NPASS Compound

Structure

NPC222244 OpenBabel07101719152D 35 36 0 0 1 0 0 0 0 0999 V2000 4.4347 5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2614 4.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5327 2.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0327 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4817 4.0267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4328 4.3357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2738 3.0485 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 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 24 2 0 0 0 0 14 26 1 0 0 0 0 16 29 1 0 0 0 0 17 25 2 0 0 0 0 17 28 1 0 0 0 0 18 24 1 0 0 0 0 18 33 1 0 0 0 0 19 25 1 0 0 0 0 19 34 1 0 0 0 0 21 26 2 0 0 0 0 22 30 2 0 0 0 0 22 33 1 0 0 0 0 23 31 2 0 0 0 0 23 34 1 0 0 0 0 25 27 1 0 0 0 0 26 29 1 0 0 0 0 27 15 1 1 0 0 0 27 35 1 0 0 0 0 28 32 2 0 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.3
Volume:	527.313
LogP:	5.56
LogD:	4.769
LogS:	-4.468
# Rotatable Bonds:	14
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.25
Synthetic Accessibility Score:	3.654
Fsp3:	0.586
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.928
MDCK Permeability:	2.4536033379263245e-05
Pgp-inhibitor:	0.668
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.831
30% Bioavailability (F30%):	0.249

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.564
Plasma Protein Binding (PPB):	91.49354553222656%
Volume Distribution (VD):	2.001
Pgp-substrate:	2.659219264984131%

ADMET: Metabolism

CYP1A2-inhibitor:	0.154
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.283
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.291
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.585
CYP2D6-substrate:	0.628
CYP3A4-inhibitor:	0.481
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	2.978
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.413
Drug-inuced Liver Injury (DILI):	0.841
AMES Toxicity:	0.186
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.373
Carcinogencity:	0.346
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.21

Download Data

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

Natural Product: NPC222244

Natural Product ID:	NPC222244
*Common Name:**	(Z)-Neomanoalide 24,25-Diacetate
IUPAC Name:	[(2R)-2-[(2Z,6E)-3-(acetyloxymethyl)-7-methyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,6-dienyl]-5-oxo-2H-furan-3-yl]methyl acetate
Synonyms:	(Z)-Neomanoalide 24,25-Diacetate
Standard InCHIKey:	HUOUTXIIOOBRPE-VWPGDHEVSA-N
Standard InCHI:	InChI=1S/C29H42O6/c1-20(12-14-26-21(2)10-8-16-29(26,5)6)9-7-11-24(18-33-22(3)30)13-15-27-25(17-28(32)35-27)19-34-23(4)31/h9,13,17,27H,7-8,10-12,14-16,18-19H2,1-6H3/b20-9+,24-13-/t27-/m1/s1
SMILES:	C/C(=CCC/C(=C/C[C@@H]1C(=CC(=O)O1)COC(=O)C)/COC(=O)C)/CCC1=C(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520505
PubChem CID:	6479921
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33331	brachiaster sp.	Species	n.a.	n.a.	n.a.	Thai	n.a.	PMID[15497961]

☑ 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
MIC	1
Others	3

Activity Type	# Activity
Cell Line	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	5990.0	nM	PMID[492583]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	80.0	%	PMID[492583]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	80.0	%	PMID[492583]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	80.0	%	PMID[492583]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	26000.0	nM	PMID[492583]

☑ 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 NPC222244 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	178
0.1-0.2	1407
0.2-0.3	6762
0.3-0.4	17613
0.4-0.5	8301
0.5-0.6	6013
0.6-0.7	2133
0.7-0.8	259
0.8-0.85	16
0.85-0.9	9
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC16349
0.9306	High Similarity	NPC474816
0.9306	High Similarity	NPC209135
0.9178	High Similarity	NPC471299
0.9167	High Similarity	NPC262747
0.8933	High Similarity	NPC475944
0.8816	High Similarity	NPC323251
0.8732	High Similarity	NPC257618
0.8701	High Similarity	NPC12283
0.8701	High Similarity	NPC474193
0.8701	High Similarity	NPC474809
0.8611	High Similarity	NPC476489
0.8611	High Similarity	NPC476490
0.8592	High Similarity	NPC469660
0.859	High Similarity	NPC474865
0.859	High Similarity	NPC126518
0.859	High Similarity	NPC31086
0.8571	High Similarity	NPC471218
0.8514	High Similarity	NPC27205
0.8481	Intermediate Similarity	NPC163606
0.8429	Intermediate Similarity	NPC472266
0.8333	Intermediate Similarity	NPC471298
0.8272	Intermediate Similarity	NPC476600
0.8228	Intermediate Similarity	NPC42476
0.8228	Intermediate Similarity	NPC471297
0.8158	Intermediate Similarity	NPC473756
0.8101	Intermediate Similarity	NPC324170
0.8056	Intermediate Similarity	NPC276290
0.8052	Intermediate Similarity	NPC471220
0.8052	Intermediate Similarity	NPC184737
0.8	Intermediate Similarity	NPC477204
0.8	Intermediate Similarity	NPC226066
0.8	Intermediate Similarity	NPC472377
0.8	Intermediate Similarity	NPC474758
0.8	Intermediate Similarity	NPC193198
0.7952	Intermediate Similarity	NPC474629
0.7952	Intermediate Similarity	NPC472378
0.7917	Intermediate Similarity	NPC203335
0.7901	Intermediate Similarity	NPC471301
0.7901	Intermediate Similarity	NPC96055
0.7887	Intermediate Similarity	NPC182794
0.7848	Intermediate Similarity	NPC268827
0.7805	Intermediate Similarity	NPC474013
0.7805	Intermediate Similarity	NPC472442
0.7805	Intermediate Similarity	NPC474860
0.7805	Intermediate Similarity	NPC471300
0.7792	Intermediate Similarity	NPC477202
0.7791	Intermediate Similarity	NPC476598
0.7791	Intermediate Similarity	NPC476597
0.7778	Intermediate Similarity	NPC311070
0.7778	Intermediate Similarity	NPC472440
0.7778	Intermediate Similarity	NPC477124
0.7765	Intermediate Similarity	NPC78973
0.775	Intermediate Similarity	NPC471325
0.775	Intermediate Similarity	NPC25554
0.7746	Intermediate Similarity	NPC329698
0.7738	Intermediate Similarity	NPC93411
0.7711	Intermediate Similarity	NPC131813
0.7711	Intermediate Similarity	NPC220478
0.7703	Intermediate Similarity	NPC151481
0.7703	Intermediate Similarity	NPC101622
0.7701	Intermediate Similarity	NPC298973
0.7701	Intermediate Similarity	NPC104925
0.7701	Intermediate Similarity	NPC476596
0.7692	Intermediate Similarity	NPC189206
0.7692	Intermediate Similarity	NPC187568
0.7692	Intermediate Similarity	NPC41780
0.7692	Intermediate Similarity	NPC477203
0.7683	Intermediate Similarity	NPC471302
0.7647	Intermediate Similarity	NPC470734
0.7647	Intermediate Similarity	NPC177141
0.7639	Intermediate Similarity	NPC282760
0.7619	Intermediate Similarity	NPC312561
0.7606	Intermediate Similarity	NPC217940
0.76	Intermediate Similarity	NPC37929
0.76	Intermediate Similarity	NPC4299
0.76	Intermediate Similarity	NPC64234
0.7595	Intermediate Similarity	NPC474005
0.759	Intermediate Similarity	NPC189311
0.759	Intermediate Similarity	NPC471795
0.7571	Intermediate Similarity	NPC19241
0.7564	Intermediate Similarity	NPC469880
0.7564	Intermediate Similarity	NPC4509
0.7558	Intermediate Similarity	NPC232426
0.7558	Intermediate Similarity	NPC281942
0.7534	Intermediate Similarity	NPC248125
0.7534	Intermediate Similarity	NPC116013
0.7534	Intermediate Similarity	NPC185587
0.7532	Intermediate Similarity	NPC117746
0.7532	Intermediate Similarity	NPC294434
0.7532	Intermediate Similarity	NPC15499
0.7532	Intermediate Similarity	NPC259599
0.7529	Intermediate Similarity	NPC226863
0.7529	Intermediate Similarity	NPC472810
0.7529	Intermediate Similarity	NPC472809
0.7529	Intermediate Similarity	NPC471956
0.75	Intermediate Similarity	NPC178277
0.75	Intermediate Similarity	NPC471219
0.75	Intermediate Similarity	NPC477084
0.75	Intermediate Similarity	NPC181587
0.75	Intermediate Similarity	NPC242767
0.75	Intermediate Similarity	NPC96663
0.75	Intermediate Similarity	NPC469697
0.75	Intermediate Similarity	NPC139712
0.7471	Intermediate Similarity	NPC141831
0.747	Intermediate Similarity	NPC149869
0.747	Intermediate Similarity	NPC160517
0.747	Intermediate Similarity	NPC318515
0.747	Intermediate Similarity	NPC474359
0.747	Intermediate Similarity	NPC186155
0.747	Intermediate Similarity	NPC78673
0.7468	Intermediate Similarity	NPC54996
0.7468	Intermediate Similarity	NPC473825
0.7468	Intermediate Similarity	NPC471225
0.7467	Intermediate Similarity	NPC232812
0.7439	Intermediate Similarity	NPC471296
0.7439	Intermediate Similarity	NPC200513
0.7439	Intermediate Similarity	NPC268122
0.7439	Intermediate Similarity	NPC256112
0.7439	Intermediate Similarity	NPC35556
0.7436	Intermediate Similarity	NPC228978
0.7436	Intermediate Similarity	NPC329852
0.7432	Intermediate Similarity	NPC194871
0.7429	Intermediate Similarity	NPC286189
0.7416	Intermediate Similarity	NPC276110
0.7412	Intermediate Similarity	NPC199382
0.7407	Intermediate Similarity	NPC233332
0.7407	Intermediate Similarity	NPC472470
0.7407	Intermediate Similarity	NPC469802
0.7386	Intermediate Similarity	NPC472812
0.7386	Intermediate Similarity	NPC475657
0.7386	Intermediate Similarity	NPC162615
0.7386	Intermediate Similarity	NPC53555
0.7386	Intermediate Similarity	NPC205034
0.7386	Intermediate Similarity	NPC152778
0.7381	Intermediate Similarity	NPC35933
0.7381	Intermediate Similarity	NPC30984
0.7375	Intermediate Similarity	NPC128276
0.7361	Intermediate Similarity	NPC44343
0.7361	Intermediate Similarity	NPC210303
0.7361	Intermediate Similarity	NPC179087
0.7356	Intermediate Similarity	NPC220454
0.7356	Intermediate Similarity	NPC469595
0.7356	Intermediate Similarity	NPC471818
0.7356	Intermediate Similarity	NPC212679
0.7356	Intermediate Similarity	NPC280149
0.7356	Intermediate Similarity	NPC273199
0.7356	Intermediate Similarity	NPC221111
0.7349	Intermediate Similarity	NPC161045
0.7349	Intermediate Similarity	NPC475947
0.7349	Intermediate Similarity	NPC30502
0.7349	Intermediate Similarity	NPC23748
0.7349	Intermediate Similarity	NPC49208
0.7349	Intermediate Similarity	NPC118423
0.7342	Intermediate Similarity	NPC123360
0.7342	Intermediate Similarity	NPC301525
0.7333	Intermediate Similarity	NPC162346
0.7333	Intermediate Similarity	NPC470256
0.7333	Intermediate Similarity	NPC16967
0.7324	Intermediate Similarity	NPC79756
0.7317	Intermediate Similarity	NPC170303
0.7308	Intermediate Similarity	NPC476355
0.7308	Intermediate Similarity	NPC470686
0.7308	Intermediate Similarity	NPC140287
0.7303	Intermediate Similarity	NPC161998
0.7303	Intermediate Similarity	NPC140277
0.7303	Intermediate Similarity	NPC477722
0.7303	Intermediate Similarity	NPC471994
0.7303	Intermediate Similarity	NPC166143
0.7303	Intermediate Similarity	NPC120351
0.7297	Intermediate Similarity	NPC191233
0.7294	Intermediate Similarity	NPC102996
0.7294	Intermediate Similarity	NPC211892
0.7294	Intermediate Similarity	NPC168248
0.7294	Intermediate Similarity	NPC286153
0.7294	Intermediate Similarity	NPC61527
0.7284	Intermediate Similarity	NPC271632
0.7284	Intermediate Similarity	NPC150646
0.7284	Intermediate Similarity	NPC5908
0.7284	Intermediate Similarity	NPC469690
0.7284	Intermediate Similarity	NPC110373
0.7284	Intermediate Similarity	NPC325869
0.7284	Intermediate Similarity	NPC80471
0.7284	Intermediate Similarity	NPC469620
0.7273	Intermediate Similarity	NPC472254
0.7273	Intermediate Similarity	NPC72845
0.7273	Intermediate Similarity	NPC84038
0.7273	Intermediate Similarity	NPC316185
0.7273	Intermediate Similarity	NPC472811
0.7273	Intermediate Similarity	NPC329842
0.7273	Intermediate Similarity	NPC473944
0.7262	Intermediate Similarity	NPC475100
0.726	Intermediate Similarity	NPC34883
0.7253	Intermediate Similarity	NPC53844
0.725	Intermediate Similarity	NPC57744
0.725	Intermediate Similarity	NPC97516
0.7241	Intermediate Similarity	NPC5509
0.7241	Intermediate Similarity	NPC284561
0.7241	Intermediate Similarity	NPC293044
0.7241	Intermediate Similarity	NPC174342

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 NPC222244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1898
0.2-0.3	4325
0.3-0.4	2073
0.4-0.5	454
0.5-0.6	218
0.6-0.7	30
0.7-0.8	3
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.859	High Similarity	NPD6400	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD8039	Approved
0.7045	Intermediate Similarity	NPD6051	Approved
0.7024	Intermediate Similarity	NPD5209	Approved
0.6986	Remote Similarity	NPD4194	Approved
0.6986	Remote Similarity	NPD4192	Approved
0.6986	Remote Similarity	NPD4193	Approved
0.6986	Remote Similarity	NPD4191	Approved
0.6809	Remote Similarity	NPD4225	Approved
0.6782	Remote Similarity	NPD1694	Approved
0.6778	Remote Similarity	NPD46	Approved
0.6778	Remote Similarity	NPD6698	Approved
0.6705	Remote Similarity	NPD7521	Approved
0.6705	Remote Similarity	NPD7334	Approved
0.6705	Remote Similarity	NPD6409	Approved
0.6705	Remote Similarity	NPD7146	Approved
0.6705	Remote Similarity	NPD6684	Approved
0.6705	Remote Similarity	NPD5330	Approved
0.6703	Remote Similarity	NPD7637	Suspended
0.6632	Remote Similarity	NPD7638	Approved
0.6593	Remote Similarity	NPD7838	Discovery
0.6593	Remote Similarity	NPD5785	Approved
0.6562	Remote Similarity	NPD7639	Approved
0.6562	Remote Similarity	NPD7640	Approved
0.6556	Remote Similarity	NPD6903	Approved
0.6556	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5737	Approved
0.6556	Remote Similarity	NPD6672	Approved
0.6552	Remote Similarity	NPD7154	Phase 3
0.6522	Remote Similarity	NPD6927	Phase 3
0.6436	Remote Similarity	NPD6686	Approved
0.6404	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6648	Approved
0.6353	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD5693	Phase 1
0.6344	Remote Similarity	NPD6411	Approved
0.6327	Remote Similarity	NPD5344	Discontinued
0.6316	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5778	Approved
0.6277	Remote Similarity	NPD6399	Phase 3
0.6277	Remote Similarity	NPD5779	Approved
0.6222	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7900	Approved
0.6211	Remote Similarity	NPD7748	Approved
0.6211	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4821	Approved
0.6207	Remote Similarity	NPD4819	Approved
0.6207	Remote Similarity	NPD4822	Approved
0.6207	Remote Similarity	NPD4820	Approved
0.619	Remote Similarity	NPD8264	Approved
0.6186	Remote Similarity	NPD6083	Phase 2
0.6186	Remote Similarity	NPD6084	Phase 2
0.618	Remote Similarity	NPD6695	Phase 3
0.618	Remote Similarity	NPD5362	Discontinued
0.6163	Remote Similarity	NPD4271	Approved
0.6163	Remote Similarity	NPD4268	Approved
0.6146	Remote Similarity	NPD5695	Phase 3
0.6129	Remote Similarity	NPD6673	Approved
0.6129	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6904	Approved
0.6129	Remote Similarity	NPD6080	Approved
0.6129	Remote Similarity	NPD6101	Approved
0.6122	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7115	Discovery
0.6111	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD4219	Approved
0.6047	Remote Similarity	NPD5776	Phase 2
0.6047	Remote Similarity	NPD6925	Approved
0.6044	Remote Similarity	NPD5363	Approved
0.6038	Remote Similarity	NPD6053	Discontinued
0.6023	Remote Similarity	NPD7332	Phase 2
0.6023	Remote Similarity	NPD7514	Phase 3
0.602	Remote Similarity	NPD7902	Approved
0.6019	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5331	Approved
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD6371	Approved
0.6	Remote Similarity	NPD5332	Approved
0.5979	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD7145	Approved
0.5976	Remote Similarity	NPD6923	Approved
0.5976	Remote Similarity	NPD6922	Approved
0.596	Remote Similarity	NPD5696	Approved
0.5957	Remote Similarity	NPD1695	Approved
0.5955	Remote Similarity	NPD4790	Discontinued
0.5955	Remote Similarity	NPD6902	Approved
0.5941	Remote Similarity	NPD7632	Discontinued
0.5922	Remote Similarity	NPD6675	Approved
0.5922	Remote Similarity	NPD5739	Approved
0.5922	Remote Similarity	NPD7128	Approved
0.5922	Remote Similarity	NPD6402	Approved
0.5918	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7524	Approved
0.5914	Remote Similarity	NPD4251	Approved
0.5914	Remote Similarity	NPD7750	Discontinued
0.5914	Remote Similarity	NPD4250	Approved
0.5909	Remote Similarity	NPD6929	Approved
0.5909	Remote Similarity	NPD7328	Approved
0.5909	Remote Similarity	NPD7327	Approved
0.5905	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD7144	Approved
0.5904	Remote Similarity	NPD7143	Approved
0.5895	Remote Similarity	NPD5692	Phase 3
0.5893	Remote Similarity	NPD8033	Approved
0.5889	Remote Similarity	NPD6435	Approved
0.5889	Remote Similarity	NPD4270	Approved
0.5889	Remote Similarity	NPD4269	Approved
0.5882	Remote Similarity	NPD6926	Approved
0.5882	Remote Similarity	NPD6924	Approved
0.5865	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4756	Discovery
0.5862	Remote Similarity	NPD6932	Approved
0.5856	Remote Similarity	NPD7516	Approved
0.5851	Remote Similarity	NPD5208	Approved
0.5849	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD6930	Phase 2
0.5843	Remote Similarity	NPD6931	Approved
0.5843	Remote Similarity	NPD4252	Approved
0.5833	Remote Similarity	NPD7983	Approved
0.5833	Remote Similarity	NPD7152	Approved
0.5833	Remote Similarity	NPD5694	Approved
0.5833	Remote Similarity	NPD7151	Approved
0.5833	Remote Similarity	NPD7150	Approved
0.5814	Remote Similarity	NPD7339	Approved
0.5814	Remote Similarity	NPD6942	Approved
0.581	Remote Similarity	NPD7320	Approved
0.581	Remote Similarity	NPD6881	Approved
0.581	Remote Similarity	NPD6899	Approved
0.5806	Remote Similarity	NPD6098	Approved
0.5806	Remote Similarity	NPD4249	Approved
0.5806	Remote Similarity	NPD5786	Approved
0.5804	Remote Similarity	NPD8294	Approved
0.5804	Remote Similarity	NPD8377	Approved
0.5802	Remote Similarity	NPD7331	Phase 2
0.5789	Remote Similarity	NPD8779	Phase 3
0.5783	Remote Similarity	NPD4137	Phase 3
0.5778	Remote Similarity	NPD5369	Approved
0.5778	Remote Similarity	NPD6898	Phase 1
0.5769	Remote Similarity	NPD6008	Approved
0.5769	Remote Similarity	NPD4211	Phase 1
0.5761	Remote Similarity	NPD3665	Phase 1
0.5761	Remote Similarity	NPD3668	Phase 3
0.5761	Remote Similarity	NPD4786	Approved
0.5761	Remote Similarity	NPD3666	Approved
0.5761	Remote Similarity	NPD3133	Approved
0.5758	Remote Similarity	NPD7839	Suspended
0.5755	Remote Similarity	NPD6373	Approved
0.5755	Remote Similarity	NPD6372	Approved
0.5752	Remote Similarity	NPD8296	Approved
0.5752	Remote Similarity	NPD8378	Approved
0.5752	Remote Similarity	NPD8380	Approved
0.5752	Remote Similarity	NPD8379	Approved
0.5752	Remote Similarity	NPD7503	Approved
0.5752	Remote Similarity	NPD8335	Approved
0.5747	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD6933	Approved
0.5745	Remote Similarity	NPD3573	Approved
0.5745	Remote Similarity	NPD1282	Approved
0.573	Remote Similarity	NPD6683	Phase 2
0.573	Remote Similarity	NPD7645	Phase 2
0.5729	Remote Similarity	NPD5207	Approved
0.5714	Remote Similarity	NPD4691	Approved
0.5714	Remote Similarity	NPD5282	Discontinued
0.5714	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD4747	Approved
0.5714	Remote Similarity	NPD3667	Approved
0.5714	Remote Similarity	NPD5701	Approved
0.5701	Remote Similarity	NPD6883	Approved
0.5701	Remote Similarity	NPD7290	Approved
0.5701	Remote Similarity	NPD2067	Discontinued
0.5701	Remote Similarity	NPD7102	Approved
0.5699	Remote Similarity	NPD1696	Phase 3
0.5698	Remote Similarity	NPD5733	Approved
0.5696	Remote Similarity	NPD368	Approved
0.5676	Remote Similarity	NPD7505	Discontinued
0.567	Remote Similarity	NPD7087	Discontinued
0.5667	Remote Similarity	NPD5368	Approved
0.5667	Remote Similarity	NPD4695	Discontinued
0.5648	Remote Similarity	NPD6869	Approved
0.5648	Remote Similarity	NPD6847	Approved
0.5648	Remote Similarity	NPD8130	Phase 1
0.5648	Remote Similarity	NPD6617	Approved
0.5648	Remote Similarity	NPD6649	Approved
0.5648	Remote Similarity	NPD6650	Approved
0.5647	Remote Similarity	NPD5276	Approved
0.5638	Remote Similarity	NPD3618	Phase 1
0.5638	Remote Similarity	NPD6422	Discontinued
0.5638	Remote Similarity	NPD5279	Phase 3
0.5634	Remote Similarity	NPD5343	Approved
0.5625	Remote Similarity	NPD5328	Approved
0.5625	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4753	Phase 2
0.561	Remote Similarity	NPD6108	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