NPASS Compound

Structure

CID281134 OpenBabel06191716092D 35 39 0 0 1 0 0 0 0 0999 V2000 2.0517 3.3761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0004 3.1719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0967 -0.8941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4347 -1.6423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6673 -1.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3968 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5475 0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8488 1.4701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3963 -2.9416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -1.4711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -2.4517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8748 1.6885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2459 -1.4710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8488 -0.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4504 2.4812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4248 2.3791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6979 0.0008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5393 -2.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3968 -0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2456 -2.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 -0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8493 0.4904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6982 -0.9811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8488 0.4901 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2736 0.7936 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8236 1.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5475 -1.4715 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4368 -3.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1115 -2.9515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7979 1.3821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7464 -1.4648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2479 0.6915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 4 20 1 0 0 0 0 6 7 1 0 0 0 0 6 21 1 0 0 0 0 8 9 1 0 0 0 0 8 24 1 0 0 0 0 9 26 1 0 0 0 0 10 12 2 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 17 1 0 0 0 0 14 27 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 34 1 0 0 0 0 17 18 2 0 0 0 0 18 28 1 0 0 0 0 19 3 1 1 0 0 0 19 24 1 0 0 0 0 20 31 2 0 0 0 0 20 34 1 0 0 0 0 21 29 1 0 0 0 0 22 32 2 0 0 0 0 23 7 1 1 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 30 1 6 0 0 0 25 29 1 6 0 0 0 26 30 1 6 0 0 0 27 19 1 1 0 0 0 27 35 1 0 0 0 0 28 33 2 0 0 0 0 28 35 1 0 0 0 0 29 5 1 6 0 0 0 30 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.29
Volume:	512.786
LogP:	5.805
LogD:	4.469
LogS:	-5.102
# Rotatable Bonds:	5
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.387
Synthetic Accessibility Score:	5.284
Fsp3:	0.7
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:	-4.771
MDCK Permeability:	3.581773489713669e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.048
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.546
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.193
Plasma Protein Binding (PPB):	87.1964340209961%
Volume Distribution (VD):	1.63
Pgp-substrate:	6.505484104156494%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.526
CYP2C19-substrate:	0.45
CYP2C9-inhibitor:	0.31
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.269
CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.944
CYP3A4-substrate:	0.657

ADMET: Excretion

Clearance (CL):	6.06
Half-life (T1/2):	0.08

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.3
Drug-inuced Liver Injury (DILI):	0.849
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.827
Maximum Recommended Daily Dose:	0.84
Skin Sensitization:	0.909
Carcinogencity:	0.43
Eye Corrosion:	0.237
Eye Irritation:	0.145
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC281134

Natural Product ID:	NPC281134
*Common Name:**	Minabeolide 2
IUPAC Name:	[(8R,9S,10R,13R,14S,17R)-17-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10-methyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-13-yl]methyl acetate
Synonyms:	Minabeolide 2
Standard InCHIKey:	FGHNAYQOKIGUIZ-OYMMUSFMSA-N
Standard InCHI:	InChI=1S/C30H40O5/c1-17-14-27(35-28(33)18(17)2)19(3)24-8-9-26-23-7-6-21-15-22(32)10-12-29(21,5)25(23)11-13-30(24,26)16-34-20(4)31/h10,12,15,19,23-27H,6-9,11,13-14,16H2,1-5H3/t19-,23+,24+,25-,26-,27+,29-,30-/m0/s1
SMILES:	CC1=C(C)C(=O)O[C@H](C1)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782227
PubChem CID:	53262729
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	Eukaryota	n.a.	the western coast of Pingtung county, Taiwan, at a depth of 10 m	2009-MAY	PMID[21425785]
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21425785]
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	45.7	%	PMID[447907]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	51.2	%	PMID[447907]

☑ 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 NPC281134 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	210
0.1-0.2	1206
0.2-0.3	4555
0.3-0.4	11292
0.4-0.5	10594
0.5-0.6	7159
0.6-0.7	5918
0.7-0.8	1691
0.8-0.85	64
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC273199
0.9432	High Similarity	NPC177141
0.8854	High Similarity	NPC310981
0.8723	High Similarity	NPC33473
0.8632	High Similarity	NPC58052
0.8632	High Similarity	NPC111684
0.8617	High Similarity	NPC128488
0.8617	High Similarity	NPC304968
0.8602	High Similarity	NPC234335
0.8469	Intermediate Similarity	NPC298233
0.8454	Intermediate Similarity	NPC98868
0.8421	Intermediate Similarity	NPC471994
0.8421	Intermediate Similarity	NPC120351
0.8421	Intermediate Similarity	NPC166143
0.8384	Intermediate Similarity	NPC471993
0.8365	Intermediate Similarity	NPC236217
0.8295	Intermediate Similarity	NPC190211
0.8235	Intermediate Similarity	NPC91034
0.8211	Intermediate Similarity	NPC177641
0.8211	Intermediate Similarity	NPC218301
0.8208	Intermediate Similarity	NPC474181
0.82	Intermediate Similarity	NPC475320
0.8191	Intermediate Similarity	NPC474844
0.8182	Intermediate Similarity	NPC105197
0.8163	Intermediate Similarity	NPC202705
0.8155	Intermediate Similarity	NPC61411
0.8144	Intermediate Similarity	NPC474909
0.8131	Intermediate Similarity	NPC190286
0.8125	Intermediate Similarity	NPC475657
0.8125	Intermediate Similarity	NPC38232
0.8125	Intermediate Similarity	NPC229976
0.8119	Intermediate Similarity	NPC254202
0.8119	Intermediate Similarity	NPC297617
0.8105	Intermediate Similarity	NPC302280
0.81	Intermediate Similarity	NPC194028
0.81	Intermediate Similarity	NPC168319
0.8095	Intermediate Similarity	NPC474315
0.8095	Intermediate Similarity	NPC470076
0.809	Intermediate Similarity	NPC44083
0.809	Intermediate Similarity	NPC153987
0.8085	Intermediate Similarity	NPC470612
0.8085	Intermediate Similarity	NPC470613
0.8081	Intermediate Similarity	NPC218107
0.8073	Intermediate Similarity	NPC475520
0.8065	Intermediate Similarity	NPC286153
0.8058	Intermediate Similarity	NPC475294
0.8041	Intermediate Similarity	NPC279410
0.8041	Intermediate Similarity	NPC477722
0.8041	Intermediate Similarity	NPC119562
0.8039	Intermediate Similarity	NPC189616
0.8022	Intermediate Similarity	NPC471218
0.8021	Intermediate Similarity	NPC190442
0.8	Intermediate Similarity	NPC103491
0.8	Intermediate Similarity	NPC469802
0.8	Intermediate Similarity	NPC473627
0.8	Intermediate Similarity	NPC146554
0.8	Intermediate Similarity	NPC37116
0.8	Intermediate Similarity	NPC251680
0.8	Intermediate Similarity	NPC227865
0.7982	Intermediate Similarity	NPC153440
0.7982	Intermediate Similarity	NPC475913
0.7981	Intermediate Similarity	NPC220155
0.798	Intermediate Similarity	NPC110937
0.798	Intermediate Similarity	NPC108078
0.798	Intermediate Similarity	NPC99726
0.7963	Intermediate Similarity	NPC176840
0.7961	Intermediate Similarity	NPC189863
0.7957	Intermediate Similarity	NPC474013
0.7957	Intermediate Similarity	NPC189311
0.7955	Intermediate Similarity	NPC474463
0.7944	Intermediate Similarity	NPC122056
0.7941	Intermediate Similarity	NPC470954
0.7941	Intermediate Similarity	NPC85742
0.7938	Intermediate Similarity	NPC473678
0.7938	Intermediate Similarity	NPC470923
0.7935	Intermediate Similarity	NPC470046
0.7935	Intermediate Similarity	NPC470047
0.7928	Intermediate Similarity	NPC67569
0.7925	Intermediate Similarity	NPC471484
0.7925	Intermediate Similarity	NPC262083
0.7921	Intermediate Similarity	NPC268829
0.7921	Intermediate Similarity	NPC25177
0.7921	Intermediate Similarity	NPC247701
0.7921	Intermediate Similarity	NPC222875
0.7921	Intermediate Similarity	NPC295110
0.7921	Intermediate Similarity	NPC475617
0.7917	Intermediate Similarity	NPC212679
0.7917	Intermediate Similarity	NPC220454
0.7917	Intermediate Similarity	NPC469595
0.7909	Intermediate Similarity	NPC474179
0.7909	Intermediate Similarity	NPC5292
0.7909	Intermediate Similarity	NPC475834
0.7905	Intermediate Similarity	NPC475274
0.79	Intermediate Similarity	NPC252295
0.79	Intermediate Similarity	NPC176845
0.79	Intermediate Similarity	NPC92275
0.7895	Intermediate Similarity	NPC473879
0.7895	Intermediate Similarity	NPC106332
0.7885	Intermediate Similarity	NPC471601
0.7879	Intermediate Similarity	NPC475380
0.7879	Intermediate Similarity	NPC8954
0.7879	Intermediate Similarity	NPC94905
0.7879	Intermediate Similarity	NPC276103
0.7879	Intermediate Similarity	NPC54248
0.7879	Intermediate Similarity	NPC209297
0.7872	Intermediate Similarity	NPC195640
0.7872	Intermediate Similarity	NPC470051
0.7872	Intermediate Similarity	NPC220478
0.7872	Intermediate Similarity	NPC471219
0.7872	Intermediate Similarity	NPC264127
0.7872	Intermediate Similarity	NPC470050
0.787	Intermediate Similarity	NPC147912
0.787	Intermediate Similarity	NPC67259
0.7864	Intermediate Similarity	NPC165969
0.7864	Intermediate Similarity	NPC228669
0.7864	Intermediate Similarity	NPC164835
0.7857	Intermediate Similarity	NPC470265
0.7857	Intermediate Similarity	NPC474922
0.7857	Intermediate Similarity	NPC23786
0.7857	Intermediate Similarity	NPC170538
0.7857	Intermediate Similarity	NPC88507
0.785	Intermediate Similarity	NPC191620
0.785	Intermediate Similarity	NPC44537
0.7849	Intermediate Similarity	NPC33913
0.7843	Intermediate Similarity	NPC476471
0.7843	Intermediate Similarity	NPC475344
0.7838	Intermediate Similarity	NPC79579
0.7838	Intermediate Similarity	NPC474585
0.7835	Intermediate Similarity	NPC477574
0.7835	Intermediate Similarity	NPC473944
0.7835	Intermediate Similarity	NPC221282
0.783	Intermediate Similarity	NPC181298
0.783	Intermediate Similarity	NPC197428
0.783	Intermediate Similarity	NPC29133
0.7826	Intermediate Similarity	NPC100297
0.7822	Intermediate Similarity	NPC290802
0.7822	Intermediate Similarity	NPC54705
0.7818	Intermediate Similarity	NPC473720
0.7812	Intermediate Similarity	NPC262858
0.7812	Intermediate Similarity	NPC285982
0.7812	Intermediate Similarity	NPC284561
0.7812	Intermediate Similarity	NPC472240
0.7812	Intermediate Similarity	NPC293044
0.781	Intermediate Similarity	NPC470269
0.781	Intermediate Similarity	NPC304276
0.781	Intermediate Similarity	NPC472825
0.781	Intermediate Similarity	NPC137462
0.781	Intermediate Similarity	NPC189075
0.781	Intermediate Similarity	NPC275539
0.7802	Intermediate Similarity	NPC233332
0.78	Intermediate Similarity	NPC2049
0.78	Intermediate Similarity	NPC151488
0.78	Intermediate Similarity	NPC51499
0.78	Intermediate Similarity	NPC475446
0.78	Intermediate Similarity	NPC141401
0.78	Intermediate Similarity	NPC84335
0.78	Intermediate Similarity	NPC311241
0.78	Intermediate Similarity	NPC38530
0.78	Intermediate Similarity	NPC253826
0.7798	Intermediate Similarity	NPC148458
0.7798	Intermediate Similarity	NPC470075
0.7798	Intermediate Similarity	NPC207637
0.7789	Intermediate Similarity	NPC477228
0.7789	Intermediate Similarity	NPC102640
0.7788	Intermediate Similarity	NPC204812
0.7788	Intermediate Similarity	NPC127790
0.7788	Intermediate Similarity	NPC119855
0.7788	Intermediate Similarity	NPC220217
0.7788	Intermediate Similarity	NPC11895
0.7788	Intermediate Similarity	NPC469789
0.7788	Intermediate Similarity	NPC96377
0.7788	Intermediate Similarity	NPC266570
0.7778	Intermediate Similarity	NPC293052
0.7778	Intermediate Similarity	NPC25909
0.7778	Intermediate Similarity	NPC171126
0.7778	Intermediate Similarity	NPC171395
0.7768	Intermediate Similarity	NPC46570
0.7767	Intermediate Similarity	NPC187302
0.7767	Intermediate Similarity	NPC10232
0.7767	Intermediate Similarity	NPC189588
0.7767	Intermediate Similarity	NPC97487
0.7767	Intermediate Similarity	NPC160583
0.7767	Intermediate Similarity	NPC36688
0.7767	Intermediate Similarity	NPC95899
0.7767	Intermediate Similarity	NPC196471
0.7767	Intermediate Similarity	NPC474124
0.7767	Intermediate Similarity	NPC171014
0.7766	Intermediate Similarity	NPC137493
0.7766	Intermediate Similarity	NPC323765
0.7757	Intermediate Similarity	NPC284162
0.7757	Intermediate Similarity	NPC470960
0.7757	Intermediate Similarity	NPC470961
0.7757	Intermediate Similarity	NPC255401
0.7755	Intermediate Similarity	NPC79117
0.7755	Intermediate Similarity	NPC7349
0.7748	Intermediate Similarity	NPC475041
0.7748	Intermediate Similarity	NPC305260
0.7748	Intermediate Similarity	NPC476960
0.7748	Intermediate Similarity	NPC270850
0.7745	Intermediate Similarity	NPC99411

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 NPC281134 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1306
0.2-0.3	3975
0.3-0.4	2499
0.4-0.5	731
0.5-0.6	182
0.6-0.7	219
0.7-0.8	64
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
0.8081	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD7639	Approved
0.8	Intermediate Similarity	NPD6051	Approved
0.7895	Intermediate Similarity	NPD6672	Approved
0.7895	Intermediate Similarity	NPD5737	Approved
0.7895	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD7521	Approved
0.7872	Intermediate Similarity	NPD7334	Approved
0.7872	Intermediate Similarity	NPD6409	Approved
0.7872	Intermediate Similarity	NPD7146	Approved
0.7872	Intermediate Similarity	NPD5330	Approved
0.7872	Intermediate Similarity	NPD6684	Approved
0.7727	Intermediate Similarity	NPD7115	Discovery
0.7708	Intermediate Similarity	NPD6903	Approved
0.7653	Intermediate Similarity	NPD5693	Phase 1
0.7634	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6399	Phase 3
0.7456	Intermediate Similarity	NPD7503	Approved
0.7453	Intermediate Similarity	NPD6008	Approved
0.7449	Intermediate Similarity	NPD6673	Approved
0.7449	Intermediate Similarity	NPD6080	Approved
0.7449	Intermediate Similarity	NPD6904	Approved
0.7396	Intermediate Similarity	NPD1694	Approved
0.7333	Intermediate Similarity	NPD7632	Discontinued
0.73	Intermediate Similarity	NPD7637	Suspended
0.7282	Intermediate Similarity	NPD6083	Phase 2
0.7282	Intermediate Similarity	NPD6084	Phase 2
0.7255	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6053	Discontinued
0.7172	Intermediate Similarity	NPD5208	Approved
0.7157	Intermediate Similarity	NPD7748	Approved
0.7157	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7900	Approved
0.7156	Intermediate Similarity	NPD6881	Approved
0.7156	Intermediate Similarity	NPD6899	Approved
0.7156	Intermediate Similarity	NPD6686	Approved
0.7143	Intermediate Similarity	NPD6098	Approved
0.7129	Intermediate Similarity	NPD6079	Approved
0.7129	Intermediate Similarity	NPD6050	Approved
0.7129	Intermediate Similarity	NPD5694	Approved
0.7128	Intermediate Similarity	NPD4195	Approved
0.7113	Intermediate Similarity	NPD4786	Approved
0.7087	Intermediate Similarity	NPD5695	Phase 3
0.7071	Intermediate Similarity	NPD3573	Approved
0.7064	Intermediate Similarity	NPD5697	Approved
0.7064	Intermediate Similarity	NPD6412	Phase 2
0.7048	Intermediate Similarity	NPD4225	Approved
0.7048	Intermediate Similarity	NPD5696	Approved
0.7043	Intermediate Similarity	NPD7327	Approved
0.7043	Intermediate Similarity	NPD7328	Approved
0.703	Intermediate Similarity	NPD5692	Phase 3
0.703	Intermediate Similarity	NPD5207	Approved
0.7027	Intermediate Similarity	NPD7290	Approved
0.7027	Intermediate Similarity	NPD6883	Approved
0.7027	Intermediate Similarity	NPD7102	Approved
0.7009	Intermediate Similarity	NPD8033	Approved
0.7	Intermediate Similarity	NPD6011	Approved
0.6991	Remote Similarity	NPD4632	Approved
0.6983	Remote Similarity	NPD7516	Approved
0.6972	Remote Similarity	NPD7128	Approved
0.6972	Remote Similarity	NPD6675	Approved
0.6972	Remote Similarity	NPD6402	Approved
0.6972	Remote Similarity	NPD5739	Approved
0.6964	Remote Similarity	NPD6869	Approved
0.6964	Remote Similarity	NPD6649	Approved
0.6964	Remote Similarity	NPD6847	Approved
0.6964	Remote Similarity	NPD8130	Phase 1
0.6964	Remote Similarity	NPD6617	Approved
0.6964	Remote Similarity	NPD6650	Approved
0.6961	Remote Similarity	NPD7515	Phase 2
0.6952	Remote Similarity	NPD7902	Approved
0.6939	Remote Similarity	NPD3668	Phase 3
0.6939	Remote Similarity	NPD3133	Approved
0.6939	Remote Similarity	NPD3666	Approved
0.6939	Remote Similarity	NPD3665	Phase 1
0.6937	Remote Similarity	NPD6012	Approved
0.6937	Remote Similarity	NPD6014	Approved
0.6937	Remote Similarity	NPD6013	Approved
0.6931	Remote Similarity	NPD5328	Approved
0.6923	Remote Similarity	NPD8377	Approved
0.6923	Remote Similarity	NPD8294	Approved
0.6907	Remote Similarity	NPD3667	Approved
0.6903	Remote Similarity	NPD8297	Approved
0.6903	Remote Similarity	NPD6882	Approved
0.6882	Remote Similarity	NPD7339	Approved
0.6882	Remote Similarity	NPD6942	Approved
0.6864	Remote Similarity	NPD8380	Approved
0.6864	Remote Similarity	NPD8379	Approved
0.6864	Remote Similarity	NPD8296	Approved
0.6864	Remote Similarity	NPD8378	Approved
0.6864	Remote Similarity	NPD8335	Approved
0.6863	Remote Similarity	NPD5785	Approved
0.6857	Remote Similarity	NPD5221	Approved
0.6857	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5222	Approved
0.6847	Remote Similarity	NPD7320	Approved
0.6837	Remote Similarity	NPD6695	Phase 3
0.6827	Remote Similarity	NPD6001	Approved
0.681	Remote Similarity	NPD6009	Approved
0.68	Remote Similarity	NPD3618	Phase 1
0.6796	Remote Similarity	NPD5284	Approved
0.6796	Remote Similarity	NPD5281	Approved
0.6792	Remote Similarity	NPD5173	Approved
0.6786	Remote Similarity	NPD6372	Approved
0.6786	Remote Similarity	NPD6373	Approved
0.678	Remote Similarity	NPD6319	Approved
0.6777	Remote Similarity	NPD7507	Approved
0.6768	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4753	Phase 2
0.6762	Remote Similarity	NPD5210	Approved
0.6762	Remote Similarity	NPD4629	Approved
0.6757	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5701	Approved
0.6757	Remote Similarity	NPD6614	Approved
0.675	Remote Similarity	NPD7604	Phase 2
0.6735	Remote Similarity	NPD5209	Approved
0.6735	Remote Similarity	NPD4221	Approved
0.6735	Remote Similarity	NPD4223	Phase 3
0.6733	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6868	Approved
0.6723	Remote Similarity	NPD5983	Phase 2
0.67	Remote Similarity	NPD5329	Approved
0.6699	Remote Similarity	NPD7838	Discovery
0.6697	Remote Similarity	NPD5211	Phase 2
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.664	Remote Similarity	NPD7260	Phase 2
0.6639	Remote Similarity	NPD6336	Discontinued
0.6639	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6637	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6052	Approved
0.6635	Remote Similarity	NPD8035	Phase 2
0.6635	Remote Similarity	NPD8034	Phase 2
0.6634	Remote Similarity	NPD5690	Phase 2
0.6634	Remote Similarity	NPD5279	Phase 3
0.6632	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4691	Approved
0.663	Remote Similarity	NPD4747	Approved
0.6613	Remote Similarity	NPD7319	Approved
0.661	Remote Similarity	NPD6335	Approved
0.6606	Remote Similarity	NPD5223	Approved
0.6606	Remote Similarity	NPD5344	Discontinued
0.6604	Remote Similarity	NPD5654	Approved
0.6602	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4197	Approved
0.6598	Remote Similarity	NPD6929	Approved
0.6596	Remote Similarity	NPD4784	Approved
0.6596	Remote Similarity	NPD4785	Approved
0.6596	Remote Similarity	NPD4058	Approved
0.6585	Remote Similarity	NPD7078	Approved
0.6579	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5141	Approved
0.6571	Remote Similarity	NPD4202	Approved
0.6569	Remote Similarity	NPD7524	Approved
0.6569	Remote Similarity	NPD7750	Discontinued
0.6555	Remote Similarity	NPD7101	Approved
0.6555	Remote Similarity	NPD7100	Approved
0.6552	Remote Similarity	NPD6858	Approved
0.6552	Remote Similarity	NPD7094	Approved
0.6545	Remote Similarity	NPD5226	Approved
0.6545	Remote Similarity	NPD5225	Approved
0.6545	Remote Similarity	NPD5224	Approved
0.6545	Remote Similarity	NPD4633	Approved
0.6542	Remote Similarity	NPD7732	Phase 3
0.6542	Remote Similarity	NPD4697	Phase 3
0.6535	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7514	Phase 3
0.6531	Remote Similarity	NPD6930	Phase 2
0.6531	Remote Similarity	NPD7525	Registered
0.6531	Remote Similarity	NPD6931	Approved
0.6531	Remote Similarity	NPD4695	Discontinued
0.6529	Remote Similarity	NPD6370	Approved
0.6526	Remote Similarity	NPD8039	Approved
0.6525	Remote Similarity	NPD6317	Approved
0.6522	Remote Similarity	NPD4137	Phase 3
0.6495	Remote Similarity	NPD7145	Approved
0.6495	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5175	Approved
0.6486	Remote Similarity	NPD5174	Approved
0.6481	Remote Similarity	NPD5959	Approved
0.6481	Remote Similarity	NPD4755	Approved
0.6471	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4690	Approved
0.6471	Remote Similarity	NPD5205	Approved
0.6471	Remote Similarity	NPD4689	Approved
0.6471	Remote Similarity	NPD6314	Approved
0.6471	Remote Similarity	NPD4138	Approved
0.6471	Remote Similarity	NPD6313	Approved
0.6471	Remote Similarity	NPD4623	Approved
0.6471	Remote Similarity	NPD4688	Approved
0.6471	Remote Similarity	NPD4693	Phase 3
0.6471	Remote Similarity	NPD4519	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