NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.15
Volume:	280.954
LogP:	2.322
LogD:	1.945
LogS:	-3.992
# Rotatable Bonds:	0
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	5.409
Fsp3:	0.812
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:	-4.944
MDCK Permeability:	2.92299737338908e-05
Pgp-inhibitor:	0.238
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.118
30% Bioavailability (F30%):	0.241

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.84
Plasma Protein Binding (PPB):	58.20919418334961%
Volume Distribution (VD):	1.131
Pgp-substrate:	43.81830978393555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.394
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.401

ADMET: Excretion

Clearance (CL):	10.614
Half-life (T1/2):	0.256

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.402
Drug-inuced Liver Injury (DILI):	0.188
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.581
Skin Sensitization:	0.423
Carcinogencity:	0.954
Eye Corrosion:	0.015
Eye Irritation:	0.032
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC181645

Natural Product ID:	NPC181645
*Common Name:**	Pestaloficiol A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BRIZKGNSBNBPFG-MVNLRDQZSA-N
Standard InCHI:	InChI=1S/C16H22O4/c1-14(2)6-10(18)8-5-9(17)13-16(12(8)19-14)7-11(16)15(3,4)20-13/h9,11,13,17H,5-7H2,1-4H3/t9-,11+,13-,16+/m0/s1
SMILES:	O=C1CC(C)(C)OC2=C1C[C@H](O)[C@H]1[C@]32C[C@@H]3C(O1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519156
PubChem CID:	25022540
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18468908]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19101157]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19618920]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	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
EC50	1
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	26000.0	nM	PMID[521593]
NPT27	Others	Unspecified		CC50	>	200000.0	nM	PMID[521593]

☑ 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 NPC181645 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	247
0.1-0.2	1553
0.2-0.3	5623
0.3-0.4	9922
0.4-0.5	12953
0.5-0.6	7908
0.6-0.7	3991
0.7-0.8	483
0.8-0.85	14
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC20078
0.9677	High Similarity	NPC473574
0.8438	Intermediate Similarity	NPC469464
0.8165	Intermediate Similarity	NPC247069
0.8095	Intermediate Similarity	NPC471332
0.8095	Intermediate Similarity	NPC471333
0.8039	Intermediate Similarity	NPC306908
0.8037	Intermediate Similarity	NPC101018
0.7941	Intermediate Similarity	NPC27105
0.79	Intermediate Similarity	NPC61275
0.7864	Intermediate Similarity	NPC472687
0.7864	Intermediate Similarity	NPC99657
0.7864	Intermediate Similarity	NPC471330
0.7864	Intermediate Similarity	NPC203388
0.7864	Intermediate Similarity	NPC35717
0.7864	Intermediate Similarity	NPC471331
0.7857	Intermediate Similarity	NPC122033
0.7857	Intermediate Similarity	NPC287343
0.7857	Intermediate Similarity	NPC474654
0.7857	Intermediate Similarity	NPC478204
0.7857	Intermediate Similarity	NPC470854
0.7857	Intermediate Similarity	NPC97908
0.7838	Intermediate Similarity	NPC143268
0.7838	Intermediate Similarity	NPC323821
0.7838	Intermediate Similarity	NPC45218
0.7838	Intermediate Similarity	NPC268238
0.7822	Intermediate Similarity	NPC469819
0.7822	Intermediate Similarity	NPC114162
0.7818	Intermediate Similarity	NPC472002
0.78	Intermediate Similarity	NPC146852
0.7798	Intermediate Similarity	NPC99760
0.7788	Intermediate Similarity	NPC478206
0.7788	Intermediate Similarity	NPC108581
0.7788	Intermediate Similarity	NPC478205
0.7768	Intermediate Similarity	NPC173686
0.7768	Intermediate Similarity	NPC207217
0.7768	Intermediate Similarity	NPC16081
0.7748	Intermediate Similarity	NPC478212
0.7739	Intermediate Similarity	NPC477046
0.7739	Intermediate Similarity	NPC102822
0.7727	Intermediate Similarity	NPC474229
0.7719	Intermediate Similarity	NPC470777
0.7706	Intermediate Similarity	NPC471400
0.7699	Intermediate Similarity	NPC27999
0.7699	Intermediate Similarity	NPC53396
0.7699	Intermediate Similarity	NPC477116
0.7699	Intermediate Similarity	NPC98249
0.7699	Intermediate Similarity	NPC58662
0.7699	Intermediate Similarity	NPC469684
0.7685	Intermediate Similarity	NPC473165
0.7677	Intermediate Similarity	NPC476707
0.7677	Intermediate Similarity	NPC476706
0.767	Intermediate Similarity	NPC472734
0.767	Intermediate Similarity	NPC135576
0.767	Intermediate Similarity	NPC8803
0.767	Intermediate Similarity	NPC91439
0.767	Intermediate Similarity	NPC93271
0.767	Intermediate Similarity	NPC472733
0.7664	Intermediate Similarity	NPC65523
0.7652	Intermediate Similarity	NPC478051
0.7642	Intermediate Similarity	NPC478176
0.7636	Intermediate Similarity	NPC478209
0.7632	Intermediate Similarity	NPC188667
0.7632	Intermediate Similarity	NPC204552
0.7632	Intermediate Similarity	NPC284707
0.7632	Intermediate Similarity	NPC17772
0.7611	Intermediate Similarity	NPC179626
0.7596	Intermediate Similarity	NPC472731
0.7596	Intermediate Similarity	NPC472732
0.7593	Intermediate Similarity	NPC102352
0.7593	Intermediate Similarity	NPC181357
0.7593	Intermediate Similarity	NPC470587
0.7589	Intermediate Similarity	NPC7921
0.7589	Intermediate Similarity	NPC208998
0.7589	Intermediate Similarity	NPC477266
0.7589	Intermediate Similarity	NPC49451
0.757	Intermediate Similarity	NPC159533
0.7568	Intermediate Similarity	NPC469655
0.7568	Intermediate Similarity	NPC469656
0.7568	Intermediate Similarity	NPC171888
0.7568	Intermediate Similarity	NPC474846
0.7568	Intermediate Similarity	NPC146945
0.7547	Intermediate Similarity	NPC471401
0.7545	Intermediate Similarity	NPC20192
0.7524	Intermediate Similarity	NPC472729
0.7524	Intermediate Similarity	NPC153776
0.7524	Intermediate Similarity	NPC472730
0.7524	Intermediate Similarity	NPC177680
0.7523	Intermediate Similarity	NPC3316
0.7523	Intermediate Similarity	NPC144854
0.7522	Intermediate Similarity	NPC117712
0.75	Intermediate Similarity	NPC268530
0.75	Intermediate Similarity	NPC154491
0.75	Intermediate Similarity	NPC474516
0.75	Intermediate Similarity	NPC269677
0.75	Intermediate Similarity	NPC112038
0.75	Intermediate Similarity	NPC476708
0.75	Intermediate Similarity	NPC251226
0.75	Intermediate Similarity	NPC269530
0.7479	Intermediate Similarity	NPC225049
0.7478	Intermediate Similarity	NPC251310
0.7478	Intermediate Similarity	NPC106644
0.7477	Intermediate Similarity	NPC295791
0.7477	Intermediate Similarity	NPC478211
0.7456	Intermediate Similarity	NPC328374
0.7456	Intermediate Similarity	NPC251236
0.7456	Intermediate Similarity	NPC40632
0.7456	Intermediate Similarity	NPC96312
0.7455	Intermediate Similarity	NPC154608
0.7455	Intermediate Similarity	NPC192813
0.7455	Intermediate Similarity	NPC277017
0.7455	Intermediate Similarity	NPC94942
0.7453	Intermediate Similarity	NPC472727
0.7453	Intermediate Similarity	NPC472728
0.7451	Intermediate Similarity	NPC476705
0.7436	Intermediate Similarity	NPC4021
0.7436	Intermediate Similarity	NPC159456
0.7434	Intermediate Similarity	NPC198539
0.7434	Intermediate Similarity	NPC475966
0.7429	Intermediate Similarity	NPC20066
0.7414	Intermediate Similarity	NPC230513
0.7414	Intermediate Similarity	NPC469488
0.7414	Intermediate Similarity	NPC42673
0.7414	Intermediate Similarity	NPC268958
0.7411	Intermediate Similarity	NPC132790
0.7411	Intermediate Similarity	NPC97939
0.7411	Intermediate Similarity	NPC38159
0.7411	Intermediate Similarity	NPC471243
0.7411	Intermediate Similarity	NPC100329
0.7411	Intermediate Similarity	NPC247031
0.7411	Intermediate Similarity	NPC317107
0.7411	Intermediate Similarity	NPC476023
0.7395	Intermediate Similarity	NPC24651
0.7391	Intermediate Similarity	NPC176513
0.7391	Intermediate Similarity	NPC470775
0.7391	Intermediate Similarity	NPC13713
0.7387	Intermediate Similarity	NPC478210
0.7387	Intermediate Similarity	NPC87335
0.7373	Intermediate Similarity	NPC312833
0.7368	Intermediate Similarity	NPC238667
0.7368	Intermediate Similarity	NPC472400
0.7368	Intermediate Similarity	NPC473798
0.7364	Intermediate Similarity	NPC112780
0.7364	Intermediate Similarity	NPC202524
0.7358	Intermediate Similarity	NPC300584
0.7355	Intermediate Similarity	NPC477712
0.7355	Intermediate Similarity	NPC477713
0.7345	Intermediate Similarity	NPC317687
0.7345	Intermediate Similarity	NPC42658
0.7345	Intermediate Similarity	NPC90769
0.7339	Intermediate Similarity	NPC146731
0.7339	Intermediate Similarity	NPC296950
0.7339	Intermediate Similarity	NPC203659
0.7339	Intermediate Similarity	NPC40170
0.7333	Intermediate Similarity	NPC272411
0.7333	Intermediate Similarity	NPC87662
0.7333	Intermediate Similarity	NPC293112
0.7328	Intermediate Similarity	NPC240509
0.7328	Intermediate Similarity	NPC297179
0.7327	Intermediate Similarity	NPC87189
0.7327	Intermediate Similarity	NPC476704
0.7327	Intermediate Similarity	NPC228415
0.7321	Intermediate Similarity	NPC210005
0.7321	Intermediate Similarity	NPC474567
0.7315	Intermediate Similarity	NPC474747
0.7315	Intermediate Similarity	NPC225353
0.7311	Intermediate Similarity	NPC11895
0.7311	Intermediate Similarity	NPC91693
0.7311	Intermediate Similarity	NPC469789
0.7311	Intermediate Similarity	NPC18945
0.7311	Intermediate Similarity	NPC105926
0.7311	Intermediate Similarity	NPC265557
0.7308	Intermediate Similarity	NPC477241
0.7308	Intermediate Similarity	NPC103527
0.7308	Intermediate Similarity	NPC196227
0.7304	Intermediate Similarity	NPC478216
0.7304	Intermediate Similarity	NPC270478
0.73	Intermediate Similarity	NPC475729
0.73	Intermediate Similarity	NPC474215
0.7297	Intermediate Similarity	NPC469916
0.7297	Intermediate Similarity	NPC151393
0.7297	Intermediate Similarity	NPC472439
0.7288	Intermediate Similarity	NPC472401
0.7288	Intermediate Similarity	NPC472000
0.7288	Intermediate Similarity	NPC471999
0.7282	Intermediate Similarity	NPC475441
0.7282	Intermediate Similarity	NPC111883
0.7281	Intermediate Similarity	NPC317210
0.7281	Intermediate Similarity	NPC194273
0.7281	Intermediate Similarity	NPC472757
0.7273	Intermediate Similarity	NPC478208
0.7273	Intermediate Similarity	NPC253223
0.7273	Intermediate Similarity	NPC128828
0.7264	Intermediate Similarity	NPC190080
0.7264	Intermediate Similarity	NPC111187
0.7264	Intermediate Similarity	NPC236176
0.7264	Intermediate Similarity	NPC239895
0.7264	Intermediate Similarity	NPC134454
0.7264	Intermediate Similarity	NPC17326
0.7257	Intermediate Similarity	NPC472003

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 NPC181645 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	2278
0.2-0.3	3886
0.3-0.4	1859
0.4-0.5	510
0.5-0.6	271
0.6-0.7	114
0.7-0.8	2
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
0.7647	Intermediate Similarity	NPD5282	Discontinued
0.7232	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6371	Approved
0.7018	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6319	Approved
0.6917	Remote Similarity	NPD6054	Approved
0.6917	Remote Similarity	NPD6059	Approved
0.687	Remote Similarity	NPD4634	Approved
0.686	Remote Similarity	NPD6016	Approved
0.686	Remote Similarity	NPD6015	Approved
0.6842	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6008	Approved
0.6807	Remote Similarity	NPD7115	Discovery
0.6803	Remote Similarity	NPD5988	Approved
0.6803	Remote Similarity	NPD6370	Approved
0.6759	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4225	Approved
0.6695	Remote Similarity	NPD4632	Approved
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6616	Approved
0.6636	Remote Similarity	NPD4755	Approved
0.6636	Remote Similarity	NPD6411	Approved
0.6613	Remote Similarity	NPD8328	Phase 3
0.6609	Remote Similarity	NPD6412	Phase 2
0.6587	Remote Similarity	NPD7078	Approved
0.6587	Remote Similarity	NPD8293	Discontinued
0.6585	Remote Similarity	NPD8513	Phase 3
0.6574	Remote Similarity	NPD5778	Approved
0.6574	Remote Similarity	NPD5779	Approved
0.6542	Remote Similarity	NPD46	Approved
0.6542	Remote Similarity	NPD6698	Approved
0.6535	Remote Similarity	NPD7736	Approved
0.6522	Remote Similarity	NPD6402	Approved
0.6522	Remote Similarity	NPD5739	Approved
0.6522	Remote Similarity	NPD7128	Approved
0.6522	Remote Similarity	NPD6675	Approved
0.6518	Remote Similarity	NPD5285	Approved
0.6518	Remote Similarity	NPD5286	Approved
0.6518	Remote Similarity	NPD4700	Approved
0.6518	Remote Similarity	NPD4696	Approved
0.6496	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6372	Approved
0.6496	Remote Similarity	NPD6373	Approved
0.6481	Remote Similarity	NPD7983	Approved
0.648	Remote Similarity	NPD7604	Phase 2
0.6476	Remote Similarity	NPD3618	Phase 1
0.6471	Remote Similarity	NPD6053	Discontinued
0.6471	Remote Similarity	NPD8297	Approved
0.6466	Remote Similarity	NPD5697	Approved
0.6466	Remote Similarity	NPD5701	Approved
0.6466	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8515	Approved
0.6452	Remote Similarity	NPD8517	Approved
0.6452	Remote Similarity	NPD8516	Approved
0.6449	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6101	Approved
0.6449	Remote Similarity	NPD5328	Approved
0.641	Remote Similarity	NPD6881	Approved
0.641	Remote Similarity	NPD7320	Approved
0.641	Remote Similarity	NPD6899	Approved
0.6408	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6033	Approved
0.6404	Remote Similarity	NPD5224	Approved
0.6404	Remote Similarity	NPD4633	Approved
0.6404	Remote Similarity	NPD5211	Phase 2
0.6404	Remote Similarity	NPD5225	Approved
0.6404	Remote Similarity	NPD5226	Approved
0.64	Remote Similarity	NPD8080	Discontinued
0.6396	Remote Similarity	NPD4697	Phase 3
0.6393	Remote Similarity	NPD6009	Approved
0.6387	Remote Similarity	NPD6650	Approved
0.6387	Remote Similarity	NPD6649	Approved
0.6357	Remote Similarity	NPD7319	Approved
0.6356	Remote Similarity	NPD6014	Approved
0.6356	Remote Similarity	NPD6013	Approved
0.6356	Remote Similarity	NPD6012	Approved
0.6348	Remote Similarity	NPD5175	Approved
0.6348	Remote Similarity	NPD5174	Approved
0.6346	Remote Similarity	NPD6110	Phase 1
0.633	Remote Similarity	NPD6079	Approved
0.6321	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.632	Remote Similarity	NPD5983	Phase 2
0.6316	Remote Similarity	NPD5344	Discontinued
0.6316	Remote Similarity	NPD5223	Approved
0.6303	Remote Similarity	NPD7290	Approved
0.6303	Remote Similarity	NPD7102	Approved
0.6303	Remote Similarity	NPD6883	Approved
0.6293	Remote Similarity	NPD5141	Approved
0.6277	Remote Similarity	NPD7341	Phase 2
0.6273	Remote Similarity	NPD6399	Phase 3
0.6273	Remote Similarity	NPD4202	Approved
0.6271	Remote Similarity	NPD6686	Approved
0.6271	Remote Similarity	NPD6011	Approved
0.626	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD4768	Approved
0.6239	Remote Similarity	NPD4767	Approved
0.6226	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4754	Approved
0.6202	Remote Similarity	NPD8074	Phase 3
0.6198	Remote Similarity	NPD6882	Approved
0.6195	Remote Similarity	NPD5173	Approved
0.6195	Remote Similarity	NPD7902	Approved
0.619	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6921	Approved
0.6174	Remote Similarity	NPD1700	Approved
0.6147	Remote Similarity	NPD4753	Phase 2
0.6134	Remote Similarity	NPD5128	Approved
0.6134	Remote Similarity	NPD4730	Approved
0.6134	Remote Similarity	NPD4729	Approved
0.6132	Remote Similarity	NPD3665	Phase 1
0.6132	Remote Similarity	NPD4786	Approved
0.6132	Remote Similarity	NPD3666	Approved
0.6132	Remote Similarity	NPD3133	Approved
0.6124	Remote Similarity	NPD7507	Approved
0.6124	Remote Similarity	NPD6336	Discontinued
0.6116	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7524	Approved
0.6075	Remote Similarity	NPD1694	Approved
0.6075	Remote Similarity	NPD1696	Phase 3
0.6071	Remote Similarity	NPD7748	Approved
0.6058	Remote Similarity	NPD4695	Discontinued
0.6053	Remote Similarity	NPD6083	Phase 2
0.6053	Remote Similarity	NPD6084	Phase 2
0.6048	Remote Similarity	NPD6274	Approved
0.6042	Remote Similarity	NPD3704	Approved
0.6036	Remote Similarity	NPD7515	Phase 2
0.6033	Remote Similarity	NPD5247	Approved
0.6033	Remote Similarity	NPD5251	Approved
0.6033	Remote Similarity	NPD5250	Approved
0.6033	Remote Similarity	NPD5248	Approved
0.6033	Remote Similarity	NPD5249	Phase 3
0.6019	Remote Similarity	NPD3617	Approved
0.6019	Remote Similarity	NPD5279	Phase 3
0.6018	Remote Similarity	NPD5695	Phase 3
0.6018	Remote Similarity	NPD4629	Approved
0.6018	Remote Similarity	NPD5210	Approved
0.6018	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD5369	Approved
0.5984	Remote Similarity	NPD5215	Approved
0.5984	Remote Similarity	NPD5216	Approved
0.5984	Remote Similarity	NPD5217	Approved
0.5981	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6067	Discontinued
0.5948	Remote Similarity	NPD6648	Approved
0.5948	Remote Similarity	NPD7639	Approved
0.5948	Remote Similarity	NPD7640	Approved
0.5946	Remote Similarity	NPD5785	Approved
0.5946	Remote Similarity	NPD7838	Discovery
0.5943	Remote Similarity	NPD6435	Approved
0.594	Remote Similarity	NPD5956	Approved
0.5938	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7900	Approved
0.5906	Remote Similarity	NPD7100	Approved
0.5906	Remote Similarity	NPD7101	Approved
0.5906	Remote Similarity	NPD4522	Approved
0.5905	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5135	Approved
0.5902	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5169	Approved
0.5893	Remote Similarity	NPD7637	Suspended
0.5888	Remote Similarity	NPD6695	Phase 3
0.5876	Remote Similarity	NPD7331	Phase 2
0.5873	Remote Similarity	NPD6317	Approved
0.5872	Remote Similarity	NPD4249	Approved
0.5872	Remote Similarity	NPD5786	Approved
0.5856	Remote Similarity	NPD1695	Approved
0.5854	Remote Similarity	NPD5127	Approved
0.5852	Remote Similarity	NPD6845	Suspended
0.5847	Remote Similarity	NPD7632	Discontinued
0.5846	Remote Similarity	NPD7642	Approved
0.5833	Remote Similarity	NPD3668	Phase 3
0.5827	Remote Similarity	NPD6335	Approved
0.5827	Remote Similarity	NPD6313	Approved
0.5827	Remote Similarity	NPD7327	Approved
0.5827	Remote Similarity	NPD7328	Approved
0.5827	Remote Similarity	NPD6314	Approved
0.5818	Remote Similarity	NPD4250	Approved
0.5818	Remote Similarity	NPD4251	Approved
0.5818	Remote Similarity	NPD3573	Approved
0.5814	Remote Similarity	NPD7503	Approved
0.5814	Remote Similarity	NPD6908	Approved
0.5814	Remote Similarity	NPD6909	Approved
0.5804	Remote Similarity	NPD3168	Discontinued
0.5794	Remote Similarity	NPD4221	Approved
0.5794	Remote Similarity	NPD4223	Phase 3
0.5789	Remote Similarity	NPD6001	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