NPASS Compound

Structure

CID256720 OpenBabel06191716062D 23 24 0 0 1 0 0 0 0 0999 V2000 -5.9449 -0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4550 3.8698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4006 2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6085 1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6574 2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3357 -0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3902 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2018 0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6629 2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7969 2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0538 3.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 14 1 0 0 0 0 2 15 2 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 17 2 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 1 0 0 0 18 21 1 6 0 0 0 19 20 1 1 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	355.825
LogP:	3.749
LogD:	3.297
LogS:	-3.756
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	4.922
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.631
MDCK Permeability:	1.137751587521052e-05
Pgp-inhibitor:	0.665
Pgp-substrate:	0.106
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.188

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.803
Plasma Protein Binding (PPB):	77.03892517089844%
Volume Distribution (VD):	1.232
Pgp-substrate:	14.455190658569336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.222
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	5.12
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.382
Drug-inuced Liver Injury (DILI):	0.213
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.624
Carcinogencity:	0.868
Eye Corrosion:	0.023
Eye Irritation:	0.553
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC256720

Natural Product ID:	NPC256720
*Common Name:**	Lobocompactol A
IUPAC Name:	(1R,5E,9S)-9-[(2R)-2-(2-hydroxypropan-2-yl)-3,6-dihydro-2H-pyran-5-yl]-6-methyl-2-methylidenecyclodec-5-en-1-ol
Synonyms:	Lobocompactol A
Standard InCHIKey:	UQFRWBRHRWRNEJ-BVSRWBKESA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-14-6-5-7-15(2)18(21)12-16(9-8-14)17-10-11-19(23-13-17)20(3,4)22/h6,10,16,18-19,21-22H,2,5,7-9,11-13H2,1,3-4H3/b14-6+/t16-,18+,19+/m0/s1
SMILES:	C/C/1=CCCC(=C)[C@@H](C[C@H](CC1)C1=CC[C@@H](OC1)C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1762125
PubChem CID:	54583411
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002456] Germacrane 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
NPO14070	Spongosorites genitrix	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10217734]
NPO13780	Mesua racemosa	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13780	Mesua racemosa	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14478	Helenium laciniatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5349	Citrus hybrid	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13946	Dolichospermum spiroides	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12200	Eucalyptus carnea	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13780	Mesua racemosa	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4141	Gaillardia arizonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14070	Spongosorites genitrix	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3043	Plocamium hamatum	Species	Plocamiaceae	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	2
Others	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[536616]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	48240.0	nM	PMID[536616]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.4	uM	PMID[536616]

☑ 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 NPC256720 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	186
0.1-0.2	1681
0.2-0.3	5435
0.3-0.4	16025
0.4-0.5	11662
0.5-0.6	5954
0.6-0.7	1599
0.7-0.8	143
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC236228
0.9	High Similarity	NPC272961
0.8472	Intermediate Similarity	NPC305698
0.8442	Intermediate Similarity	NPC477089
0.8333	Intermediate Similarity	NPC259299
0.8333	Intermediate Similarity	NPC86971
0.8194	Intermediate Similarity	NPC311736
0.8182	Intermediate Similarity	NPC170148
0.8171	Intermediate Similarity	NPC471494
0.8158	Intermediate Similarity	NPC471525
0.8158	Intermediate Similarity	NPC190859
0.8101	Intermediate Similarity	NPC476701
0.8082	Intermediate Similarity	NPC163290
0.8077	Intermediate Similarity	NPC84360
0.8028	Intermediate Similarity	NPC473508
0.8026	Intermediate Similarity	NPC477085
0.8	Intermediate Similarity	NPC129630
0.7927	Intermediate Similarity	NPC231601
0.7895	Intermediate Similarity	NPC477086
0.7895	Intermediate Similarity	NPC477087
0.7895	Intermediate Similarity	NPC472254
0.7875	Intermediate Similarity	NPC233295
0.7867	Intermediate Similarity	NPC472947
0.7857	Intermediate Similarity	NPC311163
0.7857	Intermediate Similarity	NPC122239
0.7848	Intermediate Similarity	NPC476703
0.7838	Intermediate Similarity	NPC82337
0.7808	Intermediate Similarity	NPC308844
0.7778	Intermediate Similarity	NPC474592
0.7763	Intermediate Similarity	NPC4299
0.7703	Intermediate Similarity	NPC267027
0.7701	Intermediate Similarity	NPC3952
0.7654	Intermediate Similarity	NPC139712
0.7632	Intermediate Similarity	NPC304690
0.7632	Intermediate Similarity	NPC16964
0.7632	Intermediate Similarity	NPC74722
0.7632	Intermediate Similarity	NPC101622
0.7625	Intermediate Similarity	NPC40049
0.7619	Intermediate Similarity	NPC186155
0.7619	Intermediate Similarity	NPC160517
0.7619	Intermediate Similarity	NPC78673
0.7619	Intermediate Similarity	NPC83702
0.76	Intermediate Similarity	NPC73603
0.7595	Intermediate Similarity	NPC12696
0.759	Intermediate Similarity	NPC477385
0.759	Intermediate Similarity	NPC477390
0.7586	Intermediate Similarity	NPC133450
0.7564	Intermediate Similarity	NPC476709
0.7561	Intermediate Similarity	NPC474739
0.7558	Intermediate Similarity	NPC476948
0.7531	Intermediate Similarity	NPC68119
0.7531	Intermediate Similarity	NPC13823
0.7531	Intermediate Similarity	NPC181838
0.7531	Intermediate Similarity	NPC137345
0.75	Intermediate Similarity	NPC177668
0.75	Intermediate Similarity	NPC476004
0.75	Intermediate Similarity	NPC474761
0.75	Intermediate Similarity	NPC329626
0.75	Intermediate Similarity	NPC99487
0.747	Intermediate Similarity	NPC474894
0.7467	Intermediate Similarity	NPC326310
0.7465	Intermediate Similarity	NPC155025
0.7465	Intermediate Similarity	NPC226848
0.7442	Intermediate Similarity	NPC61527
0.7442	Intermediate Similarity	NPC255143
0.7439	Intermediate Similarity	NPC471537
0.7439	Intermediate Similarity	NPC477088
0.7436	Intermediate Similarity	NPC477084
0.7436	Intermediate Similarity	NPC306085
0.7432	Intermediate Similarity	NPC300593
0.7412	Intermediate Similarity	NPC474776
0.7403	Intermediate Similarity	NPC329989
0.7403	Intermediate Similarity	NPC239373
0.7403	Intermediate Similarity	NPC269841
0.7386	Intermediate Similarity	NPC299527
0.7386	Intermediate Similarity	NPC474032
0.7386	Intermediate Similarity	NPC115607
0.7381	Intermediate Similarity	NPC471408
0.7361	Intermediate Similarity	NPC475931
0.7349	Intermediate Similarity	NPC186072
0.7342	Intermediate Similarity	NPC143576
0.7333	Intermediate Similarity	NPC472195
0.7333	Intermediate Similarity	NPC238090
0.7333	Intermediate Similarity	NPC472196
0.7333	Intermediate Similarity	NPC471200
0.7326	Intermediate Similarity	NPC137033
0.7326	Intermediate Similarity	NPC298595
0.7317	Intermediate Similarity	NPC4436
0.7317	Intermediate Similarity	NPC248775
0.7308	Intermediate Similarity	NPC329904
0.7308	Intermediate Similarity	NPC473361
0.7294	Intermediate Similarity	NPC23748
0.7294	Intermediate Similarity	NPC49208
0.7294	Intermediate Similarity	NPC471340
0.7284	Intermediate Similarity	NPC469880
0.7284	Intermediate Similarity	NPC229655
0.7284	Intermediate Similarity	NPC271070
0.7283	Intermediate Similarity	NPC472995
0.7273	Intermediate Similarity	NPC248312
0.7273	Intermediate Similarity	NPC474471
0.7273	Intermediate Similarity	NPC153805
0.7273	Intermediate Similarity	NPC224532
0.7273	Intermediate Similarity	NPC227379
0.726	Intermediate Similarity	NPC469694
0.726	Intermediate Similarity	NPC240506
0.7253	Intermediate Similarity	NPC159698
0.7253	Intermediate Similarity	NPC256368
0.7253	Intermediate Similarity	NPC472467
0.7241	Intermediate Similarity	NPC477387
0.7241	Intermediate Similarity	NPC477389
0.7229	Intermediate Similarity	NPC180725
0.7229	Intermediate Similarity	NPC470149
0.7229	Intermediate Similarity	NPC470148
0.7222	Intermediate Similarity	NPC30515
0.7209	Intermediate Similarity	NPC70424
0.7209	Intermediate Similarity	NPC243618
0.7209	Intermediate Similarity	NPC116613
0.7195	Intermediate Similarity	NPC471454
0.7195	Intermediate Similarity	NPC475711
0.7191	Intermediate Similarity	NPC97103
0.7191	Intermediate Similarity	NPC246028
0.7191	Intermediate Similarity	NPC49783
0.7179	Intermediate Similarity	NPC473893
0.7174	Intermediate Similarity	NPC36954
0.7159	Intermediate Similarity	NPC316138
0.7159	Intermediate Similarity	NPC248602
0.7159	Intermediate Similarity	NPC477386
0.7159	Intermediate Similarity	NPC477388
0.7159	Intermediate Similarity	NPC474765
0.7159	Intermediate Similarity	NPC471055
0.7159	Intermediate Similarity	NPC313658
0.7159	Intermediate Similarity	NPC471056
0.7143	Intermediate Similarity	NPC114651
0.7143	Intermediate Similarity	NPC470147
0.7143	Intermediate Similarity	NPC475912
0.7143	Intermediate Similarity	NPC133226
0.7143	Intermediate Similarity	NPC190008
0.7143	Intermediate Similarity	NPC100697
0.7126	Intermediate Similarity	NPC471223
0.7126	Intermediate Similarity	NPC67081
0.7126	Intermediate Similarity	NPC11804
0.7126	Intermediate Similarity	NPC290731
0.7125	Intermediate Similarity	NPC329763
0.7113	Intermediate Similarity	NPC220964
0.7113	Intermediate Similarity	NPC475676
0.7111	Intermediate Similarity	NPC191323
0.7111	Intermediate Similarity	NPC51004
0.7111	Intermediate Similarity	NPC202886
0.7108	Intermediate Similarity	NPC470944
0.7108	Intermediate Similarity	NPC3852
0.7105	Intermediate Similarity	NPC250836
0.7105	Intermediate Similarity	NPC473722
0.7097	Intermediate Similarity	NPC279621
0.7093	Intermediate Similarity	NPC11620
0.7093	Intermediate Similarity	NPC161045
0.7093	Intermediate Similarity	NPC44261
0.7083	Intermediate Similarity	NPC52012
0.7079	Intermediate Similarity	NPC231784
0.7073	Intermediate Similarity	NPC293223
0.7065	Intermediate Similarity	NPC303942
0.7065	Intermediate Similarity	NPC469491
0.7065	Intermediate Similarity	NPC81386
0.7065	Intermediate Similarity	NPC57405
0.7065	Intermediate Similarity	NPC474035
0.7059	Intermediate Similarity	NPC112868
0.7059	Intermediate Similarity	NPC15978
0.7059	Intermediate Similarity	NPC246621
0.7059	Intermediate Similarity	NPC315731
0.7059	Intermediate Similarity	NPC471661
0.7059	Intermediate Similarity	NPC184208
0.7059	Intermediate Similarity	NPC8538
0.7045	Intermediate Similarity	NPC476217
0.7045	Intermediate Similarity	NPC247826
0.7045	Intermediate Similarity	NPC281316
0.7045	Intermediate Similarity	NPC47220
0.7045	Intermediate Similarity	NPC186332
0.7045	Intermediate Similarity	NPC164393
0.7042	Intermediate Similarity	NPC281590
0.7042	Intermediate Similarity	NPC227135
0.7037	Intermediate Similarity	NPC306727
0.7033	Intermediate Similarity	NPC158061
0.7033	Intermediate Similarity	NPC472197
0.7033	Intermediate Similarity	NPC302584
0.7033	Intermediate Similarity	NPC472468
0.7033	Intermediate Similarity	NPC208839
0.7033	Intermediate Similarity	NPC472199
0.7033	Intermediate Similarity	NPC184463
0.7033	Intermediate Similarity	NPC473321
0.7033	Intermediate Similarity	NPC475972
0.7027	Intermediate Similarity	NPC66020
0.7027	Intermediate Similarity	NPC127824
0.7024	Intermediate Similarity	NPC325869
0.7021	Intermediate Similarity	NPC26307
0.7021	Intermediate Similarity	NPC475332
0.7011	Intermediate Similarity	NPC9868
0.701	Intermediate Similarity	NPC4620
0.701	Intermediate Similarity	NPC474165
0.701	Intermediate Similarity	NPC69171
0.7	Intermediate Similarity	NPC20946
0.7	Intermediate Similarity	NPC307411

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 NPC256720 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	2197
0.2-0.3	3840
0.3-0.4	2157
0.4-0.5	612
0.5-0.6	137
0.6-0.7	31
0.7-0.8	1
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
0.7303	Intermediate Similarity	NPD6698	Approved
0.7303	Intermediate Similarity	NPD46	Approved
0.7159	Intermediate Similarity	NPD7524	Approved
0.7111	Intermediate Similarity	NPD7838	Discovery
0.6979	Remote Similarity	NPD5344	Discontinued
0.6947	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD368	Approved
0.6897	Remote Similarity	NPD6695	Phase 3
0.6848	Remote Similarity	NPD7983	Approved
0.6818	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6930	Phase 2
0.6744	Remote Similarity	NPD6931	Approved
0.6744	Remote Similarity	NPD7332	Phase 2
0.6744	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD6933	Approved
0.6628	Remote Similarity	NPD6929	Approved
0.6593	Remote Similarity	NPD7750	Discontinued
0.6588	Remote Similarity	NPD5776	Phase 2
0.6588	Remote Similarity	NPD6925	Approved
0.6575	Remote Similarity	NPD342	Phase 1
0.6556	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD8264	Approved
0.6538	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6648	Approved
0.6517	Remote Similarity	NPD6110	Phase 1
0.6512	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7145	Approved
0.6506	Remote Similarity	NPD4732	Discontinued
0.6477	Remote Similarity	NPD6902	Approved
0.6477	Remote Similarity	NPD6898	Phase 1
0.6456	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6924	Approved
0.6429	Remote Similarity	NPD6926	Approved
0.6395	Remote Similarity	NPD6932	Approved
0.6374	Remote Similarity	NPD6893	Approved
0.6373	Remote Similarity	NPD6640	Phase 3
0.6333	Remote Similarity	NPD7154	Phase 3
0.6316	Remote Similarity	NPD7087	Discontinued
0.6286	Remote Similarity	NPD6371	Approved
0.6263	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD6683	Phase 2
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6237	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4250	Approved
0.6237	Remote Similarity	NPD4251	Approved
0.6224	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7640	Approved
0.62	Remote Similarity	NPD7639	Approved
0.6196	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4822	Approved
0.618	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4819	Approved
0.618	Remote Similarity	NPD4820	Approved
0.618	Remote Similarity	NPD4821	Approved
0.6154	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5362	Discontinued
0.6146	Remote Similarity	NPD7637	Suspended
0.6145	Remote Similarity	NPD6923	Approved
0.6145	Remote Similarity	NPD6922	Approved
0.6129	Remote Similarity	NPD4249	Approved
0.6104	Remote Similarity	NPD585	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7638	Approved
0.6095	Remote Similarity	NPD6686	Approved
0.6071	Remote Similarity	NPD7144	Approved
0.6071	Remote Similarity	NPD7143	Approved
0.6061	Remote Similarity	NPD7839	Suspended
0.6042	Remote Similarity	NPD3168	Discontinued
0.6018	Remote Similarity	NPD8513	Phase 3
0.6	Remote Similarity	NPD7150	Approved
0.6	Remote Similarity	NPD4265	Approved
0.6	Remote Similarity	NPD7152	Approved
0.6	Remote Similarity	NPD7151	Approved
0.6	Remote Similarity	NPD7509	Discontinued
0.5978	Remote Similarity	NPD5331	Approved
0.5978	Remote Similarity	NPD5332	Approved
0.5977	Remote Similarity	NPD6942	Approved
0.5977	Remote Similarity	NPD7339	Approved
0.5955	Remote Similarity	NPD4271	Approved
0.5955	Remote Similarity	NPD4268	Approved
0.5934	Remote Similarity	NPD4790	Discontinued
0.5909	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD7645	Phase 2
0.5877	Remote Similarity	NPD8517	Approved
0.5877	Remote Similarity	NPD8516	Approved
0.5877	Remote Similarity	NPD8515	Approved
0.5876	Remote Similarity	NPD5785	Approved
0.5872	Remote Similarity	NPD6053	Discontinued
0.587	Remote Similarity	NPD4269	Approved
0.587	Remote Similarity	NPD4270	Approved
0.5844	Remote Similarity	NPD4219	Approved
0.5824	Remote Similarity	NPD7525	Registered
0.5804	Remote Similarity	NPD7115	Discovery
0.5795	Remote Similarity	NPD8039	Approved
0.5789	Remote Similarity	NPD5786	Approved
0.5783	Remote Similarity	NPD7331	Phase 2
0.5778	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD5369	Approved
0.5752	Remote Similarity	NPD7328	Approved
0.5752	Remote Similarity	NPD7327	Approved
0.575	Remote Similarity	NPD1145	Discontinued
0.5739	Remote Similarity	NPD7503	Approved
0.5739	Remote Similarity	NPD8033	Approved
0.5732	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7136	Phase 2
0.5702	Remote Similarity	NPD7516	Approved
0.57	Remote Similarity	NPD5282	Discontinued
0.5684	Remote Similarity	NPD5363	Approved
0.5678	Remote Similarity	NPD8273	Phase 1
0.5673	Remote Similarity	NPD4159	Approved
0.5652	Remote Similarity	NPD4252	Approved
0.5652	Remote Similarity	NPD8377	Approved
0.5652	Remote Similarity	NPD8294	Approved
0.5636	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.563	Remote Similarity	NPD8074	Phase 3
0.5619	Remote Similarity	NPD7632	Discontinued
0.5612	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD6051	Approved
0.5612	Remote Similarity	NPD6101	Approved
0.5612	Remote Similarity	NPD1695	Approved
0.5607	Remote Similarity	NPD5357	Phase 1
0.5603	Remote Similarity	NPD8378	Approved
0.5603	Remote Similarity	NPD8380	Approved
0.5603	Remote Similarity	NPD8296	Approved
0.5603	Remote Similarity	NPD8379	Approved
0.5603	Remote Similarity	NPD8335	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