NPASS Compound

Structure

CID322966 OpenBabel06191716172D 27 27 0 0 1 0 0 0 0 0999 V2000 -6.6913 -6.2631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 -1.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8135 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2202 -2.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 -5.3495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5103 -4.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5158 -4.6450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9280 -3.8360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9334 -3.9406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3457 -3.1315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3511 -3.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7634 -2.4271 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.1810 -1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6324 -3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7688 -2.5316 0.0000 C 0 0 1 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 -1.2601 1.2601 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 1.0392 -4.4632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.7045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 0.5909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4680 2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3621 -3.4451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 15 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 16 3 1 1 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 23 2 0 0 0 0 17 27 1 0 0 0 0 18 21 1 6 0 0 0 18 22 1 0 0 0 0 19 27 1 1 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	383.27
Volume:	410.254
LogP:	4.382
LogD:	2.51
LogS:	-3.781
# Rotatable Bonds:	14
TPSA:	83.91
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	3.51
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.091
MDCK Permeability:	3.313409615657292e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.11
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.15
Plasma Protein Binding (PPB):	95.94571685791016%
Volume Distribution (VD):	0.422
Pgp-substrate:	3.3503928184509277%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.131
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.147
CYP3A4-substrate:	0.093

ADMET: Excretion

Clearance (CL):	2.9
Half-life (T1/2):	0.655

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.81
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.079
Skin Sensitization:	0.262
Carcinogencity:	0.057
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.068

Download Data

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

Natural Product: NPC322966

Natural Product ID:	NPC322966
*Common Name:**	Tumonoic Acid F
IUPAC Name:	(2S)-1-[(2S,3S)-3-acetyloxy-2,4-dimethyldodecanoyl]pyrrolidine-2-carboxylic acid
Synonyms:	Tumonoic Acid F
Standard InCHIKey:	PFYSYVJVRRSPAP-PVRLSMEHSA-N
Standard InCHI:	InChI=1S/C21H37NO5/c1-5-6-7-8-9-10-12-15(2)19(27-17(4)23)16(3)20(24)22-14-11-13-18(22)21(25)26/h15-16,18-19H,5-14H2,1-4H3,(H,25,26)/t15?,16-,18-,19-/m0/s1
SMILES:	CCCCCCCCC([C@@H]([C@@H](C(=O)N1CCC[C@H]1C(=O)O)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497483
PubChem CID:	25058103
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004322] Proline and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33134	blennothrix cantharidosmum	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18698821]
NPO5066	Oscillatoria margaritifera	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21488639]
NPO5066	Oscillatoria margaritifera	Species	Oscillatoriaceae	Bacteria	n.a.	Isla Canales de Afuera on the Pacific coast of Panama (741.617'N, 8138.379'E)	n.a.	PMID[21488639]
NPO5066	Oscillatoria margaritifera	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21751786]
NPO5066.1	Oscillatoria margaritifera nac8-54	Subspecies	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21751786]
NPO5066.2	Oscillatoria margaritifera nac8-55	Subspecies	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21751786]
NPO5066	Oscillatoria margaritifera	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1726	Organism	Vibrio harveyi	Vibrio harveyi	IC50	=	62000.0	nM	PMID[481667]

☑ 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 NPC322966 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	148
0.1-0.2	2828
0.2-0.3	19638
0.3-0.4	13948
0.4-0.5	5181
0.5-0.6	744
0.6-0.7	173
0.7-0.8	34
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8652	High Similarity	NPC476019
0.7778	Intermediate Similarity	NPC277918
0.7677	Intermediate Similarity	NPC188785
0.7653	Intermediate Similarity	NPC220234
0.7449	Intermediate Similarity	NPC47076
0.7449	Intermediate Similarity	NPC134504
0.7396	Intermediate Similarity	NPC471098
0.7396	Intermediate Similarity	NPC62263
0.7396	Intermediate Similarity	NPC173763
0.7292	Intermediate Similarity	NPC474576
0.7282	Intermediate Similarity	NPC323720
0.7255	Intermediate Similarity	NPC301148
0.7255	Intermediate Similarity	NPC5864
0.7255	Intermediate Similarity	NPC124554
0.7238	Intermediate Similarity	NPC67009
0.7222	Intermediate Similarity	NPC216090
0.7191	Intermediate Similarity	NPC477145
0.7191	Intermediate Similarity	NPC473741
0.7188	Intermediate Similarity	NPC474593
0.7188	Intermediate Similarity	NPC475801
0.7184	Intermediate Similarity	NPC265094
0.713	Intermediate Similarity	NPC309525
0.7115	Intermediate Similarity	NPC124549
0.7019	Intermediate Similarity	NPC198344
0.6981	Remote Similarity	NPC271562
0.6979	Remote Similarity	NPC52533
0.6931	Remote Similarity	NPC471843
0.6916	Remote Similarity	NPC171734
0.6887	Remote Similarity	NPC471844
0.6881	Remote Similarity	NPC476875
0.6854	Remote Similarity	NPC327272
0.6833	Remote Similarity	NPC120335
0.6752	Remote Similarity	NPC477518
0.6742	Remote Similarity	NPC178919
0.6742	Remote Similarity	NPC263281
0.6729	Remote Similarity	NPC241394
0.67	Remote Similarity	NPC315237
0.6636	Remote Similarity	NPC128303
0.6635	Remote Similarity	NPC475440
0.6633	Remote Similarity	NPC324506
0.6632	Remote Similarity	NPC47135
0.663	Remote Similarity	NPC233108
0.6604	Remote Similarity	NPC475149
0.6604	Remote Similarity	NPC471097
0.6604	Remote Similarity	NPC287638
0.6604	Remote Similarity	NPC233274
0.6604	Remote Similarity	NPC194750
0.6602	Remote Similarity	NPC473597
0.66	Remote Similarity	NPC17143
0.66	Remote Similarity	NPC47230
0.6588	Remote Similarity	NPC160661
0.6566	Remote Similarity	NPC203170
0.6555	Remote Similarity	NPC474371
0.6542	Remote Similarity	NPC476877
0.6512	Remote Similarity	NPC325117
0.6512	Remote Similarity	NPC322319
0.6512	Remote Similarity	NPC326651
0.6496	Remote Similarity	NPC160688
0.6491	Remote Similarity	NPC471845
0.6491	Remote Similarity	NPC471846
0.6491	Remote Similarity	NPC39041
0.6491	Remote Similarity	NPC202722
0.6491	Remote Similarity	NPC241294
0.6471	Remote Similarity	NPC470654
0.6471	Remote Similarity	NPC470650
0.6471	Remote Similarity	NPC470653
0.646	Remote Similarity	NPC469597
0.6444	Remote Similarity	NPC477643
0.6444	Remote Similarity	NPC320865
0.6444	Remote Similarity	NPC477641
0.6422	Remote Similarity	NPC475637
0.6422	Remote Similarity	NPC476876
0.6421	Remote Similarity	NPC470783
0.6415	Remote Similarity	NPC13175
0.6415	Remote Similarity	NPC475791
0.6374	Remote Similarity	NPC43219
0.6364	Remote Similarity	NPC10716
0.6364	Remote Similarity	NPC322672
0.6348	Remote Similarity	NPC296043
0.6321	Remote Similarity	NPC475758
0.6316	Remote Similarity	NPC63191
0.6316	Remote Similarity	NPC471202
0.6316	Remote Similarity	NPC474702
0.6304	Remote Similarity	NPC86064
0.63	Remote Similarity	NPC168017
0.63	Remote Similarity	NPC473525
0.6296	Remote Similarity	NPC227622
0.6293	Remote Similarity	NPC329216
0.6292	Remote Similarity	NPC322274
0.6292	Remote Similarity	NPC212866
0.6292	Remote Similarity	NPC29598
0.6292	Remote Similarity	NPC15864
0.6283	Remote Similarity	NPC474411
0.6283	Remote Similarity	NPC474431
0.6277	Remote Similarity	NPC316242
0.6275	Remote Similarity	NPC477538
0.6271	Remote Similarity	NPC470652
0.6271	Remote Similarity	NPC11379
0.6263	Remote Similarity	NPC319913
0.625	Remote Similarity	NPC475542
0.6224	Remote Similarity	NPC472351
0.6222	Remote Similarity	NPC477642
0.6211	Remote Similarity	NPC315131
0.6211	Remote Similarity	NPC478017
0.6211	Remote Similarity	NPC315535
0.6211	Remote Similarity	NPC473984
0.6207	Remote Similarity	NPC271115
0.6207	Remote Similarity	NPC314103
0.6176	Remote Similarity	NPC178632
0.6174	Remote Similarity	NPC309731
0.6161	Remote Similarity	NPC15413
0.6161	Remote Similarity	NPC207820
0.6154	Remote Similarity	NPC28542
0.6154	Remote Similarity	NPC469998
0.6147	Remote Similarity	NPC470592
0.6146	Remote Similarity	NPC476137
0.6146	Remote Similarity	NPC476156
0.6146	Remote Similarity	NPC476117
0.6146	Remote Similarity	NPC476243
0.6136	Remote Similarity	NPC287693
0.6129	Remote Similarity	NPC25327
0.6087	Remote Similarity	NPC76660
0.6087	Remote Similarity	NPC276995
0.6087	Remote Similarity	NPC314550
0.6083	Remote Similarity	NPC315188
0.6082	Remote Similarity	NPC476302
0.6082	Remote Similarity	NPC23984
0.6071	Remote Similarity	NPC137453
0.6061	Remote Similarity	NPC124359
0.605	Remote Similarity	NPC477237
0.6044	Remote Similarity	NPC478256
0.6042	Remote Similarity	NPC31756
0.6042	Remote Similarity	NPC312315
0.6038	Remote Similarity	NPC150041
0.6023	Remote Similarity	NPC472609
0.6022	Remote Similarity	NPC208657
0.6022	Remote Similarity	NPC266888
0.6022	Remote Similarity	NPC256312
0.6022	Remote Similarity	NPC209156
0.6022	Remote Similarity	NPC161774
0.6022	Remote Similarity	NPC320221
0.602	Remote Similarity	NPC246005
0.602	Remote Similarity	NPC84128
0.602	Remote Similarity	NPC53858
0.6015	Remote Similarity	NPC956
0.6	Remote Similarity	NPC469925
0.6	Remote Similarity	NPC8325
0.6	Remote Similarity	NPC470593
0.6	Remote Similarity	NPC227051
0.6	Remote Similarity	NPC319991
0.6	Remote Similarity	NPC470594
0.6	Remote Similarity	NPC58281
0.6	Remote Similarity	NPC330017
0.5984	Remote Similarity	NPC50520
0.5984	Remote Similarity	NPC473477
0.596	Remote Similarity	NPC473810
0.595	Remote Similarity	NPC477238
0.5941	Remote Similarity	NPC90476
0.5941	Remote Similarity	NPC69374
0.5938	Remote Similarity	NPC120420
0.5929	Remote Similarity	NPC176773
0.5926	Remote Similarity	NPC476344
0.5922	Remote Similarity	NPC275715
0.592	Remote Similarity	NPC470651
0.592	Remote Similarity	NPC470655
0.5913	Remote Similarity	NPC469603
0.59	Remote Similarity	NPC145748
0.59	Remote Similarity	NPC155670
0.59	Remote Similarity	NPC95478
0.59	Remote Similarity	NPC320936
0.5895	Remote Similarity	NPC470782
0.5891	Remote Similarity	NPC99864
0.5889	Remote Similarity	NPC135539
0.5889	Remote Similarity	NPC221764
0.5889	Remote Similarity	NPC196359
0.5889	Remote Similarity	NPC78312
0.5882	Remote Similarity	NPC477728
0.5877	Remote Similarity	NPC474099
0.5865	Remote Similarity	NPC477729
0.5854	Remote Similarity	NPC8488
0.5854	Remote Similarity	NPC274499
0.5854	Remote Similarity	NPC333075
0.5833	Remote Similarity	NPC174463
0.5833	Remote Similarity	NPC88943
0.5827	Remote Similarity	NPC313657
0.5824	Remote Similarity	NPC74555
0.5824	Remote Similarity	NPC266242
0.5824	Remote Similarity	NPC254617
0.5824	Remote Similarity	NPC306763
0.5821	Remote Similarity	NPC269398
0.5821	Remote Similarity	NPC263493
0.582	Remote Similarity	NPC266910
0.582	Remote Similarity	NPC23963
0.5812	Remote Similarity	NPC60432
0.5812	Remote Similarity	NPC1111
0.5812	Remote Similarity	NPC469466
0.5812	Remote Similarity	NPC261750
0.581	Remote Similarity	NPC159568
0.5806	Remote Similarity	NPC169976
0.5806	Remote Similarity	NPC321197

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 NPC322966 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	113
0.1-0.2	1587
0.2-0.3	4245
0.3-0.4	2389
0.4-0.5	563
0.5-0.6	214
0.6-0.7	34
0.7-0.8	5
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
0.7917	Intermediate Similarity	NPD3714	Approved
0.7917	Intermediate Similarity	NPD3713	Approved
0.7917	Intermediate Similarity	NPD3715	Approved
0.7474	Intermediate Similarity	NPD2682	Approved
0.7176	Intermediate Similarity	NPD2697	Approved
0.7176	Intermediate Similarity	NPD2695	Approved
0.7176	Intermediate Similarity	NPD2694	Approved
0.7176	Intermediate Similarity	NPD2696	Approved
0.7128	Intermediate Similarity	NPD3723	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4780	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD617	Approved
0.6667	Remote Similarity	NPD8140	Approved
0.6632	Remote Similarity	NPD7345	Approved
0.6607	Remote Similarity	NPD1376	Discontinued
0.6591	Remote Similarity	NPD9649	Approved
0.6514	Remote Similarity	NPD8307	Discontinued
0.6458	Remote Similarity	NPD883	Phase 2
0.6458	Remote Similarity	NPD882	Phase 2
0.6444	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4261	Phase 1
0.64	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3176	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3177	Phase 3
0.6296	Remote Similarity	NPD8085	Approved
0.6296	Remote Similarity	NPD8139	Approved
0.6296	Remote Similarity	NPD8086	Approved
0.6296	Remote Similarity	NPD8084	Approved
0.6296	Remote Similarity	NPD8138	Approved
0.6296	Remote Similarity	NPD8082	Approved
0.6296	Remote Similarity	NPD8083	Approved
0.6292	Remote Similarity	NPD7840	Approved
0.6277	Remote Similarity	NPD8143	Approved
0.6277	Remote Similarity	NPD8144	Approved
0.6263	Remote Similarity	NPD7759	Phase 2
0.6263	Remote Similarity	NPD7760	Phase 2
0.6261	Remote Similarity	NPD7916	Approved
0.6261	Remote Similarity	NPD7915	Approved
0.625	Remote Similarity	NPD7763	Phase 2
0.625	Remote Similarity	NPD612	Discontinued
0.625	Remote Similarity	NPD7762	Phase 2
0.6239	Remote Similarity	NPD8276	Approved
0.6239	Remote Similarity	NPD8275	Approved
0.6239	Remote Similarity	NPD6122	Discontinued
0.6222	Remote Similarity	NPD3726	Approved
0.6222	Remote Similarity	NPD3725	Approved
0.622	Remote Similarity	NPD4281	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD8087	Discontinued
0.6186	Remote Similarity	NPD2683	Discontinued
0.6182	Remote Similarity	NPD8081	Approved
0.6126	Remote Similarity	NPD8393	Approved
0.6111	Remote Similarity	NPD620	Approved
0.6075	Remote Similarity	NPD8038	Phase 2
0.6038	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.602	Remote Similarity	NPD1125	Discovery
0.6015	Remote Similarity	NPD5193	Discontinued
0.6	Remote Similarity	NPD8345	Approved
0.6	Remote Similarity	NPD8347	Approved
0.6	Remote Similarity	NPD8346	Approved
0.5965	Remote Similarity	NPD8305	Approved
0.5965	Remote Similarity	NPD8306	Approved
0.5963	Remote Similarity	NPD5359	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6937	Approved
0.5917	Remote Similarity	NPD3159	Discontinued
0.5895	Remote Similarity	NPD2257	Approved
0.5891	Remote Similarity	NPD8415	Approved
0.5889	Remote Similarity	NPD8868	Approved
0.5887	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD3103	Approved
0.5872	Remote Similarity	NPD4825	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD3104	Approved
0.5872	Remote Similarity	NPD3102	Approved
0.5872	Remote Similarity	NPD3101	Approved
0.5856	Remote Similarity	NPD8300	Approved
0.5856	Remote Similarity	NPD8301	Approved
0.5851	Remote Similarity	NPD355	Phase 2
0.5846	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6920	Discontinued
0.5833	Remote Similarity	NPD1773	Discontinued
0.5833	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD9676	Phase 3
0.5789	Remote Similarity	NPD1828	Approved
0.5789	Remote Similarity	NPD1827	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD1829	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD4177	Approved
0.5781	Remote Similarity	NPD4175	Approved
0.5763	Remote Similarity	NPD8298	Phase 2
0.575	Remote Similarity	NPD961	Discontinued
0.5738	Remote Similarity	NPD2645	Approved
0.5714	Remote Similarity	NPD6073	Approved
0.5714	Remote Similarity	NPD5725	Approved
0.5714	Remote Similarity	NPD8172	Phase 2
0.5714	Remote Similarity	NPD8173	Phase 2
0.5704	Remote Similarity	NPD7511	Approved
0.5704	Remote Similarity	NPD7512	Approved
0.5699	Remote Similarity	NPD8277	Approved
0.5691	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD3191	Approved
0.5688	Remote Similarity	NPD3190	Approved
0.5688	Remote Similarity	NPD3189	Approved
0.5688	Remote Similarity	NPD1784	Approved
0.5673	Remote Similarity	NPD621	Discontinued
0.5667	Remote Similarity	NPD4272	Discontinued
0.5652	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD8175	Discontinued
0.5648	Remote Similarity	NPD2637	Approved
0.5648	Remote Similarity	NPD2636	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD7652	Discontinued
0.5638	Remote Similarity	NPD7535	Discontinued
0.563	Remote Similarity	NPD8384	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