NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	855.48
Volume:	878.89
LogP:	5.906
LogD:	3.954
LogS:	-4.922
# Rotatable Bonds:	6
TPSA:	184.9
# H-Bond Aceptor:	14
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.24
Synthetic Accessibility Score:	7.046
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.148
MDCK Permeability:	1.6828562365844846e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.054
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	89.7488021850586%
Volume Distribution (VD):	0.754
Pgp-substrate:	9.545661926269531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.382
CYP2C19-substrate:	0.721
CYP2C9-inhibitor:	0.664
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.976
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	8.232
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.7
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.44
Carcinogencity:	0.324
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC477527

Natural Product ID:	NPC477527
*Common Name:**	Apratoxin A sulfoxide
IUPAC Name:	(2S,3S,5S,7S,10S,16S,19S,22S,25E,27S)-16-[(2S)-butan-2-yl]-7-tert-butyl-3-hydroxy-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-29-oxo-8-oxa-29lambda4-thia-14,17,20,23,30-pentazatricyclo[25.2.1.010,14]triaconta-1(30),25-diene-9,15,18,21,24-pentone
Synonyms:
Standard InCHIKey:	XQTNLJKLCLNKBG-BJAMGVOOSA-N
Standard InCHI:	InChI=1S/C45H69N5O9S/c1-13-27(3)38-43(55)50-20-14-15-35(50)44(56)59-37(45(7,8)9)22-26(2)21-36(51)29(5)40-46-32(25-60(40)57)23-28(4)39(52)47-34(24-31-16-18-33(58-12)19-17-31)42(54)48(10)30(6)41(53)49(38)11/h16-19,23,26-27,29-30,32,34-38,51H,13-15,20-22,24-25H2,1-12H3,(H,47,52)/b28-23+/t26-,27-,29-,30-,32-,34-,35-,36-,37-,38-,60?/m0/s1
SMILES:	CC[C@H](C)[C@H]1C(=O)N2CCC[C@H]2C(=O)O[C@@H](C[C@H](C[C@@H]([C@@H](C3=N[C@H](CS3=O)/C=C(/C(=O)N[C@H](C(=O)N([C@H](C(=O)N1C)C)C)CC4=CC=C(C=C4)OC)\C)C)O)C)C(C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	73353722
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO30482	Moorea producens	Species	Oscillatoriaceae	Bacteria	n.a.	Nabq Mangroves in the Gulf of Aqaba (Red Sea)	n.a.	PMID[24016099]
NPO30482	Moorea producens	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24044577]
NPO30482	Moorea producens	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25421266]

☑ 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
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	89.9	nM	PMID[24016099]

☑ 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 NPC477527 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	222
0.1-0.2	1221
0.2-0.3	4900
0.3-0.4	12545
0.4-0.5	14514
0.5-0.6	8326
0.6-0.7	799
0.7-0.8	162
0.8-0.85	2
0.85-0.9	0
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9829	High Similarity	NPC59827
0.9829	High Similarity	NPC184933
0.9486	High Similarity	NPC329731
0.9375	High Similarity	NPC4910
0.9326	High Similarity	NPC477526
0.8202	Intermediate Similarity	NPC472923
0.7957	Intermediate Similarity	NPC475421
0.7926	Intermediate Similarity	NPC167763
0.7926	Intermediate Similarity	NPC470112
0.7926	Intermediate Similarity	NPC470903
0.7796	Intermediate Similarity	NPC26108
0.7749	Intermediate Similarity	NPC299806
0.7742	Intermediate Similarity	NPC137627
0.773	Intermediate Similarity	NPC196091
0.7717	Intermediate Similarity	NPC473502
0.7676	Intermediate Similarity	NPC186617
0.7656	Intermediate Similarity	NPC315542
0.7634	Intermediate Similarity	NPC471568
0.7634	Intermediate Similarity	NPC475123
0.7634	Intermediate Similarity	NPC475204
0.7634	Intermediate Similarity	NPC473693
0.7627	Intermediate Similarity	NPC283783
0.7598	Intermediate Similarity	NPC262166
0.7568	Intermediate Similarity	NPC254700
0.7553	Intermediate Similarity	NPC306804
0.7527	Intermediate Similarity	NPC107938
0.7527	Intermediate Similarity	NPC294516
0.7513	Intermediate Similarity	NPC159767
0.7513	Intermediate Similarity	NPC471165
0.7513	Intermediate Similarity	NPC155506
0.7513	Intermediate Similarity	NPC476227
0.7513	Intermediate Similarity	NPC279871
0.7487	Intermediate Similarity	NPC269750
0.7487	Intermediate Similarity	NPC194671
0.7462	Intermediate Similarity	NPC473407
0.7462	Intermediate Similarity	NPC473378
0.7447	Intermediate Similarity	NPC46009
0.7421	Intermediate Similarity	NPC473402
0.7421	Intermediate Similarity	NPC318930
0.7421	Intermediate Similarity	NPC317362
0.7419	Intermediate Similarity	NPC63931
0.7415	Intermediate Similarity	NPC246303
0.7407	Intermediate Similarity	NPC230611
0.7391	Intermediate Similarity	NPC287757
0.7391	Intermediate Similarity	NPC319320
0.7389	Intermediate Similarity	NPC324081
0.7368	Intermediate Similarity	NPC273755
0.7354	Intermediate Similarity	NPC40234
0.7333	Intermediate Similarity	NPC471049
0.7333	Intermediate Similarity	NPC471048
0.7333	Intermediate Similarity	NPC471050
0.733	Intermediate Similarity	NPC317725
0.733	Intermediate Similarity	NPC326407
0.7318	Intermediate Similarity	NPC16188
0.7316	Intermediate Similarity	NPC89831
0.7308	Intermediate Similarity	NPC5194
0.7308	Intermediate Similarity	NPC261934
0.7308	Intermediate Similarity	NPC202198
0.7286	Intermediate Similarity	NPC248822
0.7268	Intermediate Similarity	NPC153554
0.7263	Intermediate Similarity	NPC81026
0.7253	Intermediate Similarity	NPC233702
0.7249	Intermediate Similarity	NPC302597
0.7245	Intermediate Similarity	NPC294951
0.7243	Intermediate Similarity	NPC326349
0.7243	Intermediate Similarity	NPC323336
0.7241	Intermediate Similarity	NPC477552
0.7241	Intermediate Similarity	NPC477550
0.724	Intermediate Similarity	NPC473354
0.7231	Intermediate Similarity	NPC477637
0.7216	Intermediate Similarity	NPC45037
0.7214	Intermediate Similarity	NPC328763
0.7207	Intermediate Similarity	NPC266741
0.7207	Intermediate Similarity	NPC322878
0.7207	Intermediate Similarity	NPC5620
0.7202	Intermediate Similarity	NPC50016
0.7198	Intermediate Similarity	NPC473491
0.7192	Intermediate Similarity	NPC144314
0.7174	Intermediate Similarity	NPC39431
0.7171	Intermediate Similarity	NPC477551
0.7167	Intermediate Similarity	NPC314358
0.7157	Intermediate Similarity	NPC50548
0.7151	Intermediate Similarity	NPC476978
0.715	Intermediate Similarity	NPC164608
0.715	Intermediate Similarity	NPC163961
0.715	Intermediate Similarity	NPC174122
0.715	Intermediate Similarity	NPC64140
0.715	Intermediate Similarity	NPC473305
0.7143	Intermediate Similarity	NPC473404
0.7143	Intermediate Similarity	NPC14877
0.7143	Intermediate Similarity	NPC476321
0.7143	Intermediate Similarity	NPC149962
0.7143	Intermediate Similarity	NPC475350
0.7143	Intermediate Similarity	NPC145178
0.7135	Intermediate Similarity	NPC328494
0.7135	Intermediate Similarity	NPC244509
0.712	Intermediate Similarity	NPC286551
0.712	Intermediate Similarity	NPC56685
0.7111	Intermediate Similarity	NPC313867
0.7111	Intermediate Similarity	NPC316008
0.7107	Intermediate Similarity	NPC471526
0.71	Intermediate Similarity	NPC234069
0.7095	Intermediate Similarity	NPC478005
0.7095	Intermediate Similarity	NPC161069
0.7094	Intermediate Similarity	NPC477638
0.7094	Intermediate Similarity	NPC477632
0.7092	Intermediate Similarity	NPC32064
0.7088	Intermediate Similarity	NPC189908
0.7087	Intermediate Similarity	NPC473450
0.7085	Intermediate Similarity	NPC276120
0.7073	Intermediate Similarity	NPC323662
0.7068	Intermediate Similarity	NPC141957
0.7065	Intermediate Similarity	NPC29531
0.7062	Intermediate Similarity	NPC136797
0.7056	Intermediate Similarity	NPC315283
0.7056	Intermediate Similarity	NPC314388
0.7049	Intermediate Similarity	NPC129666
0.7049	Intermediate Similarity	NPC2501
0.7042	Intermediate Similarity	NPC251036
0.7039	Intermediate Similarity	NPC476989
0.7039	Intermediate Similarity	NPC123859
0.7037	Intermediate Similarity	NPC241794
0.7033	Intermediate Similarity	NPC83790
0.7033	Intermediate Similarity	NPC128237
0.7031	Intermediate Similarity	NPC129486
0.7022	Intermediate Similarity	NPC89489
0.7021	Intermediate Similarity	NPC244336
0.7016	Intermediate Similarity	NPC61004
0.701	Intermediate Similarity	NPC248670
0.7005	Intermediate Similarity	NPC242728
0.7	Intermediate Similarity	NPC469360
0.7	Intermediate Similarity	NPC91953
0.6995	Remote Similarity	NPC105717
0.6995	Remote Similarity	NPC477631
0.6995	Remote Similarity	NPC326333
0.698	Remote Similarity	NPC240130
0.698	Remote Similarity	NPC477636
0.698	Remote Similarity	NPC61332
0.6976	Remote Similarity	NPC477639
0.6974	Remote Similarity	NPC477462
0.6968	Remote Similarity	NPC56635
0.6965	Remote Similarity	NPC94862
0.6961	Remote Similarity	NPC52748
0.6961	Remote Similarity	NPC314083
0.6961	Remote Similarity	NPC302715
0.6952	Remote Similarity	NPC476268
0.6952	Remote Similarity	NPC473580
0.695	Remote Similarity	NPC138083
0.6944	Remote Similarity	NPC263493
0.6944	Remote Similarity	NPC197921
0.6944	Remote Similarity	NPC269398
0.694	Remote Similarity	NPC138775
0.694	Remote Similarity	NPC145113
0.694	Remote Similarity	NPC225648
0.694	Remote Similarity	NPC135121
0.694	Remote Similarity	NPC329761
0.6935	Remote Similarity	NPC122590
0.6932	Remote Similarity	NPC246079
0.6931	Remote Similarity	NPC102959
0.693	Remote Similarity	NPC326027
0.6927	Remote Similarity	NPC242159
0.6927	Remote Similarity	NPC471563
0.6927	Remote Similarity	NPC313694
0.6923	Remote Similarity	NPC475532
0.6912	Remote Similarity	NPC204970
0.6907	Remote Similarity	NPC198254
0.6907	Remote Similarity	NPC274198
0.6902	Remote Similarity	NPC471821
0.6902	Remote Similarity	NPC471820
0.6902	Remote Similarity	NPC9373
0.6898	Remote Similarity	NPC470902
0.6897	Remote Similarity	NPC283207
0.6897	Remote Similarity	NPC60516
0.6895	Remote Similarity	NPC469243
0.6895	Remote Similarity	NPC478007
0.6893	Remote Similarity	NPC470392
0.6891	Remote Similarity	NPC328649
0.6888	Remote Similarity	NPC165285
0.6888	Remote Similarity	NPC17698
0.6888	Remote Similarity	NPC158277
0.6882	Remote Similarity	NPC214239
0.6872	Remote Similarity	NPC257511
0.6865	Remote Similarity	NPC132771
0.6857	Remote Similarity	NPC311357
0.6856	Remote Similarity	NPC315388
0.6856	Remote Similarity	NPC469505
0.6856	Remote Similarity	NPC280022
0.6839	Remote Similarity	NPC469479
0.6833	Remote Similarity	NPC476133
0.6833	Remote Similarity	NPC92784
0.6833	Remote Similarity	NPC478008
0.6833	Remote Similarity	NPC470884
0.6833	Remote Similarity	NPC178662
0.6833	Remote Similarity	NPC98424
0.6831	Remote Similarity	NPC477217
0.6831	Remote Similarity	NPC201244
0.6831	Remote Similarity	NPC471680
0.6831	Remote Similarity	NPC209509
0.6828	Remote Similarity	NPC7817
0.6828	Remote Similarity	NPC475168

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 NPC477527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	487
0.2-0.3	893
0.3-0.4	2143
0.4-0.5	3131
0.5-0.6	2033
0.6-0.7	295
0.7-0.8	22
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
0.774	Intermediate Similarity	NPD6390	Discontinued
0.7577	Intermediate Similarity	NPD6089	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD2517	Approved
0.7527	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2516	Approved
0.7487	Intermediate Similarity	NPD5484	Approved
0.7487	Intermediate Similarity	NPD5485	Approved
0.7403	Intermediate Similarity	NPD7131	Phase 3
0.7374	Intermediate Similarity	NPD6505	Approved
0.7374	Intermediate Similarity	NPD6504	Approved
0.7326	Intermediate Similarity	NPD2098	Approved
0.7312	Intermediate Similarity	NPD2097	Approved
0.7273	Intermediate Similarity	NPD4435	Approved
0.7263	Intermediate Similarity	NPD4652	Approved
0.7249	Intermediate Similarity	NPD7133	Discontinued
0.7243	Intermediate Similarity	NPD2513	Approved
0.7222	Intermediate Similarity	NPD4434	Approved
0.7204	Intermediate Similarity	NPD2515	Approved
0.7204	Intermediate Similarity	NPD3007	Approved
0.7196	Intermediate Similarity	NPD8303	Discontinued
0.7135	Intermediate Similarity	NPD2052	Approved
0.7122	Intermediate Similarity	NPD7811	Phase 3
0.7122	Intermediate Similarity	NPD7810	Phase 3
0.7097	Intermediate Similarity	NPD22	Approved
0.7097	Intermediate Similarity	NPD2053	Approved
0.7065	Intermediate Similarity	NPD7303	Discontinued
0.7031	Intermediate Similarity	NPD7484	Phase 3
0.7031	Intermediate Similarity	NPD7485	Phase 3
0.7021	Intermediate Similarity	NPD5355	Approved
0.7021	Intermediate Similarity	NPD5356	Approved
0.6995	Remote Similarity	NPD7608	Discontinued
0.698	Remote Similarity	NPD7861	Discontinued
0.6914	Remote Similarity	NPD4125	Approved
0.6893	Remote Similarity	NPD3659	Discontinued
0.6893	Remote Similarity	NPD5745	Approved
0.6856	Remote Similarity	NPD2890	Approved
0.6856	Remote Similarity	NPD2888	Approved
0.6856	Remote Similarity	NPD2889	Approved
0.6856	Remote Similarity	NPD2017	Approved
0.6835	Remote Similarity	NPD8255	Phase 2
0.6816	Remote Similarity	NPD7281	Phase 3
0.6816	Remote Similarity	NPD7280	Phase 3
0.6806	Remote Similarity	NPD5773	Approved
0.6806	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5772	Approved
0.6784	Remote Similarity	NPD5557	Phase 1
0.6784	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5746	Approved
0.6751	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD8124	Phase 3
0.6739	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5264	Approved
0.6739	Remote Similarity	NPD5265	Approved
0.6738	Remote Similarity	NPD7967	Discontinued
0.6719	Remote Similarity	NPD4557	Approved
0.67	Remote Similarity	NPD6853	Approved
0.67	Remote Similarity	NPD6851	Approved
0.6699	Remote Similarity	NPD5994	Discontinued
0.6685	Remote Similarity	NPD8172	Phase 2
0.6685	Remote Similarity	NPD8173	Phase 2
0.6684	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3987	Approved
0.6684	Remote Similarity	NPD5967	Approved
0.6684	Remote Similarity	NPD3988	Approved
0.6683	Remote Similarity	NPD3909	Discontinued
0.6683	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5852	Approved
0.6683	Remote Similarity	NPD5851	Approved
0.6682	Remote Similarity	NPD3878	Approved
0.6667	Remote Similarity	NPD1670	Discontinued
0.6651	Remote Similarity	NPD3879	Approved
0.665	Remote Similarity	NPD5114	Approved
0.665	Remote Similarity	NPD5113	Approved
0.665	Remote Similarity	NPD5112	Approved
0.6649	Remote Similarity	NPD4739	Approved
0.6648	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4508	Discontinued
0.6632	Remote Similarity	NPD7972	Discontinued
0.6632	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4210	Discontinued
0.6632	Remote Similarity	NPD4647	Approved
0.6632	Remote Similarity	NPD4646	Approved
0.6632	Remote Similarity	NPD4648	Approved
0.6631	Remote Similarity	NPD6666	Approved
0.6631	Remote Similarity	NPD6667	Approved
0.663	Remote Similarity	NPD2022	Approved
0.6618	Remote Similarity	NPD4483	Discontinued
0.6615	Remote Similarity	NPD8031	Discontinued
0.6614	Remote Similarity	NPD5230	Approved
0.6614	Remote Similarity	NPD7613	Discontinued
0.6614	Remote Similarity	NPD5229	Approved
0.6612	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD8161	Suspended
0.6599	Remote Similarity	NPD6303	Approved
0.6599	Remote Similarity	NPD6304	Approved
0.6595	Remote Similarity	NPD2437	Approved
0.6595	Remote Similarity	NPD2436	Approved
0.6595	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7965	Phase 2
0.6583	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD8359	Phase 2
0.6566	Remote Similarity	NPD7315	Approved
0.6562	Remote Similarity	NPD2891	Approved
0.6559	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7565	Approved
0.6553	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6863	Phase 2
0.6541	Remote Similarity	NPD2088	Approved
0.6541	Remote Similarity	NPD2087	Approved
0.6538	Remote Similarity	NPD5076	Approved
0.6538	Remote Similarity	NPD5077	Approved
0.6537	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6971	Discontinued
0.6528	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6253	Approved
0.6524	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3480	Approved
0.6512	Remote Similarity	NPD3802	Phase 3
0.6502	Remote Similarity	NPD6297	Approved
0.65	Remote Similarity	NPD2048	Approved
0.65	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.65	Remote Similarity	NPD21	Approved
0.65	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2045	Approved
0.65	Remote Similarity	NPD2044	Approved
0.65	Remote Similarity	NPD2051	Approved
0.65	Remote Similarity	NPD2046	Approved
0.65	Remote Similarity	NPD2047	Approved
0.65	Remote Similarity	NPD2043	Approved
0.6495	Remote Similarity	NPD6256	Approved
0.6495	Remote Similarity	NPD6255	Approved
0.6495	Remote Similarity	NPD6254	Approved
0.6493	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD8416	Discontinued
0.6484	Remote Similarity	NPD5323	Approved
0.6477	Remote Similarity	NPD2584	Suspended
0.6476	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6751	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4126	Approved
0.6462	Remote Similarity	NPD4566	Approved
0.6462	Remote Similarity	NPD5564	Approved
0.6462	Remote Similarity	NPD4567	Approved
0.6443	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD7438	Suspended
0.6442	Remote Similarity	NPD4157	Discontinued
0.6435	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3479	Discontinued
0.6429	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7318	Phase 3
0.6425	Remote Similarity	NPD3111	Phase 1
0.6421	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5614	Approved
0.6421	Remote Similarity	NPD5613	Approved
0.6417	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD1986	Approved
0.641	Remote Similarity	NPD8019	Approved
0.641	Remote Similarity	NPD7495	Discontinued
0.6409	Remote Similarity	NPD3136	Phase 2
0.6409	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD2239	Approved
0.6398	Remote Similarity	NPD2240	Approved
0.6396	Remote Similarity	NPD3674	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4236	Phase 3
0.6383	Remote Similarity	NPD4237	Approved
0.6382	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5299	Approved
0.6374	Remote Similarity	NPD1330	Phase 2
0.6374	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3687	Approved
0.6373	Remote Similarity	NPD3686	Approved
0.6368	Remote Similarity	NPD5137	Approved
0.6368	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7978	Discontinued
0.6364	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.636	Remote Similarity	NPD7820	Phase 3
0.6359	Remote Similarity	NPD6677	Suspended
0.6359	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.635	Remote Similarity	NPD5262	Discontinued
0.6349	Remote Similarity	NPD5481	Discontinued
0.6344	Remote Similarity	NPD3152	Clinical (unspecified phase)
0.634	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5025	Approved
0.6335	Remote Similarity	NPD1785	Approved
0.6335	Remote Similarity	NPD1787	Approved
0.6335	Remote Similarity	NPD1786	Approved
0.6333	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6681	Discovery

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