NPASS Compound

Structure

NPC473747 OpenBabel07101718292D 41 45 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 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 22 1 0 0 0 0 2 22 1 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 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 24 2 0 0 0 0 10 12 1 0 0 0 0 10 22 2 0 0 0 0 11 13 1 0 0 0 0 11 23 2 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 15 31 1 0 0 0 0 16 18 1 0 0 0 0 16 32 1 0 0 0 0 17 36 1 0 0 0 0 18 37 1 0 0 0 0 19 25 2 0 0 0 0 19 28 1 0 0 0 0 20 27 1 0 0 0 0 20 29 1 0 0 0 0 21 26 2 0 0 0 0 21 30 1 0 0 0 0 24 35 1 0 0 0 0 25 26 1 0 0 0 0 27 14 1 6 0 0 0 27 33 1 0 0 0 0 28 29 1 0 0 0 0 28 30 2 0 0 0 0 29 34 2 0 0 0 0 30 38 1 0 0 0 0 31 36 1 1 0 0 0 31 37 1 0 0 0 0 32 36 1 1 0 0 0 32 39 1 0 0 0 0 33 34 1 0 0 0 0 33 37 1 1 0 0 0 34 38 1 0 0 0 0 35 40 2 0 0 0 0 35 41 1 0 0 0 0 36 6 1 1 0 0 0 37 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	557.39
Volume:	622.001
LogP:	8.589
LogD:	5.401
LogS:	-2.84
# Rotatable Bonds:	8
TPSA:	73.32
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.284
Synthetic Accessibility Score:	5.15
Fsp3:	0.595
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:	-5.017
MDCK Permeability:	1.546935527585447e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.602
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.863
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	87.46542358398438%
Volume Distribution (VD):	2.586
Pgp-substrate:	6.419078826904297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.153
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.283
CYP2C9-inhibitor:	0.421
CYP2C9-substrate:	0.489
CYP2D6-inhibitor:	0.383
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.429
CYP3A4-substrate:	0.138

ADMET: Excretion

Clearance (CL):	12.642
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.459
Human Hepatotoxicity (H-HT):	0.702
Drug-inuced Liver Injury (DILI):	0.139
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.777
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.542
Carcinogencity:	0.326
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC473747

Natural Product ID:	NPC473747
*Common Name:**	Nodulisporic Acid E
IUPAC Name:	n.a.
Synonyms:	Nodulisporic Acid E
Standard InCHIKey:	MZNVFBWGMTXXDI-RDUGODHGSA-N
Standard InCHI:	InChI=1S/C37H51NO3/c1-22(2)10-12-25-19-28-29-20-27-14-15-31-36(6,17-8-9-24(5)35(40)41)32(39)16-18-37(31,7)33(27)34(29)38-30(28)21-26(25)13-11-23(3)4/h9-11,19,21,27,31-33,38-39H,8,12-18,20H2,1-7H3,(H,40,41)/b24-9+/t27-,31-,32-,33+,36-,37-/m0/s1
SMILES:	CC(=CCc1cc2[nH]c3c(c2cc1CC=C(C)C)C[C@H]1[C@H]3[C@@]2(C)CC[C@@H]([C@@]([C@@H]2CC1)(C)CC/C=C(/C(=O)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450791
PubChem CID:	44584353
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
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	=	17.5	uM	PMID[474077]
NPT2	Others	Unspecified		IC50	=	2143.0	nM	PMID[474077]

☑ 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 NPC473747 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	293
0.1-0.2	1390
0.2-0.3	4800
0.3-0.4	21716
0.4-0.5	10004
0.5-0.6	2857
0.6-0.7	1406
0.7-0.8	176
0.8-0.85	33
0.85-0.9	15
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC475151
0.9489	High Similarity	NPC206967
0.9358	High Similarity	NPC250129
0.9305	High Similarity	NPC475165
0.9194	High Similarity	NPC187456
0.911	High Similarity	NPC97388
0.9058	High Similarity	NPC473547
0.8927	High Similarity	NPC198339
0.8814	High Similarity	NPC160527
0.8814	High Similarity	NPC473650
0.875	High Similarity	NPC284102
0.875	High Similarity	NPC97525
0.8656	High Similarity	NPC181502
0.8656	High Similarity	NPC85066
0.8636	High Similarity	NPC242446
0.8636	High Similarity	NPC475476
0.85	High Similarity	NPC61813
0.8462	Intermediate Similarity	NPC302191
0.8382	Intermediate Similarity	NPC79107
0.8382	Intermediate Similarity	NPC475424
0.837	Intermediate Similarity	NPC165201
0.8352	Intermediate Similarity	NPC6093
0.8333	Intermediate Similarity	NPC119700
0.8289	Intermediate Similarity	NPC34271
0.8259	Intermediate Similarity	NPC96131
0.8247	Intermediate Similarity	NPC123019
0.8221	Intermediate Similarity	NPC282033
0.8182	Intermediate Similarity	NPC99428
0.8122	Intermediate Similarity	NPC18661
0.8069	Intermediate Similarity	NPC471284
0.8066	Intermediate Similarity	NPC154293
0.806	Intermediate Similarity	NPC235900
0.8031	Intermediate Similarity	NPC231342
0.8031	Intermediate Similarity	NPC205403
0.801	Intermediate Similarity	NPC204303
0.8	Intermediate Similarity	NPC473806
0.8	Intermediate Similarity	NPC471634
0.7978	Intermediate Similarity	NPC126492
0.7971	Intermediate Similarity	NPC469312
0.7971	Intermediate Similarity	NPC41318
0.7963	Intermediate Similarity	NPC94541
0.7963	Intermediate Similarity	NPC470843
0.7914	Intermediate Similarity	NPC300688
0.7895	Intermediate Similarity	NPC245756
0.7842	Intermediate Similarity	NPC476319
0.7838	Intermediate Similarity	NPC34508
0.782	Intermediate Similarity	NPC183426
0.7737	Intermediate Similarity	NPC19679
0.7722	Intermediate Similarity	NPC184476
0.7705	Intermediate Similarity	NPC472587
0.7672	Intermediate Similarity	NPC270009
0.7638	Intermediate Similarity	NPC32200
0.7634	Intermediate Similarity	NPC280548
0.7619	Intermediate Similarity	NPC151939
0.7596	Intermediate Similarity	NPC204491
0.7596	Intermediate Similarity	NPC203614
0.7592	Intermediate Similarity	NPC192270
0.7588	Intermediate Similarity	NPC477041
0.7588	Intermediate Similarity	NPC477044
0.7574	Intermediate Similarity	NPC477135
0.7574	Intermediate Similarity	NPC98715
0.7559	Intermediate Similarity	NPC235885
0.755	Intermediate Similarity	NPC477045
0.7538	Intermediate Similarity	NPC46413
0.7512	Intermediate Similarity	NPC258062
0.7512	Intermediate Similarity	NPC61637
0.7512	Intermediate Similarity	NPC127677
0.75	Intermediate Similarity	NPC278540
0.7487	Intermediate Similarity	NPC201700
0.7487	Intermediate Similarity	NPC213468
0.7475	Intermediate Similarity	NPC300183
0.7474	Intermediate Similarity	NPC280290
0.7466	Intermediate Similarity	NPC471782
0.7466	Intermediate Similarity	NPC471583
0.7463	Intermediate Similarity	NPC225821
0.7463	Intermediate Similarity	NPC46225
0.7453	Intermediate Similarity	NPC470874
0.7444	Intermediate Similarity	NPC124005
0.7427	Intermediate Similarity	NPC470280
0.7426	Intermediate Similarity	NPC79129
0.7426	Intermediate Similarity	NPC249150
0.7426	Intermediate Similarity	NPC49196
0.7426	Intermediate Similarity	NPC195461
0.7426	Intermediate Similarity	NPC81654
0.7426	Intermediate Similarity	NPC313985
0.7413	Intermediate Similarity	NPC50503
0.7411	Intermediate Similarity	NPC106833
0.7411	Intermediate Similarity	NPC469497
0.7407	Intermediate Similarity	NPC6982
0.7405	Intermediate Similarity	NPC473320
0.7404	Intermediate Similarity	NPC9894
0.7391	Intermediate Similarity	NPC271862
0.738	Intermediate Similarity	NPC470508
0.7377	Intermediate Similarity	NPC38736
0.7376	Intermediate Similarity	NPC476175
0.7368	Intermediate Similarity	NPC151976
0.7368	Intermediate Similarity	NPC87856
0.7366	Intermediate Similarity	NPC477043
0.7366	Intermediate Similarity	NPC16667
0.736	Intermediate Similarity	NPC128751
0.736	Intermediate Similarity	NPC246700
0.7356	Intermediate Similarity	NPC234999
0.7356	Intermediate Similarity	NPC475422
0.7349	Intermediate Similarity	NPC147446
0.7346	Intermediate Similarity	NPC132211
0.7344	Intermediate Similarity	NPC293472
0.7336	Intermediate Similarity	NPC2395
0.7333	Intermediate Similarity	NPC311451
0.7333	Intermediate Similarity	NPC129042
0.7333	Intermediate Similarity	NPC267965
0.7323	Intermediate Similarity	NPC95783
0.7315	Intermediate Similarity	NPC141428
0.7313	Intermediate Similarity	NPC11445
0.7306	Intermediate Similarity	NPC472443
0.7306	Intermediate Similarity	NPC176199
0.7306	Intermediate Similarity	NPC215795
0.7293	Intermediate Similarity	NPC477134
0.7292	Intermediate Similarity	NPC288785
0.7283	Intermediate Similarity	NPC470507
0.7282	Intermediate Similarity	NPC472444
0.7277	Intermediate Similarity	NPC153042
0.7277	Intermediate Similarity	NPC229332
0.7265	Intermediate Similarity	NPC473565
0.7264	Intermediate Similarity	NPC157828
0.7264	Intermediate Similarity	NPC195239
0.726	Intermediate Similarity	NPC87755
0.7259	Intermediate Similarity	NPC160381
0.7258	Intermediate Similarity	NPC67056
0.7248	Intermediate Similarity	NPC57690
0.7248	Intermediate Similarity	NPC470873
0.724	Intermediate Similarity	NPC329688
0.724	Intermediate Similarity	NPC189812
0.7234	Intermediate Similarity	NPC271734
0.723	Intermediate Similarity	NPC293151
0.7222	Intermediate Similarity	NPC242556
0.7204	Intermediate Similarity	NPC475778
0.7202	Intermediate Similarity	NPC112547
0.7191	Intermediate Similarity	NPC312092
0.7189	Intermediate Similarity	NPC51388
0.7189	Intermediate Similarity	NPC471458
0.7178	Intermediate Similarity	NPC195314
0.7169	Intermediate Similarity	NPC249342
0.7164	Intermediate Similarity	NPC67551
0.7158	Intermediate Similarity	NPC187951
0.7158	Intermediate Similarity	NPC37548
0.7157	Intermediate Similarity	NPC190007
0.7151	Intermediate Similarity	NPC285469
0.715	Intermediate Similarity	NPC472586
0.7149	Intermediate Similarity	NPC474701
0.7129	Intermediate Similarity	NPC474177
0.7121	Intermediate Similarity	NPC94943
0.712	Intermediate Similarity	NPC33421
0.7109	Intermediate Similarity	NPC303951
0.7105	Intermediate Similarity	NPC71132
0.7101	Intermediate Similarity	NPC193761
0.7098	Intermediate Similarity	NPC313791
0.7097	Intermediate Similarity	NPC207726
0.7095	Intermediate Similarity	NPC39679
0.7094	Intermediate Similarity	NPC133366
0.7089	Intermediate Similarity	NPC31700
0.7077	Intermediate Similarity	NPC68354
0.7075	Intermediate Similarity	NPC23294
0.7072	Intermediate Similarity	NPC311330
0.7068	Intermediate Similarity	NPC470509
0.7065	Intermediate Similarity	NPC329858
0.7062	Intermediate Similarity	NPC275305
0.7062	Intermediate Similarity	NPC37423
0.7053	Intermediate Similarity	NPC40779
0.7053	Intermediate Similarity	NPC8104
0.7053	Intermediate Similarity	NPC311276
0.7048	Intermediate Similarity	NPC193777
0.7048	Intermediate Similarity	NPC477065
0.7045	Intermediate Similarity	NPC267926
0.7043	Intermediate Similarity	NPC200743
0.7041	Intermediate Similarity	NPC88363
0.7039	Intermediate Similarity	NPC473441
0.7039	Intermediate Similarity	NPC131273
0.7035	Intermediate Similarity	NPC473189
0.7032	Intermediate Similarity	NPC266192
0.7021	Intermediate Similarity	NPC76982
0.7021	Intermediate Similarity	NPC299594
0.7021	Intermediate Similarity	NPC469762
0.702	Intermediate Similarity	NPC212535
0.7019	Intermediate Similarity	NPC474116
0.7019	Intermediate Similarity	NPC162730
0.7018	Intermediate Similarity	NPC280799
0.7015	Intermediate Similarity	NPC175474
0.7	Intermediate Similarity	NPC476106
0.6995	Remote Similarity	NPC87413
0.6995	Remote Similarity	NPC47190
0.699	Remote Similarity	NPC52557
0.6986	Remote Similarity	NPC165599
0.6986	Remote Similarity	NPC476115
0.6982	Remote Similarity	NPC274640
0.6968	Remote Similarity	NPC469785
0.6967	Remote Similarity	NPC323927
0.6967	Remote Similarity	NPC474905
0.6965	Remote Similarity	NPC317030
0.6944	Remote Similarity	NPC330009
0.6944	Remote Similarity	NPC3207

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 NPC473747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	582
0.2-0.3	620
0.3-0.4	2012
0.4-0.5	3301
0.5-0.6	1902
0.6-0.7	509
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
0.7732	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4600	Approved
0.7426	Intermediate Similarity	NPD4601	Approved
0.7263	Intermediate Similarity	NPD1326	Approved
0.7263	Intermediate Similarity	NPD1325	Approved
0.7246	Intermediate Similarity	NPD7957	Phase 1
0.7246	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6995	Phase 1
0.7211	Intermediate Similarity	NPD5021	Discontinued
0.7136	Intermediate Similarity	NPD8431	Approved
0.7128	Intermediate Similarity	NPD4079	Approved
0.7128	Intermediate Similarity	NPD4076	Approved
0.712	Intermediate Similarity	NPD4462	Approved
0.712	Intermediate Similarity	NPD4463	Approved
0.712	Intermediate Similarity	NPD2844	Phase 3
0.7115	Intermediate Similarity	NPD5901	Discontinued
0.7108	Intermediate Similarity	NPD5003	Discontinued
0.7077	Intermediate Similarity	NPD3506	Approved
0.7077	Intermediate Similarity	NPD3505	Approved
0.7072	Intermediate Similarity	NPD7688	Phase 1
0.7053	Intermediate Similarity	NPD4511	Phase 1
0.7041	Intermediate Similarity	NPD8386	Phase 2
0.7033	Intermediate Similarity	NPD5254	Discontinued
0.7028	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5936	Approved
0.6995	Remote Similarity	NPD7474	Suspended
0.6995	Remote Similarity	NPD5939	Approved
0.6986	Remote Similarity	NPD2920	Discontinued
0.6977	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD1534	Approved
0.6923	Remote Similarity	NPD7418	Discontinued
0.6923	Remote Similarity	NPD43	Approved
0.6923	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6182	Approved
0.6923	Remote Similarity	NPD1592	Phase 3
0.6919	Remote Similarity	NPD5898	Approved
0.6919	Remote Similarity	NPD5897	Approved
0.6919	Remote Similarity	NPD5899	Approved
0.6919	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6176	Phase 1
0.6904	Remote Similarity	NPD2144	Approved
0.69	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7707	Approved
0.6897	Remote Similarity	NPD4499	Approved
0.6897	Remote Similarity	NPD2564	Approved
0.6897	Remote Similarity	NPD2565	Phase 2
0.6884	Remote Similarity	NPD7454	Approved
0.6884	Remote Similarity	NPD7455	Approved
0.6884	Remote Similarity	NPD3038	Discontinued
0.6875	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8094	Discontinued
0.6831	Remote Similarity	NPD5020	Approved
0.6827	Remote Similarity	NPD7777	Approved
0.6827	Remote Similarity	NPD7778	Approved
0.6827	Remote Similarity	NPD53	Approved
0.6806	Remote Similarity	NPD8093	Discontinued
0.6804	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7878	Phase 2
0.6798	Remote Similarity	NPD4948	Discontinued
0.6792	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6987	Phase 1
0.6786	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6376	Discontinued
0.6769	Remote Similarity	NPD4639	Approved
0.6769	Remote Similarity	NPD4640	Approved
0.6769	Remote Similarity	NPD4638	Approved
0.6768	Remote Similarity	NPD2381	Approved
0.6768	Remote Similarity	NPD4075	Phase 2
0.6768	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD2382	Approved
0.6768	Remote Similarity	NPD2380	Approved
0.6766	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7233	Approved
0.6765	Remote Similarity	NPD7234	Approved
0.6762	Remote Similarity	NPD4501	Approved
0.6762	Remote Similarity	NPD4500	Approved
0.6758	Remote Similarity	NPD5164	Discontinued
0.6757	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6595	Phase 3
0.6745	Remote Similarity	NPD8072	Approved
0.6744	Remote Similarity	NPD5834	Phase 3
0.6744	Remote Similarity	NPD5835	Phase 3
0.6736	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6281	Approved
0.6729	Remote Similarity	NPD5429	Discontinued
0.6717	Remote Similarity	NPD482	Approved
0.6717	Remote Similarity	NPD5065	Approved
0.6716	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD56	Approved
0.6714	Remote Similarity	NPD8283	Approved
0.6714	Remote Similarity	NPD8282	Approved
0.6701	Remote Similarity	NPD6635	Approved
0.6701	Remote Similarity	NPD3323	Discontinued
0.6699	Remote Similarity	NPD5913	Phase 3
0.6699	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7948	Phase 1
0.6698	Remote Similarity	NPD7187	Phase 2
0.6698	Remote Similarity	NPD8423	Phase 2
0.6698	Remote Similarity	NPD8399	Phase 1
0.6684	Remote Similarity	NPD5086	Approved
0.6683	Remote Similarity	NPD3319	Phase 1
0.6683	Remote Similarity	NPD3318	Approved
0.6683	Remote Similarity	NPD5596	Phase 2
0.6683	Remote Similarity	NPD2094	Phase 2
0.6683	Remote Similarity	NPD5501	Discontinued
0.6683	Remote Similarity	NPD3320	Approved
0.6683	Remote Similarity	NPD2092	Phase 2
0.6683	Remote Similarity	NPD2095	Phase 2
0.6682	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6479	Discontinued
0.6682	Remote Similarity	NPD7470	Discontinued
0.6682	Remote Similarity	NPD7010	Phase 3
0.6667	Remote Similarity	NPD5473	Discontinued
0.6667	Remote Similarity	NPD7946	Pre-registration
0.6667	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7824	Approved
0.6651	Remote Similarity	NPD7931	Approved
0.6651	Remote Similarity	NPD7932	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD8322	Phase 2
0.6651	Remote Similarity	NPD7934	Discovery
0.6651	Remote Similarity	NPD7933	Approved
0.6651	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6145	Phase 1
0.665	Remote Similarity	NPD2096	Phase 2
0.665	Remote Similarity	NPD4181	Approved
0.665	Remote Similarity	NPD2091	Phase 2
0.665	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6978	Phase 2
0.6637	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD8114	Approved
0.6636	Remote Similarity	NPD8115	Approved
0.6636	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3961	Discontinued
0.6632	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6158	Phase 2
0.6622	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2510	Approved
0.662	Remote Similarity	NPD8073	Approved
0.662	Remote Similarity	NPD2509	Approved
0.6619	Remote Similarity	NPD6664	Approved
0.6617	Remote Similarity	NPD3417	Phase 1
0.6615	Remote Similarity	NPD6026	Approved
0.6615	Remote Similarity	NPD5138	Approved
0.6615	Remote Similarity	NPD5140	Approved
0.6612	Remote Similarity	NPD1262	Discovery
0.6608	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7767	Approved
0.6606	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7941	Phase 3
0.6579	Remote Similarity	NPD2172	Phase 1
0.6577	Remote Similarity	NPD7395	Discontinued
0.6564	Remote Similarity	NPD7730	Approved
0.6564	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7731	Approved
0.6564	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD8160	Phase 2
0.6558	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8395	Approved
0.6557	Remote Similarity	NPD6248	Phase 2
0.6557	Remote Similarity	NPD8396	Approved
0.6557	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD2177	Approved
0.6557	Remote Similarity	NPD2176	Approved
0.6557	Remote Similarity	NPD6249	Phase 2
0.6557	Remote Similarity	NPD2175	Phase 3
0.6552	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.655	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.655	Remote Similarity	NPD4128	Approved
0.6549	Remote Similarity	NPD7271	Approved
0.6545	Remote Similarity	NPD7276	Approved
0.6545	Remote Similarity	NPD2882	Phase 1
0.6545	Remote Similarity	NPD7277	Approved
0.6544	Remote Similarity	NPD2916	Discontinued
0.6542	Remote Similarity	NPD6975	Discontinued
0.6535	Remote Similarity	NPD6555	Clinical (unspecified phase)
0.653	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD2580	Discontinued
0.6524	Remote Similarity	NPD3525	Discontinued
0.6524	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7944	Discontinued
0.6522	Remote Similarity	NPD4334	Discontinued
0.6522	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5104	Approved
0.6511	Remote Similarity	NPD7770	Phase 3

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