NPASS Compound

Structure

NPC270009 OpenBabel07101718232D 31 33 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 -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 -5.5495 3.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0495 2.3512 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 -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 -4.1835 0.8512 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 -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 -5.0495 1.3512 0.0000 C 0 0 2 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 -5.0495 2.3512 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 -5.9156 0.8512 0.0000 O 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 -4.1835 2.8512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 23 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 18 2 0 0 0 0 13 2 1 6 0 0 0 13 21 1 0 0 0 0 13 25 1 0 0 0 0 15 16 1 0 0 0 0 15 17 2 0 0 0 0 16 20 2 0 0 0 0 17 26 1 0 0 0 0 18 22 1 0 0 0 0 18 27 1 0 0 0 0 19 24 1 0 0 0 0 19 28 1 1 0 0 0 20 23 1 0 0 0 0 20 26 1 0 0 0 0 21 27 2 0 0 0 0 21 29 1 0 0 0 0 22 25 2 0 0 0 0 22 30 1 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	425.23
Volume:	445.05
LogP:	2.613
LogD:	2.068
LogS:	-3.974
# Rotatable Bonds:	7
TPSA:	122.23
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.373
Synthetic Accessibility Score:	3.925
Fsp3:	0.417
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:	-5.452
MDCK Permeability:	1.0768897482194006e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.897
Human Intestinal Absorption (HIA):	0.178
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	97.18677520751953%
Volume Distribution (VD):	0.33
Pgp-substrate:	2.5618958473205566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.085
CYP1A2-substrate:	0.508
CYP2C19-inhibitor:	0.111
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.441
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.41
CYP2D6-substrate:	0.391
CYP3A4-inhibitor:	0.513
CYP3A4-substrate:	0.744

ADMET: Excretion

Clearance (CL):	3.379
Half-life (T1/2):	0.71

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.334
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.087
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC270009

Natural Product ID:	NPC270009
*Common Name:**	Dihydroxyisoechinulin A
IUPAC Name:	(3Z,6S)-3-[[5-[(2R)-2,3-dihydroxy-3-methylbutyl]-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene]-6-methylpiperazine-2,5-dione
Synonyms:
Standard InCHIKey:	ICDCJXUIMDWCFI-RKFKHAPCSA-N
Standard InCHI:	InChI=1S/C24H31N3O4/c1-7-23(3,4)20-16(12-18-22(30)25-13(2)21(29)27-18)15-10-14(8-9-17(15)26-20)11-19(28)24(5,6)31/h7-10,12-13,19,26,28,31H,1,11H2,2-6H3,(H,25,30)(H,27,29)/b18-12-/t13-,19+/m0/s1
SMILES:	C=CC(c1[nH]c2c(c1/C=C/1N=C(O)[C@@H](N=C1O)C)cc(cc2)C[C@H](C(O)(C)C)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251228
PubChem CID:	10071070
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]
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	1
LD50	1
MIC	1

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	79000.0	nM	PMID[517863]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	15.2	uM	PMID[517864]
NPT1845	Organism	Vibrio alginolyticus	Vibrio alginolyticus	MIC	=	16.0	ug.mL-1	PMID[517864]

☑ 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 NPC270009 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	303
0.1-0.2	1512
0.2-0.3	10080
0.3-0.4	19998
0.4-0.5	5971
0.5-0.6	2881
0.6-0.7	1492
0.7-0.8	415
0.8-0.85	19
0.85-0.9	18
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC34508
0.9509	High Similarity	NPC472443
0.9394	High Similarity	NPC192270
0.9337	High Similarity	NPC472444
0.929	High Similarity	NPC46413
0.9207	High Similarity	NPC472586
0.9096	High Similarity	NPC293472
0.8994	High Similarity	NPC38736
0.8951	High Similarity	NPC16667
0.8927	High Similarity	NPC32200
0.8922	High Similarity	NPC288785
0.8889	High Similarity	NPC473320
0.8875	High Similarity	NPC470507
0.8841	High Similarity	NPC470508
0.8742	High Similarity	NPC124005
0.8742	High Similarity	NPC187951
0.8742	High Similarity	NPC37548
0.8712	High Similarity	NPC67056
0.8704	High Similarity	NPC285469
0.8683	High Similarity	NPC280548
0.8642	High Similarity	NPC207726
0.8642	High Similarity	NPC471458
0.8521	High Similarity	NPC6982
0.85	High Similarity	NPC129042
0.8491	Intermediate Similarity	NPC242556
0.8476	Intermediate Similarity	NPC184476
0.8443	Intermediate Similarity	NPC472587
0.8364	Intermediate Similarity	NPC141353
0.8343	Intermediate Similarity	NPC19679
0.8294	Intermediate Similarity	NPC154293
0.8229	Intermediate Similarity	NPC198339
0.8225	Intermediate Similarity	NPC40779
0.8225	Intermediate Similarity	NPC271734
0.8198	Intermediate Similarity	NPC470498
0.8187	Intermediate Similarity	NPC133366
0.8132	Intermediate Similarity	NPC474177
0.8129	Intermediate Similarity	NPC474561
0.8129	Intermediate Similarity	NPC49954
0.8129	Intermediate Similarity	NPC54988
0.8118	Intermediate Similarity	NPC311276
0.8118	Intermediate Similarity	NPC194640
0.8114	Intermediate Similarity	NPC151939
0.8111	Intermediate Similarity	NPC34271
0.8103	Intermediate Similarity	NPC329688
0.8103	Intermediate Similarity	NPC189812
0.8081	Intermediate Similarity	NPC201700
0.8079	Intermediate Similarity	NPC314394
0.8059	Intermediate Similarity	NPC282231
0.8056	Intermediate Similarity	NPC317030
0.8043	Intermediate Similarity	NPC205403
0.8	Intermediate Similarity	NPC279918
0.7988	Intermediate Similarity	NPC469762
0.7988	Intermediate Similarity	NPC299594
0.7977	Intermediate Similarity	NPC63751
0.7977	Intermediate Similarity	NPC317430
0.7956	Intermediate Similarity	NPC204565
0.7944	Intermediate Similarity	NPC476319
0.7943	Intermediate Similarity	NPC97525
0.7929	Intermediate Similarity	NPC469785
0.7921	Intermediate Similarity	NPC300688
0.7919	Intermediate Similarity	NPC160105
0.7912	Intermediate Similarity	NPC65215
0.7912	Intermediate Similarity	NPC173028
0.791	Intermediate Similarity	NPC68354
0.7907	Intermediate Similarity	NPC102423
0.7889	Intermediate Similarity	NPC165201
0.7886	Intermediate Similarity	NPC158129
0.7877	Intermediate Similarity	NPC302191
0.7869	Intermediate Similarity	NPC95783
0.7865	Intermediate Similarity	NPC314957
0.7865	Intermediate Similarity	NPC72980
0.7865	Intermediate Similarity	NPC215795
0.7865	Intermediate Similarity	NPC127677
0.7865	Intermediate Similarity	NPC176199
0.7857	Intermediate Similarity	NPC119700
0.7841	Intermediate Similarity	NPC472123
0.7841	Intermediate Similarity	NPC313791
0.7833	Intermediate Similarity	NPC163055
0.7833	Intermediate Similarity	NPC139291
0.7833	Intermediate Similarity	NPC472108
0.7812	Intermediate Similarity	NPC46225
0.7811	Intermediate Similarity	NPC259644
0.7811	Intermediate Similarity	NPC469760
0.7811	Intermediate Similarity	NPC469763
0.7811	Intermediate Similarity	NPC73952
0.7811	Intermediate Similarity	NPC469765
0.7811	Intermediate Similarity	NPC25008
0.7811	Intermediate Similarity	NPC469786
0.7807	Intermediate Similarity	NPC232130
0.7802	Intermediate Similarity	NPC474707
0.7797	Intermediate Similarity	NPC275305
0.7797	Intermediate Similarity	NPC37423
0.7791	Intermediate Similarity	NPC131718
0.779	Intermediate Similarity	NPC190007
0.7778	Intermediate Similarity	NPC470497
0.7772	Intermediate Similarity	NPC206967
0.7765	Intermediate Similarity	NPC88363
0.7765	Intermediate Similarity	NPC211572
0.7765	Intermediate Similarity	NPC80597
0.7765	Intermediate Similarity	NPC70922
0.7765	Intermediate Similarity	NPC133261
0.7765	Intermediate Similarity	NPC212376
0.7765	Intermediate Similarity	NPC75540
0.7747	Intermediate Similarity	NPC94943
0.774	Intermediate Similarity	NPC314603
0.7737	Intermediate Similarity	NPC300183
0.7736	Intermediate Similarity	NPC22079
0.7735	Intermediate Similarity	NPC48938
0.7733	Intermediate Similarity	NPC230869
0.7709	Intermediate Similarity	NPC59269
0.7709	Intermediate Similarity	NPC326575
0.7709	Intermediate Similarity	NPC248454
0.7701	Intermediate Similarity	NPC476118
0.7692	Intermediate Similarity	NPC105818
0.7692	Intermediate Similarity	NPC24678
0.7692	Intermediate Similarity	NPC475422
0.768	Intermediate Similarity	NPC233936
0.768	Intermediate Similarity	NPC258062
0.7672	Intermediate Similarity	NPC473747
0.7672	Intermediate Similarity	NPC470499
0.7668	Intermediate Similarity	NPC476106
0.766	Intermediate Similarity	NPC231342
0.7656	Intermediate Similarity	NPC98715
0.7653	Intermediate Similarity	NPC250129
0.765	Intermediate Similarity	NPC473189
0.765	Intermediate Similarity	NPC188387
0.765	Intermediate Similarity	NPC163421
0.7637	Intermediate Similarity	NPC212535
0.7634	Intermediate Similarity	NPC243716
0.7629	Intermediate Similarity	NPC225821
0.7627	Intermediate Similarity	NPC194411
0.7622	Intermediate Similarity	NPC246700
0.7619	Intermediate Similarity	NPC229332
0.7614	Intermediate Similarity	NPC151976
0.7606	Intermediate Similarity	NPC181502
0.7606	Intermediate Similarity	NPC85066
0.7604	Intermediate Similarity	NPC123019
0.7602	Intermediate Similarity	NPC475165
0.7596	Intermediate Similarity	NPC472294
0.7592	Intermediate Similarity	NPC249040
0.759	Intermediate Similarity	NPC87755
0.759	Intermediate Similarity	NPC61637
0.7588	Intermediate Similarity	NPC204491
0.7581	Intermediate Similarity	NPC314333
0.7578	Intermediate Similarity	NPC179365
0.7578	Intermediate Similarity	NPC475450
0.7569	Intermediate Similarity	NPC213468
0.7569	Intermediate Similarity	NPC6093
0.7565	Intermediate Similarity	NPC477135
0.7565	Intermediate Similarity	NPC476115
0.756	Intermediate Similarity	NPC314372
0.756	Intermediate Similarity	NPC159856
0.7556	Intermediate Similarity	NPC134586
0.7554	Intermediate Similarity	NPC62510
0.755	Intermediate Similarity	NPC96131
0.7541	Intermediate Similarity	NPC472109
0.7541	Intermediate Similarity	NPC472110
0.7541	Intermediate Similarity	NPC469358
0.7539	Intermediate Similarity	NPC128823
0.753	Intermediate Similarity	NPC2949
0.7526	Intermediate Similarity	NPC243834
0.7526	Intermediate Similarity	NPC70956
0.7514	Intermediate Similarity	NPC211997
0.7514	Intermediate Similarity	NPC315555
0.7514	Intermediate Similarity	NPC235684
0.7513	Intermediate Similarity	NPC234999
0.7512	Intermediate Similarity	NPC469594
0.75	Intermediate Similarity	NPC165495
0.75	Intermediate Similarity	NPC475151
0.7487	Intermediate Similarity	NPC471080
0.7487	Intermediate Similarity	NPC329858
0.7487	Intermediate Similarity	NPC265576
0.7487	Intermediate Similarity	NPC306376
0.7487	Intermediate Similarity	NPC469592
0.7485	Intermediate Similarity	NPC33421
0.7462	Intermediate Similarity	NPC477548
0.7462	Intermediate Similarity	NPC271862
0.7459	Intermediate Similarity	NPC15102
0.7459	Intermediate Similarity	NPC203754
0.7459	Intermediate Similarity	NPC150048
0.7459	Intermediate Similarity	NPC314002
0.7453	Intermediate Similarity	NPC473587
0.745	Intermediate Similarity	NPC471284
0.7449	Intermediate Similarity	NPC474905
0.7448	Intermediate Similarity	NPC476175
0.7446	Intermediate Similarity	NPC176127
0.744	Intermediate Similarity	NPC190296
0.7437	Intermediate Similarity	NPC87856
0.7437	Intermediate Similarity	NPC235900
0.7435	Intermediate Similarity	NPC153042
0.7433	Intermediate Similarity	NPC128751
0.7432	Intermediate Similarity	NPC91179
0.7429	Intermediate Similarity	NPC92796
0.7429	Intermediate Similarity	NPC135141
0.7423	Intermediate Similarity	NPC291535
0.7423	Intermediate Similarity	NPC475112
0.7423	Intermediate Similarity	NPC193761
0.7423	Intermediate Similarity	NPC475085
0.7421	Intermediate Similarity	NPC195314
0.7419	Intermediate Similarity	NPC171171

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 NPC270009 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	531
0.2-0.3	773
0.3-0.4	1441
0.4-0.5	2972
0.5-0.6	2534
0.6-0.7	630
0.7-0.8	99
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD1326	Approved
0.8462	Intermediate Similarity	NPD1325	Approved
0.8057	Intermediate Similarity	NPD2380	Approved
0.8057	Intermediate Similarity	NPD2381	Approved
0.8057	Intermediate Similarity	NPD2382	Approved
0.7966	Intermediate Similarity	NPD8386	Phase 2
0.7966	Intermediate Similarity	NPD4076	Approved
0.7966	Intermediate Similarity	NPD4079	Approved
0.7933	Intermediate Similarity	NPD5596	Phase 2
0.7914	Intermediate Similarity	NPD1592	Phase 3
0.791	Intermediate Similarity	NPD2144	Approved
0.791	Intermediate Similarity	NPD3506	Approved
0.791	Intermediate Similarity	NPD3505	Approved
0.7904	Intermediate Similarity	NPD4463	Approved
0.7904	Intermediate Similarity	NPD4462	Approved
0.7882	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD5065	Approved
0.7778	Intermediate Similarity	NPD3038	Discontinued
0.7759	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6595	Phase 3
0.7701	Intermediate Similarity	NPD5140	Approved
0.7701	Intermediate Similarity	NPD5138	Approved
0.767	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5021	Discontinued
0.765	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6158	Phase 2
0.7647	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4511	Phase 1
0.7633	Intermediate Similarity	NPD3100	Discontinued
0.7624	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD4499	Approved
0.7571	Intermediate Similarity	NPD4640	Approved
0.7571	Intermediate Similarity	NPD4639	Approved
0.7571	Intermediate Similarity	NPD4638	Approved
0.7568	Intermediate Similarity	NPD8431	Approved
0.7544	Intermediate Similarity	NPD2882	Phase 1
0.7543	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7948	Phase 1
0.7487	Intermediate Similarity	NPD3003	Approved
0.7485	Intermediate Similarity	NPD2172	Phase 1
0.7473	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD2383	Phase 1
0.7472	Intermediate Similarity	NPD2844	Phase 3
0.746	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5913	Phase 3
0.7447	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5901	Discontinued
0.7411	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5254	Discontinued
0.7394	Intermediate Similarity	NPD2564	Approved
0.7394	Intermediate Similarity	NPD2565	Phase 2
0.7358	Intermediate Similarity	NPD1768	Approved
0.7358	Intermediate Similarity	NPD6248	Phase 2
0.7358	Intermediate Similarity	NPD6249	Phase 2
0.7351	Intermediate Similarity	NPD2094	Phase 2
0.7351	Intermediate Similarity	NPD2092	Phase 2
0.7351	Intermediate Similarity	NPD2095	Phase 2
0.7348	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5003	Discontinued
0.734	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5897	Approved
0.7337	Intermediate Similarity	NPD5898	Approved
0.7337	Intermediate Similarity	NPD3525	Discontinued
0.7337	Intermediate Similarity	NPD5899	Approved
0.733	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4600	Approved
0.732	Intermediate Similarity	NPD4601	Approved
0.7312	Intermediate Similarity	NPD2091	Phase 2
0.7312	Intermediate Similarity	NPD2096	Phase 2
0.731	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6492	Phase 2
0.7308	Intermediate Similarity	NPD482	Approved
0.7292	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3835	Phase 3
0.7283	Intermediate Similarity	NPD3833	Phase 3
0.7268	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD2175	Phase 3
0.7268	Intermediate Similarity	NPD2177	Approved
0.7268	Intermediate Similarity	NPD2176	Approved
0.7267	Intermediate Similarity	NPD4702	Approved
0.7267	Intermediate Similarity	NPD4703	Approved
0.7264	Intermediate Similarity	NPD3330	Phase 1
0.7262	Intermediate Similarity	NPD786	Approved
0.7241	Intermediate Similarity	NPD5612	Discontinued
0.7228	Intermediate Similarity	NPD6159	Phase 2
0.7225	Intermediate Similarity	NPD3404	Approved
0.7222	Intermediate Similarity	NPD7957	Phase 1
0.7222	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5067	Phase 2
0.7214	Intermediate Similarity	NPD5066	Phase 2
0.7213	Intermediate Similarity	NPD4128	Approved
0.7209	Intermediate Similarity	NPD1683	Approved
0.7192	Intermediate Similarity	NPD5902	Approved
0.7192	Intermediate Similarity	NPD5903	Approved
0.7188	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1038	Approved
0.7186	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD8322	Phase 2
0.7179	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5100	Phase 3
0.7166	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6978	Phase 2
0.7143	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5255	Approved
0.7129	Intermediate Similarity	NPD7470	Discontinued
0.7129	Intermediate Similarity	NPD6220	Phase 3
0.7129	Intermediate Similarity	NPD5939	Approved
0.7129	Intermediate Similarity	NPD5936	Approved
0.7126	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5487	Phase 1
0.7121	Intermediate Similarity	NPD6176	Phase 1
0.7114	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3961	Discontinued
0.71	Intermediate Similarity	NPD1392	Approved
0.7095	Intermediate Similarity	NPD1403	Approved
0.7095	Intermediate Similarity	NPD1404	Approved
0.7092	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD3814	Phase 1
0.709	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD2640	Approved
0.7088	Intermediate Similarity	NPD2641	Approved
0.7083	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4075	Phase 2
0.7076	Intermediate Similarity	NPD1722	Approved
0.7071	Intermediate Similarity	NPD8073	Approved
0.7068	Intermediate Similarity	NPD4334	Discontinued
0.7065	Intermediate Similarity	NPD750	Phase 2
0.7059	Intermediate Similarity	NPD6452	Discontinued
0.7056	Intermediate Similarity	NPD484	Approved
0.7053	Intermediate Similarity	NPD6455	Phase 3
0.705	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8123	Approved
0.7043	Intermediate Similarity	NPD8122	Approved
0.7035	Intermediate Similarity	NPD2920	Discontinued
0.7035	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8072	Approved
0.7033	Intermediate Similarity	NPD2639	Approved
0.7033	Intermediate Similarity	NPD2642	Approved
0.7031	Intermediate Similarity	NPD6281	Approved
0.703	Intermediate Similarity	NPD5835	Phase 3
0.703	Intermediate Similarity	NPD5834	Phase 3
0.7026	Intermediate Similarity	NPD7935	Phase 2
0.7019	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4948	Discontinued
0.701	Intermediate Similarity	NPD802	Phase 2
0.701	Intermediate Similarity	NPD8093	Discontinued
0.7	Intermediate Similarity	NPD8272	Phase 2
0.6995	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6206	Phase 1
0.6989	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5104	Approved
0.6979	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2915	Discontinued
0.6977	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7944	Discontinued
0.697	Remote Similarity	NPD4501	Approved
0.697	Remote Similarity	NPD4500	Approved
0.697	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7777	Approved
0.6954	Remote Similarity	NPD6261	Phase 3
0.6954	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7778	Approved
0.6954	Remote Similarity	NPD53	Approved
0.6952	Remote Similarity	NPD4181	Approved
0.6947	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1262	Discovery
0.6931	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4204	Approved
0.6931	Remote Similarity	NPD4203	Approved
0.6928	Remote Similarity	NPD3654	Approved
0.6927	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3323	Discontinued
0.6923	Remote Similarity	NPD6985	Discontinued
0.6919	Remote Similarity	NPD8395	Approved
0.6919	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8396	Approved
0.6912	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5075	Discontinued
0.6911	Remote Similarity	NPD3082	Discontinued
0.6909	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4699	Discontinued
0.6902	Remote Similarity	NPD5862	Discovery
0.69	Remote Similarity	NPD5721	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