NPASS Compound

Structure

NPC475151 OpenBabel07101719252D 42 46 0 0 1 0 0 0 0 0999 V2000 5.2812 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6369 -1.4841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 -0.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6369 -4.9482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6369 -1.4841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1369 -2.3501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.8820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6369 -1.4841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 0.3820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1369 -2.3501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.1180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -1.1180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1369 0.3820 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 -1.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6369 -3.2161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -0.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4049 -0.6180 0.0000 C 0 0 2 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 -5.0029 0.8820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6369 -3.2161 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1369 -4.0821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 8 42 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 25 2 0 0 0 0 11 13 1 0 0 0 0 11 23 2 0 0 0 0 12 14 1 0 0 0 0 12 24 2 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 16 32 1 0 0 0 0 17 19 1 0 0 0 0 17 33 1 0 0 0 0 18 37 1 0 0 0 0 19 38 1 0 0 0 0 20 26 2 0 0 0 0 20 29 1 0 0 0 0 21 28 1 0 0 0 0 21 30 1 0 0 0 0 22 27 2 0 0 0 0 22 31 1 0 0 0 0 25 36 1 0 0 0 0 26 27 1 0 0 0 0 28 15 1 6 0 0 0 28 34 1 0 0 0 0 29 30 1 0 0 0 0 29 31 2 0 0 0 0 30 35 2 0 0 0 0 31 39 1 0 0 0 0 32 37 1 1 0 0 0 32 38 1 0 0 0 0 33 37 1 1 0 0 0 33 40 1 0 0 0 0 34 35 1 0 0 0 0 34 38 1 1 0 0 0 35 39 1 0 0 0 0 36 41 2 0 0 0 0 36 42 1 0 0 0 0 37 6 1 1 0 0 0 38 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	571.4
Volume:	639.297
LogP:	9.143
LogD:	5.732
LogS:	-5.581
# Rotatable Bonds:	9
TPSA:	62.32
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.189
Synthetic Accessibility Score:	4.949
Fsp3:	0.605
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.14
MDCK Permeability:	1.6847236111061648e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.35
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	86.69452667236328%
Volume Distribution (VD):	5.392
Pgp-substrate:	5.842865467071533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.183
CYP1A2-substrate:	0.197
CYP2C19-inhibitor:	0.354
CYP2C19-substrate:	0.341
CYP2C9-inhibitor:	0.755
CYP2C9-substrate:	0.275
CYP2D6-inhibitor:	0.55
CYP2D6-substrate:	0.369
CYP3A4-inhibitor:	0.911
CYP3A4-substrate:	0.298

ADMET: Excretion

Clearance (CL):	15.62
Half-life (T1/2):	0.018

ADMET: Toxicity

hERG Blockers:	0.974
Human Hepatotoxicity (H-HT):	0.669
Drug-inuced Liver Injury (DILI):	0.549
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.846
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.958
Carcinogencity:	0.124
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC475151

Natural Product ID:	NPC475151
*Common Name:**	Nodulisporic Acid E Methyl Ester
IUPAC Name:	n.a.
Synonyms:	Nodulisporic Acid E Methyl Ester
Standard InCHIKey:	GVTNUENKWZJLQE-UEUAPDDSSA-N
Standard InCHI:	InChI=1S/C38H53NO3/c1-23(2)11-13-26-20-29-30-21-28-15-16-32-37(6,18-9-10-25(5)36(41)42-8)33(40)17-19-38(32,7)34(28)35(30)39-31(29)22-27(26)14-12-24(3)4/h10-12,20,22,28,32-34,39-40H,9,13-19,21H2,1-8H3/b25-10+/t28-,32-,33-,34+,37-,38-/m0/s1
SMILES:	CC(=CCC1=CC2=C(C=C1CC=C(C)C)NC3=C2CC4C3C5(CCC(C(C5CC4)(C)CCC=C(C)C(=O)OC)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499440
PubChem CID:	44584354
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO32628	nodulisporium	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387649]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	100.0	nM	PMID[476667]

☑ 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 NPC475151 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	290
0.1-0.2	1401
0.2-0.3	4088
0.3-0.4	20533
0.4-0.5	11689
0.5-0.6	3041
0.6-0.7	1427
0.7-0.8	171
0.8-0.85	35
0.85-0.9	14
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC473747
0.9516	High Similarity	NPC475165
0.9465	High Similarity	NPC250129
0.9301	High Similarity	NPC187456
0.9274	High Similarity	NPC206967
0.9263	High Similarity	NPC473547
0.9215	High Similarity	NPC97388
0.8918	High Similarity	NPC160527
0.8918	High Similarity	NPC473650
0.8854	High Similarity	NPC284102
0.8737	High Similarity	NPC242446
0.8737	High Similarity	NPC475476
0.8722	High Similarity	NPC198339
0.8652	High Similarity	NPC97525
0.86	High Similarity	NPC61813
0.8571	High Similarity	NPC475424
0.8571	High Similarity	NPC79107
0.8564	High Similarity	NPC181502
0.8564	High Similarity	NPC6093
0.8564	High Similarity	NPC85066
0.8495	Intermediate Similarity	NPC34271
0.8446	Intermediate Similarity	NPC123019
0.8378	Intermediate Similarity	NPC165201
0.837	Intermediate Similarity	NPC302191
0.8358	Intermediate Similarity	NPC96131
0.8342	Intermediate Similarity	NPC119700
0.8317	Intermediate Similarity	NPC282033
0.8168	Intermediate Similarity	NPC471284
0.8159	Intermediate Similarity	NPC235900
0.8131	Intermediate Similarity	NPC18661
0.8095	Intermediate Similarity	NPC471634
0.8095	Intermediate Similarity	NPC473806
0.8095	Intermediate Similarity	NPC99428
0.8068	Intermediate Similarity	NPC469312
0.8068	Intermediate Similarity	NPC41318
0.8056	Intermediate Similarity	NPC470843
0.8056	Intermediate Similarity	NPC94541
0.8041	Intermediate Similarity	NPC231342
0.799	Intermediate Similarity	NPC245756
0.7989	Intermediate Similarity	NPC126492
0.7978	Intermediate Similarity	NPC154293
0.7931	Intermediate Similarity	NPC204303
0.7915	Intermediate Similarity	NPC183426
0.7857	Intermediate Similarity	NPC205403
0.7831	Intermediate Similarity	NPC300688
0.7739	Intermediate Similarity	NPC32200
0.7668	Intermediate Similarity	NPC476319
0.7668	Intermediate Similarity	NPC280290
0.766	Intermediate Similarity	NPC34508
0.7656	Intermediate Similarity	NPC19679
0.7653	Intermediate Similarity	NPC235885
0.761	Intermediate Similarity	NPC470280
0.7591	Intermediate Similarity	NPC278540
0.7557	Intermediate Similarity	NPC471583
0.7557	Intermediate Similarity	NPC471782
0.7553	Intermediate Similarity	NPC280548
0.7547	Intermediate Similarity	NPC470874
0.7541	Intermediate Similarity	NPC184476
0.7539	Intermediate Similarity	NPC151939
0.7527	Intermediate Similarity	NPC472587
0.7512	Intermediate Similarity	NPC477044
0.7512	Intermediate Similarity	NPC477041
0.75	Intermediate Similarity	NPC477135
0.75	Intermediate Similarity	NPC270009
0.7475	Intermediate Similarity	NPC477045
0.7462	Intermediate Similarity	NPC46413
0.7449	Intermediate Similarity	NPC160381
0.7441	Intermediate Similarity	NPC203614
0.7441	Intermediate Similarity	NPC204491
0.7438	Intermediate Similarity	NPC79129
0.7438	Intermediate Similarity	NPC249150
0.7438	Intermediate Similarity	NPC49196
0.7438	Intermediate Similarity	NPC195461
0.7438	Intermediate Similarity	NPC313985
0.7438	Intermediate Similarity	NPC81654
0.743	Intermediate Similarity	NPC2395
0.7423	Intermediate Similarity	NPC192270
0.7422	Intermediate Similarity	NPC311451
0.7415	Intermediate Similarity	NPC98715
0.7409	Intermediate Similarity	NPC213468
0.7407	Intermediate Similarity	NPC201700
0.7368	Intermediate Similarity	NPC234999
0.7356	Intermediate Similarity	NPC127677
0.7356	Intermediate Similarity	NPC258062
0.7356	Intermediate Similarity	NPC61637
0.7354	Intermediate Similarity	NPC473565
0.734	Intermediate Similarity	NPC50503
0.7339	Intermediate Similarity	NPC470873
0.7339	Intermediate Similarity	NPC249342
0.7326	Intermediate Similarity	NPC473320
0.7317	Intermediate Similarity	NPC300183
0.7308	Intermediate Similarity	NPC46225
0.7308	Intermediate Similarity	NPC225821
0.7302	Intermediate Similarity	NPC470508
0.7295	Intermediate Similarity	NPC477043
0.7287	Intermediate Similarity	NPC16667
0.7281	Intermediate Similarity	NPC51388
0.7268	Intermediate Similarity	NPC124005
0.7263	Intermediate Similarity	NPC470509
0.7251	Intermediate Similarity	NPC9894
0.725	Intermediate Similarity	NPC95783
0.725	Intermediate Similarity	NPC469497
0.725	Intermediate Similarity	NPC106833
0.7249	Intermediate Similarity	NPC8104
0.7241	Intermediate Similarity	NPC11445
0.724	Intermediate Similarity	NPC6982
0.724	Intermediate Similarity	NPC474701
0.7238	Intermediate Similarity	NPC271862
0.7222	Intermediate Similarity	NPC473189
0.722	Intermediate Similarity	NPC476175
0.7217	Intermediate Similarity	NPC151976
0.7217	Intermediate Similarity	NPC87856
0.7217	Intermediate Similarity	NPC475778
0.7213	Intermediate Similarity	NPC477134
0.7208	Intermediate Similarity	NPC472444
0.7206	Intermediate Similarity	NPC229332
0.7204	Intermediate Similarity	NPC38736
0.7204	Intermediate Similarity	NPC475422
0.7202	Intermediate Similarity	NPC147446
0.72	Intermediate Similarity	NPC128751
0.72	Intermediate Similarity	NPC246700
0.7196	Intermediate Similarity	NPC132211
0.7192	Intermediate Similarity	NPC157828
0.7192	Intermediate Similarity	NPC195239
0.719	Intermediate Similarity	NPC39679
0.7189	Intermediate Similarity	NPC280799
0.7183	Intermediate Similarity	NPC267965
0.7182	Intermediate Similarity	NPC57690
0.7181	Intermediate Similarity	NPC67056
0.7179	Intermediate Similarity	NPC293472
0.7169	Intermediate Similarity	NPC141428
0.7165	Intermediate Similarity	NPC189812
0.7165	Intermediate Similarity	NPC329688
0.7158	Intermediate Similarity	NPC129042
0.7143	Intermediate Similarity	NPC176199
0.7143	Intermediate Similarity	NPC474905
0.7143	Intermediate Similarity	NPC472443
0.7143	Intermediate Similarity	NPC193777
0.7143	Intermediate Similarity	NPC215795
0.7128	Intermediate Similarity	NPC288785
0.7124	Intermediate Similarity	NPC473441
0.7124	Intermediate Similarity	NPC131273
0.7122	Intermediate Similarity	NPC153042
0.7115	Intermediate Similarity	NPC193761
0.7114	Intermediate Similarity	NPC196251
0.7114	Intermediate Similarity	NPC111602
0.7114	Intermediate Similarity	NPC102338
0.7114	Intermediate Similarity	NPC63199
0.7112	Intermediate Similarity	NPC471458
0.7112	Intermediate Similarity	NPC470507
0.7111	Intermediate Similarity	NPC312092
0.7109	Intermediate Similarity	NPC87755
0.7095	Intermediate Similarity	NPC476106
0.7094	Intermediate Similarity	NPC67551
0.7094	Intermediate Similarity	NPC55493
0.7089	Intermediate Similarity	NPC87413
0.7085	Intermediate Similarity	NPC474688
0.7083	Intermediate Similarity	NPC293151
0.7079	Intermediate Similarity	NPC329858
0.7078	Intermediate Similarity	NPC144452
0.7077	Intermediate Similarity	NPC472586
0.7074	Intermediate Similarity	NPC285469
0.7072	Intermediate Similarity	NPC274640
0.7068	Intermediate Similarity	NPC271734
0.7068	Intermediate Similarity	NPC311276
0.7062	Intermediate Similarity	NPC477065
0.7061	Intermediate Similarity	NPC475844
0.7059	Intermediate Similarity	NPC112547
0.7059	Intermediate Similarity	NPC267926
0.7056	Intermediate Similarity	NPC473180
0.7053	Intermediate Similarity	NPC241024
0.7049	Intermediate Similarity	NPC242556
0.7045	Intermediate Similarity	NPC266192
0.7043	Intermediate Similarity	NPC33421
0.7042	Intermediate Similarity	NPC126066
0.7039	Intermediate Similarity	NPC70956
0.7039	Intermediate Similarity	NPC243834
0.7037	Intermediate Similarity	NPC3207
0.7033	Intermediate Similarity	NPC474116
0.7033	Intermediate Similarity	NPC162730
0.7031	Intermediate Similarity	NPC71132
0.703	Intermediate Similarity	NPC175474
0.7024	Intermediate Similarity	NPC220151
0.7024	Intermediate Similarity	NPC19692
0.7024	Intermediate Similarity	NPC195314
0.7021	Intermediate Similarity	NPC207726
0.7014	Intermediate Similarity	NPC300156
0.7005	Intermediate Similarity	NPC52557
0.7005	Intermediate Similarity	NPC68354
0.7	Intermediate Similarity	NPC190007
0.6995	Remote Similarity	NPC311330
0.6991	Remote Similarity	NPC118228
0.699	Remote Similarity	NPC275305
0.699	Remote Similarity	NPC37423
0.6989	Remote Similarity	NPC187951
0.6989	Remote Similarity	NPC37548
0.6986	Remote Similarity	NPC225279
0.6986	Remote Similarity	NPC476044
0.6986	Remote Similarity	NPC267423
0.6981	Remote Similarity	NPC4687

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 NPC475151 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	582
0.2-0.3	613
0.3-0.4	1897
0.4-0.5	3359
0.5-0.6	1968
0.6-0.7	502
0.7-0.8	17
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
0.7653	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4601	Approved
0.7438	Intermediate Similarity	NPD4600	Approved
0.7395	Intermediate Similarity	NPD6995	Phase 1
0.7394	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD5003	Discontinued
0.726	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7957	Phase 1
0.724	Intermediate Similarity	NPD7688	Phase 1
0.7163	Intermediate Similarity	NPD2920	Discontinued
0.7135	Intermediate Similarity	NPD5021	Discontinued
0.7098	Intermediate Similarity	NPD1325	Approved
0.7098	Intermediate Similarity	NPD1326	Approved
0.7081	Intermediate Similarity	NPD6176	Phase 1
0.7079	Intermediate Similarity	NPD2564	Approved
0.7079	Intermediate Similarity	NPD2565	Phase 2
0.7065	Intermediate Similarity	NPD8431	Approved
0.7056	Intermediate Similarity	NPD4079	Approved
0.7056	Intermediate Similarity	NPD4076	Approved
0.7033	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3506	Approved
0.7005	Intermediate Similarity	NPD3505	Approved
0.6991	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8386	Phase 2
0.6967	Remote Similarity	NPD5901	Discontinued
0.6963	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2844	Phase 3
0.6957	Remote Similarity	NPD5254	Discontinued
0.6952	Remote Similarity	NPD4463	Approved
0.6952	Remote Similarity	NPD4462	Approved
0.6939	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD4500	Approved
0.6938	Remote Similarity	NPD4501	Approved
0.6923	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2144	Approved
0.6912	Remote Similarity	NPD4499	Approved
0.6912	Remote Similarity	NPD6281	Approved
0.6912	Remote Similarity	NPD7707	Approved
0.6905	Remote Similarity	NPD4511	Phase 1
0.6901	Remote Similarity	NPD5429	Discontinued
0.69	Remote Similarity	NPD3038	Discontinued
0.6898	Remote Similarity	NPD7454	Approved
0.6898	Remote Similarity	NPD7455	Approved
0.689	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD8282	Approved
0.6887	Remote Similarity	NPD56	Approved
0.6887	Remote Similarity	NPD8283	Approved
0.6878	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5913	Phase 3
0.6869	Remote Similarity	NPD8399	Phase 1
0.6869	Remote Similarity	NPD8423	Phase 2
0.6866	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1534	Approved
0.6857	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6479	Discontinued
0.6854	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7010	Phase 3
0.6852	Remote Similarity	NPD5936	Approved
0.6852	Remote Similarity	NPD7470	Discontinued
0.6852	Remote Similarity	NPD5939	Approved
0.685	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5164	Discontinued
0.6837	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5834	Phase 3
0.6837	Remote Similarity	NPD5835	Phase 3
0.6837	Remote Similarity	NPD7474	Suspended
0.6832	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2509	Approved
0.6791	Remote Similarity	NPD2510	Approved
0.6784	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7234	Approved
0.678	Remote Similarity	NPD7233	Approved
0.6768	Remote Similarity	NPD6182	Approved
0.6768	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7418	Discontinued
0.6768	Remote Similarity	NPD43	Approved
0.6766	Remote Similarity	NPD5899	Approved
0.6766	Remote Similarity	NPD5898	Approved
0.6766	Remote Similarity	NPD5897	Approved
0.6762	Remote Similarity	NPD7946	Pre-registration
0.6761	Remote Similarity	NPD8072	Approved
0.6757	Remote Similarity	NPD1592	Phase 3
0.6729	Remote Similarity	NPD6987	Phase 1
0.6727	Remote Similarity	NPD8160	Phase 2
0.6718	Remote Similarity	NPD6635	Approved
0.6716	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD8094	Discontinued
0.6701	Remote Similarity	NPD4640	Approved
0.6701	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4639	Approved
0.6701	Remote Similarity	NPD4638	Approved
0.67	Remote Similarity	NPD749	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5104	Approved
0.67	Remote Similarity	NPD4075	Phase 2
0.6696	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3835	Phase 3
0.6684	Remote Similarity	NPD2915	Discontinued
0.6684	Remote Similarity	NPD3833	Phase 3
0.6683	Remote Similarity	NPD6595	Phase 3
0.6682	Remote Similarity	NPD53	Approved
0.6682	Remote Similarity	NPD7777	Approved
0.6682	Remote Similarity	NPD7778	Approved
0.6667	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5020	Approved
0.6667	Remote Similarity	NPD7824	Approved
0.6667	Remote Similarity	NPD5512	Phase 3
0.6667	Remote Similarity	NPD7395	Discontinued
0.6667	Remote Similarity	NPD7878	Phase 2
0.6667	Remote Similarity	NPD8093	Discontinued
0.6652	Remote Similarity	NPD3394	Approved
0.6652	Remote Similarity	NPD3389	Approved
0.6652	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD3393	Approved
0.6651	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6248	Phase 2
0.6651	Remote Similarity	NPD6249	Phase 2
0.665	Remote Similarity	NPD4948	Discontinued
0.665	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.665	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.665	Remote Similarity	NPD482	Approved
0.6636	Remote Similarity	NPD7187	Phase 2
0.6636	Remote Similarity	NPD8073	Approved
0.6636	Remote Similarity	NPD6376	Discontinued
0.6633	Remote Similarity	NPD3323	Discontinued
0.6624	Remote Similarity	NPD8358	Approved
0.6618	Remote Similarity	NPD3320	Approved
0.6618	Remote Similarity	NPD3318	Approved
0.6618	Remote Similarity	NPD5596	Phase 2
0.6618	Remote Similarity	NPD2094	Phase 2
0.6618	Remote Similarity	NPD2092	Phase 2
0.6618	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3319	Phase 1
0.6618	Remote Similarity	NPD4334	Discontinued
0.6618	Remote Similarity	NPD2095	Phase 2
0.6617	Remote Similarity	NPD5501	Discontinued
0.6617	Remote Similarity	NPD2380	Approved
0.6617	Remote Similarity	NPD2381	Approved
0.6617	Remote Similarity	NPD2382	Approved
0.6606	Remote Similarity	NPD7941	Phase 3
0.6606	Remote Similarity	NPD4506	Discontinued
0.6605	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5473	Discontinued
0.659	Remote Similarity	NPD8322	Phase 2
0.6585	Remote Similarity	NPD2096	Phase 2
0.6585	Remote Similarity	NPD2091	Phase 2
0.6584	Remote Similarity	NPD4181	Approved
0.6583	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7731	Approved
0.6579	Remote Similarity	NPD6978	Phase 2
0.6579	Remote Similarity	NPD7730	Approved
0.6579	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD8114	Approved
0.6574	Remote Similarity	NPD8115	Approved
0.6573	Remote Similarity	NPD8364	Approved
0.6573	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD8363	Approved
0.657	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3961	Discontinued
0.6567	Remote Similarity	NPD5065	Approved
0.6564	Remote Similarity	NPD7271	Approved
0.6564	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6770	Approved
0.6561	Remote Similarity	NPD7276	Approved
0.6561	Remote Similarity	NPD7277	Approved
0.6561	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3795	Approved
0.6561	Remote Similarity	NPD3794	Approved
0.6557	Remote Similarity	NPD7948	Phase 1
0.6557	Remote Similarity	NPD6664	Approved
0.6552	Remote Similarity	NPD6555	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD6026	Approved
0.6545	Remote Similarity	NPD5475	Discontinued
0.6544	Remote Similarity	NPD6245	Phase 2
0.6541	Remote Similarity	NPD1262	Discovery
0.654	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5086	Approved
0.6524	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4315	Phase 2
0.652	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7069	Discontinued
0.6514	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6145	Phase 1
0.6512	Remote Similarity	NPD7931	Approved
0.6512	Remote Similarity	NPD7934	Discovery
0.6512	Remote Similarity	NPD7932	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7933	Approved
0.651	Remote Similarity	NPD2172	Phase 1
0.6509	Remote Similarity	NPD7952	Approved
0.6509	Remote Similarity	NPD7951	Approved
0.6509	Remote Similarity	NPD7789	Approved
0.6509	Remote Similarity	NPD7791	Approved
0.6509	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7953	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