NPASS Compound

Structure

NPC38736 OpenBabel07101719252D 29 31 0 0 1 0 0 0 0 0999 V2000 -3.9811 -4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 2.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9156 2.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6150 -4.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6150 -3.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9811 -4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 1.3512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 0.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 -0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 -1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 -0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 2.3512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1835 -0.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 -1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -2.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 -2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9811 -3.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4811 -4.0975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9756 -3.1270 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 -0.4158 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3164 1.2784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 24 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 9 16 1 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 15 4 1 6 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 18 21 2 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 26 1 0 0 0 0 22 27 2 0 0 0 0 22 28 1 0 0 0 0 23 25 2 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	391.23
Volume:	424.833
LogP:	5.114
LogD:	3.822
LogS:	-3.085
# Rotatable Bonds:	6
TPSA:	81.77
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	3.443
Fsp3:	0.333
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:	-5.087
MDCK Permeability:	1.4421562809729949e-05
Pgp-inhibitor:	0.814
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.062

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	99.4694595336914%
Volume Distribution (VD):	0.24
Pgp-substrate:	1.2089887857437134%

ADMET: Metabolism

CYP1A2-inhibitor:	0.547
CYP1A2-substrate:	0.781
CYP2C19-inhibitor:	0.765
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.876
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.884
CYP2D6-substrate:	0.692
CYP3A4-inhibitor:	0.825
CYP3A4-substrate:	0.665

ADMET: Excretion

Clearance (CL):	3.162
Half-life (T1/2):	0.605

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.796
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.757
Maximum Recommended Daily Dose:	0.118
Skin Sensitization:	0.086
Carcinogencity:	0.095
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC38736

Natural Product ID:	NPC38736
*Common Name:**	Isoechinulin A
IUPAC Name:	(3S,6Z)-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-5-(3-methylbut-2-enyl)-1H-indol-3-yl]methylidene]piperazine-2,5-dione
Synonyms:
Standard InCHIKey:	ZHKHUDVCZTVZPU-HYTQYMIGSA-N
Standard InCHI:	InChI=1S/C24H29N3O2/c1-7-24(5,6)21-18(13-20-23(29)25-15(4)22(28)27-20)17-12-16(9-8-14(2)3)10-11-19(17)26-21/h7-8,10-13,15,26H,1,9H2,2-6H3,(H,25,29)(H,27,28)/b20-13-/t15-/m0/s1
SMILES:	C=CC(c1[nH]c2c(c1/C=C/1N=C(O)[C@@H](N=C1O)C)cc(cc2)CC=C(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL250697
PubChem CID:	44445553
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids 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
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00010a040]
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17896816]
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17965475]
NPO32843	eurotium cristatum en-220	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22727636]
NPO32640	eurotium rubrum ma-150	Species	Aspergillaceae	Eukaryota	Fungus Obtained from Marine Mangrove-Derived Rhizospheric Soil.	n.a.	n.a.	PMID[25730346]

☑ 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	2
LD50	2
Others	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	>	200000.0	nM	PMID[473230]
NPT35	Others	n.a.		IC50	=	98000.0	nM	PMID[473228]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	16.9	ug ml-1	PMID[473229]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	42700.0	nM	PMID[473230]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	77.58	%	PMID[473230]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	11.7	uM	PMID[473231]

☑ 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 NPC38736 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	448
0.1-0.2	3495
0.2-0.3	17827
0.3-0.4	13674
0.4-0.5	3383
0.5-0.6	2127
0.6-0.7	1313
0.7-0.8	365
0.8-0.85	41
0.85-0.9	9
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC187951
0.972	High Similarity	NPC37548
0.972	High Similarity	NPC124005
0.9456	High Similarity	NPC470507
0.9444	High Similarity	NPC129042
0.9441	High Similarity	NPC242556
0.9392	High Similarity	NPC184476
0.9338	High Similarity	NPC472587
0.9333	High Similarity	NPC473320
0.9286	High Similarity	NPC6982
0.9272	High Similarity	NPC16667
0.9226	High Similarity	NPC34508
0.9108	High Similarity	NPC288785
0.9085	High Similarity	NPC271734
0.9067	High Similarity	NPC471458
0.9013	High Similarity	NPC67056
0.9007	High Similarity	NPC285469
0.8994	High Similarity	NPC270009
0.8974	High Similarity	NPC280548
0.894	High Similarity	NPC207726
0.8882	High Similarity	NPC192270
0.8824	High Similarity	NPC299594
0.8782	High Similarity	NPC470508
0.8601	High Similarity	NPC22079
0.858	High Similarity	NPC293472
0.8563	High Similarity	NPC46413
0.8528	High Similarity	NPC472443
0.8516	High Similarity	NPC141353
0.8497	Intermediate Similarity	NPC105818
0.8497	Intermediate Similarity	NPC24678
0.8414	Intermediate Similarity	NPC179365
0.8414	Intermediate Similarity	NPC475450
0.8375	Intermediate Similarity	NPC49954
0.8375	Intermediate Similarity	NPC474561
0.8373	Intermediate Similarity	NPC472444
0.8365	Intermediate Similarity	NPC194640
0.8355	Intermediate Similarity	NPC159856
0.8355	Intermediate Similarity	NPC314372
0.8333	Intermediate Similarity	NPC2949
0.8303	Intermediate Similarity	NPC176199
0.8303	Intermediate Similarity	NPC215795
0.8302	Intermediate Similarity	NPC282231
0.8276	Intermediate Similarity	NPC473587
0.8272	Intermediate Similarity	NPC194411
0.8258	Intermediate Similarity	NPC33421
0.8242	Intermediate Similarity	NPC68354
0.8239	Intermediate Similarity	NPC279918
0.8232	Intermediate Similarity	NPC472586
0.8224	Intermediate Similarity	NPC190296
0.8221	Intermediate Similarity	NPC470498
0.8219	Intermediate Similarity	NPC475428
0.821	Intermediate Similarity	NPC63751
0.8207	Intermediate Similarity	NPC473762
0.8188	Intermediate Similarity	NPC325252
0.8176	Intermediate Similarity	NPC92796
0.8176	Intermediate Similarity	NPC135141
0.8158	Intermediate Similarity	NPC63157
0.8158	Intermediate Similarity	NPC473868
0.8153	Intermediate Similarity	NPC25008
0.8153	Intermediate Similarity	NPC469765
0.8153	Intermediate Similarity	NPC469763
0.8153	Intermediate Similarity	NPC469760
0.8153	Intermediate Similarity	NPC469786
0.8153	Intermediate Similarity	NPC73952
0.8153	Intermediate Similarity	NPC259644
0.8129	Intermediate Similarity	NPC21605
0.8125	Intermediate Similarity	NPC32200
0.8121	Intermediate Similarity	NPC198988
0.8121	Intermediate Similarity	NPC275305
0.8121	Intermediate Similarity	NPC37423
0.8108	Intermediate Similarity	NPC473930
0.8101	Intermediate Similarity	NPC75540
0.8101	Intermediate Similarity	NPC80597
0.8101	Intermediate Similarity	NPC212376
0.8101	Intermediate Similarity	NPC70922
0.8101	Intermediate Similarity	NPC211572
0.8092	Intermediate Similarity	NPC59084
0.8069	Intermediate Similarity	NPC250361
0.8067	Intermediate Similarity	NPC218268
0.8042	Intermediate Similarity	NPC41174
0.8037	Intermediate Similarity	NPC160105
0.8037	Intermediate Similarity	NPC54988
0.8026	Intermediate Similarity	NPC88097
0.8	Intermediate Similarity	NPC470440
0.8	Intermediate Similarity	NPC469762
0.7988	Intermediate Similarity	NPC201700
0.7974	Intermediate Similarity	NPC469768
0.7974	Intermediate Similarity	NPC469767
0.7974	Intermediate Similarity	NPC469779
0.7974	Intermediate Similarity	NPC469784
0.7974	Intermediate Similarity	NPC469783
0.7974	Intermediate Similarity	NPC469761
0.7974	Intermediate Similarity	NPC469780
0.7965	Intermediate Similarity	NPC317030
0.795	Intermediate Similarity	NPC206819
0.795	Intermediate Similarity	NPC318065
0.7937	Intermediate Similarity	NPC469785
0.7929	Intermediate Similarity	NPC91179
0.7927	Intermediate Similarity	NPC109447
0.7922	Intermediate Similarity	NPC469766
0.7917	Intermediate Similarity	NPC59269
0.7917	Intermediate Similarity	NPC248454
0.7914	Intermediate Similarity	NPC311276
0.791	Intermediate Similarity	NPC232130
0.7908	Intermediate Similarity	NPC73767
0.7904	Intermediate Similarity	NPC329688
0.7904	Intermediate Similarity	NPC189812
0.7901	Intermediate Similarity	NPC131718
0.7898	Intermediate Similarity	NPC471957
0.7898	Intermediate Similarity	NPC133366
0.7898	Intermediate Similarity	NPC477134
0.7895	Intermediate Similarity	NPC125746
0.7895	Intermediate Similarity	NPC84911
0.7879	Intermediate Similarity	NPC154293
0.787	Intermediate Similarity	NPC11126
0.7861	Intermediate Similarity	NPC204565
0.7857	Intermediate Similarity	NPC115611
0.7848	Intermediate Similarity	NPC2272
0.7844	Intermediate Similarity	NPC314603
0.7841	Intermediate Similarity	NPC474177
0.784	Intermediate Similarity	NPC41257
0.7836	Intermediate Similarity	NPC19679
0.7829	Intermediate Similarity	NPC261195
0.7829	Intermediate Similarity	NPC96102
0.7829	Intermediate Similarity	NPC29886
0.7824	Intermediate Similarity	NPC198339
0.7818	Intermediate Similarity	NPC49217
0.7818	Intermediate Similarity	NPC470509
0.7816	Intermediate Similarity	NPC173028
0.7816	Intermediate Similarity	NPC65215
0.7805	Intermediate Similarity	NPC476118
0.7805	Intermediate Similarity	NPC40779
0.7792	Intermediate Similarity	NPC104483
0.7792	Intermediate Similarity	NPC110126
0.7792	Intermediate Similarity	NPC312092
0.7791	Intermediate Similarity	NPC228835
0.7778	Intermediate Similarity	NPC286427
0.7778	Intermediate Similarity	NPC105127
0.7771	Intermediate Similarity	NPC204141
0.7771	Intermediate Similarity	NPC317430
0.7765	Intermediate Similarity	NPC213468
0.7765	Intermediate Similarity	NPC72980
0.7756	Intermediate Similarity	NPC20144
0.7746	Intermediate Similarity	NPC476319
0.7738	Intermediate Similarity	NPC472123
0.7733	Intermediate Similarity	NPC163055
0.773	Intermediate Similarity	NPC475990
0.773	Intermediate Similarity	NPC56765
0.7722	Intermediate Similarity	NPC143872
0.7706	Intermediate Similarity	NPC151939
0.7701	Intermediate Similarity	NPC474707
0.7697	Intermediate Similarity	NPC90723
0.7697	Intermediate Similarity	NPC271797
0.7697	Intermediate Similarity	NPC21174
0.7697	Intermediate Similarity	NPC102423
0.7688	Intermediate Similarity	NPC53947
0.7688	Intermediate Similarity	NPC190007
0.7688	Intermediate Similarity	NPC148592
0.7688	Intermediate Similarity	NPC165495
0.7684	Intermediate Similarity	NPC304187
0.7684	Intermediate Similarity	NPC477166
0.7683	Intermediate Similarity	NPC215584
0.7683	Intermediate Similarity	NPC44773
0.7661	Intermediate Similarity	NPC88363
0.7655	Intermediate Similarity	NPC215519
0.7644	Intermediate Similarity	NPC94943
0.764	Intermediate Similarity	NPC216713
0.7633	Intermediate Similarity	NPC97525
0.7633	Intermediate Similarity	NPC313791
0.7628	Intermediate Similarity	NPC279081
0.7616	Intermediate Similarity	NPC300688
0.761	Intermediate Similarity	NPC288838
0.7593	Intermediate Similarity	NPC200214
0.7586	Intermediate Similarity	NPC472294
0.7574	Intermediate Similarity	NPC158129
0.7572	Intermediate Similarity	NPC233936
0.7569	Intermediate Similarity	NPC265576
0.7568	Intermediate Similarity	NPC122718
0.7566	Intermediate Similarity	NPC82295
0.7562	Intermediate Similarity	NPC179787
0.7562	Intermediate Similarity	NPC201380
0.7561	Intermediate Similarity	NPC76982
0.7558	Intermediate Similarity	NPC219336
0.7557	Intermediate Similarity	NPC17059
0.7544	Intermediate Similarity	NPC267885
0.7543	Intermediate Similarity	NPC15102
0.7543	Intermediate Similarity	NPC280290
0.7529	Intermediate Similarity	NPC64055
0.7529	Intermediate Similarity	NPC212535
0.7529	Intermediate Similarity	NPC472108
0.7529	Intermediate Similarity	NPC161861
0.7529	Intermediate Similarity	NPC139291
0.7516	Intermediate Similarity	NPC230002
0.7516	Intermediate Similarity	NPC321911
0.7515	Intermediate Similarity	NPC221786
0.7515	Intermediate Similarity	NPC230869
0.7515	Intermediate Similarity	NPC474880
0.7514	Intermediate Similarity	NPC246700
0.7514	Intermediate Similarity	NPC229332
0.7514	Intermediate Similarity	NPC34271

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 NPC38736 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	602
0.2-0.3	999
0.3-0.4	1561
0.4-0.5	2810
0.5-0.6	2180
0.6-0.7	646
0.7-0.8	110
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8742	High Similarity	NPD4462	Approved
0.8742	High Similarity	NPD4463	Approved
0.85	High Similarity	NPD1325	Approved
0.85	High Similarity	NPD1326	Approved
0.8431	Intermediate Similarity	NPD3100	Discontinued
0.8428	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD2172	Phase 1
0.8242	Intermediate Similarity	NPD3505	Approved
0.8242	Intermediate Similarity	NPD3506	Approved
0.8193	Intermediate Similarity	NPD4076	Approved
0.8193	Intermediate Similarity	NPD4079	Approved
0.8193	Intermediate Similarity	NPD8386	Phase 2
0.817	Intermediate Similarity	NPD5254	Discontinued
0.8098	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD5021	Discontinued
0.8092	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1592	Phase 3
0.8026	Intermediate Similarity	NPD786	Approved
0.8024	Intermediate Similarity	NPD2144	Approved
0.7949	Intermediate Similarity	NPD1683	Approved
0.7939	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD5065	Approved
0.7904	Intermediate Similarity	NPD4128	Approved
0.7882	Intermediate Similarity	NPD3038	Discontinued
0.7849	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1722	Approved
0.7805	Intermediate Similarity	NPD5138	Approved
0.7805	Intermediate Similarity	NPD5140	Approved
0.7799	Intermediate Similarity	NPD3835	Phase 3
0.7799	Intermediate Similarity	NPD3833	Phase 3
0.7791	Intermediate Similarity	NPD1403	Approved
0.7791	Intermediate Similarity	NPD1404	Approved
0.7771	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4640	Approved
0.7771	Intermediate Similarity	NPD4639	Approved
0.7771	Intermediate Similarity	NPD2640	Approved
0.7771	Intermediate Similarity	NPD2641	Approved
0.7771	Intermediate Similarity	NPD4638	Approved
0.7759	Intermediate Similarity	NPD3961	Discontinued
0.7756	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD4075	Phase 2
0.7727	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6595	Phase 3
0.7711	Intermediate Similarity	NPD2639	Approved
0.7711	Intermediate Similarity	NPD2642	Approved
0.7667	Intermediate Similarity	NPD3654	Approved
0.7662	Intermediate Similarity	NPD1262	Discovery
0.7657	Intermediate Similarity	NPD8431	Approved
0.764	Intermediate Similarity	NPD6158	Phase 2
0.764	Intermediate Similarity	NPD2882	Phase 1
0.764	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD4181	Approved
0.759	Intermediate Similarity	NPD3323	Discontinued
0.7582	Intermediate Similarity	NPD3385	Approved
0.758	Intermediate Similarity	NPD5020	Approved
0.7557	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD2915	Discontinued
0.7544	Intermediate Similarity	NPD2381	Approved
0.7544	Intermediate Similarity	NPD2382	Approved
0.7544	Intermediate Similarity	NPD2380	Approved
0.7541	Intermediate Similarity	NPD4511	Phase 1
0.753	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD482	Approved
0.7485	Intermediate Similarity	NPD2837	Discontinued
0.7472	Intermediate Similarity	NPD4499	Approved
0.7468	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2844	Phase 3
0.7455	Intermediate Similarity	NPD4326	Phase 2
0.7453	Intermediate Similarity	NPD4547	Phase 3
0.7442	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5104	Approved
0.744	Intermediate Similarity	NPD2720	Phase 1
0.744	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5596	Phase 2
0.7429	Intermediate Similarity	NPD5106	Approved
0.7429	Intermediate Similarity	NPD2095	Phase 2
0.7429	Intermediate Similarity	NPD5105	Approved
0.7429	Intermediate Similarity	NPD2094	Phase 2
0.7429	Intermediate Similarity	NPD2092	Phase 2
0.7419	Intermediate Similarity	NPD5901	Discontinued
0.7416	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7619	Phase 3
0.7403	Intermediate Similarity	NPD7618	Phase 3
0.7386	Intermediate Similarity	NPD2096	Phase 2
0.7386	Intermediate Similarity	NPD2091	Phase 2
0.7368	Intermediate Similarity	NPD3609	Approved
0.7368	Intermediate Similarity	NPD3610	Approved
0.7363	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4703	Approved
0.7346	Intermediate Similarity	NPD4702	Approved
0.7337	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7948	Phase 1
0.732	Intermediate Similarity	NPD947	Approved
0.7314	Intermediate Similarity	NPD5473	Discontinued
0.7312	Intermediate Similarity	NPD4047	Discontinued
0.7308	Intermediate Similarity	NPD4880	Discontinued
0.7308	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3404	Approved
0.7289	Intermediate Similarity	NPD2580	Discontinued
0.7283	Intermediate Similarity	NPD6492	Phase 2
0.7278	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1255	Approved
0.7261	Intermediate Similarity	NPD1253	Approved
0.7261	Intermediate Similarity	NPD1256	Approved
0.7261	Intermediate Similarity	NPD1254	Approved
0.7251	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD750	Phase 2
0.7207	Intermediate Similarity	NPD6217	Discontinued
0.7186	Intermediate Similarity	NPD2150	Discontinued
0.7178	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5075	Discontinued
0.7151	Intermediate Similarity	NPD6248	Phase 2
0.7151	Intermediate Similarity	NPD6249	Phase 2
0.7143	Intermediate Similarity	NPD5100	Phase 3
0.7143	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6664	Approved
0.712	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5897	Approved
0.7119	Intermediate Similarity	NPD5899	Approved
0.7119	Intermediate Similarity	NPD5898	Approved
0.7119	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1251	Discontinued
0.7107	Intermediate Similarity	NPD6554	Approved
0.7107	Intermediate Similarity	NPD45	Approved
0.7105	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6159	Phase 2
0.7095	Intermediate Similarity	NPD4957	Phase 2
0.7079	Intermediate Similarity	NPD4399	Phase 2
0.7073	Intermediate Similarity	NPD7469	Discontinued
0.7072	Intermediate Similarity	NPD2383	Phase 1
0.7069	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6828	Phase 2
0.7062	Intermediate Similarity	NPD8093	Discontinued
0.7062	Intermediate Similarity	NPD3330	Phase 1
0.7059	Intermediate Similarity	NPD3814	Phase 1
0.7051	Intermediate Similarity	NPD3476	Approved
0.7051	Intermediate Similarity	NPD3475	Approved
0.7049	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5913	Phase 3
0.7049	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3318	Approved
0.7039	Intermediate Similarity	NPD3320	Approved
0.7039	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3319	Phase 1
0.7033	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1661	Suspended
0.7022	Intermediate Similarity	NPD6452	Discontinued
0.7021	Intermediate Similarity	NPD4600	Approved
0.7021	Intermediate Similarity	NPD4601	Approved
0.7011	Intermediate Similarity	NPD4615	Phase 2
0.7011	Intermediate Similarity	NPD5436	Phase 1
0.7	Intermediate Similarity	NPD5255	Approved
0.6995	Remote Similarity	NPD2564	Approved
0.6995	Remote Similarity	NPD2565	Phase 2
0.6994	Remote Similarity	NPD2006	Phase 2
0.6988	Remote Similarity	NPD2430	Phase 2
0.6983	Remote Similarity	NPD1707	Approved
0.6983	Remote Similarity	NPD1708	Approved
0.6978	Remote Similarity	NPD4948	Discontinued
0.6978	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD1038	Approved
0.6973	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3117	Approved
0.6971	Remote Similarity	NPD3116	Approved
0.6968	Remote Similarity	NPD2119	Approved
0.6968	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2118	Approved
0.6968	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD991	Phase 2
0.6961	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5003	Discontinued
0.6947	Remote Similarity	NPD8073	Approved
0.694	Remote Similarity	NPD4334	Discontinued
0.6939	Remote Similarity	NPD8094	Discontinued
0.6937	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4999	Phase 3
0.6935	Remote Similarity	NPD4998	Phase 3
0.6931	Remote Similarity	NPD484	Approved
0.6927	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3003	Approved
0.6927	Remote Similarity	NPD7957	Phase 1

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