NPASS Compound

Structure

CID328070 OpenBabel06191716202D 28 29 0 0 1 0 0 0 0 0999 V2000 -7.5375 3.2544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5430 3.1499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5594 2.8363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9716 3.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5540 2.9408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9771 3.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1417 2.1318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5704 2.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7240 1.4273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1363 2.2363 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.5759 2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 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 -7.7186 1.5319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 1.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0119 3.3317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5522 2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 15 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 8 2 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 16 2 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 27 2 0 0 0 0 22 23 2 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	383.17
Volume:	403.175
LogP:	3.657
LogD:	2.523
LogS:	-3.796
# Rotatable Bonds:	9
TPSA:	113.78
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	3.845
Fsp3:	0.227
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.086
MDCK Permeability:	7.386030119960196e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.11

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	99.98785400390625%
Volume Distribution (VD):	0.21
Pgp-substrate:	1.2648862600326538%

ADMET: Metabolism

CYP1A2-inhibitor:	0.427
CYP1A2-substrate:	0.418
CYP2C19-inhibitor:	0.191
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.692
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.893
CYP2D6-substrate:	0.882
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.411

ADMET: Excretion

Clearance (CL):	4.952
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.368
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.891
Rat Oral Acute Toxicity:	0.724
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.929
Carcinogencity:	0.495
Eye Corrosion:	0.003
Eye Irritation:	0.113
Respiratory Toxicity:	0.313

Download Data

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

Natural Product: NPC328070

Natural Product ID:	NPC328070
*Common Name:**	Torrubiellone D
IUPAC Name:	(3E)-3-[(2E,4E,6E)-1-hydroxy-8-(hydroxymethyl)deca-2,4,6-trienylidene]-5-[(4-hydroxyphenyl)methyl]pyrrolidine-2,4-dione
Synonyms:	Torrubiellone D
Standard InCHIKey:	TVSMLVYMTMBUHC-KGPDSPOASA-N
Standard InCHI:	InChI=1S/C22H25NO5/c1-2-15(14-24)7-5-3-4-6-8-19(26)20-21(27)18(23-22(20)28)13-16-9-11-17(25)12-10-16/h3-12,15,18,24-26H,2,13-14H2,1H3,(H,23,28)/b4-3+,7-5+,8-6+,20-19+
SMILES:	CCC(/C=C/C=C/C=C/C(=C/1C(=NC(C1=O)Cc1ccc(cc1)O)O)/O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651335
PubChem CID:	54729463
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO31149	Torrubiella	Genus	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21090800]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	44000.0	nM	PMID[457128]

☑ 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 NPC328070 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	138
0.1-0.2	812
0.2-0.3	3581
0.3-0.4	11003
0.4-0.5	8767
0.5-0.6	14456
0.6-0.7	3711
0.7-0.8	208
0.8-0.85	13
0.85-0.9	1
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC473055
0.9688	High Similarity	NPC473052
0.9612	High Similarity	NPC322526
0.9313	High Similarity	NPC471201
0.8516	High Similarity	NPC473051
0.8516	High Similarity	NPC473050
0.8485	Intermediate Similarity	NPC296712
0.845	Intermediate Similarity	NPC474862
0.8421	Intermediate Similarity	NPC478147
0.8243	Intermediate Similarity	NPC476194
0.8217	Intermediate Similarity	NPC319950
0.8134	Intermediate Similarity	NPC476353
0.803	Intermediate Similarity	NPC142577
0.8029	Intermediate Similarity	NPC45191
0.7958	Intermediate Similarity	NPC91953
0.7937	Intermediate Similarity	NPC474149
0.792	Intermediate Similarity	NPC317305
0.7914	Intermediate Similarity	NPC169766
0.7907	Intermediate Similarity	NPC317254
0.7895	Intermediate Similarity	NPC27581
0.7887	Intermediate Similarity	NPC197921
0.7883	Intermediate Similarity	NPC325651
0.7842	Intermediate Similarity	NPC244866
0.7829	Intermediate Similarity	NPC285350
0.781	Intermediate Similarity	NPC116057
0.7801	Intermediate Similarity	NPC6570
0.777	Intermediate Similarity	NPC326966
0.7769	Intermediate Similarity	NPC23402
0.7769	Intermediate Similarity	NPC188010
0.776	Intermediate Similarity	NPC231705
0.7734	Intermediate Similarity	NPC177576
0.773	Intermediate Similarity	NPC473360
0.7717	Intermediate Similarity	NPC258056
0.7714	Intermediate Similarity	NPC470392
0.7708	Intermediate Similarity	NPC469360
0.7698	Intermediate Similarity	NPC142297
0.7692	Intermediate Similarity	NPC118202
0.7681	Intermediate Similarity	NPC472413
0.7676	Intermediate Similarity	NPC208725
0.7671	Intermediate Similarity	NPC473804
0.7669	Intermediate Similarity	NPC283760
0.7656	Intermediate Similarity	NPC252544
0.7656	Intermediate Similarity	NPC321252
0.7639	Intermediate Similarity	NPC150712
0.763	Intermediate Similarity	NPC268348
0.7619	Intermediate Similarity	NPC119569
0.7612	Intermediate Similarity	NPC190663
0.7609	Intermediate Similarity	NPC305717
0.7586	Intermediate Similarity	NPC251439
0.7576	Intermediate Similarity	NPC106551
0.7576	Intermediate Similarity	NPC188867
0.7576	Intermediate Similarity	NPC281686
0.7552	Intermediate Similarity	NPC6913
0.7532	Intermediate Similarity	NPC471203
0.752	Intermediate Similarity	NPC178902
0.7519	Intermediate Similarity	NPC38458
0.7519	Intermediate Similarity	NPC311737
0.75	Intermediate Similarity	NPC96224
0.75	Intermediate Similarity	NPC24101
0.75	Intermediate Similarity	NPC16188
0.75	Intermediate Similarity	NPC153690
0.75	Intermediate Similarity	NPC160493
0.7481	Intermediate Similarity	NPC80150
0.748	Intermediate Similarity	NPC70843
0.7467	Intermediate Similarity	NPC473491
0.7463	Intermediate Similarity	NPC249435
0.7462	Intermediate Similarity	NPC114682
0.7452	Intermediate Similarity	NPC71205
0.7447	Intermediate Similarity	NPC120251
0.7444	Intermediate Similarity	NPC82963
0.7442	Intermediate Similarity	NPC88141
0.7434	Intermediate Similarity	NPC39431
0.7407	Intermediate Similarity	NPC239697
0.74	Intermediate Similarity	NPC476444
0.7394	Intermediate Similarity	NPC257390
0.7386	Intermediate Similarity	NPC244509
0.7379	Intermediate Similarity	NPC313694
0.7379	Intermediate Similarity	NPC242159
0.7379	Intermediate Similarity	NPC236795
0.7368	Intermediate Similarity	NPC262166
0.7348	Intermediate Similarity	NPC309808
0.7347	Intermediate Similarity	NPC33011
0.7344	Intermediate Similarity	NPC188677
0.7344	Intermediate Similarity	NPC95178
0.7344	Intermediate Similarity	NPC69332
0.7344	Intermediate Similarity	NPC29989
0.7342	Intermediate Similarity	NPC15506
0.7339	Intermediate Similarity	NPC260000
0.7338	Intermediate Similarity	NPC472414
0.7329	Intermediate Similarity	NPC471316
0.7324	Intermediate Similarity	NPC183722
0.7323	Intermediate Similarity	NPC261573
0.7323	Intermediate Similarity	NPC8931
0.7323	Intermediate Similarity	NPC120693
0.7319	Intermediate Similarity	NPC472415
0.7319	Intermediate Similarity	NPC86900
0.7315	Intermediate Similarity	NPC81026
0.7313	Intermediate Similarity	NPC28951
0.7313	Intermediate Similarity	NPC325646
0.731	Intermediate Similarity	NPC109580
0.7308	Intermediate Similarity	NPC95172
0.7303	Intermediate Similarity	NPC233702
0.7299	Intermediate Similarity	NPC56634
0.7287	Intermediate Similarity	NPC228737
0.728	Intermediate Similarity	NPC280869
0.7279	Intermediate Similarity	NPC43275
0.7279	Intermediate Similarity	NPC182240
0.7273	Intermediate Similarity	NPC17693
0.7266	Intermediate Similarity	NPC307020
0.7261	Intermediate Similarity	NPC156348
0.7255	Intermediate Similarity	NPC202198
0.7254	Intermediate Similarity	NPC469930
0.7248	Intermediate Similarity	NPC266741
0.7244	Intermediate Similarity	NPC244336
0.7237	Intermediate Similarity	NPC324081
0.7231	Intermediate Similarity	NPC31274
0.7226	Intermediate Similarity	NPC34634
0.7226	Intermediate Similarity	NPC478015
0.7226	Intermediate Similarity	NPC478016
0.7226	Intermediate Similarity	NPC478014
0.7226	Intermediate Similarity	NPC265454
0.7215	Intermediate Similarity	NPC67080
0.7214	Intermediate Similarity	NPC171372
0.7214	Intermediate Similarity	NPC4974
0.7208	Intermediate Similarity	NPC68967
0.7206	Intermediate Similarity	NPC142638
0.7206	Intermediate Similarity	NPC5932
0.7206	Intermediate Similarity	NPC317784
0.7205	Intermediate Similarity	NPC314693
0.7197	Intermediate Similarity	NPC212718
0.7194	Intermediate Similarity	NPC469927
0.7192	Intermediate Similarity	NPC64205
0.719	Intermediate Similarity	NPC153644
0.7185	Intermediate Similarity	NPC128249
0.7183	Intermediate Similarity	NPC71271
0.7174	Intermediate Similarity	NPC86966
0.7174	Intermediate Similarity	NPC98305
0.7174	Intermediate Similarity	NPC326079
0.7172	Intermediate Similarity	NPC477680
0.7171	Intermediate Similarity	NPC132771
0.7165	Intermediate Similarity	NPC472585
0.7163	Intermediate Similarity	NPC29477
0.7162	Intermediate Similarity	NPC476989
0.7161	Intermediate Similarity	NPC123011
0.7161	Intermediate Similarity	NPC256689
0.7161	Intermediate Similarity	NPC476268
0.7154	Intermediate Similarity	NPC226699
0.7153	Intermediate Similarity	NPC473767
0.7153	Intermediate Similarity	NPC268572
0.7153	Intermediate Similarity	NPC42423
0.7143	Intermediate Similarity	NPC101207
0.7143	Intermediate Similarity	NPC56685
0.7132	Intermediate Similarity	NPC211551
0.7123	Intermediate Similarity	NPC113325
0.7123	Intermediate Similarity	NPC470441
0.7123	Intermediate Similarity	NPC279045
0.7121	Intermediate Similarity	NPC222905
0.7121	Intermediate Similarity	NPC21162
0.7117	Intermediate Similarity	NPC12890
0.7113	Intermediate Similarity	NPC71610
0.7111	Intermediate Similarity	NPC322197
0.7103	Intermediate Similarity	NPC88667
0.7101	Intermediate Similarity	NPC112823
0.7099	Intermediate Similarity	NPC224584
0.7097	Intermediate Similarity	NPC478189
0.7095	Intermediate Similarity	NPC471283
0.7095	Intermediate Similarity	NPC48202
0.7095	Intermediate Similarity	NPC249899
0.7092	Intermediate Similarity	NPC62101
0.7092	Intermediate Similarity	NPC474803
0.7092	Intermediate Similarity	NPC95733
0.709	Intermediate Similarity	NPC242136
0.709	Intermediate Similarity	NPC11824
0.7087	Intermediate Similarity	NPC155847
0.7087	Intermediate Similarity	NPC289381
0.7086	Intermediate Similarity	NPC297322
0.7081	Intermediate Similarity	NPC209463
0.708	Intermediate Similarity	NPC122009
0.708	Intermediate Similarity	NPC41567
0.7077	Intermediate Similarity	NPC6984
0.7073	Intermediate Similarity	NPC26108
0.7073	Intermediate Similarity	NPC136797
0.707	Intermediate Similarity	NPC56635
0.7068	Intermediate Similarity	NPC163674
0.7068	Intermediate Similarity	NPC227553
0.7068	Intermediate Similarity	NPC166837
0.7067	Intermediate Similarity	NPC13696
0.7063	Intermediate Similarity	NPC63931
0.7063	Intermediate Similarity	NPC16031
0.7063	Intermediate Similarity	NPC161593
0.7063	Intermediate Similarity	NPC145888
0.7059	Intermediate Similarity	NPC19290
0.7059	Intermediate Similarity	NPC146097
0.7059	Intermediate Similarity	NPC227905
0.7059	Intermediate Similarity	NPC339338
0.7059	Intermediate Similarity	NPC2672
0.7059	Intermediate Similarity	NPC477453
0.7055	Intermediate Similarity	NPC132308
0.7055	Intermediate Similarity	NPC228511
0.7055	Intermediate Similarity	NPC328494

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 NPC328070 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	116
0.1-0.2	499
0.2-0.3	900
0.3-0.4	1929
0.4-0.5	2901
0.5-0.6	2234
0.6-0.7	542
0.7-0.8	28
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
0.8222	Intermediate Similarity	NPD3136	Phase 2
0.7842	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1759	Phase 1
0.7708	Intermediate Similarity	NPD7978	Discontinued
0.7671	Intermediate Similarity	NPD3400	Discontinued
0.7652	Intermediate Similarity	NPD1758	Phase 1
0.7576	Intermediate Similarity	NPD9568	Approved
0.7517	Intermediate Similarity	NPD7450	Phase 2
0.75	Intermediate Similarity	NPD256	Approved
0.75	Intermediate Similarity	NPD255	Approved
0.7415	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6325	Discontinued
0.7303	Intermediate Similarity	NPD6390	Discontinued
0.729	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4659	Approved
0.7266	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD2228	Approved
0.7218	Intermediate Similarity	NPD2234	Approved
0.7218	Intermediate Similarity	NPD2229	Approved
0.7211	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7972	Discontinued
0.7194	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD9610	Approved
0.7188	Intermediate Similarity	NPD9608	Approved
0.7185	Intermediate Similarity	NPD3123	Discovery
0.7162	Intermediate Similarity	NPD9570	Approved
0.7143	Intermediate Similarity	NPD7131	Phase 3
0.7143	Intermediate Similarity	NPD7523	Phase 3
0.7134	Intermediate Similarity	NPD7495	Discontinued
0.7132	Intermediate Similarity	NPD317	Approved
0.7132	Intermediate Similarity	NPD318	Approved
0.7123	Intermediate Similarity	NPD555	Phase 2
0.7113	Intermediate Similarity	NPD7451	Discontinued
0.7103	Intermediate Similarity	NPD259	Phase 1
0.7101	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2562	Approved
0.7071	Intermediate Similarity	NPD2561	Approved
0.7063	Intermediate Similarity	NPD9569	Approved
0.7055	Intermediate Similarity	NPD825	Approved
0.7055	Intermediate Similarity	NPD826	Approved
0.7045	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4103	Phase 2
0.7027	Intermediate Similarity	NPD3553	Approved
0.7027	Intermediate Similarity	NPD3552	Approved
0.7027	Intermediate Similarity	NPD3555	Approved
0.7027	Intermediate Similarity	NPD3554	Approved
0.7021	Intermediate Similarity	NPD1755	Approved
0.7021	Intermediate Similarity	NPD5159	Phase 2
0.7021	Intermediate Similarity	NPD5157	Phase 1
0.7021	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD16	Approved
0.7007	Intermediate Similarity	NPD856	Approved
0.6993	Remote Similarity	NPD257	Approved
0.6993	Remote Similarity	NPD258	Approved
0.6982	Remote Similarity	NPD5035	Approved
0.6972	Remote Similarity	NPD196	Phase 1
0.6957	Remote Similarity	NPD5304	Approved
0.6957	Remote Similarity	NPD5303	Approved
0.6947	Remote Similarity	NPD1444	Approved
0.6947	Remote Similarity	NPD1445	Approved
0.6933	Remote Similarity	NPD2161	Phase 2
0.6929	Remote Similarity	NPD3421	Phase 3
0.6928	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD8019	Approved
0.6912	Remote Similarity	NPD9618	Approved
0.6912	Remote Similarity	NPD9614	Approved
0.6899	Remote Similarity	NPD6502	Phase 2
0.6866	Remote Similarity	NPD3642	Approved
0.6866	Remote Similarity	NPD3644	Approved
0.6866	Remote Similarity	NPD3643	Approved
0.6857	Remote Similarity	NPD2932	Approved
0.6857	Remote Similarity	NPD3019	Approved
0.6849	Remote Similarity	NPD9537	Phase 1
0.6849	Remote Similarity	NPD9536	Phase 1
0.6835	Remote Similarity	NPD3455	Phase 2
0.6829	Remote Similarity	NPD3286	Discontinued
0.6828	Remote Similarity	NPD4208	Discontinued
0.6824	Remote Similarity	NPD5028	Approved
0.6824	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD36	Approved
0.6824	Remote Similarity	NPD5026	Approved
0.6824	Remote Similarity	NPD4954	Approved
0.6824	Remote Similarity	NPD4955	Approved
0.6824	Remote Similarity	NPD6346	Approved
0.6824	Remote Similarity	NPD5034	Approved
0.6809	Remote Similarity	NPD3143	Discontinued
0.6806	Remote Similarity	NPD1135	Approved
0.6806	Remote Similarity	NPD1133	Approved
0.6806	Remote Similarity	NPD1131	Approved
0.6806	Remote Similarity	NPD1129	Approved
0.6806	Remote Similarity	NPD1134	Approved
0.6805	Remote Similarity	NPD3823	Discontinued
0.6791	Remote Similarity	NPD1792	Phase 2
0.6788	Remote Similarity	NPD7315	Approved
0.6786	Remote Similarity	NPD5981	Approved
0.6786	Remote Similarity	NPD4093	Discontinued
0.6783	Remote Similarity	NPD3685	Discontinued
0.6781	Remote Similarity	NPD4207	Discontinued
0.6774	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2860	Approved
0.6772	Remote Similarity	NPD2859	Approved
0.6765	Remote Similarity	NPD5030	Phase 2
0.6761	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2674	Phase 3
0.6752	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5557	Phase 1
0.6744	Remote Similarity	NPD3020	Approved
0.6738	Remote Similarity	NPD2668	Approved
0.6738	Remote Similarity	NPD2667	Approved
0.6735	Remote Similarity	NPD4738	Phase 2
0.6732	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3909	Discontinued
0.6725	Remote Similarity	NPD5032	Approved
0.6714	Remote Similarity	NPD2217	Approved
0.6714	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD2218	Phase 2
0.6711	Remote Similarity	NPD468	Phase 1
0.6711	Remote Similarity	NPD3140	Approved
0.6711	Remote Similarity	NPD3142	Approved
0.6708	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD2934	Approved
0.6693	Remote Similarity	NPD2933	Approved
0.6689	Remote Similarity	NPD3145	Approved
0.6689	Remote Similarity	NPD3144	Approved
0.6688	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7608	Discontinued
0.6667	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3300	Phase 2
0.6667	Remote Similarity	NPD5037	Approved
0.6667	Remote Similarity	NPD6746	Phase 2
0.6667	Remote Similarity	NPD2614	Approved
0.6667	Remote Similarity	NPD9622	Approved
0.6667	Remote Similarity	NPD274	Approved
0.6667	Remote Similarity	NPD275	Approved
0.6667	Remote Similarity	NPD5038	Approved
0.6644	Remote Similarity	NPD7477	Discontinued
0.6644	Remote Similarity	NPD5745	Approved
0.6644	Remote Similarity	NPD520	Approved
0.6643	Remote Similarity	NPD4217	Approved
0.6643	Remote Similarity	NPD9616	Approved
0.6643	Remote Similarity	NPD2611	Approved
0.6643	Remote Similarity	NPD2612	Approved
0.6643	Remote Similarity	NPD9613	Approved
0.6643	Remote Similarity	NPD2608	Approved
0.6643	Remote Similarity	NPD9615	Approved
0.6643	Remote Similarity	NPD3131	Approved
0.6643	Remote Similarity	NPD4218	Approved
0.6643	Remote Similarity	NPD2609	Approved
0.6643	Remote Similarity	NPD4216	Approved
0.6643	Remote Similarity	NPD2610	Approved
0.6643	Remote Similarity	NPD4215	Approved
0.6643	Remote Similarity	NPD3132	Approved
0.6641	Remote Similarity	NPD855	Approved
0.6641	Remote Similarity	NPD854	Approved
0.6626	Remote Similarity	NPD7318	Phase 3
0.6626	Remote Similarity	NPD5967	Approved
0.6626	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD4357	Discontinued
0.6623	Remote Similarity	NPD2157	Approved
0.6623	Remote Similarity	NPD8173	Phase 2
0.6623	Remote Similarity	NPD2568	Approved
0.6623	Remote Similarity	NPD8172	Phase 2
0.6622	Remote Similarity	NPD9718	Approved
0.6621	Remote Similarity	NPD3125	Approved
0.661	Remote Similarity	NPD5968	Phase 3
0.6609	Remote Similarity	NPD5036	Approved
0.6606	Remote Similarity	NPD8303	Discontinued
0.6606	Remote Similarity	NPD6862	Phase 2
0.6605	Remote Similarity	NPD7577	Discontinued
0.6604	Remote Similarity	NPD1670	Discontinued
0.6601	Remote Similarity	NPD1538	Phase 1
0.6601	Remote Similarity	NPD1519	Approved
0.6601	Remote Similarity	NPD2239	Approved
0.6601	Remote Similarity	NPD5712	Approved
0.6601	Remote Similarity	NPD2240	Approved
0.6601	Remote Similarity	NPD1537	Approved
0.6599	Remote Similarity	NPD3636	Approved
0.6599	Remote Similarity	NPD1712	Approved
0.6599	Remote Similarity	NPD3637	Approved
0.6599	Remote Similarity	NPD3635	Approved
0.6597	Remote Similarity	NPD6624	Discontinued
0.6597	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD3070	Discontinued
0.6596	Remote Similarity	NPD9545	Approved
0.6596	Remote Similarity	NPD316	Approved
0.6582	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2654	Approved
0.6577	Remote Similarity	NPD598	Approved
0.6577	Remote Similarity	NPD601	Approved
0.6577	Remote Similarity	NPD597	Approved
0.6575	Remote Similarity	NPD2628	Approved
0.6575	Remote Similarity	NPD2625	Approved
0.6575	Remote Similarity	NPD2159	Approved
0.6575	Remote Similarity	NPD2627	Approved
0.6575	Remote Similarity	NPD3053	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