NPASS Compound

Structure

NPC4436 OpenBabel07101719142D 23 24 0 0 1 0 0 0 0 0999 V2000 4.9917 -2.0825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8748 1.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2257 0.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5677 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3596 0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3596 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3748 -1.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2257 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3748 0.7660 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 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 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 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 12 2 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 16 17 1 0 0 0 0 17 11 1 6 0 0 0 17 18 1 0 0 0 0 18 15 1 1 0 0 0 18 19 1 0 0 0 0 19 21 1 6 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	2.371
LogD:	2.897
LogS:	-3.868
# 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:	0.759
Synthetic Accessibility Score:	5.137
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.511
MDCK Permeability:	3.0170718673616648e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.097
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.284
30% Bioavailability (F30%):	0.087

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.969
Plasma Protein Binding (PPB):	77.42557525634766%
Volume Distribution (VD):	0.795
Pgp-substrate:	24.450458526611328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.58
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.596
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.803
CYP3A4-inhibitor:	0.18
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	3.116
Half-life (T1/2):	0.375

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.337
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.294
Carcinogencity:	0.887
Eye Corrosion:	0.004
Eye Irritation:	0.164
Respiratory Toxicity:	0.335

Download Data

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

Natural Product: NPC4436

Natural Product ID:	NPC4436
*Common Name:**	9-Deoxyxenialactol-C
IUPAC Name:	(1S,4E,4aS,7E,11aR)-4-[(E)-4-hydroxy-4-methylpent-2-enylidene]-7-methyl-11-methylidene-4a,5,6,9,10,11a-hexahydro-1H-cyclonona[c]pyran-1-ol
Synonyms:	9-Deoxyxenialactol-C
Standard InCHIKey:	GVOYGZRFVYIDGT-FZAJABQISA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-14-7-5-8-15(2)18-17(11-10-14)16(13-23-19(18)21)9-6-12-20(3,4)22/h6-7,9,12,17-19,21-22H,2,5,8,10-11,13H2,1,3-4H3/b12-6+,14-7+,16-9-/t17-,18+,19+/m1/s1
SMILES:	C/C/1=CCCC(=C)[C@H]2[C@H](CC1)/C(=CC=CC(C)(C)O)/CO[C@@H]2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465844
PubChem CID:	10860114
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002012] Oxanes

*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
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[12502332]
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562830]
NPO14298	Xenia umbellata	Species	Xeniidae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	4.85	ug ml-1	PMID[524837]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	12.9	ug ml-1	PMID[524837]
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.45	ug ml-1	PMID[524837]

☑ 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 NPC4436 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	171
0.1-0.2	1184
0.2-0.3	4923
0.3-0.4	14988
0.4-0.5	13016
0.5-0.6	6855
0.6-0.7	1463
0.7-0.8	94
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC190008
0.7683	Intermediate Similarity	NPC204270
0.7674	Intermediate Similarity	NPC116575
0.7647	Intermediate Similarity	NPC196487
0.7647	Intermediate Similarity	NPC14575
0.7586	Intermediate Similarity	NPC316138
0.7586	Intermediate Similarity	NPC313658
0.7561	Intermediate Similarity	NPC470944
0.7558	Intermediate Similarity	NPC471494
0.7556	Intermediate Similarity	NPC476049
0.7532	Intermediate Similarity	NPC470040
0.7471	Intermediate Similarity	NPC311163
0.7471	Intermediate Similarity	NPC234038
0.7439	Intermediate Similarity	NPC107668
0.7416	Intermediate Similarity	NPC212598
0.7416	Intermediate Similarity	NPC309310
0.7368	Intermediate Similarity	NPC308844
0.7356	Intermediate Similarity	NPC474369
0.7356	Intermediate Similarity	NPC119001
0.7342	Intermediate Similarity	NPC4299
0.7317	Intermediate Similarity	NPC256720
0.7317	Intermediate Similarity	NPC12740
0.7317	Intermediate Similarity	NPC236228
0.7317	Intermediate Similarity	NPC152017
0.7317	Intermediate Similarity	NPC110461
0.7317	Intermediate Similarity	NPC61863
0.7317	Intermediate Similarity	NPC229655
0.7308	Intermediate Similarity	NPC305698
0.7294	Intermediate Similarity	NPC246621
0.7283	Intermediate Similarity	NPC470255
0.7273	Intermediate Similarity	NPC267027
0.7262	Intermediate Similarity	NPC321728
0.7262	Intermediate Similarity	NPC17550
0.7262	Intermediate Similarity	NPC471537
0.725	Intermediate Similarity	NPC472254
0.7241	Intermediate Similarity	NPC471302
0.7241	Intermediate Similarity	NPC471301
0.7234	Intermediate Similarity	NPC98112
0.7229	Intermediate Similarity	NPC84360
0.7215	Intermediate Similarity	NPC74722
0.7215	Intermediate Similarity	NPC101622
0.7215	Intermediate Similarity	NPC329989
0.7215	Intermediate Similarity	NPC304690
0.7215	Intermediate Similarity	NPC239373
0.7209	Intermediate Similarity	NPC324170
0.7204	Intermediate Similarity	NPC272050
0.7195	Intermediate Similarity	NPC215215
0.7195	Intermediate Similarity	NPC265921
0.7195	Intermediate Similarity	NPC85831
0.7179	Intermediate Similarity	NPC259299
0.7176	Intermediate Similarity	NPC186072
0.7162	Intermediate Similarity	NPC122239
0.716	Intermediate Similarity	NPC477085
0.7143	Intermediate Similarity	NPC477089
0.7143	Intermediate Similarity	NPC475980
0.7143	Intermediate Similarity	NPC470817
0.7111	Intermediate Similarity	NPC248312
0.7105	Intermediate Similarity	NPC473508
0.7093	Intermediate Similarity	NPC315731
0.7079	Intermediate Similarity	NPC198314
0.7067	Intermediate Similarity	NPC240506
0.7067	Intermediate Similarity	NPC66020
0.7059	Intermediate Similarity	NPC86971
0.7045	Intermediate Similarity	NPC470800
0.7045	Intermediate Similarity	NPC474776
0.7037	Intermediate Similarity	NPC477087
0.7037	Intermediate Similarity	NPC477086
0.7033	Intermediate Similarity	NPC470819
0.7033	Intermediate Similarity	NPC106040
0.7033	Intermediate Similarity	NPC115179
0.7033	Intermediate Similarity	NPC299527
0.7024	Intermediate Similarity	NPC315394
0.7024	Intermediate Similarity	NPC476439
0.7021	Intermediate Similarity	NPC13924
0.7013	Intermediate Similarity	NPC300593
0.7013	Intermediate Similarity	NPC110241
0.7011	Intermediate Similarity	NPC122945
0.7011	Intermediate Similarity	NPC477385
0.7011	Intermediate Similarity	NPC471298
0.7011	Intermediate Similarity	NPC109938
0.7011	Intermediate Similarity	NPC477390
0.7	Intermediate Similarity	NPC475678
0.7	Intermediate Similarity	NPC199382
0.6989	Remote Similarity	NPC472196
0.6989	Remote Similarity	NPC474792
0.6989	Remote Similarity	NPC67398
0.6989	Remote Similarity	NPC472195
0.6989	Remote Similarity	NPC91654
0.6989	Remote Similarity	NPC238090
0.6979	Remote Similarity	NPC203627
0.6977	Remote Similarity	NPC206062
0.6977	Remote Similarity	NPC100697
0.6977	Remote Similarity	NPC474592
0.6974	Remote Similarity	NPC225342
0.6966	Remote Similarity	NPC42586
0.6966	Remote Similarity	NPC473251
0.6966	Remote Similarity	NPC470658
0.6966	Remote Similarity	NPC329630
0.6962	Remote Similarity	NPC73603
0.6957	Remote Similarity	NPC469403
0.6957	Remote Similarity	NPC202886
0.6957	Remote Similarity	NPC477865
0.6957	Remote Similarity	NPC477866
0.6951	Remote Similarity	NPC135703
0.6951	Remote Similarity	NPC329763
0.6951	Remote Similarity	NPC130665
0.6941	Remote Similarity	NPC474341
0.6933	Remote Similarity	NPC475931
0.6932	Remote Similarity	NPC23748
0.6932	Remote Similarity	NPC471297
0.6923	Remote Similarity	NPC472809
0.6923	Remote Similarity	NPC60765
0.6923	Remote Similarity	NPC472810
0.6915	Remote Similarity	NPC159698
0.6914	Remote Similarity	NPC329904
0.6914	Remote Similarity	NPC129630
0.6914	Remote Similarity	NPC473361
0.6907	Remote Similarity	NPC475053
0.6897	Remote Similarity	NPC112868
0.6897	Remote Similarity	NPC474894
0.6897	Remote Similarity	NPC184208
0.6897	Remote Similarity	NPC8538
0.6897	Remote Similarity	NPC15978
0.6889	Remote Similarity	NPC61527
0.6889	Remote Similarity	NPC281316
0.6889	Remote Similarity	NPC173917
0.6889	Remote Similarity	NPC471480
0.6889	Remote Similarity	NPC472379
0.6883	Remote Similarity	NPC473759
0.6883	Remote Similarity	NPC474155
0.6882	Remote Similarity	NPC302584
0.6882	Remote Similarity	NPC472811
0.6882	Remote Similarity	NPC324157
0.6875	Remote Similarity	NPC272961
0.6875	Remote Similarity	NPC224532
0.6867	Remote Similarity	NPC471525
0.686	Remote Similarity	NPC476701
0.686	Remote Similarity	NPC233295
0.686	Remote Similarity	NPC139712
0.6854	Remote Similarity	NPC46320
0.6854	Remote Similarity	NPC116613
0.6848	Remote Similarity	NPC477748
0.6848	Remote Similarity	NPC49783
0.6848	Remote Similarity	NPC470734
0.6842	Remote Similarity	NPC127824
0.6842	Remote Similarity	NPC99487
0.6835	Remote Similarity	NPC326310
0.6835	Remote Similarity	NPC311736
0.6824	Remote Similarity	NPC40049
0.6824	Remote Similarity	NPC473756
0.6818	Remote Similarity	NPC323251
0.6813	Remote Similarity	NPC471056
0.6813	Remote Similarity	NPC45409
0.6813	Remote Similarity	NPC471055
0.6813	Remote Similarity	NPC86005
0.6809	Remote Similarity	NPC109406
0.6809	Remote Similarity	NPC59646
0.6809	Remote Similarity	NPC472812
0.6804	Remote Similarity	NPC474440
0.68	Remote Similarity	NPC155025
0.68	Remote Similarity	NPC226848
0.68	Remote Similarity	NPC181872
0.679	Remote Similarity	NPC473893
0.679	Remote Similarity	NPC471560
0.6786	Remote Similarity	NPC313179
0.6786	Remote Similarity	NPC23231
0.6786	Remote Similarity	NPC171148
0.6786	Remote Similarity	NPC69383
0.6786	Remote Similarity	NPC60818
0.6774	Remote Similarity	NPC182136
0.6774	Remote Similarity	NPC3436
0.6774	Remote Similarity	NPC253186
0.6771	Remote Similarity	NPC57664
0.6771	Remote Similarity	NPC288350
0.6771	Remote Similarity	NPC173329
0.6768	Remote Similarity	NPC471889
0.6768	Remote Similarity	NPC470571
0.6753	Remote Similarity	NPC321867
0.6753	Remote Similarity	NPC207007
0.6753	Remote Similarity	NPC68679
0.675	Remote Similarity	NPC82337
0.675	Remote Similarity	NPC163290
0.675	Remote Similarity	NPC114651
0.6742	Remote Similarity	NPC474809
0.6742	Remote Similarity	NPC49208
0.6742	Remote Similarity	NPC44261
0.6739	Remote Similarity	NPC474629
0.6739	Remote Similarity	NPC233997
0.6739	Remote Similarity	NPC473151
0.6739	Remote Similarity	NPC472378
0.6737	Remote Similarity	NPC475572
0.6737	Remote Similarity	NPC469697
0.6737	Remote Similarity	NPC104925
0.6737	Remote Similarity	NPC469491
0.6737	Remote Similarity	NPC298973
0.6737	Remote Similarity	NPC470521
0.6737	Remote Similarity	NPC189513
0.6735	Remote Similarity	NPC477720
0.6707	Remote Similarity	NPC316029
0.6706	Remote Similarity	NPC469880

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 NPC4436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1436
0.2-0.3	3860
0.3-0.4	2551
0.4-0.5	941
0.5-0.6	152
0.6-0.7	52
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
0.6979	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8264	Approved
0.6782	Remote Similarity	NPD7332	Phase 2
0.6782	Remote Similarity	NPD7514	Phase 3
0.6753	Remote Similarity	NPD368	Approved
0.6744	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7839	Suspended
0.6591	Remote Similarity	NPD6931	Approved
0.6591	Remote Similarity	NPD6930	Phase 2
0.6552	Remote Similarity	NPD7145	Approved
0.6548	Remote Similarity	NPD4732	Discontinued
0.6517	Remote Similarity	NPD6902	Approved
0.6477	Remote Similarity	NPD6929	Approved
0.6471	Remote Similarity	NPD6924	Approved
0.6471	Remote Similarity	NPD6926	Approved
0.6458	Remote Similarity	NPD5778	Approved
0.6458	Remote Similarity	NPD5779	Approved
0.6452	Remote Similarity	NPD7750	Discontinued
0.6452	Remote Similarity	NPD7524	Approved
0.6437	Remote Similarity	NPD5776	Phase 2
0.6437	Remote Similarity	NPD6925	Approved
0.6437	Remote Similarity	NPD6932	Approved
0.6421	Remote Similarity	NPD7838	Discovery
0.64	Remote Similarity	NPD342	Phase 1
0.6354	Remote Similarity	NPD7637	Suspended
0.6333	Remote Similarity	NPD6898	Phase 1
0.6322	Remote Similarity	NPD6933	Approved
0.6316	Remote Similarity	NPD4219	Approved
0.631	Remote Similarity	NPD7143	Approved
0.631	Remote Similarity	NPD7144	Approved
0.6296	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.625	Remote Similarity	NPD46	Approved
0.625	Remote Similarity	NPD6698	Approved
0.6238	Remote Similarity	NPD6648	Approved
0.6237	Remote Similarity	NPD6893	Approved
0.6235	Remote Similarity	NPD7150	Approved
0.6235	Remote Similarity	NPD7151	Approved
0.6235	Remote Similarity	NPD7152	Approved
0.6222	Remote Similarity	NPD4822	Approved
0.6222	Remote Similarity	NPD4820	Approved
0.6222	Remote Similarity	NPD4821	Approved
0.6222	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4819	Approved
0.6207	Remote Similarity	NPD8039	Approved
0.6196	Remote Similarity	NPD5362	Discontinued
0.6196	Remote Similarity	NPD7154	Phase 3
0.6195	Remote Similarity	NPD8513	Phase 3
0.6195	Remote Similarity	NPD8515	Approved
0.6195	Remote Similarity	NPD8516	Approved
0.6195	Remote Similarity	NPD8517	Approved
0.619	Remote Similarity	NPD6922	Approved
0.619	Remote Similarity	NPD6923	Approved
0.6186	Remote Similarity	NPD7983	Approved
0.6186	Remote Similarity	NPD7087	Discontinued
0.6176	Remote Similarity	NPD5344	Discontinued
0.6173	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6101	Approved
0.6146	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6683	Phase 2
0.6064	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD7509	Discontinued
0.6022	Remote Similarity	NPD5331	Approved
0.6022	Remote Similarity	NPD5332	Approved
0.602	Remote Similarity	NPD6411	Approved
0.6	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD4268	Approved
0.6	Remote Similarity	NPD4271	Approved
0.5981	Remote Similarity	NPD6686	Approved
0.5978	Remote Similarity	NPD4790	Discontinued
0.5963	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4250	Approved
0.5938	Remote Similarity	NPD4251	Approved
0.5938	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5785	Approved
0.5914	Remote Similarity	NPD4270	Approved
0.5914	Remote Similarity	NPD4269	Approved
0.5913	Remote Similarity	NPD7503	Approved
0.5833	Remote Similarity	NPD5786	Approved
0.5825	Remote Similarity	NPD4225	Approved
0.5824	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5369	Approved
0.5802	Remote Similarity	NPD1145	Discontinued
0.5802	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6640	Phase 3
0.5784	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7640	Approved
0.5769	Remote Similarity	NPD7639	Approved
0.5758	Remote Similarity	NPD3168	Discontinued
0.5758	Remote Similarity	NPD7136	Phase 2
0.5745	Remote Similarity	NPD5209	Approved
0.5732	Remote Similarity	NPD4192	Approved
0.5732	Remote Similarity	NPD4191	Approved
0.5732	Remote Similarity	NPD4194	Approved
0.5732	Remote Similarity	NPD4193	Approved
0.5729	Remote Similarity	NPD1696	Phase 3
0.5729	Remote Similarity	NPD5363	Approved
0.5699	Remote Similarity	NPD4252	Approved
0.5676	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD7638	Approved
0.5667	Remote Similarity	NPD6942	Approved
0.5667	Remote Similarity	NPD8074	Phase 3
0.5667	Remote Similarity	NPD7339	Approved
0.5652	Remote Similarity	NPD7328	Approved
0.5652	Remote Similarity	NPD7327	Approved
0.5641	Remote Similarity	NPD8444	Approved
0.5641	Remote Similarity	NPD8033	Approved
0.5616	Remote Similarity	NPD4265	Approved
0.5603	Remote Similarity	NPD7516	Approved
0.56	Remote Similarity	NPD8522	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