NPASS Compound

Structure

NPC474341 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.7905 -0.9982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4489 3.5584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5917 0.9263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9489 0.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5917 1.9263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.4866 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 -2.7561 1.4263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.0134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9489 2.6924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 2.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.9641 2.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 4.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 4.3660 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 14 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 13 2 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 15 16 1 0 0 0 0 16 10 1 1 0 0 0 16 18 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 0 0 0 0 18 14 1 6 0 0 0 18 19 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	4.599
LogD:	4.29
LogS:	-5.427
# Rotatable Bonds:	2
TPSA:	38.83
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	4.761
Fsp3:	0.65
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:	-4.775
MDCK Permeability:	2.710900480451528e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.881

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	96.8598861694336%
Volume Distribution (VD):	1.092
Pgp-substrate:	1.3174793720245361%

ADMET: Metabolism

CYP1A2-inhibitor:	0.229
CYP1A2-substrate:	0.206
CYP2C19-inhibitor:	0.716
CYP2C19-substrate:	0.469
CYP2C9-inhibitor:	0.823
CYP2C9-substrate:	0.126
CYP2D6-inhibitor:	0.231
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.692
CYP3A4-substrate:	0.407

ADMET: Excretion

Clearance (CL):	3.955
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.306
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.805
Carcinogencity:	0.265
Eye Corrosion:	0.013
Eye Irritation:	0.115
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC474341

Natural Product ID:	NPC474341
*Common Name:**	9-Deoxyxeniloide-E
IUPAC Name:	(4E,4aS,7E,11aR)-4-[2-(3,3-dimethyloxiran-2-yl)ethylidene]-7-methyl-11-methylidene-4a,5,6,9,10,11a-hexahydrocyclonona[c]pyran-1-one
Synonyms:	9-Deoxyxeniloide-E
Standard InCHIKey:	SLBDTTJOIFSXFG-DACSYXBRSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-13-6-5-7-14(2)18-16(10-8-13)15(12-22-19(18)21)9-11-17-20(3,4)23-17/h6,9,16-18H,2,5,7-8,10-12H2,1,3-4H3/b13-6+,15-9-/t16-,17?,18+/m1/s1
SMILES:	C/C/1=CCCC(=C)[C@H]2[C@H](CC1)/C(=CCC1OC1(C)C)/COC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465479
PubChem CID:	21603533
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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	=	11.2	ug ml-1	PMID[523892]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	21.1	ug ml-1	PMID[523892]
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.87	ug ml-1	PMID[523892]

☑ 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 NPC474341 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	199
0.1-0.2	1263
0.2-0.3	5643
0.3-0.4	15552
0.4-0.5	9923
0.5-0.6	7000
0.6-0.7	2841
0.7-0.8	253
0.8-0.85	14
0.85-0.9	6
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9306	High Similarity	NPC135703
0.9221	High Similarity	NPC475936
0.9103	High Similarity	NPC53867
0.9054	High Similarity	NPC475861
0.8816	High Similarity	NPC107668
0.8625	High Similarity	NPC475842
0.8608	High Similarity	NPC475481
0.8608	High Similarity	NPC79277
0.8519	High Similarity	NPC196487
0.8519	High Similarity	NPC14575
0.8452	Intermediate Similarity	NPC115179
0.8452	Intermediate Similarity	NPC106040
0.8442	Intermediate Similarity	NPC110461
0.8442	Intermediate Similarity	NPC12740
0.8442	Intermediate Similarity	NPC61863
0.8415	Intermediate Similarity	NPC474369
0.8313	Intermediate Similarity	NPC116575
0.8313	Intermediate Similarity	NPC234038
0.8293	Intermediate Similarity	NPC474776
0.8267	Intermediate Similarity	NPC475310
0.8214	Intermediate Similarity	NPC474765
0.8193	Intermediate Similarity	NPC474547
0.8148	Intermediate Similarity	NPC141810
0.8125	Intermediate Similarity	NPC617
0.8072	Intermediate Similarity	NPC72464
0.8025	Intermediate Similarity	NPC233377
0.8023	Intermediate Similarity	NPC212598
0.7975	Intermediate Similarity	NPC271070
0.7955	Intermediate Similarity	NPC476049
0.7952	Intermediate Similarity	NPC475989
0.7952	Intermediate Similarity	NPC272814
0.7952	Intermediate Similarity	NPC170377
0.7922	Intermediate Similarity	NPC129665
0.7922	Intermediate Similarity	NPC477084
0.7922	Intermediate Similarity	NPC163003
0.7895	Intermediate Similarity	NPC269841
0.7882	Intermediate Similarity	NPC198314
0.7875	Intermediate Similarity	NPC187568
0.7875	Intermediate Similarity	NPC41780
0.7857	Intermediate Similarity	NPC70424
0.7857	Intermediate Similarity	NPC243618
0.7848	Intermediate Similarity	NPC324762
0.7831	Intermediate Similarity	NPC35556
0.7805	Intermediate Similarity	NPC474510
0.7791	Intermediate Similarity	NPC231889
0.7791	Intermediate Similarity	NPC475703
0.7778	Intermediate Similarity	NPC471220
0.7778	Intermediate Similarity	NPC128276
0.7763	Intermediate Similarity	NPC276290
0.775	Intermediate Similarity	NPC474447
0.775	Intermediate Similarity	NPC235906
0.7738	Intermediate Similarity	NPC193198
0.7738	Intermediate Similarity	NPC222358
0.7727	Intermediate Similarity	NPC51653
0.7722	Intermediate Similarity	NPC476355
0.7722	Intermediate Similarity	NPC140287
0.7722	Intermediate Similarity	NPC474551
0.7711	Intermediate Similarity	NPC325031
0.7711	Intermediate Similarity	NPC471325
0.7683	Intermediate Similarity	NPC178277
0.7683	Intermediate Similarity	NPC469690
0.7683	Intermediate Similarity	NPC469617
0.7674	Intermediate Similarity	NPC474045
0.7674	Intermediate Similarity	NPC50637
0.7674	Intermediate Similarity	NPC261253
0.7674	Intermediate Similarity	NPC220478
0.7674	Intermediate Similarity	NPC122502
0.7662	Intermediate Similarity	NPC199557
0.7654	Intermediate Similarity	NPC470240
0.7654	Intermediate Similarity	NPC57744
0.7654	Intermediate Similarity	NPC476794
0.7654	Intermediate Similarity	NPC65603
0.7654	Intermediate Similarity	NPC474760
0.7647	Intermediate Similarity	NPC82297
0.7647	Intermediate Similarity	NPC9868
0.764	Intermediate Similarity	NPC49420
0.7634	Intermediate Similarity	NPC475053
0.7625	Intermediate Similarity	NPC226669
0.7625	Intermediate Similarity	NPC155587
0.7625	Intermediate Similarity	NPC138408
0.7625	Intermediate Similarity	NPC193351
0.7619	Intermediate Similarity	NPC471159
0.7619	Intermediate Similarity	NPC173609
0.7619	Intermediate Similarity	NPC123880
0.7614	Intermediate Similarity	NPC166919
0.7595	Intermediate Similarity	NPC269206
0.7595	Intermediate Similarity	NPC238425
0.7595	Intermediate Similarity	NPC58956
0.7595	Intermediate Similarity	NPC474543
0.7595	Intermediate Similarity	NPC295633
0.7595	Intermediate Similarity	NPC472018
0.759	Intermediate Similarity	NPC103634
0.759	Intermediate Similarity	NPC47747
0.7586	Intermediate Similarity	NPC74139
0.7582	Intermediate Similarity	NPC272050
0.7582	Intermediate Similarity	NPC107476
0.7568	Intermediate Similarity	NPC217940
0.7564	Intermediate Similarity	NPC472955
0.7564	Intermediate Similarity	NPC69462
0.7561	Intermediate Similarity	NPC222210
0.7561	Intermediate Similarity	NPC63445
0.7561	Intermediate Similarity	NPC267231
0.7561	Intermediate Similarity	NPC299235
0.7558	Intermediate Similarity	NPC319795
0.7558	Intermediate Similarity	NPC50362
0.7558	Intermediate Similarity	NPC38468
0.7531	Intermediate Similarity	NPC474527
0.7531	Intermediate Similarity	NPC301525
0.7531	Intermediate Similarity	NPC123360
0.7531	Intermediate Similarity	NPC471726
0.7529	Intermediate Similarity	NPC170286
0.7529	Intermediate Similarity	NPC474703
0.7528	Intermediate Similarity	NPC62815
0.7528	Intermediate Similarity	NPC475748
0.75	Intermediate Similarity	NPC301477
0.75	Intermediate Similarity	NPC475902
0.75	Intermediate Similarity	NPC25684
0.75	Intermediate Similarity	NPC473151
0.75	Intermediate Similarity	NPC281949
0.75	Intermediate Similarity	NPC474758
0.7473	Intermediate Similarity	NPC38830
0.7471	Intermediate Similarity	NPC469676
0.747	Intermediate Similarity	NPC89128
0.747	Intermediate Similarity	NPC471740
0.747	Intermediate Similarity	NPC182550
0.747	Intermediate Similarity	NPC469620
0.7467	Intermediate Similarity	NPC34883
0.7444	Intermediate Similarity	NPC20713
0.7444	Intermediate Similarity	NPC475972
0.7444	Intermediate Similarity	NPC219874
0.7442	Intermediate Similarity	NPC295799
0.7442	Intermediate Similarity	NPC474359
0.7442	Intermediate Similarity	NPC149869
0.7439	Intermediate Similarity	NPC116177
0.7439	Intermediate Similarity	NPC171204
0.7439	Intermediate Similarity	NPC320630
0.7439	Intermediate Similarity	NPC97516
0.7439	Intermediate Similarity	NPC476028
0.7439	Intermediate Similarity	NPC7563
0.7439	Intermediate Similarity	NPC141789
0.7439	Intermediate Similarity	NPC84360
0.7436	Intermediate Similarity	NPC107130
0.7436	Intermediate Similarity	NPC101622
0.7436	Intermediate Similarity	NPC261398
0.7436	Intermediate Similarity	NPC477448
0.7436	Intermediate Similarity	NPC477449
0.7436	Intermediate Similarity	NPC296522
0.7436	Intermediate Similarity	NPC144511
0.7416	Intermediate Similarity	NPC151770
0.7416	Intermediate Similarity	NPC475971
0.7416	Intermediate Similarity	NPC83423
0.7412	Intermediate Similarity	NPC89555
0.7412	Intermediate Similarity	NPC474291
0.7412	Intermediate Similarity	NPC85772
0.7407	Intermediate Similarity	NPC244166
0.7407	Intermediate Similarity	NPC329852
0.7407	Intermediate Similarity	NPC60718
0.7407	Intermediate Similarity	NPC228978
0.7403	Intermediate Similarity	NPC472266
0.7386	Intermediate Similarity	NPC312561
0.7381	Intermediate Similarity	NPC195424
0.7381	Intermediate Similarity	NPC304795
0.7381	Intermediate Similarity	NPC276356
0.7381	Intermediate Similarity	NPC474739
0.7375	Intermediate Similarity	NPC167145
0.7375	Intermediate Similarity	NPC107783
0.7375	Intermediate Similarity	NPC92909
0.7356	Intermediate Similarity	NPC78089
0.7356	Intermediate Similarity	NPC197903
0.7356	Intermediate Similarity	NPC99395
0.7356	Intermediate Similarity	NPC96621
0.7349	Intermediate Similarity	NPC474056
0.7349	Intermediate Similarity	NPC93763
0.7349	Intermediate Similarity	NPC108816
0.7349	Intermediate Similarity	NPC474005
0.7349	Intermediate Similarity	NPC121200
0.7349	Intermediate Similarity	NPC472960
0.7342	Intermediate Similarity	NPC4299
0.7342	Intermediate Similarity	NPC469660
0.7333	Intermediate Similarity	NPC469718
0.7333	Intermediate Similarity	NPC312042
0.7333	Intermediate Similarity	NPC329857
0.7326	Intermediate Similarity	NPC39588
0.7326	Intermediate Similarity	NPC108045
0.7326	Intermediate Similarity	NPC52609
0.7326	Intermediate Similarity	NPC250315
0.7326	Intermediate Similarity	NPC475622
0.7326	Intermediate Similarity	NPC318468
0.7326	Intermediate Similarity	NPC1761
0.7317	Intermediate Similarity	NPC226242
0.7317	Intermediate Similarity	NPC473223
0.7308	Intermediate Similarity	NPC218477
0.7303	Intermediate Similarity	NPC477128
0.7303	Intermediate Similarity	NPC281516
0.7294	Intermediate Similarity	NPC229584
0.7294	Intermediate Similarity	NPC286229
0.7294	Intermediate Similarity	NPC42470
0.7294	Intermediate Similarity	NPC14203
0.7294	Intermediate Similarity	NPC207188
0.7294	Intermediate Similarity	NPC52861

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 NPC474341 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1647
0.2-0.3	4024
0.3-0.4	2236
0.4-0.5	702
0.5-0.6	303
0.6-0.7	52
0.7-0.8	5
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
0.7838	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD46	Approved
0.7528	Intermediate Similarity	NPD6698	Approved
0.7407	Intermediate Similarity	NPD8039	Approved
0.7222	Intermediate Similarity	NPD1695	Approved
0.7209	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1694	Approved
0.6932	Remote Similarity	NPD5362	Discontinued
0.6932	Remote Similarity	NPD7154	Phase 3
0.6848	Remote Similarity	NPD6101	Approved
0.6848	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5209	Approved
0.6809	Remote Similarity	NPD5778	Approved
0.6809	Remote Similarity	NPD5779	Approved
0.6705	Remote Similarity	NPD5369	Approved
0.6703	Remote Similarity	NPD6422	Discontinued
0.6703	Remote Similarity	NPD5786	Approved
0.6702	Remote Similarity	NPD6411	Approved
0.6629	Remote Similarity	NPD4269	Approved
0.6629	Remote Similarity	NPD4270	Approved
0.6629	Remote Similarity	NPD6435	Approved
0.6598	Remote Similarity	NPD7839	Suspended
0.6596	Remote Similarity	NPD5785	Approved
0.6593	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4822	Approved
0.6591	Remote Similarity	NPD4819	Approved
0.6591	Remote Similarity	NPD4821	Approved
0.6591	Remote Similarity	NPD4820	Approved
0.6552	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7983	Approved
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD7521	Approved
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6522	Remote Similarity	NPD6409	Approved
0.6495	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3573	Approved
0.6421	Remote Similarity	NPD7838	Discovery
0.642	Remote Similarity	NPD7331	Phase 2
0.6413	Remote Similarity	NPD5363	Approved
0.6404	Remote Similarity	NPD5368	Approved
0.6404	Remote Similarity	NPD4252	Approved
0.6383	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6903	Approved
0.6375	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5331	Approved
0.6374	Remote Similarity	NPD5332	Approved
0.6364	Remote Similarity	NPD4271	Approved
0.6364	Remote Similarity	NPD4268	Approved
0.6354	Remote Similarity	NPD5693	Phase 1
0.6333	Remote Similarity	NPD4790	Discontinued
0.6316	Remote Similarity	NPD6051	Approved
0.6301	Remote Similarity	NPD6927	Phase 3
0.63	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD6008	Approved
0.6238	Remote Similarity	NPD6648	Approved
0.6211	Remote Similarity	NPD6672	Approved
0.6211	Remote Similarity	NPD5737	Approved
0.6204	Remote Similarity	NPD6053	Discontinued
0.619	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5344	Discontinued
0.617	Remote Similarity	NPD4249	Approved
0.617	Remote Similarity	NPD6098	Approved
0.6168	Remote Similarity	NPD6371	Approved
0.6139	Remote Similarity	NPD7638	Approved
0.6139	Remote Similarity	NPD4225	Approved
0.6132	Remote Similarity	NPD6686	Approved
0.6126	Remote Similarity	NPD7115	Discovery
0.6111	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4251	Approved
0.6105	Remote Similarity	NPD4250	Approved
0.6098	Remote Similarity	NPD7341	Phase 2
0.6087	Remote Similarity	NPD3667	Approved
0.6081	Remote Similarity	NPD28	Approved
0.6081	Remote Similarity	NPD29	Approved
0.6078	Remote Similarity	NPD7639	Approved
0.6078	Remote Similarity	NPD7640	Approved
0.6067	Remote Similarity	NPD4756	Discovery
0.6061	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7748	Approved
0.6061	Remote Similarity	NPD7900	Approved
0.6061	Remote Similarity	NPD5282	Discontinued
0.6042	Remote Similarity	NPD5208	Approved
0.6038	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5695	Phase 3
0.5979	Remote Similarity	NPD6080	Approved
0.5979	Remote Similarity	NPD6904	Approved
0.5979	Remote Similarity	NPD6673	Approved
0.5976	Remote Similarity	NPD3197	Phase 1
0.5957	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD3668	Phase 3
0.5957	Remote Similarity	NPD4786	Approved
0.5941	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD368	Approved
0.5921	Remote Similarity	NPD3172	Approved
0.5918	Remote Similarity	NPD5207	Approved
0.5918	Remote Similarity	NPD3673	Approved
0.5918	Remote Similarity	NPD5692	Phase 3
0.5918	Remote Similarity	NPD3672	Approved
0.5913	Remote Similarity	NPD8516	Approved
0.5913	Remote Similarity	NPD8517	Approved
0.5913	Remote Similarity	NPD8515	Approved
0.5913	Remote Similarity	NPD8513	Phase 3
0.59	Remote Similarity	NPD6001	Approved
0.5882	Remote Similarity	NPD6083	Phase 2
0.5882	Remote Similarity	NPD7902	Approved
0.5882	Remote Similarity	NPD6084	Phase 2
0.5872	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5694	Approved
0.5859	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7515	Phase 2
0.5859	Remote Similarity	NPD6050	Approved
0.5844	Remote Similarity	NPD3196	Approved
0.5844	Remote Similarity	NPD4266	Approved
0.5844	Remote Similarity	NPD3195	Phase 2
0.5844	Remote Similarity	NPD3194	Approved
0.5833	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5696	Approved
0.5818	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5370	Suspended
0.5802	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6675	Approved
0.5794	Remote Similarity	NPD7128	Approved
0.5794	Remote Similarity	NPD5739	Approved
0.5794	Remote Similarity	NPD6402	Approved
0.5789	Remote Similarity	NPD3133	Approved
0.5789	Remote Similarity	NPD3665	Phase 1
0.5789	Remote Similarity	NPD3666	Approved
0.5765	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5697	Approved
0.5741	Remote Similarity	NPD5701	Approved
0.5729	Remote Similarity	NPD1696	Phase 3
0.5727	Remote Similarity	NPD2067	Discontinued
0.5714	Remote Similarity	NPD8273	Phase 1
0.5701	Remote Similarity	NPD5909	Discontinued
0.5699	Remote Similarity	NPD4695	Discontinued
0.5688	Remote Similarity	NPD6881	Approved
0.5688	Remote Similarity	NPD6899	Approved
0.5688	Remote Similarity	NPD6011	Approved
0.5688	Remote Similarity	NPD7320	Approved
0.5678	Remote Similarity	NPD7642	Approved
0.5678	Remote Similarity	NPD7829	Approved
0.5678	Remote Similarity	NPD7830	Approved
0.5676	Remote Similarity	NPD5343	Approved
0.567	Remote Similarity	NPD4519	Discontinued
0.567	Remote Similarity	NPD4623	Approved
0.567	Remote Similarity	NPD5279	Phase 3
0.567	Remote Similarity	NPD3618	Phase 1
0.5667	Remote Similarity	NPD8074	Phase 3
0.5657	Remote Similarity	NPD5328	Approved
0.5636	Remote Similarity	NPD6372	Approved
0.5636	Remote Similarity	NPD6014	Approved
0.5636	Remote Similarity	NPD6013	Approved
0.5636	Remote Similarity	NPD6012	Approved
0.5636	Remote Similarity	NPD6373	Approved
0.5631	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD1989	Approved
0.5616	Remote Similarity	NPD3174	Discontinued

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