NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	364.15
Volume:	353.94
LogP:	0.802
LogD:	0.593
LogS:	-3.957
# Rotatable Bonds:	1
TPSA:	117.2
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	4.984
Fsp3:	0.684
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:	-5.473
MDCK Permeability:	5.418821456260048e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.06
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.882

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.175
Plasma Protein Binding (PPB):	65.86095428466797%
Volume Distribution (VD):	0.951
Pgp-substrate:	24.085769653320312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.89
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	5.032
Half-life (T1/2):	0.253

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.644
Drug-inuced Liver Injury (DILI):	0.389
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.135
Skin Sensitization:	0.24
Carcinogencity:	0.08
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC132790

Natural Product ID:	NPC132790
*Common Name:**	nagilactone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AEGWYWSJGKOLGB-ZLNDBNLZSA-N
Standard InCHI:	InChI=1S/C19H24O7/c1-7(2)13-11-8(5-10(21)25-13)19(4)15-14(12(11)22)26-17(24)18(15,3)6-9(20)16(19)23/h5,7,9,12,14-16,20,22-23H,6H2,1-4H3/t9-,12-,14-,15+,16-,18+,19-/m1/s1
SMILES:	O=c1oc(C(C)C)c2c(c1)[C@@]1(C)[C@H](O)[C@H](O)C[C@]3([C@@H]1[C@@H]([C@@H]2O)OC3=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	3084329
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO33703	Podocarpus nagi	Species	Podocarpaceae	Eukaryota	Seeds	Aihua, Lincang, Yunnan Province, China	2103-OCT	PMID[28719204]
NPO5234	Myrica nagi	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28711	Artabotrys hexapetalus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5234	Myrica nagi	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28711	Artabotrys hexapetalus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15008	Smilax bockii	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5234	Myrica nagi	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28711	Artabotrys hexapetalus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7473	Spermatochnus paradoxus	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28711	Artabotrys hexapetalus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5234	Myrica nagi	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4298	Mycobacterium liflandii	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15008	Smilax bockii	Species	Staphylinidae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC132790 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	331
0.1-0.2	1278
0.2-0.3	2797
0.3-0.4	5312
0.4-0.5	10219
0.5-0.6	8167
0.6-0.7	6419
0.7-0.8	7639
0.8-0.85	485
0.85-0.9	46
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC247031
1.0	High Similarity	NPC100329
1.0	High Similarity	NPC97939
0.9902	High Similarity	NPC478211
0.9808	High Similarity	NPC475966
0.9804	High Similarity	NPC478210
0.9623	High Similarity	NPC478216
0.951	High Similarity	NPC478208
0.9444	High Similarity	NPC478206
0.9444	High Similarity	NPC478205
0.9444	High Similarity	NPC108581
0.9434	High Similarity	NPC478212
0.9352	High Similarity	NPC478204
0.9151	High Similarity	NPC478209
0.8952	High Similarity	NPC469607
0.8889	High Similarity	NPC469656
0.8889	High Similarity	NPC474846
0.8889	High Similarity	NPC188738
0.8889	High Similarity	NPC469655
0.8829	High Similarity	NPC53396
0.8829	High Similarity	NPC98249
0.875	High Similarity	NPC284707
0.8692	High Similarity	NPC230541
0.8667	High Similarity	NPC273005
0.8667	High Similarity	NPC469606
0.8667	High Similarity	NPC31058
0.8661	High Similarity	NPC58662
0.8661	High Similarity	NPC13713
0.8636	High Similarity	NPC472002
0.8636	High Similarity	NPC269530
0.8598	High Similarity	NPC102352
0.8532	High Similarity	NPC141350
0.8519	High Similarity	NPC144854
0.8519	High Similarity	NPC3316
0.8519	High Similarity	NPC180744
0.8509	High Similarity	NPC475041
0.8496	Intermediate Similarity	NPC469684
0.8496	Intermediate Similarity	NPC473968
0.8491	Intermediate Similarity	NPC295791
0.8475	Intermediate Similarity	NPC478207
0.8455	Intermediate Similarity	NPC210005
0.844	Intermediate Similarity	NPC277017
0.844	Intermediate Similarity	NPC192813
0.844	Intermediate Similarity	NPC189075
0.844	Intermediate Similarity	NPC154608
0.844	Intermediate Similarity	NPC275539
0.8393	Intermediate Similarity	NPC469496
0.8393	Intermediate Similarity	NPC25909
0.8393	Intermediate Similarity	NPC469463
0.8393	Intermediate Similarity	NPC469454
0.839	Intermediate Similarity	NPC477745
0.8378	Intermediate Similarity	NPC304180
0.8378	Intermediate Similarity	NPC179798
0.8364	Intermediate Similarity	NPC143706
0.8364	Intermediate Similarity	NPC472534
0.8349	Intermediate Similarity	NPC187435
0.8349	Intermediate Similarity	NPC67321
0.8349	Intermediate Similarity	NPC110496
0.8319	Intermediate Similarity	NPC476008
0.8318	Intermediate Similarity	NPC235369
0.8291	Intermediate Similarity	NPC269642
0.8288	Intermediate Similarity	NPC5103
0.8288	Intermediate Similarity	NPC286880
0.8286	Intermediate Similarity	NPC474343
0.8273	Intermediate Similarity	NPC50124
0.8257	Intermediate Similarity	NPC181357
0.8257	Intermediate Similarity	NPC127609
0.8257	Intermediate Similarity	NPC34768
0.8241	Intermediate Similarity	NPC159533
0.823	Intermediate Similarity	NPC51978
0.823	Intermediate Similarity	NPC471204
0.823	Intermediate Similarity	NPC56448
0.8224	Intermediate Similarity	NPC303559
0.822	Intermediate Similarity	NPC67251
0.8198	Intermediate Similarity	NPC469370
0.819	Intermediate Similarity	NPC230513
0.819	Intermediate Similarity	NPC256227
0.819	Intermediate Similarity	NPC475775
0.819	Intermediate Similarity	NPC476529
0.8182	Intermediate Similarity	NPC302788
0.8174	Intermediate Similarity	NPC473590
0.8174	Intermediate Similarity	NPC284068
0.8173	Intermediate Similarity	NPC57117
0.8165	Intermediate Similarity	NPC296950
0.8165	Intermediate Similarity	NPC146731
0.8165	Intermediate Similarity	NPC258532
0.8158	Intermediate Similarity	NPC117712
0.8151	Intermediate Similarity	NPC24651
0.8151	Intermediate Similarity	NPC476729
0.8142	Intermediate Similarity	NPC12046
0.8142	Intermediate Similarity	NPC476801
0.8142	Intermediate Similarity	NPC302146
0.8142	Intermediate Similarity	NPC194951
0.8142	Intermediate Similarity	NPC222834
0.8136	Intermediate Similarity	NPC312833
0.8131	Intermediate Similarity	NPC47024
0.8125	Intermediate Similarity	NPC253906
0.812	Intermediate Similarity	NPC107338
0.812	Intermediate Similarity	NPC478051
0.812	Intermediate Similarity	NPC268530
0.812	Intermediate Similarity	NPC109607
0.812	Intermediate Similarity	NPC154491
0.8108	Intermediate Similarity	NPC306265
0.8108	Intermediate Similarity	NPC88701
0.8087	Intermediate Similarity	NPC179626
0.8087	Intermediate Similarity	NPC474734
0.8087	Intermediate Similarity	NPC49492
0.8087	Intermediate Similarity	NPC266728
0.8083	Intermediate Similarity	NPC293112
0.8073	Intermediate Similarity	NPC254202
0.8073	Intermediate Similarity	NPC99266
0.807	Intermediate Similarity	NPC49451
0.807	Intermediate Similarity	NPC157441
0.807	Intermediate Similarity	NPC250109
0.807	Intermediate Similarity	NPC474271
0.807	Intermediate Similarity	NPC962
0.8067	Intermediate Similarity	NPC265557
0.8067	Intermediate Similarity	NPC105926
0.8067	Intermediate Similarity	NPC469789
0.8067	Intermediate Similarity	NPC18945
0.8067	Intermediate Similarity	NPC91693
0.8056	Intermediate Similarity	NPC471412
0.8053	Intermediate Similarity	NPC201992
0.8051	Intermediate Similarity	NPC4021
0.8051	Intermediate Similarity	NPC159456
0.8037	Intermediate Similarity	NPC159763
0.8037	Intermediate Similarity	NPC278386
0.8037	Intermediate Similarity	NPC124512
0.8037	Intermediate Similarity	NPC23364
0.8036	Intermediate Similarity	NPC27814
0.8036	Intermediate Similarity	NPC474243
0.8036	Intermediate Similarity	NPC153239
0.8034	Intermediate Similarity	NPC42673
0.8034	Intermediate Similarity	NPC122971
0.8019	Intermediate Similarity	NPC134072
0.8019	Intermediate Similarity	NPC234993
0.8019	Intermediate Similarity	NPC473153
0.8018	Intermediate Similarity	NPC179380
0.8018	Intermediate Similarity	NPC133422
0.8017	Intermediate Similarity	NPC176513
0.8017	Intermediate Similarity	NPC55296
0.8017	Intermediate Similarity	NPC470775
0.8017	Intermediate Similarity	NPC23046
0.8	Intermediate Similarity	NPC81736
0.8	Intermediate Similarity	NPC172154
0.8	Intermediate Similarity	NPC470922
0.8	Intermediate Similarity	NPC8369
0.8	Intermediate Similarity	NPC469877
0.8	Intermediate Similarity	NPC470919
0.8	Intermediate Similarity	NPC250075
0.7982	Intermediate Similarity	NPC289312
0.7982	Intermediate Similarity	NPC476081
0.7982	Intermediate Similarity	NPC137430
0.7982	Intermediate Similarity	NPC162973
0.7982	Intermediate Similarity	NPC474516
0.7982	Intermediate Similarity	NPC11252
0.7982	Intermediate Similarity	NPC165250
0.7966	Intermediate Similarity	NPC475003
0.7966	Intermediate Similarity	NPC475885
0.7966	Intermediate Similarity	NPC251226
0.7965	Intermediate Similarity	NPC235014
0.7963	Intermediate Similarity	NPC471413
0.7963	Intermediate Similarity	NPC476767
0.7949	Intermediate Similarity	NPC470776
0.7949	Intermediate Similarity	NPC251310
0.7946	Intermediate Similarity	NPC19412
0.7946	Intermediate Similarity	NPC37628
0.7946	Intermediate Similarity	NPC293850
0.7944	Intermediate Similarity	NPC134454
0.7944	Intermediate Similarity	NPC17326
0.7934	Intermediate Similarity	NPC159499
0.7931	Intermediate Similarity	NPC106228
0.7931	Intermediate Similarity	NPC259306
0.7931	Intermediate Similarity	NPC196931
0.7931	Intermediate Similarity	NPC251236
0.7931	Intermediate Similarity	NPC207217
0.7931	Intermediate Similarity	NPC328374
0.7931	Intermediate Similarity	NPC96312
0.7931	Intermediate Similarity	NPC40632
0.7931	Intermediate Similarity	NPC176840
0.7931	Intermediate Similarity	NPC471816
0.7931	Intermediate Similarity	NPC474046
0.7931	Intermediate Similarity	NPC470628
0.7931	Intermediate Similarity	NPC138372
0.7928	Intermediate Similarity	NPC266570
0.7928	Intermediate Similarity	NPC471206
0.7928	Intermediate Similarity	NPC478052
0.7928	Intermediate Similarity	NPC477125
0.7917	Intermediate Similarity	NPC11895
0.7913	Intermediate Similarity	NPC264153
0.7909	Intermediate Similarity	NPC99510
0.7909	Intermediate Similarity	NPC471208
0.7909	Intermediate Similarity	NPC264048
0.7909	Intermediate Similarity	NPC61442
0.7909	Intermediate Similarity	NPC8196
0.7909	Intermediate Similarity	NPC72842
0.7905	Intermediate Similarity	NPC53555
0.7899	Intermediate Similarity	NPC470779
0.7899	Intermediate Similarity	NPC67569
0.7895	Intermediate Similarity	NPC473921

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 NPC132790 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	799
0.2-0.3	1784
0.3-0.4	2519
0.4-0.5	2162
0.5-0.6	1062
0.6-0.7	401
0.7-0.8	133
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8037	Intermediate Similarity	NPD4225	Approved
0.7876	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7640	Approved
0.7798	Intermediate Similarity	NPD7639	Approved
0.7706	Intermediate Similarity	NPD7638	Approved
0.7652	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6686	Approved
0.7563	Intermediate Similarity	NPD7115	Discovery
0.7478	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7507	Approved
0.7345	Intermediate Similarity	NPD7632	Discontinued
0.7317	Intermediate Similarity	NPD8513	Phase 3
0.7311	Intermediate Similarity	NPD4632	Approved
0.7304	Intermediate Similarity	NPD6008	Approved
0.7227	Intermediate Similarity	NPD6053	Discontinued
0.7188	Intermediate Similarity	NPD7319	Approved
0.7177	Intermediate Similarity	NPD8516	Approved
0.7177	Intermediate Similarity	NPD8515	Approved
0.7177	Intermediate Similarity	NPD8517	Approved
0.7177	Intermediate Similarity	NPD7503	Approved
0.7105	Intermediate Similarity	NPD5344	Discontinued
0.7097	Intermediate Similarity	NPD6319	Approved
0.7091	Intermediate Similarity	NPD5778	Approved
0.7091	Intermediate Similarity	NPD5779	Approved
0.7064	Intermediate Similarity	NPD6698	Approved
0.7064	Intermediate Similarity	NPD46	Approved
0.7018	Intermediate Similarity	NPD6648	Approved
0.7009	Intermediate Similarity	NPD5739	Approved
0.7009	Intermediate Similarity	NPD6675	Approved
0.7009	Intermediate Similarity	NPD6402	Approved
0.7009	Intermediate Similarity	NPD7128	Approved
0.7	Intermediate Similarity	NPD7983	Approved
0.6992	Remote Similarity	NPD6009	Approved
0.6991	Remote Similarity	NPD7902	Approved
0.6975	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6373	Approved
0.6975	Remote Similarity	NPD6372	Approved
0.6952	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5701	Approved
0.6949	Remote Similarity	NPD5697	Approved
0.6947	Remote Similarity	NPD7260	Phase 2
0.6942	Remote Similarity	NPD8297	Approved
0.6937	Remote Similarity	NPD6399	Phase 3
0.6929	Remote Similarity	NPD8328	Phase 3
0.6917	Remote Similarity	NPD6371	Approved
0.6916	Remote Similarity	NPD1694	Approved
0.6905	Remote Similarity	NPD5983	Phase 2
0.6899	Remote Similarity	NPD8074	Phase 3
0.6894	Remote Similarity	NPD6845	Suspended
0.6891	Remote Similarity	NPD6881	Approved
0.6891	Remote Similarity	NPD6899	Approved
0.6891	Remote Similarity	NPD7320	Approved
0.6891	Remote Similarity	NPD6011	Approved
0.688	Remote Similarity	NPD7516	Approved
0.6875	Remote Similarity	NPD7748	Approved
0.6875	Remote Similarity	NPD7492	Approved
0.686	Remote Similarity	NPD6650	Approved
0.686	Remote Similarity	NPD6649	Approved
0.686	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3618	Phase 1
0.6847	Remote Similarity	NPD6411	Approved
0.6847	Remote Similarity	NPD7515	Phase 2
0.6833	Remote Similarity	NPD6012	Approved
0.6833	Remote Similarity	NPD6014	Approved
0.6833	Remote Similarity	NPD6013	Approved
0.6825	Remote Similarity	NPD6059	Approved
0.6825	Remote Similarity	NPD6054	Approved
0.6822	Remote Similarity	NPD6616	Approved
0.6818	Remote Similarity	NPD5328	Approved
0.6814	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6412	Phase 2
0.68	Remote Similarity	NPD7328	Approved
0.68	Remote Similarity	NPD7327	Approved
0.6797	Remote Similarity	NPD7604	Phase 2
0.6783	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7102	Approved
0.6777	Remote Similarity	NPD6883	Approved
0.6777	Remote Similarity	NPD7290	Approved
0.6772	Remote Similarity	NPD6016	Approved
0.6772	Remote Similarity	NPD8033	Approved
0.6772	Remote Similarity	NPD6015	Approved
0.6772	Remote Similarity	NPD6921	Approved
0.6769	Remote Similarity	NPD7078	Approved
0.6769	Remote Similarity	NPD8293	Discontinued
0.6757	Remote Similarity	NPD7838	Discovery
0.6754	Remote Similarity	NPD4697	Phase 3
0.6752	Remote Similarity	NPD5211	Phase 2
0.6726	Remote Similarity	NPD7900	Approved
0.6726	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8130	Phase 1
0.6721	Remote Similarity	NPD6869	Approved
0.6721	Remote Similarity	NPD6847	Approved
0.6721	Remote Similarity	NPD6617	Approved
0.6721	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6370	Approved
0.6719	Remote Similarity	NPD5988	Approved
0.6718	Remote Similarity	NPD7736	Approved
0.6696	Remote Similarity	NPD7637	Suspended
0.6696	Remote Similarity	NPD4755	Approved
0.6696	Remote Similarity	NPD6079	Approved
0.6693	Remote Similarity	NPD8294	Approved
0.6693	Remote Similarity	NPD8377	Approved
0.6692	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD8378	Approved
0.6641	Remote Similarity	NPD8380	Approved
0.6641	Remote Similarity	NPD8335	Approved
0.6641	Remote Similarity	NPD8379	Approved
0.6641	Remote Similarity	NPD8296	Approved
0.6639	Remote Similarity	NPD5141	Approved
0.6639	Remote Similarity	NPD4634	Approved
0.6636	Remote Similarity	NPD7524	Approved
0.6613	Remote Similarity	NPD8133	Approved
0.6609	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5222	Approved
0.6609	Remote Similarity	NPD5221	Approved
0.6581	Remote Similarity	NPD5286	Approved
0.6581	Remote Similarity	NPD5285	Approved
0.6581	Remote Similarity	NPD4700	Approved
0.6581	Remote Similarity	NPD4696	Approved
0.6579	Remote Similarity	NPD5282	Discontinued
0.6552	Remote Similarity	NPD5173	Approved
0.6549	Remote Similarity	NPD8034	Phase 2
0.6549	Remote Similarity	NPD8035	Phase 2
0.6525	Remote Similarity	NPD5223	Approved
0.6518	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6274	Approved
0.6491	Remote Similarity	NPD4202	Approved
0.6486	Remote Similarity	NPD3573	Approved
0.6481	Remote Similarity	NPD3667	Approved
0.6471	Remote Similarity	NPD4633	Approved
0.6471	Remote Similarity	NPD5226	Approved
0.6471	Remote Similarity	NPD5225	Approved
0.6471	Remote Similarity	NPD5224	Approved
0.6466	Remote Similarity	NPD6033	Approved
0.646	Remote Similarity	NPD5785	Approved
0.6457	Remote Similarity	NPD6317	Approved
0.6455	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6110	Phase 1
0.6417	Remote Similarity	NPD5174	Approved
0.6417	Remote Similarity	NPD5175	Approved
0.6417	Remote Similarity	NPD4754	Approved
0.6412	Remote Similarity	NPD6067	Discontinued
0.641	Remote Similarity	NPD6083	Phase 2
0.641	Remote Similarity	NPD6084	Phase 2
0.6406	Remote Similarity	NPD6314	Approved
0.6406	Remote Similarity	NPD6335	Approved
0.6406	Remote Similarity	NPD6313	Approved
0.6404	Remote Similarity	NPD5284	Approved
0.6404	Remote Similarity	NPD5281	Approved
0.6396	Remote Similarity	NPD6409	Approved
0.6396	Remote Similarity	NPD4249	Approved
0.6396	Remote Similarity	NPD7334	Approved
0.6396	Remote Similarity	NPD7146	Approved
0.6396	Remote Similarity	NPD6684	Approved
0.6396	Remote Similarity	NPD5330	Approved
0.6396	Remote Similarity	NPD5279	Phase 3
0.6396	Remote Similarity	NPD7521	Approved
0.6379	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6868	Approved
0.6364	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3666	Approved
0.6364	Remote Similarity	NPD4786	Approved
0.6364	Remote Similarity	NPD3665	Phase 1
0.6357	Remote Similarity	NPD7101	Approved
0.6357	Remote Similarity	NPD7100	Approved
0.6356	Remote Similarity	NPD5696	Approved
0.6339	Remote Similarity	NPD4250	Approved
0.6339	Remote Similarity	NPD4251	Approved
0.6311	Remote Similarity	NPD4767	Approved
0.6311	Remote Similarity	NPD4768	Approved
0.6306	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4695	Discontinued
0.6283	Remote Similarity	NPD6672	Approved
0.6283	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6903	Approved
0.6283	Remote Similarity	NPD5737	Approved
0.6273	Remote Similarity	NPD6695	Phase 3
0.6273	Remote Similarity	NPD7154	Phase 3
0.6261	Remote Similarity	NPD5693	Phase 1
0.626	Remote Similarity	NPD6909	Approved
0.626	Remote Similarity	NPD6908	Approved
0.625	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5695	Phase 3
0.6216	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5128	Approved
0.621	Remote Similarity	NPD4730	Approved
0.621	Remote Similarity	NPD4729	Approved
0.6186	Remote Similarity	NPD7839	Suspended
0.6174	Remote Similarity	NPD5207	Approved
0.6164	Remote Similarity	NPD4628	Phase 3
0.6161	Remote Similarity	NPD1696	Phase 3

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