NPASS Compound

Structure

NPC169586 OpenBabel07101718282D 25 26 0 0 0 0 0 0 0 0999 V2000 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 -5.1962 -3.0000 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 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0109 -4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5109 -3.3364 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2896 -4.6637 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 -2.5933 0.0000 N 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 2.5981 -1.5000 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 1 0 0 0 0 3 24 1 0 0 0 0 4 5 1 0 0 0 0 4 6 2 0 0 0 0 5 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 14 2 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 11 16 1 0 0 0 0 12 22 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 25 1 0 0 0 0 19 24 1 0 0 0 0 20 23 2 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	357.11
Volume:	366.214
LogP:	3.773
LogD:	3.949
LogS:	-4.94
# Rotatable Bonds:	6
TPSA:	55.23
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.726
Synthetic Accessibility Score:	3.558
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.949
MDCK Permeability:	1.2910464647575282e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.183
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.092

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	97.58661651611328%
Volume Distribution (VD):	0.617
Pgp-substrate:	4.81626558303833%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.575
CYP2C9-inhibitor:	0.912
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.622
CYP2D6-substrate:	0.936
CYP3A4-inhibitor:	0.795
CYP3A4-substrate:	0.367

ADMET: Excretion

Clearance (CL):	2.04
Half-life (T1/2):	0.159

ADMET: Toxicity

hERG Blockers:	0.657
Human Hepatotoxicity (H-HT):	0.806
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.523
Rat Oral Acute Toxicity:	0.906
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.802
Carcinogencity:	0.566
Eye Corrosion:	0.004
Eye Irritation:	0.029
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC169586

Natural Product ID:	NPC169586
*Common Name:**	12E-Isorumbrin
IUPAC Name:	6-[(2E,4E,6E,8E)-9-(3-chloro-1H-pyrrol-2-yl)nona-2,4,6,8-tetraen-2-yl]-4-methoxy-3-methylpyran-2-one
Synonyms:	12E-Isorumbrin
Standard InCHIKey:	TUFFAFAPFQNIRB-NBWHIMRISA-N
Standard InCHI:	InChI=1S/C20H20ClNO3/c1-14(18-13-19(24-3)15(2)20(23)25-18)9-7-5-4-6-8-10-17-16(21)11-12-22-17/h4-13,22H,1-3H3/b6-4+,7-5+,10-8+,14-9+
SMILES:	C/C(=CC=CC=CC=Cc1c(cc[nH]1)Cl)/c1cc(c(C)c(=O)o1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL426025
PubChem CID:	6448763
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives

*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
NPO33022	gymnoascus reessii	Species	Gymnoascaceae	Eukaryota	n.a.	Australian	n.a.	PMID[16124766]
NPO33022	gymnoascus reessii	Species	Gymnoascaceae	Eukaryota	n.a.	Australian	n.a.	PMID[16309319]
NPO33022	gymnoascus reessii	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17309300]

☑ 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
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5200.0	nM	PMID[527331]
NPT27	Others	Unspecified		LD99	=	0.034	uM	PMID[527330]

☑ 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 NPC169586 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	427
0.1-0.2	4730
0.2-0.3	12170
0.3-0.4	6486
0.4-0.5	13582
0.5-0.6	4080
0.6-0.7	1195
0.7-0.8	25
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9007	High Similarity	NPC75135
0.7908	Intermediate Similarity	NPC104049
0.7607	Intermediate Similarity	NPC477815
0.7372	Intermediate Similarity	NPC291517
0.733	Intermediate Similarity	NPC243381
0.733	Intermediate Similarity	NPC275292
0.7314	Intermediate Similarity	NPC233050
0.7314	Intermediate Similarity	NPC276540
0.7303	Intermediate Similarity	NPC280290
0.7261	Intermediate Similarity	NPC23215
0.7108	Intermediate Similarity	NPC105818
0.7108	Intermediate Similarity	NPC24678
0.7083	Intermediate Similarity	NPC33229
0.7011	Intermediate Similarity	NPC138370
0.697	Remote Similarity	NPC314372
0.697	Remote Similarity	NPC159856
0.6951	Remote Similarity	NPC190296
0.6936	Remote Similarity	NPC311276
0.6936	Remote Similarity	NPC8104
0.6933	Remote Similarity	NPC469779
0.6933	Remote Similarity	NPC469784
0.6933	Remote Similarity	NPC469780
0.6933	Remote Similarity	NPC469767
0.6933	Remote Similarity	NPC469783
0.6933	Remote Similarity	NPC469761
0.6933	Remote Similarity	NPC469768
0.6906	Remote Similarity	NPC469358
0.6902	Remote Similarity	NPC209917
0.6894	Remote Similarity	NPC261195
0.6894	Remote Similarity	NPC29886
0.689	Remote Similarity	NPC469766
0.6871	Remote Similarity	NPC73767
0.6855	Remote Similarity	NPC82295
0.6852	Remote Similarity	NPC84911
0.6852	Remote Similarity	NPC472288
0.6851	Remote Similarity	NPC71037
0.6839	Remote Similarity	NPC40779
0.6836	Remote Similarity	NPC470498
0.6833	Remote Similarity	NPC213468
0.6824	Remote Similarity	NPC259644
0.6824	Remote Similarity	NPC469765
0.6824	Remote Similarity	NPC25008
0.6824	Remote Similarity	NPC469760
0.6824	Remote Similarity	NPC469763
0.6824	Remote Similarity	NPC469786
0.6824	Remote Similarity	NPC73952
0.6818	Remote Similarity	NPC78020
0.6805	Remote Similarity	NPC471655
0.6802	Remote Similarity	NPC469762
0.6793	Remote Similarity	NPC235684
0.679	Remote Similarity	NPC96102
0.6789	Remote Similarity	NPC67288
0.6784	Remote Similarity	NPC212376
0.6784	Remote Similarity	NPC80597
0.6784	Remote Similarity	NPC211572
0.6784	Remote Similarity	NPC70922
0.6784	Remote Similarity	NPC75540
0.6778	Remote Similarity	NPC84827
0.6778	Remote Similarity	NPC145885
0.6778	Remote Similarity	NPC14113
0.6768	Remote Similarity	NPC110126
0.6763	Remote Similarity	NPC92796
0.6763	Remote Similarity	NPC135141
0.6761	Remote Similarity	NPC470509
0.6758	Remote Similarity	NPC470677
0.6748	Remote Similarity	NPC105127
0.6744	Remote Similarity	NPC469785
0.673	Remote Similarity	NPC71236
0.6725	Remote Similarity	NPC107287
0.6725	Remote Similarity	NPC200214
0.6722	Remote Similarity	NPC267885
0.6705	Remote Similarity	NPC42372
0.6705	Remote Similarity	NPC233380
0.6703	Remote Similarity	NPC477042
0.6687	Remote Similarity	NPC476454
0.6686	Remote Similarity	NPC471957
0.6684	Remote Similarity	NPC77061
0.6667	Remote Similarity	NPC110500
0.6667	Remote Similarity	NPC203468
0.6667	Remote Similarity	NPC293216
0.6667	Remote Similarity	NPC49954
0.6667	Remote Similarity	NPC149155
0.6667	Remote Similarity	NPC474561
0.6648	Remote Similarity	NPC248041
0.6648	Remote Similarity	NPC55772
0.6648	Remote Similarity	NPC126709
0.6632	Remote Similarity	NPC202812
0.6627	Remote Similarity	NPC279081
0.6624	Remote Similarity	NPC27740
0.6608	Remote Similarity	NPC53947
0.6596	Remote Similarity	NPC76748
0.6595	Remote Similarity	NPC477003
0.6593	Remote Similarity	NPC284775
0.6593	Remote Similarity	NPC111275
0.6592	Remote Similarity	NPC116961
0.6591	Remote Similarity	NPC282231
0.659	Remote Similarity	NPC229055
0.6588	Remote Similarity	NPC112741
0.6587	Remote Similarity	NPC192712
0.6585	Remote Similarity	NPC328029
0.6585	Remote Similarity	NPC200397
0.6585	Remote Similarity	NPC14448
0.6585	Remote Similarity	NPC167200
0.6585	Remote Similarity	NPC292434
0.6585	Remote Similarity	NPC64661
0.6585	Remote Similarity	NPC98156
0.6585	Remote Similarity	NPC195704
0.6585	Remote Similarity	NPC138596
0.658	Remote Similarity	NPC74413
0.6579	Remote Similarity	NPC307963
0.6578	Remote Similarity	NPC278434
0.6573	Remote Similarity	NPC160105
0.6571	Remote Similarity	NPC315062
0.6571	Remote Similarity	NPC267853
0.6571	Remote Similarity	NPC474492
0.6568	Remote Similarity	NPC467188
0.6567	Remote Similarity	NPC221100
0.6567	Remote Similarity	NPC234078
0.6566	Remote Similarity	NPC32002
0.6566	Remote Similarity	NPC315348
0.6562	Remote Similarity	NPC89490
0.6561	Remote Similarity	NPC92111
0.6557	Remote Similarity	NPC283219
0.6557	Remote Similarity	NPC176199
0.6557	Remote Similarity	NPC141377
0.6557	Remote Similarity	NPC215795
0.6557	Remote Similarity	NPC11126
0.6554	Remote Similarity	NPC102423
0.6552	Remote Similarity	NPC476464
0.655	Remote Similarity	NPC102664
0.6548	Remote Similarity	NPC82053
0.6545	Remote Similarity	NPC471312
0.6543	Remote Similarity	NPC196251
0.6543	Remote Similarity	NPC296527
0.6543	Remote Similarity	NPC102338
0.6543	Remote Similarity	NPC63199
0.6543	Remote Similarity	NPC111602
0.654	Remote Similarity	NPC244897
0.6536	Remote Similarity	NPC63751
0.6536	Remote Similarity	NPC201700
0.6534	Remote Similarity	NPC100104
0.6534	Remote Similarity	NPC131718
0.6534	Remote Similarity	NPC470680
0.6534	Remote Similarity	NPC279918
0.6529	Remote Similarity	NPC288838
0.6529	Remote Similarity	NPC143872
0.6527	Remote Similarity	NPC230002
0.6526	Remote Similarity	NPC47190
0.6524	Remote Similarity	NPC315555
0.6522	Remote Similarity	NPC475105
0.6522	Remote Similarity	NPC329896
0.6522	Remote Similarity	NPC16659
0.6522	Remote Similarity	NPC475090
0.6522	Remote Similarity	NPC314919
0.6519	Remote Similarity	NPC313791
0.6514	Remote Similarity	NPC212742
0.6508	Remote Similarity	NPC83111
0.6505	Remote Similarity	NPC228835
0.6503	Remote Similarity	NPC68354
0.65	Remote Similarity	NPC194411
0.6495	Remote Similarity	NPC103361
0.6494	Remote Similarity	NPC209362
0.6492	Remote Similarity	NPC84853
0.6491	Remote Similarity	NPC100726
0.6491	Remote Similarity	NPC105811
0.6488	Remote Similarity	NPC114033
0.6488	Remote Similarity	NPC58268
0.6488	Remote Similarity	NPC101130
0.6488	Remote Similarity	NPC129412
0.6486	Remote Similarity	NPC231655
0.6484	Remote Similarity	NPC275305
0.6484	Remote Similarity	NPC37423
0.648	Remote Similarity	NPC476874
0.648	Remote Similarity	NPC54988
0.648	Remote Similarity	NPC260900
0.648	Remote Similarity	NPC193761
0.648	Remote Similarity	NPC49217
0.6479	Remote Similarity	NPC316411
0.6477	Remote Similarity	NPC230869
0.6477	Remote Similarity	NPC156704
0.6477	Remote Similarity	NPC206819
0.6477	Remote Similarity	NPC318065
0.6474	Remote Similarity	NPC470233
0.6474	Remote Similarity	NPC216713
0.6474	Remote Similarity	NPC472260
0.6471	Remote Similarity	NPC282103
0.6467	Remote Similarity	NPC265710
0.6464	Remote Similarity	NPC262338
0.6464	Remote Similarity	NPC302647
0.6464	Remote Similarity	NPC249614
0.6461	Remote Similarity	NPC194640
0.646	Remote Similarity	NPC313823
0.6458	Remote Similarity	NPC220151
0.6458	Remote Similarity	NPC135950
0.6458	Remote Similarity	NPC19692
0.6455	Remote Similarity	NPC321708
0.6453	Remote Similarity	NPC37548
0.6453	Remote Similarity	NPC321911
0.6448	Remote Similarity	NPC476419
0.6446	Remote Similarity	NPC114310

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 NPC169586 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	769
0.2-0.3	862
0.3-0.4	1662
0.4-0.5	2854
0.5-0.6	2218
0.6-0.7	520
0.7-0.8	18
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
0.7066	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3178	Discontinued
0.6885	Remote Similarity	NPD6217	Discontinued
0.6871	Remote Similarity	NPD786	Approved
0.6821	Remote Similarity	NPD2510	Approved
0.6821	Remote Similarity	NPD2509	Approved
0.6821	Remote Similarity	NPD9392	Approved
0.6821	Remote Similarity	NPD9396	Approved
0.679	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.678	Remote Similarity	NPD565	Phase 2
0.6772	Remote Similarity	NPD1031	Discontinued
0.6768	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3100	Discontinued
0.6723	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3833	Phase 3
0.6706	Remote Similarity	NPD3835	Phase 3
0.6705	Remote Similarity	NPD820	Phase 3
0.6704	Remote Similarity	NPD2077	Approved
0.6704	Remote Similarity	NPD2076	Approved
0.6689	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5020	Approved
0.6687	Remote Similarity	NPD1722	Approved
0.6685	Remote Similarity	NPD3569	Discontinued
0.6667	Remote Similarity	NPD4529	Approved
0.6667	Remote Similarity	NPD482	Approved
0.6667	Remote Similarity	NPD4526	Approved
0.6667	Remote Similarity	NPD4528	Approved
0.6667	Remote Similarity	NPD1248	Discontinued
0.6648	Remote Similarity	NPD9548	Phase 2
0.6648	Remote Similarity	NPD5088	Discontinued
0.6647	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5092	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2095	Phase 2
0.663	Remote Similarity	NPD4075	Phase 2
0.663	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2092	Phase 2
0.663	Remote Similarity	NPD2094	Phase 2
0.6628	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD165	Phase 2
0.6612	Remote Similarity	NPD3927	Phase 2
0.6609	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2172	Phase 1
0.6597	Remote Similarity	NPD4848	Phase 1
0.6595	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD2096	Phase 2
0.6595	Remote Similarity	NPD2091	Phase 2
0.6593	Remote Similarity	NPD2144	Approved
0.6592	Remote Similarity	NPD4973	Approved
0.659	Remote Similarity	NPD2165	Phase 1
0.6588	Remote Similarity	NPD9271	Approved
0.6582	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD3947	Discontinued
0.6579	Remote Similarity	NPD1038	Approved
0.6579	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4804	Approved
0.6566	Remote Similarity	NPD2075	Approved
0.6566	Remote Similarity	NPD2074	Approved
0.6566	Remote Similarity	NPD2073	Approved
0.6566	Remote Similarity	NPD2072	Approved
0.6556	Remote Similarity	NPD3116	Approved
0.6556	Remote Similarity	NPD3117	Approved
0.6552	Remote Similarity	NPD3113	Approved
0.6552	Remote Similarity	NPD3112	Approved
0.6552	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3115	Approved
0.6552	Remote Similarity	NPD3114	Approved
0.6538	Remote Similarity	NPD9598	Discontinued
0.6532	Remote Similarity	NPD3339	Approved
0.6527	Remote Similarity	NPD9599	Approved
0.6517	Remote Similarity	NPD2915	Discontinued
0.6512	Remote Similarity	NPD4463	Approved
0.6512	Remote Similarity	NPD4462	Approved
0.6503	Remote Similarity	NPD3506	Approved
0.6503	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3505	Approved
0.6502	Remote Similarity	NPD3389	Approved
0.6502	Remote Similarity	NPD3394	Approved
0.6502	Remote Similarity	NPD3393	Approved
0.65	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4805	Approved
0.6486	Remote Similarity	NPD3038	Discontinued
0.6486	Remote Similarity	NPD9098	Phase 3
0.6486	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3476	Approved
0.6481	Remote Similarity	NPD3475	Approved
0.648	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4699	Discontinued
0.6467	Remote Similarity	NPD4076	Approved
0.6467	Remote Similarity	NPD4079	Approved
0.6464	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD803	Phase 1
0.6441	Remote Similarity	NPD1403	Approved
0.6441	Remote Similarity	NPD1404	Approved
0.6436	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD750	Phase 2
0.642	Remote Similarity	NPD2581	Approved
0.642	Remote Similarity	NPD2582	Approved
0.6418	Remote Similarity	NPD5072	Discontinued
0.6417	Remote Similarity	NPD2416	Approved
0.6417	Remote Similarity	NPD2417	Approved
0.6416	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD9357	Approved
0.6414	Remote Similarity	NPD2831	Approved
0.6414	Remote Similarity	NPD5901	Discontinued
0.6413	Remote Similarity	NPD4072	Approved
0.6413	Remote Similarity	NPD4071	Approved
0.641	Remote Similarity	NPD3825	Phase 3
0.6407	Remote Similarity	NPD2896	Discontinued
0.6407	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD991	Phase 2
0.6398	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5065	Approved
0.6389	Remote Similarity	NPD2642	Approved
0.6389	Remote Similarity	NPD2639	Approved
0.6387	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7470	Discontinued
0.6383	Remote Similarity	NPD4889	Approved
0.6378	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6479	Discontinued
0.6378	Remote Similarity	NPD4500	Approved
0.6378	Remote Similarity	NPD4501	Approved
0.6377	Remote Similarity	NPD3280	Approved
0.6377	Remote Similarity	NPD6242	Discontinued
0.6359	Remote Similarity	NPD5104	Approved
0.6354	Remote Similarity	NPD2640	Approved
0.6354	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD2641	Approved
0.6348	Remote Similarity	NPD1418	Phase 2
0.6347	Remote Similarity	NPD201	Phase 2
0.6347	Remote Similarity	NPD200	Phase 2
0.6344	Remote Similarity	NPD6595	Phase 3
0.6344	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD2837	Discontinued
0.6335	Remote Similarity	NPD9583	Approved
0.6331	Remote Similarity	NPD107	Approved
0.633	Remote Similarity	NPD1096	Discontinued
0.6329	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD268	Approved
0.6329	Remote Similarity	NPD271	Approved
0.6328	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6249	Phase 2
0.6327	Remote Similarity	NPD6248	Phase 2
0.6316	Remote Similarity	NPD3961	Discontinued
0.6316	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD8073	Approved
0.631	Remote Similarity	NPD1380	Discovery
0.631	Remote Similarity	NPD4891	Phase 2
0.6304	Remote Similarity	NPD1586	Approved
0.6304	Remote Similarity	NPD4128	Approved
0.6304	Remote Similarity	NPD2829	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7957	Phase 1
0.63	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD5611	Phase 2
0.6298	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1227	Phase 2
0.6296	Remote Similarity	NPD6735	Approved
0.6296	Remote Similarity	NPD4454	Phase 2
0.6296	Remote Similarity	NPD2118	Approved
0.6296	Remote Similarity	NPD2119	Approved
0.6294	Remote Similarity	NPD484	Approved
0.6292	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5487	Phase 1
0.6281	Remote Similarity	NPD6176	Phase 1
0.6281	Remote Similarity	NPD8072	Approved
0.6278	Remote Similarity	NPD3323	Discontinued
0.6277	Remote Similarity	NPD6194	Discontinued
0.6277	Remote Similarity	NPD5213	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4823	Approved
0.6275	Remote Similarity	NPD4824	Approved
0.6272	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD1392	Approved
0.6263	Remote Similarity	NPD5444	Phase 1
0.6257	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD9726	Discontinued
0.6239	Remote Similarity	NPD6154	Approved
0.623	Remote Similarity	NPD4024	Phase 3
0.6228	Remote Similarity	NPD272	Approved
0.6225	Remote Similarity	NPD5066	Phase 2
0.6225	Remote Similarity	NPD5475	Discontinued
0.6225	Remote Similarity	NPD5067	Phase 2
0.6218	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD2928	Phase 2
0.6215	Remote Similarity	NPD2061	Approved
0.6215	Remote Similarity	NPD2809	Approved
0.6212	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD9100	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