NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	331.14
Volume:	333.344
LogP:	2.74
LogD:	1.801
LogS:	-3.521
# Rotatable Bonds:	3
TPSA:	95.86
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	4.762
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.794
MDCK Permeability:	3.904218829120509e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996
Plasma Protein Binding (PPB):	81.40668487548828%
Volume Distribution (VD):	1.255
Pgp-substrate:	15.30138874053955%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.218
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.797
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.254
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.659

ADMET: Excretion

Clearance (CL):	7.171
Half-life (T1/2):	0.545

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.561
Rat Oral Acute Toxicity:	0.631
Maximum Recommended Daily Dose:	0.288
Skin Sensitization:	0.677
Carcinogencity:	0.328
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC477680

Natural Product ID:	NPC477680
*Common Name:**	Berkeleyamide D
IUPAC Name:	2-benzyl-8,9-dihydroxy-8-(2-methylpropyl)-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
Synonyms:	Berkeleyamide D
Standard InCHIKey:	KYPWBBBOBAOGSQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H21NO5/c1-11(2)10-17(23)15(21)18(16(22)19-17)14(20)9-13(24-18)8-12-6-4-3-5-7-12/h3-7,9,11,15,21,23H,8,10H2,1-2H3,(H,19,22)
SMILES:	CC(C)CC1(C(C2(C(=O)C=C(O2)CC3=CC=CC=C3)C(=O)N1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	24879338
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones

*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
NPO29761	Penicillium rubrum	Species	Trichocomaceae	Eukaryota	n.a.	Berkeley Pit Lake, Butte, Montana	n.a.	PMID[18330993]
NPO29761	Penicillium rubrum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO29761	Penicillium rubrum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22295871]

☑ 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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT277	Individual Protein	Caspase-1	Homo sapiens	IC50	=	610	nM	PMID[18330993]
NPT567	Individual Protein	Matrix metalloproteinase 3	Homo sapiens	IC50	=	610	nM	PMID[18330993]

☑ 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 NPC477680 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	166
0.1-0.2	673
0.2-0.3	2456
0.3-0.4	8586
0.4-0.5	17546
0.5-0.6	12418
0.6-0.7	812
0.7-0.8	31
0.8-0.85	1
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8986	High Similarity	NPC339338
0.8986	High Similarity	NPC227905
0.8986	High Similarity	NPC146097
0.8857	High Similarity	NPC185404
0.771	Intermediate Similarity	NPC188010
0.7594	Intermediate Similarity	NPC471553
0.7431	Intermediate Similarity	NPC279045
0.7431	Intermediate Similarity	NPC113325
0.7383	Intermediate Similarity	NPC49565
0.7379	Intermediate Similarity	NPC208725
0.7361	Intermediate Similarity	NPC228511
0.7279	Intermediate Similarity	NPC471201
0.7273	Intermediate Similarity	NPC183722
0.726	Intermediate Similarity	NPC175870
0.7254	Intermediate Similarity	NPC116057
0.7211	Intermediate Similarity	NPC473055
0.7211	Intermediate Similarity	NPC473052
0.7183	Intermediate Similarity	NPC81135
0.7174	Intermediate Similarity	NPC478016
0.7174	Intermediate Similarity	NPC478015
0.7174	Intermediate Similarity	NPC478014
0.7172	Intermediate Similarity	NPC328070
0.7162	Intermediate Similarity	NPC322526
0.7143	Intermediate Similarity	NPC162104
0.7133	Intermediate Similarity	NPC472413
0.7097	Intermediate Similarity	NPC4108
0.7076	Intermediate Similarity	NPC471395
0.7067	Intermediate Similarity	NPC108852
0.7067	Intermediate Similarity	NPC261709
0.7067	Intermediate Similarity	NPC111586
0.705	Intermediate Similarity	NPC105709
0.7044	Intermediate Similarity	NPC476194
0.7021	Intermediate Similarity	NPC472415
0.7014	Intermediate Similarity	NPC71271
0.7	Intermediate Similarity	NPC19136
0.6993	Remote Similarity	NPC236405
0.6986	Remote Similarity	NPC42423
0.6934	Remote Similarity	NPC235421
0.6929	Remote Similarity	NPC190663
0.6929	Remote Similarity	NPC80150
0.6923	Remote Similarity	NPC47667
0.6917	Remote Similarity	NPC475282
0.6912	Remote Similarity	NPC474544
0.6912	Remote Similarity	NPC1986
0.6906	Remote Similarity	NPC237420
0.6906	Remote Similarity	NPC310467
0.6906	Remote Similarity	NPC314992
0.6901	Remote Similarity	NPC35996
0.6892	Remote Similarity	NPC144257
0.6889	Remote Similarity	NPC477250
0.6887	Remote Similarity	NPC239770
0.6884	Remote Similarity	NPC108532
0.6883	Remote Similarity	NPC31171
0.6883	Remote Similarity	NPC237240
0.6875	Remote Similarity	NPC278097
0.6875	Remote Similarity	NPC328997
0.6875	Remote Similarity	NPC294050
0.6849	Remote Similarity	NPC69496
0.6838	Remote Similarity	NPC477245
0.6838	Remote Similarity	NPC477246
0.6835	Remote Similarity	NPC169328
0.6832	Remote Similarity	NPC471203
0.6831	Remote Similarity	NPC84281
0.6831	Remote Similarity	NPC213126
0.6831	Remote Similarity	NPC160493
0.6831	Remote Similarity	NPC317474
0.6831	Remote Similarity	NPC291027
0.6831	Remote Similarity	NPC169485
0.6821	Remote Similarity	NPC307357
0.6821	Remote Similarity	NPC46098
0.6821	Remote Similarity	NPC268841
0.6815	Remote Similarity	NPC477247
0.6806	Remote Similarity	NPC477249
0.6806	Remote Similarity	NPC477248
0.6806	Remote Similarity	NPC472414
0.6781	Remote Similarity	NPC316553
0.6781	Remote Similarity	NPC295478
0.6774	Remote Similarity	NPC145113
0.6767	Remote Similarity	NPC329705
0.6767	Remote Similarity	NPC474111
0.6767	Remote Similarity	NPC193640
0.6767	Remote Similarity	NPC25385
0.6767	Remote Similarity	NPC475905
0.6763	Remote Similarity	NPC2265
0.6752	Remote Similarity	NPC201692
0.6748	Remote Similarity	NPC67080
0.6744	Remote Similarity	NPC145052
0.6739	Remote Similarity	NPC469509
0.6731	Remote Similarity	NPC173934
0.6711	Remote Similarity	NPC245836
0.6711	Remote Similarity	NPC233910
0.6708	Remote Similarity	NPC297145
0.6708	Remote Similarity	NPC197743
0.6692	Remote Similarity	NPC474307
0.6691	Remote Similarity	NPC210531
0.669	Remote Similarity	NPC474847
0.669	Remote Similarity	NPC317163
0.6689	Remote Similarity	NPC68865
0.6667	Remote Similarity	NPC472707
0.6667	Remote Similarity	NPC213969
0.6667	Remote Similarity	NPC165726
0.6667	Remote Similarity	NPC65627
0.6667	Remote Similarity	NPC469927
0.6667	Remote Similarity	NPC15506
0.6647	Remote Similarity	NPC245741
0.6644	Remote Similarity	NPC79608
0.6644	Remote Similarity	NPC476033
0.6644	Remote Similarity	NPC65310
0.6643	Remote Similarity	NPC476281
0.6643	Remote Similarity	NPC476184
0.6641	Remote Similarity	NPC158623
0.6623	Remote Similarity	NPC136994
0.6623	Remote Similarity	NPC88255
0.6623	Remote Similarity	NPC251439
0.6621	Remote Similarity	NPC471466
0.6619	Remote Similarity	NPC472164
0.6617	Remote Similarity	NPC194390
0.6617	Remote Similarity	NPC113326
0.6617	Remote Similarity	NPC88267
0.6617	Remote Similarity	NPC224610
0.6603	Remote Similarity	NPC262216
0.66	Remote Similarity	NPC108553
0.6599	Remote Similarity	NPC146239
0.6585	Remote Similarity	NPC156348
0.6584	Remote Similarity	NPC32197
0.6579	Remote Similarity	NPC472247
0.6577	Remote Similarity	NPC262819
0.6575	Remote Similarity	NPC472165
0.6573	Remote Similarity	NPC477061
0.6573	Remote Similarity	NPC476183
0.6573	Remote Similarity	NPC45777
0.6571	Remote Similarity	NPC216387
0.6571	Remote Similarity	NPC471616
0.6566	Remote Similarity	NPC71205
0.6561	Remote Similarity	NPC135121
0.6556	Remote Similarity	NPC64897
0.6556	Remote Similarity	NPC248283
0.6556	Remote Similarity	NPC90693
0.6554	Remote Similarity	NPC103605
0.6554	Remote Similarity	NPC478165
0.6554	Remote Similarity	NPC81092
0.6554	Remote Similarity	NPC478162
0.6554	Remote Similarity	NPC477370
0.6552	Remote Similarity	NPC476278
0.6547	Remote Similarity	NPC474363
0.6533	Remote Similarity	NPC17567
0.6531	Remote Similarity	NPC477366
0.6531	Remote Similarity	NPC477363
0.6516	Remote Similarity	NPC176226
0.651	Remote Similarity	NPC469930
0.651	Remote Similarity	NPC37968
0.6507	Remote Similarity	NPC476260
0.6507	Remote Similarity	NPC138798
0.6507	Remote Similarity	NPC476241
0.6503	Remote Similarity	NPC207675
0.6503	Remote Similarity	NPC212699
0.6497	Remote Similarity	NPC45307
0.6494	Remote Similarity	NPC469973
0.6491	Remote Similarity	NPC88378
0.6491	Remote Similarity	NPC477115
0.6491	Remote Similarity	NPC211713
0.6486	Remote Similarity	NPC477365
0.6483	Remote Similarity	NPC469494
0.6478	Remote Similarity	NPC170668
0.6478	Remote Similarity	NPC477737
0.6477	Remote Similarity	NPC282092
0.6474	Remote Similarity	NPC475413
0.6474	Remote Similarity	NPC474303
0.6474	Remote Similarity	NPC473497
0.6471	Remote Similarity	NPC6570
0.6467	Remote Similarity	NPC49272
0.6467	Remote Similarity	NPC469479
0.6463	Remote Similarity	NPC246166
0.6463	Remote Similarity	NPC476125
0.6463	Remote Similarity	NPC476179
0.6456	Remote Similarity	NPC225648
0.6456	Remote Similarity	NPC329761
0.6454	Remote Similarity	NPC197470
0.6452	Remote Similarity	NPC269398
0.6452	Remote Similarity	NPC263493
0.645	Remote Similarity	NPC196091
0.6447	Remote Similarity	NPC169766
0.6439	Remote Similarity	NPC474308
0.6439	Remote Similarity	NPC476042
0.6438	Remote Similarity	NPC108286
0.6438	Remote Similarity	NPC205389
0.6434	Remote Similarity	NPC104514
0.6433	Remote Similarity	NPC201244
0.6433	Remote Similarity	NPC477217
0.6429	Remote Similarity	NPC217673
0.6429	Remote Similarity	NPC241851
0.6429	Remote Similarity	NPC52523
0.6429	Remote Similarity	NPC87069
0.6429	Remote Similarity	NPC309056
0.6425	Remote Similarity	NPC306001
0.6425	Remote Similarity	NPC473400
0.6425	Remote Similarity	NPC206211
0.6425	Remote Similarity	NPC324251
0.6425	Remote Similarity	NPC275170
0.6425	Remote Similarity	NPC471629

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 NPC477680 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	130
0.1-0.2	476
0.2-0.3	1016
0.3-0.4	2690
0.4-0.5	3252
0.5-0.6	1429
0.6-0.7	156
0.7-0.8	1
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
0.7273	Intermediate Similarity	NPD4738	Phase 2
0.7121	Intermediate Similarity	NPD2067	Discontinued
0.6906	Remote Similarity	NPD2218	Phase 2
0.6906	Remote Similarity	NPD2217	Approved
0.6892	Remote Similarity	NPD8265	Approved
0.6883	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5981	Approved
0.6849	Remote Similarity	NPD2613	Approved
0.6831	Remote Similarity	NPD3132	Approved
0.6831	Remote Similarity	NPD4215	Approved
0.6831	Remote Similarity	NPD4217	Approved
0.6831	Remote Similarity	NPD3131	Approved
0.6831	Remote Similarity	NPD2611	Approved
0.6831	Remote Similarity	NPD4216	Approved
0.6831	Remote Similarity	NPD4218	Approved
0.6831	Remote Similarity	NPD2608	Approved
0.6831	Remote Similarity	NPD2609	Approved
0.6831	Remote Similarity	NPD2612	Approved
0.6831	Remote Similarity	NPD2610	Approved
0.6818	Remote Similarity	NPD2575	Approved
0.6788	Remote Similarity	NPD2652	Approved
0.6788	Remote Similarity	NPD2650	Approved
0.6781	Remote Similarity	NPD3664	Approved
0.6781	Remote Similarity	NPD3663	Approved
0.6781	Remote Similarity	NPD3662	Phase 3
0.6781	Remote Similarity	NPD3661	Approved
0.6711	Remote Similarity	NPD3614	Approved
0.6711	Remote Similarity	NPD3088	Approved
0.6711	Remote Similarity	NPD2571	Approved
0.6711	Remote Similarity	NPD2570	Approved
0.6711	Remote Similarity	NPD2573	Approved
0.6711	Remote Similarity	NPD3615	Approved
0.6711	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3089	Approved
0.6711	Remote Similarity	NPD2574	Discontinued
0.6711	Remote Similarity	NPD4745	Approved
0.6711	Remote Similarity	NPD4746	Phase 3
0.6711	Remote Similarity	NPD2566	Approved
0.6711	Remote Similarity	NPD3616	Approved
0.6711	Remote Similarity	NPD3087	Approved
0.6711	Remote Similarity	NPD3090	Approved
0.6708	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD8173	Phase 2
0.6689	Remote Similarity	NPD8172	Phase 2
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD8417	Discontinued
0.6644	Remote Similarity	NPD2160	Approved
0.6644	Remote Similarity	NPD2627	Approved
0.6644	Remote Similarity	NPD2159	Approved
0.6644	Remote Similarity	NPD2626	Approved
0.6644	Remote Similarity	NPD2625	Approved
0.6644	Remote Similarity	NPD2628	Approved
0.6642	Remote Similarity	NPD467	Phase 1
0.6626	Remote Similarity	NPD7972	Discontinued
0.6623	Remote Similarity	NPD4684	Phase 3
0.6623	Remote Similarity	NPD4686	Approved
0.6623	Remote Similarity	NPD4685	Phase 3
0.6619	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6325	Discontinued
0.6554	Remote Similarity	NPD5204	Approved
0.6532	Remote Similarity	NPD5030	Phase 2
0.6513	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4620	Approved
0.651	Remote Similarity	NPD4617	Approved
0.651	Remote Similarity	NPD5201	Approved
0.651	Remote Similarity	NPD5203	Approved
0.65	Remote Similarity	NPD2629	Approved
0.6494	Remote Similarity	NPD4954	Approved
0.6494	Remote Similarity	NPD4955	Approved
0.6494	Remote Similarity	NPD5034	Approved
0.6494	Remote Similarity	NPD5028	Approved
0.6494	Remote Similarity	NPD5026	Approved
0.6494	Remote Similarity	NPD36	Approved
0.6483	Remote Similarity	NPD4806	Approved
0.6483	Remote Similarity	NPD4807	Approved
0.6458	Remote Similarity	NPD5305	Approved
0.6458	Remote Similarity	NPD5306	Approved
0.6454	Remote Similarity	NPD1348	Approved
0.6449	Remote Similarity	NPD3644	Approved
0.6449	Remote Similarity	NPD3642	Approved
0.6449	Remote Similarity	NPD3643	Approved
0.6449	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6309	Approved
0.6447	Remote Similarity	NPD5119	Approved
0.6447	Remote Similarity	NPD5121	Approved
0.6447	Remote Similarity	NPD5120	Approved
0.6447	Remote Similarity	NPD6311	Approved
0.6447	Remote Similarity	NPD6310	Approved
0.6438	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD4619	Approved
0.6424	Remote Similarity	NPD4621	Approved
0.642	Remote Similarity	NPD8407	Phase 2
0.6414	Remote Similarity	NPD4106	Approved
0.6414	Remote Similarity	NPD4135	Approved
0.6414	Remote Similarity	NPD4136	Approved
0.641	Remote Similarity	NPD4152	Approved
0.64	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD5036	Approved
0.6364	Remote Similarity	NPD5035	Approved
0.6348	Remote Similarity	NPD5037	Approved
0.6348	Remote Similarity	NPD5038	Approved
0.6343	Remote Similarity	NPD8368	Discontinued
0.634	Remote Similarity	NPD8416	Discontinued
0.6327	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD6852	Discontinued
0.6319	Remote Similarity	NPD4479	Discontinued
0.6296	Remote Similarity	NPD6647	Phase 2
0.6284	Remote Similarity	NPD5157	Phase 1
0.6284	Remote Similarity	NPD5159	Phase 2
0.6284	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD8435	Approved
0.6277	Remote Similarity	NPD6685	Approved
0.6276	Remote Similarity	NPD4105	Approved
0.6276	Remote Similarity	NPD4102	Approved
0.6269	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD1711	Phase 2
0.6266	Remote Similarity	NPD2424	Discontinued
0.625	Remote Similarity	NPD8485	Approved
0.6242	Remote Similarity	NPD5667	Approved
0.6242	Remote Similarity	NPD4172	Approved
0.6242	Remote Similarity	NPD4173	Approved
0.6242	Remote Similarity	NPD5712	Approved
0.6232	Remote Similarity	NPD6406	Approved
0.6193	Remote Similarity	NPD3823	Discontinued
0.6188	Remote Similarity	NPD6676	Phase 2
0.6188	Remote Similarity	NPD8361	Approved
0.6188	Remote Similarity	NPD8360	Approved
0.6183	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD3123	Discovery
0.6181	Remote Similarity	NPD4574	Approved
0.6181	Remote Similarity	NPD4576	Approved
0.6178	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.617	Remote Similarity	NPD969	Suspended
0.6167	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.615	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD8323	Discontinued
0.6149	Remote Similarity	NPD3603	Phase 3
0.6149	Remote Similarity	NPD5618	Discontinued
0.6144	Remote Similarity	NPD3136	Phase 2
0.6143	Remote Similarity	NPD4233	Approved
0.6143	Remote Similarity	NPD4234	Approved
0.6143	Remote Similarity	NPD9713	Approved
0.6139	Remote Similarity	NPD2161	Phase 2
0.6138	Remote Similarity	NPD7522	Discontinued
0.6136	Remote Similarity	NPD4814	Discontinued
0.6131	Remote Similarity	NPD1237	Approved
0.6119	Remote Similarity	NPD9495	Approved
0.6118	Remote Similarity	NPD3626	Phase 3
0.6118	Remote Similarity	NPD7084	Phase 3
0.6115	Remote Similarity	NPD2569	Approved
0.6115	Remote Similarity	NPD2567	Approved
0.6101	Remote Similarity	NPD7978	Discontinued
0.6098	Remote Similarity	NPD7613	Discontinued
0.6096	Remote Similarity	NPD7565	Approved
0.609	Remote Similarity	NPD6355	Discontinued
0.609	Remote Similarity	NPD8643	Discontinued
0.6087	Remote Similarity	NPD1040	Phase 2
0.6087	Remote Similarity	NPD3400	Discontinued
0.6087	Remote Similarity	NPD1018	Approved
0.608	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD2066	Phase 3
0.6069	Remote Similarity	NPD7315	Approved
0.6067	Remote Similarity	NPD5029	Approved
0.6067	Remote Similarity	NPD5027	Approved
0.6067	Remote Similarity	NPD5031	Approved
0.6062	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD3719	Approved
0.6061	Remote Similarity	NPD1066	Discontinued
0.6061	Remote Similarity	NPD3718	Approved
0.6058	Remote Similarity	NPD5765	Approved
0.6056	Remote Similarity	NPD6912	Phase 3
0.6054	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5647	Approved
0.6042	Remote Similarity	NPD4766	Approved
0.6037	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD4662	Approved
0.6037	Remote Similarity	NPD4661	Approved
0.6034	Remote Similarity	NPD5032	Approved
0.6028	Remote Similarity	NPD1756	Approved
0.6028	Remote Similarity	NPD1752	Approved
0.6027	Remote Similarity	NPD1758	Phase 1
0.6027	Remote Similarity	NPD6065	Approved
0.6022	Remote Similarity	NPD3154	Approved
0.6022	Remote Similarity	NPD3153	Approved
0.6015	Remote Similarity	NPD1693	Approved
0.6014	Remote Similarity	NPD2607	Approved
0.6012	Remote Similarity	NPD3300	Phase 2
0.6011	Remote Similarity	NPD6836	Approved
0.6	Remote Similarity	NPD4198	Discontinued
0.6	Remote Similarity	NPD2584	Suspended
0.6	Remote Similarity	NPD52	Approved
0.6	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7526	Approved
0.6	Remote Similarity	NPD1048	Approved
0.5986	Remote Similarity	NPD1759	Phase 1
0.5986	Remote Similarity	NPD2617	Discontinued
0.5986	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD998	Approved
0.5985	Remote Similarity	NPD4719	Phase 2

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