NPASS Compound

Structure

NPC469678 OpenBabel07101719242D 22 24 0 0 1 0 0 0 0 0999 V2000 2.1533 -3.1975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5933 -4.0288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5259 2.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0677 -0.3976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7233 -2.1690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1911 1.7284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3256 1.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8812 0.9952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2554 -1.6438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1691 0.0794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3747 -1.2617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5480 -2.2657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1133 -3.1975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1438 1.6099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5933 -2.3661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2028 -1.4891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7476 -1.3267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8221 0.4957 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9162 -0.8467 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8404 -0.4641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6246 -0.9362 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 14 1 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 8 14 2 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 15 16 1 0 0 0 0 16 19 1 1 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 20 1 6 0 0 0 18 22 1 0 0 0 0 19 4 1 1 0 0 0 20 5 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	3.929
LogD:	3.753
LogS:	-4.524
# Rotatable Bonds:	1
TPSA:	29.6
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	4.83
Fsp3:	0.75
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:	-4.746
MDCK Permeability:	2.638430851220619e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.316

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.169
Plasma Protein Binding (PPB):	96.78555297851562%
Volume Distribution (VD):	1.715
Pgp-substrate:	2.7573561668395996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.523
CYP2C19-inhibitor:	0.245
CYP2C19-substrate:	0.934
CYP2C9-inhibitor:	0.23
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.652
CYP3A4-substrate:	0.722

ADMET: Excretion

Clearance (CL):	4.953
Half-life (T1/2):	0.206

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.493
Drug-inuced Liver Injury (DILI):	0.157
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.152
Maximum Recommended Daily Dose:	0.645
Skin Sensitization:	0.569
Carcinogencity:	0.793
Eye Corrosion:	0.03
Eye Irritation:	0.413
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC469678

Natural Product ID:	NPC469678
*Common Name:**	UOOSOJLICIHJEA-SRPFAFIASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UOOSOJLICIHJEA-SRPFAFIASA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13(2)15-12-17(21)19(4)10-8-14(3)6-7-18-20(5,22-18)11-9-16(15)19/h8,12-13,16,18H,6-7,9-11H2,1-5H3/b14-8-/t16-,18-,19+,20-/m1/s1
SMILES:	CC1=CCC2(C(CCC3(C(O3)CC1)C)C(=CC2=O)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098222
PubChem CID:	46833411
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane diterpenoids

*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
NPO32701	Eunicea	Genus	Plexauridae	Eukaryota	n.a.	southwestern Caribbean	n.a.	PMID[20384296]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>=	100000.0	nM	PMID[572955]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	<=	50.0	%	PMID[572955]

☑ 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 NPC469678 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	206
0.1-0.2	1704
0.2-0.3	8255
0.3-0.4	15950
0.4-0.5	7638
0.5-0.6	6240
0.6-0.7	2474
0.7-0.8	205
0.8-0.85	13
0.85-0.9	7
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469669
1.0	High Similarity	NPC475771
0.9571	High Similarity	NPC469691
0.9571	High Similarity	NPC167049
0.9429	High Similarity	NPC107783
0.9429	High Similarity	NPC92909
0.9041	High Similarity	NPC226242
0.8553	High Similarity	NPC474056
0.8481	Intermediate Similarity	NPC108045
0.8481	Intermediate Similarity	NPC475622
0.8472	Intermediate Similarity	NPC477448
0.8472	Intermediate Similarity	NPC477449
0.8375	Intermediate Similarity	NPC475796
0.8205	Intermediate Similarity	NPC469608
0.8171	Intermediate Similarity	NPC474045
0.8171	Intermediate Similarity	NPC261253
0.8125	Intermediate Similarity	NPC145963
0.8082	Intermediate Similarity	NPC469679
0.8077	Intermediate Similarity	NPC207186
0.8028	Intermediate Similarity	NPC140233
0.8028	Intermediate Similarity	NPC287744
0.7975	Intermediate Similarity	NPC476177
0.7975	Intermediate Similarity	NPC469690
0.7973	Intermediate Similarity	NPC261398
0.7952	Intermediate Similarity	NPC469676
0.7949	Intermediate Similarity	NPC195785
0.7949	Intermediate Similarity	NPC15975
0.7922	Intermediate Similarity	NPC474011
0.7838	Intermediate Similarity	NPC469688
0.7831	Intermediate Similarity	NPC96621
0.7821	Intermediate Similarity	NPC215481
0.7821	Intermediate Similarity	NPC469646
0.7791	Intermediate Similarity	NPC49946
0.7791	Intermediate Similarity	NPC306168
0.7778	Intermediate Similarity	NPC255580
0.7778	Intermediate Similarity	NPC39411
0.775	Intermediate Similarity	NPC469620
0.7746	Intermediate Similarity	NPC228574
0.7746	Intermediate Similarity	NPC294304
0.7733	Intermediate Similarity	NPC469677
0.7714	Intermediate Similarity	NPC259261
0.7711	Intermediate Similarity	NPC475100
0.7692	Intermediate Similarity	NPC475861
0.7692	Intermediate Similarity	NPC216791
0.7692	Intermediate Similarity	NPC251435
0.7674	Intermediate Similarity	NPC170775
0.7671	Intermediate Similarity	NPC474329
0.7671	Intermediate Similarity	NPC474304
0.7662	Intermediate Similarity	NPC470237
0.7654	Intermediate Similarity	NPC304795
0.7632	Intermediate Similarity	NPC475310
0.7619	Intermediate Similarity	NPC323765
0.7614	Intermediate Similarity	NPC37816
0.7606	Intermediate Similarity	NPC25853
0.7595	Intermediate Similarity	NPC271070
0.759	Intermediate Similarity	NPC193198
0.7571	Intermediate Similarity	NPC266295
0.7571	Intermediate Similarity	NPC94991
0.7561	Intermediate Similarity	NPC475665
0.7561	Intermediate Similarity	NPC136150
0.7556	Intermediate Similarity	NPC477354
0.7534	Intermediate Similarity	NPC473902
0.7531	Intermediate Similarity	NPC229204
0.7531	Intermediate Similarity	NPC617
0.7531	Intermediate Similarity	NPC261125
0.7531	Intermediate Similarity	NPC181195
0.7529	Intermediate Similarity	NPC195640
0.75	Intermediate Similarity	NPC22301
0.75	Intermediate Similarity	NPC238197
0.75	Intermediate Similarity	NPC144511
0.75	Intermediate Similarity	NPC276769
0.75	Intermediate Similarity	NPC296522
0.75	Intermediate Similarity	NPC97322
0.75	Intermediate Similarity	NPC190442
0.75	Intermediate Similarity	NPC186109
0.75	Intermediate Similarity	NPC262870
0.75	Intermediate Similarity	NPC473246
0.75	Intermediate Similarity	NPC86917
0.75	Intermediate Similarity	NPC214043
0.75	Intermediate Similarity	NPC85774
0.7473	Intermediate Similarity	NPC151488
0.747	Intermediate Similarity	NPC256750
0.747	Intermediate Similarity	NPC20262
0.7468	Intermediate Similarity	NPC114236
0.7468	Intermediate Similarity	NPC474419
0.7468	Intermediate Similarity	NPC77501
0.7439	Intermediate Similarity	NPC74673
0.7439	Intermediate Similarity	NPC276356
0.7439	Intermediate Similarity	NPC69271
0.7439	Intermediate Similarity	NPC47747
0.7439	Intermediate Similarity	NPC302426
0.7429	Intermediate Similarity	NPC55004
0.7429	Intermediate Similarity	NPC267626
0.7429	Intermediate Similarity	NPC49575
0.7416	Intermediate Similarity	NPC229976
0.7416	Intermediate Similarity	NPC202824
0.7416	Intermediate Similarity	NPC477361
0.7412	Intermediate Similarity	NPC476678
0.7412	Intermediate Similarity	NPC179006
0.7412	Intermediate Similarity	NPC474853
0.7412	Intermediate Similarity	NPC78089
0.7412	Intermediate Similarity	NPC33570
0.7412	Intermediate Similarity	NPC300985
0.7412	Intermediate Similarity	NPC21471
0.7412	Intermediate Similarity	NPC161957
0.7407	Intermediate Similarity	NPC23778
0.7407	Intermediate Similarity	NPC253749
0.7407	Intermediate Similarity	NPC299235
0.7407	Intermediate Similarity	NPC128276
0.7407	Intermediate Similarity	NPC471220
0.7407	Intermediate Similarity	NPC469996
0.7403	Intermediate Similarity	NPC280256
0.7391	Intermediate Similarity	NPC471582
0.7391	Intermediate Similarity	NPC477355
0.7381	Intermediate Similarity	NPC215294
0.7381	Intermediate Similarity	NPC470047
0.7381	Intermediate Similarity	NPC470046
0.7381	Intermediate Similarity	NPC53867
0.7375	Intermediate Similarity	NPC472967
0.7375	Intermediate Similarity	NPC266159
0.7356	Intermediate Similarity	NPC476707
0.7356	Intermediate Similarity	NPC477710
0.7356	Intermediate Similarity	NPC476706
0.7349	Intermediate Similarity	NPC141810
0.7342	Intermediate Similarity	NPC469641
0.7342	Intermediate Similarity	NPC469643
0.7333	Intermediate Similarity	NPC174051
0.7333	Intermediate Similarity	NPC67831
0.7326	Intermediate Similarity	NPC470051
0.7326	Intermediate Similarity	NPC474732
0.7326	Intermediate Similarity	NPC70555
0.7326	Intermediate Similarity	NPC474778
0.7326	Intermediate Similarity	NPC474733
0.7326	Intermediate Similarity	NPC104961
0.7326	Intermediate Similarity	NPC107787
0.7326	Intermediate Similarity	NPC145879
0.7326	Intermediate Similarity	NPC470050
0.7326	Intermediate Similarity	NPC70422
0.7326	Intermediate Similarity	NPC31564
0.7324	Intermediate Similarity	NPC30215
0.7317	Intermediate Similarity	NPC80999
0.7317	Intermediate Similarity	NPC136033
0.7317	Intermediate Similarity	NPC471740
0.7312	Intermediate Similarity	NPC112167
0.7303	Intermediate Similarity	NPC221282
0.7303	Intermediate Similarity	NPC218301
0.7303	Intermediate Similarity	NPC290651
0.7294	Intermediate Similarity	NPC227064
0.7294	Intermediate Similarity	NPC58841
0.7294	Intermediate Similarity	NPC161423
0.7294	Intermediate Similarity	NPC329043
0.7294	Intermediate Similarity	NPC165287
0.7294	Intermediate Similarity	NPC100391
0.7294	Intermediate Similarity	NPC115786
0.7294	Intermediate Similarity	NPC321187
0.7294	Intermediate Similarity	NPC90446
0.7294	Intermediate Similarity	NPC237712
0.7284	Intermediate Similarity	NPC211279
0.7284	Intermediate Similarity	NPC197659
0.7284	Intermediate Similarity	NPC57744
0.7284	Intermediate Similarity	NPC122264
0.7284	Intermediate Similarity	NPC472300
0.7284	Intermediate Similarity	NPC476264
0.7284	Intermediate Similarity	NPC476325
0.7273	Intermediate Similarity	NPC4986
0.7273	Intermediate Similarity	NPC61702
0.7273	Intermediate Similarity	NPC119416
0.7273	Intermediate Similarity	NPC162867
0.7262	Intermediate Similarity	NPC35556
0.7262	Intermediate Similarity	NPC193347
0.7262	Intermediate Similarity	NPC142683
0.726	Intermediate Similarity	NPC475795
0.725	Intermediate Similarity	NPC113639
0.7241	Intermediate Similarity	NPC469322
0.7241	Intermediate Similarity	NPC58063
0.7241	Intermediate Similarity	NPC38885
0.7241	Intermediate Similarity	NPC471739
0.7241	Intermediate Similarity	NPC475740
0.7241	Intermediate Similarity	NPC136548
0.7234	Intermediate Similarity	NPC477356
0.7229	Intermediate Similarity	NPC472948
0.7229	Intermediate Similarity	NPC45495
0.7222	Intermediate Similarity	NPC125180
0.7215	Intermediate Similarity	NPC472956
0.7215	Intermediate Similarity	NPC300940
0.7209	Intermediate Similarity	NPC474547
0.7209	Intermediate Similarity	NPC470223
0.7209	Intermediate Similarity	NPC470574
0.7209	Intermediate Similarity	NPC202868
0.7209	Intermediate Similarity	NPC189311
0.7209	Intermediate Similarity	NPC470048
0.7209	Intermediate Similarity	NPC469948
0.7195	Intermediate Similarity	NPC474341
0.7195	Intermediate Similarity	NPC478247
0.7195	Intermediate Similarity	NPC321180
0.7195	Intermediate Similarity	NPC474005
0.7195	Intermediate Similarity	NPC475994
0.7195	Intermediate Similarity	NPC478246
0.7195	Intermediate Similarity	NPC35574
0.7191	Intermediate Similarity	NPC253144

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 NPC469678 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	2399
0.2-0.3	4099
0.3-0.4	1715
0.4-0.5	405
0.5-0.6	245
0.6-0.7	90
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
0.7529	Intermediate Similarity	NPD7334	Approved
0.7529	Intermediate Similarity	NPD5330	Approved
0.7529	Intermediate Similarity	NPD6409	Approved
0.7529	Intermediate Similarity	NPD7521	Approved
0.7529	Intermediate Similarity	NPD6684	Approved
0.7529	Intermediate Similarity	NPD7146	Approved
0.7356	Intermediate Similarity	NPD6903	Approved
0.7356	Intermediate Similarity	NPD6672	Approved
0.7356	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5737	Approved
0.7326	Intermediate Similarity	NPD5279	Phase 3
0.7294	Intermediate Similarity	NPD3665	Phase 1
0.7294	Intermediate Similarity	NPD3133	Approved
0.7294	Intermediate Similarity	NPD3666	Approved
0.7273	Intermediate Similarity	NPD1695	Approved
0.7262	Intermediate Similarity	NPD4223	Phase 3
0.7262	Intermediate Similarity	NPD4221	Approved
0.7159	Intermediate Similarity	NPD5208	Approved
0.7143	Intermediate Similarity	NPD5282	Discontinued
0.7126	Intermediate Similarity	NPD3618	Phase 1
0.7093	Intermediate Similarity	NPD4197	Approved
0.7093	Intermediate Similarity	NPD4786	Approved
0.7079	Intermediate Similarity	NPD6673	Approved
0.7079	Intermediate Similarity	NPD4753	Phase 2
0.7079	Intermediate Similarity	NPD6080	Approved
0.7079	Intermediate Similarity	NPD5328	Approved
0.7079	Intermediate Similarity	NPD6904	Approved
0.7065	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5695	Phase 3
0.7059	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5209	Approved
0.7059	Intermediate Similarity	NPD3667	Approved
0.7033	Intermediate Similarity	NPD4202	Approved
0.7011	Intermediate Similarity	NPD5329	Approved
0.7011	Intermediate Similarity	NPD1694	Approved
0.7	Intermediate Similarity	NPD5692	Phase 3
0.7	Intermediate Similarity	NPD5207	Approved
0.6988	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4747	Approved
0.6957	Remote Similarity	NPD6001	Approved
0.6939	Remote Similarity	NPD6008	Approved
0.6932	Remote Similarity	NPD4694	Approved
0.6932	Remote Similarity	NPD4138	Approved
0.6932	Remote Similarity	NPD4689	Approved
0.6932	Remote Similarity	NPD4693	Phase 3
0.6932	Remote Similarity	NPD6098	Approved
0.6932	Remote Similarity	NPD4690	Approved
0.6932	Remote Similarity	NPD5280	Approved
0.6932	Remote Similarity	NPD4688	Approved
0.6932	Remote Similarity	NPD5690	Phase 2
0.6932	Remote Similarity	NPD5205	Approved
0.6923	Remote Similarity	NPD5693	Phase 1
0.6923	Remote Similarity	NPD5694	Approved
0.6923	Remote Similarity	NPD6050	Approved
0.6923	Remote Similarity	NPD6079	Approved
0.6915	Remote Similarity	NPD6083	Phase 2
0.6915	Remote Similarity	NPD6084	Phase 2
0.6897	Remote Similarity	NPD3668	Phase 3
0.6883	Remote Similarity	NPD7331	Phase 2
0.6875	Remote Similarity	NPD5276	Approved
0.6848	Remote Similarity	NPD6399	Phase 3
0.6842	Remote Similarity	NPD5696	Approved
0.6835	Remote Similarity	NPD4137	Phase 3
0.6782	Remote Similarity	NPD5362	Discontinued
0.6778	Remote Similarity	NPD4518	Approved
0.6753	Remote Similarity	NPD7341	Phase 2
0.675	Remote Similarity	NPD4691	Approved
0.6744	Remote Similarity	NPD5369	Approved
0.6742	Remote Similarity	NPD4519	Discontinued
0.6742	Remote Similarity	NPD4623	Approved
0.6737	Remote Similarity	NPD4755	Approved
0.6707	Remote Similarity	NPD4687	Approved
0.6707	Remote Similarity	NPD5733	Approved
0.6702	Remote Similarity	NPD4629	Approved
0.6702	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6632	Remote Similarity	NPD5221	Approved
0.6632	Remote Similarity	NPD5222	Approved
0.6632	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4697	Phase 3
0.663	Remote Similarity	NPD4096	Approved
0.663	Remote Similarity	NPD5785	Approved
0.6629	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4695	Discontinued
0.66	Remote Similarity	NPD6402	Approved
0.66	Remote Similarity	NPD7128	Approved
0.66	Remote Similarity	NPD6675	Approved
0.66	Remote Similarity	NPD5739	Approved
0.6598	Remote Similarity	NPD5285	Approved
0.6598	Remote Similarity	NPD4700	Approved
0.6598	Remote Similarity	NPD5286	Approved
0.6598	Remote Similarity	NPD4696	Approved
0.6596	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7900	Approved
0.6596	Remote Similarity	NPD7748	Approved
0.6591	Remote Similarity	NPD7154	Phase 3
0.6591	Remote Similarity	NPD4788	Approved
0.6588	Remote Similarity	NPD3617	Approved
0.6562	Remote Similarity	NPD5959	Approved
0.6562	Remote Similarity	NPD5173	Approved
0.6559	Remote Similarity	NPD5284	Approved
0.6559	Remote Similarity	NPD5281	Approved
0.6556	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5697	Approved
0.6535	Remote Similarity	NPD5701	Approved
0.6531	Remote Similarity	NPD5223	Approved
0.6526	Remote Similarity	NPD5654	Approved
0.6512	Remote Similarity	NPD4195	Approved
0.6506	Remote Similarity	NPD6924	Approved
0.6506	Remote Similarity	NPD4058	Approved
0.6506	Remote Similarity	NPD6926	Approved
0.6505	Remote Similarity	NPD6371	Approved
0.6489	Remote Similarity	NPD5133	Approved
0.6471	Remote Similarity	NPD6899	Approved
0.6471	Remote Similarity	NPD7320	Approved
0.6471	Remote Similarity	NPD6881	Approved
0.6471	Remote Similarity	NPD6011	Approved
0.6465	Remote Similarity	NPD4633	Approved
0.6465	Remote Similarity	NPD5225	Approved
0.6465	Remote Similarity	NPD5224	Approved
0.6465	Remote Similarity	NPD5226	Approved
0.6465	Remote Similarity	NPD5211	Phase 2
0.6444	Remote Similarity	NPD5363	Approved
0.6437	Remote Similarity	NPD5368	Approved
0.6429	Remote Similarity	NPD8039	Approved
0.6408	Remote Similarity	NPD6373	Approved
0.6408	Remote Similarity	NPD6012	Approved
0.6408	Remote Similarity	NPD6014	Approved
0.6408	Remote Similarity	NPD6013	Approved
0.6408	Remote Similarity	NPD6372	Approved
0.64	Remote Similarity	NPD5174	Approved
0.64	Remote Similarity	NPD4754	Approved
0.64	Remote Similarity	NPD5175	Approved
0.6392	Remote Similarity	NPD7902	Approved
0.6383	Remote Similarity	NPD7515	Phase 2
0.6364	Remote Similarity	NPD4139	Approved
0.6364	Remote Similarity	NPD4692	Approved
0.6353	Remote Similarity	NPD6933	Approved
0.6346	Remote Similarity	NPD7290	Approved
0.6346	Remote Similarity	NPD7102	Approved
0.6346	Remote Similarity	NPD6883	Approved
0.6337	Remote Similarity	NPD5141	Approved
0.6296	Remote Similarity	NPD7115	Discovery
0.6296	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4270	Approved
0.6292	Remote Similarity	NPD4269	Approved
0.6292	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6649	Approved
0.6286	Remote Similarity	NPD6847	Approved
0.6286	Remote Similarity	NPD6869	Approved
0.6286	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6650	Approved
0.6286	Remote Similarity	NPD8130	Phase 1
0.6286	Remote Similarity	NPD6617	Approved
0.6277	Remote Similarity	NPD6698	Approved
0.6277	Remote Similarity	NPD46	Approved
0.6275	Remote Similarity	NPD4768	Approved
0.6275	Remote Similarity	NPD4767	Approved
0.6264	Remote Similarity	NPD1696	Phase 3
0.625	Remote Similarity	NPD7509	Discontinued
0.625	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6052	Approved
0.6226	Remote Similarity	NPD8297	Approved
0.6226	Remote Similarity	NPD6882	Approved
0.6222	Remote Similarity	NPD6695	Phase 3
0.6214	Remote Similarity	NPD6412	Phase 2
0.6211	Remote Similarity	NPD6411	Approved
0.6196	Remote Similarity	NPD5786	Approved
0.6184	Remote Similarity	NPD287	Approved
0.618	Remote Similarity	NPD857	Phase 3
0.617	Remote Similarity	NPD6051	Approved
0.6162	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD5128	Approved
0.6154	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4730	Approved
0.6154	Remote Similarity	NPD4729	Approved
0.61	Remote Similarity	NPD7640	Approved
0.61	Remote Similarity	NPD7639	Approved
0.6087	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6930	Phase 2
0.6067	Remote Similarity	NPD4819	Approved
0.6067	Remote Similarity	NPD7525	Registered
0.6067	Remote Similarity	NPD4820	Approved
0.6067	Remote Similarity	NPD6931	Approved
0.6067	Remote Similarity	NPD4252	Approved
0.6067	Remote Similarity	NPD4822	Approved
0.6067	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4821	Approved
0.6058	Remote Similarity	NPD6614	Approved
0.6058	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6274	Approved
0.6047	Remote Similarity	NPD6942	Approved
0.6047	Remote Similarity	NPD7339	Approved
0.6044	Remote Similarity	NPD5332	Approved
0.6044	Remote Similarity	NPD5331	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