NPASS Compound

Structure

NPC284102 OpenBabel07101718252D 43 49 0 0 1 0 0 0 0 0999 V2000 -4.9961 -3.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2356 2.0637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3403 2.4623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7226 -1.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5155 -0.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0361 0.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3986 -0.8953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0161 -1.3387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9961 -1.3387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 -1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5261 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0695 -1.0957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2888 -1.2828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9320 1.2828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2888 0.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4681 1.3853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4861 -2.1874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1375 -0.7928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1375 0.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4401 0.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5081 0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0695 0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6456 -0.3028 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4401 -0.7928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5461 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9320 -0.3028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4661 -2.1874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4428 1.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6202 -0.2004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5461 -0.4900 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8487 -0.4900 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5081 -1.0957 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3948 -1.9600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9561 -3.0361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9561 -1.3387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0188 0.6949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 34 1 0 0 0 0 3 34 1 0 0 0 0 4 35 1 0 0 0 0 5 35 1 0 0 0 0 7 37 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 21 2 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 30 1 0 0 0 0 13 15 1 0 0 0 0 13 31 1 0 0 0 0 14 36 1 0 0 0 0 15 37 1 0 0 0 0 16 22 1 0 0 0 0 17 22 2 0 0 0 0 17 29 1 0 0 0 0 18 23 1 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 27 2 0 0 0 0 20 34 1 0 0 0 0 21 33 1 0 0 0 0 22 24 1 0 0 0 0 23 38 1 1 0 0 0 24 27 1 0 0 0 0 25 26 1 0 0 0 0 25 29 2 0 0 0 0 26 32 2 0 0 0 0 27 28 1 0 0 0 0 28 16 1 1 0 0 0 28 35 1 0 0 0 0 29 39 1 0 0 0 0 30 36 1 6 0 0 0 30 37 1 0 0 0 0 31 36 1 0 0 0 0 31 40 2 0 0 0 0 32 38 1 0 0 0 0 32 39 1 0 0 0 0 33 41 2 0 0 0 0 33 42 1 0 0 0 0 34 43 1 0 0 0 0 35 43 1 0 0 0 0 36 6 1 6 0 0 0 37 38 1 1 0 0 0 38 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	581.35
Volume:	628.338
LogP:	7.019
LogD:	4.823
LogS:	-4.344
# Rotatable Bonds:	3
TPSA:	79.39
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.283
Synthetic Accessibility Score:	5.247
Fsp3:	0.579
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.325
MDCK Permeability:	2.1281486624502577e-05
Pgp-inhibitor:	0.096
Pgp-substrate:	0.073
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.815

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.366
Plasma Protein Binding (PPB):	93.9762954711914%
Volume Distribution (VD):	0.652
Pgp-substrate:	4.9607391357421875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.17
CYP1A2-substrate:	0.748
CYP2C19-inhibitor:	0.441
CYP2C19-substrate:	0.366
CYP2C9-inhibitor:	0.754
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.878
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.908
CYP3A4-substrate:	0.888

ADMET: Excretion

Clearance (CL):	3.587
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.139
Human Hepatotoxicity (H-HT):	0.562
Drug-inuced Liver Injury (DILI):	0.791
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.972
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.498
Carcinogencity:	0.95
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC284102

Natural Product ID:	NPC284102
*Common Name:**	Nodulisporic Acid D3
IUPAC Name:	n.a.
Synonyms:	Nodulisporic Acid D3
Standard InCHIKey:	XCPHFIHPQDNWJO-NHHJTVBZSA-N
Standard InCHI:	InChI=1S/C38H47NO4/c1-21(33(41)42)10-9-14-36(6)30-12-11-23-18-26-25-19-24-22(16-28-27(24)20-34(2,3)43-35(28,4)5)17-29(25)39-32(26)38(23,8)37(30,7)15-13-31(36)40/h9-10,14,17,19-20,23,28,30,39H,11-13,15-16,18H2,1-8H3,(H,41,42)/b14-9+,21-10+/t23-,28-,30-,36-,37-,38+/m0/s1
SMILES:	C/C(=CC=C[C@]1(C)C(=O)CC[C@]2([C@H]1CC[C@@H]1[C@]2(C)c2[nH]c3c(c2C1)cc1c(c3)C[C@H]2C1=CC(OC2(C)C)(C)C)C)/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509735
PubChem CID:	11307760
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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	>	1000.0	nM	PMID[507586]

☑ 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 NPC284102 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	352
0.1-0.2	1516
0.2-0.3	4217
0.3-0.4	18738
0.4-0.5	13025
0.5-0.6	3022
0.6-0.7	1571
0.7-0.8	205
0.8-0.85	36
0.85-0.9	11
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC250129
0.9323	High Similarity	NPC475165
0.9133	High Similarity	NPC97388
0.9082	High Similarity	NPC473547
0.9016	High Similarity	NPC187456
0.8854	High Similarity	NPC475151
0.8844	High Similarity	NPC160527
0.8844	High Similarity	NPC473650
0.875	High Similarity	NPC473747
0.8689	High Similarity	NPC475424
0.8689	High Similarity	NPC79107
0.8578	High Similarity	NPC242446
0.8578	High Similarity	NPC475476
0.8537	High Similarity	NPC61813
0.8436	Intermediate Similarity	NPC282033
0.839	Intermediate Similarity	NPC96131
0.8385	Intermediate Similarity	NPC206967
0.8384	Intermediate Similarity	NPC123019
0.8302	Intermediate Similarity	NPC471634
0.8302	Intermediate Similarity	NPC473806
0.8238	Intermediate Similarity	NPC34271
0.8199	Intermediate Similarity	NPC245756
0.8195	Intermediate Similarity	NPC235900
0.8135	Intermediate Similarity	NPC99428
0.8122	Intermediate Similarity	NPC181502
0.8122	Intermediate Similarity	NPC85066
0.8116	Intermediate Similarity	NPC471284
0.8091	Intermediate Similarity	NPC94541
0.8091	Intermediate Similarity	NPC470843
0.8079	Intermediate Similarity	NPC18661
0.8019	Intermediate Similarity	NPC469312
0.8019	Intermediate Similarity	NPC41318
0.7969	Intermediate Similarity	NPC198339
0.7919	Intermediate Similarity	NPC471583
0.7919	Intermediate Similarity	NPC471782
0.7917	Intermediate Similarity	NPC6093
0.7873	Intermediate Similarity	NPC278540
0.7846	Intermediate Similarity	NPC165201
0.7788	Intermediate Similarity	NPC183426
0.7783	Intermediate Similarity	NPC32200
0.7727	Intermediate Similarity	NPC119700
0.7708	Intermediate Similarity	NPC97525
0.7699	Intermediate Similarity	NPC311451
0.7656	Intermediate Similarity	NPC6982
0.7615	Intermediate Similarity	NPC235885
0.7588	Intermediate Similarity	NPC160381
0.7571	Intermediate Similarity	NPC470280
0.7563	Intermediate Similarity	NPC302191
0.7558	Intermediate Similarity	NPC2395
0.7556	Intermediate Similarity	NPC473565
0.7551	Intermediate Similarity	NPC213468
0.7549	Intermediate Similarity	NPC231342
0.7547	Intermediate Similarity	NPC204303
0.7512	Intermediate Similarity	NPC46413
0.75	Intermediate Similarity	NPC184476
0.7488	Intermediate Similarity	NPC127677
0.7488	Intermediate Similarity	NPC258062
0.7487	Intermediate Similarity	NPC472587
0.7464	Intermediate Similarity	NPC98715
0.7463	Intermediate Similarity	NPC11445
0.745	Intermediate Similarity	NPC476319
0.745	Intermediate Similarity	NPC280290
0.7441	Intermediate Similarity	NPC46225
0.7441	Intermediate Similarity	NPC225821
0.7423	Intermediate Similarity	NPC280548
0.7415	Intermediate Similarity	NPC195239
0.7415	Intermediate Similarity	NPC157828
0.7397	Intermediate Similarity	NPC280799
0.7393	Intermediate Similarity	NPC131273
0.7393	Intermediate Similarity	NPC473441
0.7374	Intermediate Similarity	NPC270009
0.7371	Intermediate Similarity	NPC271862
0.7371	Intermediate Similarity	NPC154293
0.7358	Intermediate Similarity	NPC474905
0.7352	Intermediate Similarity	NPC470874
0.7349	Intermediate Similarity	NPC475778
0.7347	Intermediate Similarity	NPC34508
0.7336	Intermediate Similarity	NPC234999
0.7333	Intermediate Similarity	NPC137589
0.733	Intermediate Similarity	NPC51388
0.7327	Intermediate Similarity	NPC203614
0.7327	Intermediate Similarity	NPC204491
0.7324	Intermediate Similarity	NPC39679
0.7317	Intermediate Similarity	NPC47190
0.7315	Intermediate Similarity	NPC31700
0.7296	Intermediate Similarity	NPC126492
0.7295	Intermediate Similarity	NPC205403
0.7286	Intermediate Similarity	NPC300183
0.7277	Intermediate Similarity	NPC274640
0.7269	Intermediate Similarity	NPC87856
0.7269	Intermediate Similarity	NPC151976
0.7268	Intermediate Similarity	NPC71132
0.7248	Intermediate Similarity	NPC132211
0.7235	Intermediate Similarity	NPC267965
0.7234	Intermediate Similarity	NPC124005
0.7233	Intermediate Similarity	NPC55493
0.7232	Intermediate Similarity	NPC57690
0.7222	Intermediate Similarity	NPC87413
0.7222	Intermediate Similarity	NPC9894
0.722	Intermediate Similarity	NPC329858
0.7217	Intermediate Similarity	NPC476115
0.7212	Intermediate Similarity	NPC474701
0.7211	Intermediate Similarity	NPC200743
0.7202	Intermediate Similarity	NPC473320
0.7196	Intermediate Similarity	NPC477065
0.719	Intermediate Similarity	NPC241024
0.7186	Intermediate Similarity	NPC288785
0.7178	Intermediate Similarity	NPC19679
0.7175	Intermediate Similarity	NPC147446
0.7173	Intermediate Similarity	NPC38736
0.717	Intermediate Similarity	NPC162730
0.717	Intermediate Similarity	NPC474116
0.7165	Intermediate Similarity	NPC16667
0.7156	Intermediate Similarity	NPC470873
0.7156	Intermediate Similarity	NPC214428
0.7143	Intermediate Similarity	NPC141428
0.7136	Intermediate Similarity	NPC314333
0.7136	Intermediate Similarity	NPC477135
0.7129	Intermediate Similarity	NPC192270
0.7128	Intermediate Similarity	NPC129042
0.7128	Intermediate Similarity	NPC8104
0.7123	Intermediate Similarity	NPC118228
0.7112	Intermediate Similarity	NPC475844
0.7111	Intermediate Similarity	NPC472762
0.7108	Intermediate Similarity	NPC473189
0.71	Intermediate Similarity	NPC84347
0.7098	Intermediate Similarity	NPC266192
0.7094	Intermediate Similarity	NPC472444
0.7091	Intermediate Similarity	NPC3207
0.7087	Intermediate Similarity	NPC196251
0.7087	Intermediate Similarity	NPC102338
0.7087	Intermediate Similarity	NPC63199
0.7087	Intermediate Similarity	NPC111602
0.7081	Intermediate Similarity	NPC220151
0.7081	Intermediate Similarity	NPC195314
0.7081	Intermediate Similarity	NPC19692
0.708	Intermediate Similarity	NPC469720
0.708	Intermediate Similarity	NPC476491
0.7077	Intermediate Similarity	NPC214106
0.7075	Intermediate Similarity	NPC49196
0.7075	Intermediate Similarity	NPC195461
0.7075	Intermediate Similarity	NPC79129
0.7075	Intermediate Similarity	NPC81654
0.7075	Intermediate Similarity	NPC249150
0.7075	Intermediate Similarity	NPC313985
0.7075	Intermediate Similarity	NPC252338
0.7073	Intermediate Similarity	NPC235684
0.707	Intermediate Similarity	NPC300156
0.707	Intermediate Similarity	NPC277350
0.7067	Intermediate Similarity	NPC67551
0.7062	Intermediate Similarity	NPC67056
0.7062	Intermediate Similarity	NPC477044
0.7062	Intermediate Similarity	NPC477041
0.7061	Intermediate Similarity	NPC290529
0.7059	Intermediate Similarity	NPC293151
0.7056	Intermediate Similarity	NPC470509
0.7054	Intermediate Similarity	NPC144452
0.7053	Intermediate Similarity	NPC83111
0.7053	Intermediate Similarity	NPC469497
0.7053	Intermediate Similarity	NPC106833
0.7048	Intermediate Similarity	NPC472293
0.7048	Intermediate Similarity	NPC245916
0.7041	Intermediate Similarity	NPC271734
0.704	Intermediate Similarity	NPC174760
0.7037	Intermediate Similarity	NPC4687
0.7035	Intermediate Similarity	NPC267926
0.703	Intermediate Similarity	NPC472443
0.7028	Intermediate Similarity	NPC476175
0.7027	Intermediate Similarity	NPC82070
0.7027	Intermediate Similarity	NPC184408
0.7023	Intermediate Similarity	NPC477043
0.7021	Intermediate Similarity	NPC242556
0.7018	Intermediate Similarity	NPC475422
0.7014	Intermediate Similarity	NPC469928
0.7014	Intermediate Similarity	NPC330009
0.7005	Intermediate Similarity	NPC246700
0.7005	Intermediate Similarity	NPC128751
0.7004	Intermediate Similarity	NPC249342
0.7	Intermediate Similarity	NPC477134
0.6995	Remote Similarity	NPC471458
0.6995	Remote Similarity	NPC199851
0.6995	Remote Similarity	NPC128265
0.6995	Remote Similarity	NPC312870
0.6995	Remote Similarity	NPC294909
0.6995	Remote Similarity	NPC254240
0.6995	Remote Similarity	NPC300688
0.6991	Remote Similarity	NPC476818
0.6987	Remote Similarity	NPC474688
0.6986	Remote Similarity	NPC472292
0.6983	Remote Similarity	NPC6786
0.6982	Remote Similarity	NPC312645
0.6981	Remote Similarity	NPC67288
0.6981	Remote Similarity	NPC52557
0.6981	Remote Similarity	NPC50503
0.698	Remote Similarity	NPC151939
0.6977	Remote Similarity	NPC134848
0.6971	Remote Similarity	NPC472112
0.6963	Remote Similarity	NPC471944
0.6963	Remote Similarity	NPC37548
0.6963	Remote Similarity	NPC187951

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 NPC284102 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	608
0.2-0.3	616
0.3-0.4	1900
0.4-0.5	3236
0.5-0.6	1982
0.6-0.7	548
0.7-0.8	30
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7879	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD5003	Discontinued
0.7444	Intermediate Similarity	NPD7688	Phase 1
0.7443	Intermediate Similarity	NPD6995	Phase 1
0.7381	Intermediate Similarity	NPD2920	Discontinued
0.7346	Intermediate Similarity	NPD5901	Discontinued
0.7304	Intermediate Similarity	NPD2564	Approved
0.7304	Intermediate Similarity	NPD2565	Phase 2
0.7282	Intermediate Similarity	NPD2844	Phase 3
0.7256	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD56	Approved
0.7183	Intermediate Similarity	NPD8283	Approved
0.7183	Intermediate Similarity	NPD8282	Approved
0.7179	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6176	Phase 1
0.7136	Intermediate Similarity	NPD4499	Approved
0.7114	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7455	Approved
0.711	Intermediate Similarity	NPD7454	Approved
0.7094	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1534	Approved
0.7083	Intermediate Similarity	NPD8423	Phase 2
0.7083	Intermediate Similarity	NPD8399	Phase 1
0.7078	Intermediate Similarity	NPD8094	Discontinued
0.7075	Intermediate Similarity	NPD4601	Approved
0.7075	Intermediate Similarity	NPD4600	Approved
0.7071	Intermediate Similarity	NPD1326	Approved
0.7071	Intermediate Similarity	NPD1325	Approved
0.707	Intermediate Similarity	NPD7010	Phase 3
0.7059	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5834	Phase 3
0.7051	Intermediate Similarity	NPD5835	Phase 3
0.7039	Intermediate Similarity	NPD8431	Approved
0.7032	Intermediate Similarity	NPD8093	Discontinued
0.7023	Intermediate Similarity	NPD6987	Phase 1
0.6995	Remote Similarity	NPD4501	Approved
0.6995	Remote Similarity	NPD6479	Discontinued
0.6995	Remote Similarity	NPD4500	Approved
0.6991	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7470	Discontinued
0.6959	Remote Similarity	NPD5429	Discontinued
0.6957	Remote Similarity	NPD4948	Discontinued
0.6948	Remote Similarity	NPD6248	Phase 2
0.6948	Remote Similarity	NPD6249	Phase 2
0.6948	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7824	Approved
0.6937	Remote Similarity	NPD8160	Phase 2
0.693	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7953	Approved
0.6926	Remote Similarity	NPD7952	Approved
0.6926	Remote Similarity	NPD7951	Approved
0.6926	Remote Similarity	NPD7789	Approved
0.6926	Remote Similarity	NPD7791	Approved
0.6926	Remote Similarity	NPD7790	Approved
0.6926	Remote Similarity	NPD7950	Approved
0.6923	Remote Similarity	NPD7234	Approved
0.6923	Remote Similarity	NPD4334	Discontinued
0.6923	Remote Similarity	NPD7233	Approved
0.6912	Remote Similarity	NPD5473	Discontinued
0.6912	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7957	Phase 1
0.69	Remote Similarity	NPD7781	Approved
0.69	Remote Similarity	NPD7780	Approved
0.6895	Remote Similarity	NPD7941	Phase 3
0.6892	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7707	Approved
0.6884	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7395	Discontinued
0.6866	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3394	Approved
0.6861	Remote Similarity	NPD3389	Approved
0.6861	Remote Similarity	NPD3393	Approved
0.6856	Remote Similarity	NPD7731	Approved
0.6856	Remote Similarity	NPD5086	Approved
0.6856	Remote Similarity	NPD7730	Approved
0.6849	Remote Similarity	NPD2509	Approved
0.6849	Remote Similarity	NPD2510	Approved
0.6849	Remote Similarity	NPD6376	Discontinued
0.6847	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2095	Phase 2
0.6845	Remote Similarity	NPD2092	Phase 2
0.6845	Remote Similarity	NPD2094	Phase 2
0.6839	Remote Similarity	NPD4462	Approved
0.6839	Remote Similarity	NPD4463	Approved
0.6833	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7767	Approved
0.6822	Remote Similarity	NPD7946	Pre-registration
0.6812	Remote Similarity	NPD2096	Phase 2
0.6812	Remote Similarity	NPD2091	Phase 2
0.6806	Remote Similarity	NPD4511	Phase 1
0.6806	Remote Similarity	NPD7931	Approved
0.6806	Remote Similarity	NPD7934	Discovery
0.6806	Remote Similarity	NPD7933	Approved
0.6806	Remote Similarity	NPD7932	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7716	Approved
0.6798	Remote Similarity	NPD7717	Approved
0.6798	Remote Similarity	NPD482	Approved
0.6791	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8386	Phase 2
0.678	Remote Similarity	NPD4076	Approved
0.678	Remote Similarity	NPD4079	Approved
0.6777	Remote Similarity	NPD5913	Phase 3
0.6777	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7187	Phase 2
0.6769	Remote Similarity	NPD7271	Approved
0.6763	Remote Similarity	NPD3318	Approved
0.6763	Remote Similarity	NPD3320	Approved
0.6763	Remote Similarity	NPD3319	Phase 1
0.6758	Remote Similarity	NPD6245	Phase 2
0.6754	Remote Similarity	NPD5254	Discontinued
0.675	Remote Similarity	NPD8358	Approved
0.6749	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD4315	Phase 2
0.6744	Remote Similarity	NPD53	Approved
0.6744	Remote Similarity	NPD7777	Approved
0.6744	Remote Similarity	NPD7778	Approved
0.6743	Remote Similarity	NPD5487	Phase 1
0.6743	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4506	Discontinued
0.6737	Remote Similarity	NPD1592	Phase 3
0.6735	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3506	Approved
0.6732	Remote Similarity	NPD3505	Approved
0.6732	Remote Similarity	NPD7865	Approved
0.673	Remote Similarity	NPD6281	Approved
0.6729	Remote Similarity	NPD5512	Phase 3
0.6727	Remote Similarity	NPD7562	Approved
0.6726	Remote Similarity	NPD7878	Phase 2
0.6712	Remote Similarity	NPD8098	Approved
0.6711	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6664	Approved
0.6698	Remote Similarity	NPD6206	Phase 1
0.6697	Remote Similarity	NPD8073	Approved
0.6697	Remote Similarity	NPD2916	Discontinued
0.6696	Remote Similarity	NPD6770	Approved
0.6696	Remote Similarity	NPD3925	Approved
0.6683	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5021	Discontinued
0.6682	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5475	Discontinued
0.6682	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5416	Discontinued
0.6667	Remote Similarity	NPD5898	Approved
0.6667	Remote Similarity	NPD6261	Phase 3
0.6667	Remote Similarity	NPD5897	Approved
0.6667	Remote Similarity	NPD6182	Approved
0.6667	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3746	Discontinued
0.6667	Remote Similarity	NPD43	Approved
0.6667	Remote Similarity	NPD5899	Approved
0.6667	Remote Similarity	NPD7921	Approved
0.6652	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5506	Approved
0.6638	Remote Similarity	NPD5507	Approved
0.6637	Remote Similarity	NPD6733	Discontinued
0.6636	Remote Similarity	NPD3947	Discontinued
0.6636	Remote Similarity	NPD5426	Phase 3
0.6635	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8364	Approved
0.6627	Remote Similarity	NPD8363	Approved
0.6622	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3794	Approved
0.6622	Remote Similarity	NPD3795	Approved
0.6618	Remote Similarity	NPD3417	Phase 1
0.6617	Remote Similarity	NPD1631	Approved
0.6607	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5104	Approved
0.6602	Remote Similarity	NPD4075	Phase 2
0.6593	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8072	Approved
0.659	Remote Similarity	NPD6846	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5444	Phase 1
0.6588	Remote Similarity	NPD5809	Phase 3
0.6585	Remote Similarity	NPD750	Phase 2
0.6583	Remote Similarity	NPD7770	Phase 3
0.6578	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6145	Phase 1
0.6571	Remote Similarity	NPD6178	Phase 3
0.657	Remote Similarity	NPD2144	Approved
0.6569	Remote Similarity	NPD8016	Phase 3
0.6569	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD972	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