate Similarity	NPC122239
0.7821	Intermediate Similarity	NPC84360
0.7763	Intermediate Similarity	NPC329763
0.7733	Intermediate Similarity	NPC4299
0.7722	Intermediate Similarity	NPC68119
0.7722	Intermediate Similarity	NPC13823
0.7714	Intermediate Similarity	NPC127824
0.7671	Intermediate Similarity	NPC267027
0.7619	Intermediate Similarity	NPC281316
0.7619	Intermediate Similarity	NPC255143
0.76	Intermediate Similarity	NPC16964
0.76	Intermediate Similarity	NPC329656
0.7595	Intermediate Similarity	NPC40049
0.759	Intermediate Similarity	NPC78673
0.759	Intermediate Similarity	NPC160517
0.759	Intermediate Similarity	NPC186155
0.7571	Intermediate Similarity	NPC475931
0.7571	Intermediate Similarity	NPC83838
0.7571	Intermediate Similarity	NPC143810
0.7536	Intermediate Similarity	NPC52012
0.7531	Intermediate Similarity	NPC474739
0.7529	Intermediate Similarity	NPC474765
0.75	Intermediate Similarity	NPC223604
0.7471	Intermediate Similarity	NPC3952
0.747	Intermediate Similarity	NPC23748
0.747	Intermediate Similarity	NPC49208
0.7465	Intermediate Similarity	NPC469694
0.7429	Intermediate Similarity	NPC226848
0.7412	Intermediate Similarity	NPC61527
0.7412	Intermediate Similarity	NPC311163
0.7407	Intermediate Similarity	NPC325869
0.7403	Intermediate Similarity	NPC477084
0.7403	Intermediate Similarity	NPC472254
0.7375	Intermediate Similarity	NPC471454
0.7368	Intermediate Similarity	NPC269841
0.7356	Intermediate Similarity	NPC49783
0.7349	Intermediate Similarity	NPC477385
0.7349	Intermediate Similarity	NPC477390
0.7349	Intermediate Similarity	NPC474291
0.7349	Intermediate Similarity	NPC471408
0.7342	Intermediate Similarity	NPC12696
0.7333	Intermediate Similarity	NPC33583
0.7333	Intermediate Similarity	NPC82337
0.7333	Intermediate Similarity	NPC193029
0.7333	Intermediate Similarity	NPC473357
0.7333	Intermediate Similarity	NPC161612
0.7333	Intermediate Similarity	NPC472255
0.7333	Intermediate Similarity	NPC472253
0.7333	Intermediate Similarity	NPC73603
0.7308	Intermediate Similarity	NPC477085
0.7308	Intermediate Similarity	NPC143576
0.7297	Intermediate Similarity	NPC308844
0.7294	Intermediate Similarity	NPC11804
0.7294	Intermediate Similarity	NPC298595
0.7294	Intermediate Similarity	NPC471494
0.7273	Intermediate Similarity	NPC473361
0.7273	Intermediate Similarity	NPC329904
0.725	Intermediate Similarity	NPC469880
0.725	Intermediate Similarity	NPC268111
0.7246	Intermediate Similarity	NPC281590
0.7237	Intermediate Similarity	NPC224532
0.7229	Intermediate Similarity	NPC112868
0.7222	Intermediate Similarity	NPC258788
0.72	Intermediate Similarity	NPC326310
0.72	Intermediate Similarity	NPC311736
0.72	Intermediate Similarity	NPC272125
0.7195	Intermediate Similarity	NPC86971
0.7183	Intermediate Similarity	NPC181872
0.7179	Intermediate Similarity	NPC477086
0.7179	Intermediate Similarity	NPC306085
0.7179	Intermediate Similarity	NPC477087
0.7176	Intermediate Similarity	NPC9868
0.7176	Intermediate Similarity	NPC474776
0.7176	Intermediate Similarity	NPC72464
0.7176	Intermediate Similarity	NPC83702
0.7162	Intermediate Similarity	NPC300593
0.716	Intermediate Similarity	NPC476439
0.7159	Intermediate Similarity	NPC133450
0.7159	Intermediate Similarity	NPC128066
0.7143	Intermediate Similarity	NPC155521
0.7143	Intermediate Similarity	NPC270013
0.7143	Intermediate Similarity	NPC14961
0.7126	Intermediate Similarity	NPC476948
0.7123	Intermediate Similarity	NPC64971
0.7111	Intermediate Similarity	NPC212486
0.7111	Intermediate Similarity	NPC307776
0.7105	Intermediate Similarity	NPC163290
0.7079	Intermediate Similarity	NPC177668
0.7079	Intermediate Similarity	NPC474761
0.7079	Intermediate Similarity	NPC476004
0.7079	Intermediate Similarity	NPC191323
0.7073	Intermediate Similarity	NPC474005
0.7073	Intermediate Similarity	NPC137345
0.7073	Intermediate Similarity	NPC476314
0.7073	Intermediate Similarity	NPC181838
0.7067	Intermediate Similarity	NPC471200
0.7067	Intermediate Similarity	NPC473722
0.7065	Intermediate Similarity	NPC476315
0.7065	Intermediate Similarity	NPC57664
0.7059	Intermediate Similarity	NPC44261
0.7059	Intermediate Similarity	NPC471340
0.7059	Intermediate Similarity	NPC474809
0.7059	Intermediate Similarity	NPC475842
0.7059	Intermediate Similarity	NPC161045
0.7053	Intermediate Similarity	NPC471148
0.7051	Intermediate Similarity	NPC470041
0.7045	Intermediate Similarity	NPC248312
0.7045	Intermediate Similarity	NPC281516
0.7033	Intermediate Similarity	NPC81386
0.7033	Intermediate Similarity	NPC474035
0.7027	Intermediate Similarity	NPC473508
0.7013	Intermediate Similarity	NPC310210
0.7011	Intermediate Similarity	NPC125399
0.7011	Intermediate Similarity	NPC477387
0.7011	Intermediate Similarity	NPC477389
0.7	Intermediate Similarity	NPC144995
0.7	Intermediate Similarity	NPC227814
0.7	Intermediate Similarity	NPC227135
0.7	Intermediate Similarity	NPC107654
0.7	Intermediate Similarity	NPC476705
0.7	Intermediate Similarity	NPC158061
0.7	Intermediate Similarity	NPC30515
0.7	Intermediate Similarity	NPC184463
0.6988	Remote Similarity	NPC139712
0.6988	Remote Similarity	NPC477088
0.6986	Remote Similarity	NPC240506
0.6986	Remote Similarity	NPC99487
0.6986	Remote Similarity	NPC66020
0.6977	Remote Similarity	NPC243618
0.6977	Remote Similarity	NPC70424
0.6966	Remote Similarity	NPC20946
0.6966	Remote Similarity	NPC299527
0.6962	Remote Similarity	NPC471662
0.6957	Remote Similarity	NPC36954
0.6957	Remote Similarity	NPC469583
0.6957	Remote Similarity	NPC220221
0.6957	Remote Similarity	NPC8774
0.6957	Remote Similarity	NPC107476
0.6957	Remote Similarity	NPC474496
0.6951	Remote Similarity	NPC477425
0.6951	Remote Similarity	NPC477427
0.6951	Remote Similarity	NPC477426
0.6951	Remote Similarity	NPC474826
0.6944	Remote Similarity	NPC155025
0.6941	Remote Similarity	NPC259858
0.6941	Remote Similarity	NPC475936
0.6933	Remote Similarity	NPC140233
0.6933	Remote Similarity	NPC309300
0.6933	Remote Similarity	NPC287744
0.6932	Remote Similarity	NPC477386
0.6932	Remote Similarity	NPC477388
0.6932	Remote Similarity	NPC248602
0.6923	Remote Similarity	NPC119379
0.6923	Remote Similarity	NPC473893
0.6923	Remote Similarity	NPC476300
0.6923	Remote Similarity	NPC475912
0.6915	Remote Similarity	NPC474213
0.6914	Remote Similarity	NPC93213
0.6905	Remote Similarity	NPC233332
0.6905	Remote Similarity	NPC103634
0.6905	Remote Similarity	NPC233377
0.6897	Remote Similarity	NPC137033
0.6892	Remote Similarity	NPC475251
0.6889	Remote Similarity	NPC473448
0.6889	Remote Similarity	NPC197107
0.6889	Remote Similarity	NPC51004
0.6883	Remote Similarity	NPC472266
0.6883	Remote Similarity	NPC114651
0.6882	Remote Similarity	NPC98457
0.6882	Remote Similarity	NPC279621
0.6882	Remote Similarity	NPC210717
0.6882	Remote Similarity	NPC103165
0.6882	Remote Similarity	NPC472995
0.6882	Remote Similarity	NPC227583

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 NPC471525 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	2506
0.2-0.3	3889
0.3-0.4	1973
0.4-0.5	447
0.5-0.6	111
0.6-0.7	13
0.7-0.8	3
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
0.7471	Intermediate Similarity	NPD7838	Discovery
0.7312	Intermediate Similarity	NPD5344	Discontinued
0.7273	Intermediate Similarity	NPD6698	Approved
0.7273	Intermediate Similarity	NPD46	Approved
0.7183	Intermediate Similarity	NPD585	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7524	Approved
0.6842	Remote Similarity	NPD6648	Approved
0.6829	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD368	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6591	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6924	Approved
0.6585	Remote Similarity	NPD6926	Approved
0.6528	Remote Similarity	NPD342	Phase 1
0.6522	Remote Similarity	NPD3168	Discontinued
0.6512	Remote Similarity	NPD6931	Approved
0.6512	Remote Similarity	NPD6930	Phase 2
0.6477	Remote Similarity	NPD7154	Phase 3
0.6452	Remote Similarity	NPD7983	Approved
0.6395	Remote Similarity	NPD6929	Approved
0.6392	Remote Similarity	NPD4225	Approved
0.6374	Remote Similarity	NPD7750	Discontinued
0.6333	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4820	Approved
0.6322	Remote Similarity	NPD7332	Phase 2
0.6322	Remote Similarity	NPD4819	Approved
0.6322	Remote Similarity	NPD7514	Phase 3
0.6322	Remote Similarity	NPD4821	Approved
0.6322	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4822	Approved
0.631	Remote Similarity	NPD8264	Approved
0.6279	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4159	Approved
0.625	Remote Similarity	NPD6902	Approved
0.625	Remote Similarity	NPD6371	Approved
0.6224	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7645	Phase 2
0.6163	Remote Similarity	NPD6932	Approved
0.6163	Remote Similarity	NPD5776	Phase 2
0.6163	Remote Similarity	NPD6925	Approved
0.6154	Remote Similarity	NPD6893	Approved
0.6136	Remote Similarity	NPD7509	Discontinued
0.6118	Remote Similarity	NPD6942	Approved
0.6118	Remote Similarity	NPD7339	Approved
0.6117	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5362	Discontinued
0.6105	Remote Similarity	NPD7087	Discontinued
0.6098	Remote Similarity	NPD6923	Approved
0.6098	Remote Similarity	NPD6922	Approved
0.6092	Remote Similarity	NPD4271	Approved
0.6092	Remote Similarity	NPD7145	Approved
0.6092	Remote Similarity	NPD4268	Approved
0.6071	Remote Similarity	NPD4732	Discontinued
0.6067	Remote Similarity	NPD6898	Phase 1
0.6055	Remote Similarity	NPD7115	Discovery
0.6047	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5778	Approved
0.6042	Remote Similarity	NPD5779	Approved
0.6038	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD7143	Approved
0.6024	Remote Similarity	NPD7144	Approved
0.6023	Remote Similarity	NPD6683	Phase 2
0.602	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5357	Phase 1
0.6019	Remote Similarity	NPD6640	Phase 3
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD7525	Registered
0.5952	Remote Similarity	NPD7152	Approved
0.5952	Remote Similarity	NPD7150	Approved
0.5952	Remote Similarity	NPD7151	Approved
0.5942	Remote Similarity	NPD4265	Approved
0.5934	Remote Similarity	NPD5332	Approved
0.5934	Remote Similarity	NPD5331	Approved
0.5905	Remote Similarity	NPD6686	Approved
0.5897	Remote Similarity	NPD1145	Discontinued
0.5895	Remote Similarity	NPD6101	Approved
0.5895	Remote Similarity	NPD1695	Approved
0.5895	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD4790	Discontinued
0.5889	Remote Similarity	NPD5369	Approved
0.5882	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD4251	Approved
0.5851	Remote Similarity	NPD4250	Approved
0.5833	Remote Similarity	NPD5785	Approved
0.5824	Remote Similarity	NPD6435	Approved
0.5824	Remote Similarity	NPD4270	Approved
0.5824	Remote Similarity	NPD4269	Approved
0.5773	Remote Similarity	NPD6411	Approved
0.5773	Remote Similarity	NPD7637	Suspended
0.5761	Remote Similarity	NPD6110	Phase 1
0.5758	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD8039	Approved
0.5745	Remote Similarity	NPD4249	Approved
0.5745	Remote Similarity	NPD5786	Approved
0.5743	Remote Similarity	NPD7638	Approved
0.5732	Remote Similarity	NPD7331	Phase 2
0.573	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6051	Approved
0.57	Remote Similarity	NPD7839	Suspended
0.5699	Remote Similarity	NPD4786	Approved
0.5686	Remote Similarity	NPD7639	Approved
0.5686	Remote Similarity	NPD7640	Approved
0.5679	Remote Similarity	NPD3197	Phase 1
0.5679	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD3667	Approved
0.5648	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD8273	Phase 1
0.5638	Remote Similarity	NPD5363	Approved
0.5632	Remote Similarity	NPD4784	Approved
0.5632	Remote Similarity	NPD4785	Approved
0.5625	Remote Similarity	NPD7505	Discontinued
0.561	Remote Similarity	NPD7341	Phase 2
0.5604	Remote Similarity	NPD4252	Approved
0.5604	Remote Similarity	NPD5368	Approved

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