NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	384.1
Volume:	351.855
LogP:	0.578
LogD:	0.227
LogS:	-3.019
# Rotatable Bonds:	1
TPSA:	117.2
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	5.258
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.426
MDCK Permeability:	0.00015551369870081544
Pgp-inhibitor:	0.028
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.735

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.6
Plasma Protein Binding (PPB):	82.0394058227539%
Volume Distribution (VD):	0.621
Pgp-substrate:	21.600502014160156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.518
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.783
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.14
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.252

ADMET: Excretion

Clearance (CL):	4.708
Half-life (T1/2):	0.485

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.377
Drug-inuced Liver Injury (DILI):	0.253
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.571
Maximum Recommended Daily Dose:	0.137
Skin Sensitization:	0.065
Carcinogencity:	0.588
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.323

Download Data

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

Natural Product: NPC478207

Natural Product ID:	NPC478207
*Common Name:**	1α-Chloro-2β,3β,15-trihydroxynagilactone L
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UBUSWNRZXPOPGI-DMLAFKAMSA-N
Standard InCHI:	InChI=1S/C17H19ClO7/c1-5(19)14-6-3-8-11-10(16(23)24-8)12(21)13(22)15(18)17(11,2)7(6)4-9(20)25-14/h4-5,8,10-13,15,19,21-22H,3H2,1-2H3/t5?,8-,10-,11+,12?,13?,15?,17-/m1/s1
SMILES:	[H][C@@]12[C@H]3CC4=C(C(C)O)OC(=O)C=C4[C@@]1(C)C(Cl)C(O)C(O)[C@@H]2C(=O)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds]

*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]

☑ 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 NPC478207 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	379
0.1-0.2	1522
0.2-0.3	3249
0.3-0.4	7036
0.4-0.5	11609
0.5-0.6	7443
0.6-0.7	9319
0.7-0.8	2117
0.8-0.85	19
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8512	High Similarity	NPC108581
0.8512	High Similarity	NPC478205
0.8512	High Similarity	NPC478206
0.8487	Intermediate Similarity	NPC478212
0.8475	Intermediate Similarity	NPC100329
0.8475	Intermediate Similarity	NPC97939
0.8475	Intermediate Similarity	NPC247031
0.8475	Intermediate Similarity	NPC132790
0.843	Intermediate Similarity	NPC478204
0.839	Intermediate Similarity	NPC478211
0.8333	Intermediate Similarity	NPC475966
0.8305	Intermediate Similarity	NPC478210
0.8235	Intermediate Similarity	NPC478209
0.8197	Intermediate Similarity	NPC478216
0.8125	Intermediate Similarity	NPC156797
0.8051	Intermediate Similarity	NPC478208
0.7984	Intermediate Similarity	NPC98249
0.7984	Intermediate Similarity	NPC287903
0.7984	Intermediate Similarity	NPC53396
0.7953	Intermediate Similarity	NPC282003
0.7953	Intermediate Similarity	NPC188222
0.7953	Intermediate Similarity	NPC310035
0.792	Intermediate Similarity	NPC284707
0.7891	Intermediate Similarity	NPC303006
0.784	Intermediate Similarity	NPC58662
0.7805	Intermediate Similarity	NPC269530
0.7731	Intermediate Similarity	NPC159533
0.7724	Intermediate Similarity	NPC469656
0.7724	Intermediate Similarity	NPC474846
0.7724	Intermediate Similarity	NPC469655
0.7698	Intermediate Similarity	NPC469684
0.7667	Intermediate Similarity	NPC296950
0.7667	Intermediate Similarity	NPC146731
0.7647	Intermediate Similarity	NPC31058
0.7647	Intermediate Similarity	NPC273005
0.7647	Intermediate Similarity	NPC469606
0.7634	Intermediate Similarity	NPC477745
0.7619	Intermediate Similarity	NPC329869
0.7612	Intermediate Similarity	NPC470185
0.7603	Intermediate Similarity	NPC469607
0.7581	Intermediate Similarity	NPC188738
0.7576	Intermediate Similarity	NPC476008
0.7559	Intermediate Similarity	NPC13713
0.7554	Intermediate Similarity	NPC473396
0.7542	Intermediate Similarity	NPC278386
0.7542	Intermediate Similarity	NPC124512
0.7542	Intermediate Similarity	NPC159763
0.7541	Intermediate Similarity	NPC67321
0.7541	Intermediate Similarity	NPC187435
0.7536	Intermediate Similarity	NPC473233
0.752	Intermediate Similarity	NPC472002
0.7518	Intermediate Similarity	NPC130447
0.75	Intermediate Similarity	NPC235014
0.7481	Intermediate Similarity	NPC67251
0.748	Intermediate Similarity	NPC50124
0.7479	Intermediate Similarity	NPC110897
0.7462	Intermediate Similarity	NPC67569
0.746	Intermediate Similarity	NPC264153
0.746	Intermediate Similarity	NPC89018
0.7459	Intermediate Similarity	NPC34768
0.7442	Intermediate Similarity	NPC230513
0.7438	Intermediate Similarity	NPC99510
0.7438	Intermediate Similarity	NPC72842
0.7424	Intermediate Similarity	NPC476729
0.7424	Intermediate Similarity	NPC24651
0.7422	Intermediate Similarity	NPC473968
0.7419	Intermediate Similarity	NPC322912
0.7405	Intermediate Similarity	NPC23786
0.7405	Intermediate Similarity	NPC287236
0.7405	Intermediate Similarity	NPC269642
0.7405	Intermediate Similarity	NPC470265
0.7405	Intermediate Similarity	NPC312833
0.7402	Intermediate Similarity	NPC226608
0.7402	Intermediate Similarity	NPC88867
0.7402	Intermediate Similarity	NPC117712
0.7398	Intermediate Similarity	NPC230541
0.7398	Intermediate Similarity	NPC302788
0.7398	Intermediate Similarity	NPC216636
0.7398	Intermediate Similarity	NPC180744
0.7391	Intermediate Similarity	NPC245017
0.7385	Intermediate Similarity	NPC154491
0.7385	Intermediate Similarity	NPC268530
0.7385	Intermediate Similarity	NPC478051
0.7381	Intermediate Similarity	NPC42658
0.7372	Intermediate Similarity	NPC296617
0.7368	Intermediate Similarity	NPC293112
0.7355	Intermediate Similarity	NPC295791
0.7348	Intermediate Similarity	NPC469789
0.7348	Intermediate Similarity	NPC18945
0.7348	Intermediate Similarity	NPC105926
0.7348	Intermediate Similarity	NPC265557
0.7348	Intermediate Similarity	NPC91693
0.7344	Intermediate Similarity	NPC470466
0.7339	Intermediate Similarity	NPC306265
0.7333	Intermediate Similarity	NPC47024
0.7328	Intermediate Similarity	NPC159456
0.7328	Intermediate Similarity	NPC4021
0.7323	Intermediate Similarity	NPC477126
0.7323	Intermediate Similarity	NPC469463
0.7323	Intermediate Similarity	NPC469454
0.7323	Intermediate Similarity	NPC469496
0.7323	Intermediate Similarity	NPC25909
0.7317	Intermediate Similarity	NPC102352
0.7311	Intermediate Similarity	NPC73911
0.7308	Intermediate Similarity	NPC475041
0.7308	Intermediate Similarity	NPC42673
0.7302	Intermediate Similarity	NPC179798
0.7302	Intermediate Similarity	NPC304180
0.7293	Intermediate Similarity	NPC470922
0.7293	Intermediate Similarity	NPC8369
0.7293	Intermediate Similarity	NPC172154
0.7293	Intermediate Similarity	NPC81736
0.7287	Intermediate Similarity	NPC176513
0.7287	Intermediate Similarity	NPC55296
0.7287	Intermediate Similarity	NPC473656
0.7287	Intermediate Similarity	NPC470775
0.728	Intermediate Similarity	NPC475065
0.728	Intermediate Similarity	NPC42662
0.728	Intermediate Similarity	NPC141350
0.728	Intermediate Similarity	NPC143706
0.728	Intermediate Similarity	NPC472534
0.728	Intermediate Similarity	NPC474243
0.7273	Intermediate Similarity	NPC303559
0.7273	Intermediate Similarity	NPC244456
0.7273	Intermediate Similarity	NPC308824
0.7273	Intermediate Similarity	NPC469657
0.7266	Intermediate Similarity	NPC110861
0.7266	Intermediate Similarity	NPC67259
0.7266	Intermediate Similarity	NPC73314
0.7266	Intermediate Similarity	NPC147912
0.7258	Intermediate Similarity	NPC330011
0.7258	Intermediate Similarity	NPC319438
0.7258	Intermediate Similarity	NPC179380
0.7258	Intermediate Similarity	NPC3316
0.7258	Intermediate Similarity	NPC329048
0.7258	Intermediate Similarity	NPC144854
0.7252	Intermediate Similarity	NPC251226
0.7252	Intermediate Similarity	NPC475003
0.7244	Intermediate Similarity	NPC476801
0.7236	Intermediate Similarity	NPC283850
0.7231	Intermediate Similarity	NPC470776
0.7231	Intermediate Similarity	NPC709
0.7231	Intermediate Similarity	NPC50774
0.7231	Intermediate Similarity	NPC476714
0.7231	Intermediate Similarity	NPC251310
0.7227	Intermediate Similarity	NPC134072
0.7227	Intermediate Similarity	NPC242848
0.7227	Intermediate Similarity	NPC234993
0.7222	Intermediate Similarity	NPC11491
0.7222	Intermediate Similarity	NPC210005
0.7222	Intermediate Similarity	NPC472666
0.7222	Intermediate Similarity	NPC5103
0.7222	Intermediate Similarity	NPC140409
0.7222	Intermediate Similarity	NPC156248
0.7218	Intermediate Similarity	NPC11895
0.7213	Intermediate Similarity	NPC476081
0.7213	Intermediate Similarity	NPC165250
0.7209	Intermediate Similarity	NPC44170
0.7209	Intermediate Similarity	NPC207217
0.7209	Intermediate Similarity	NPC268954
0.7209	Intermediate Similarity	NPC64318
0.7206	Intermediate Similarity	NPC473593
0.7203	Intermediate Similarity	NPC57117
0.72	Intermediate Similarity	NPC475418
0.72	Intermediate Similarity	NPC88701
0.72	Intermediate Similarity	NPC37628
0.72	Intermediate Similarity	NPC151393
0.72	Intermediate Similarity	NPC192813
0.72	Intermediate Similarity	NPC94377
0.72	Intermediate Similarity	NPC154608
0.72	Intermediate Similarity	NPC318363
0.72	Intermediate Similarity	NPC128210
0.72	Intermediate Similarity	NPC275539
0.72	Intermediate Similarity	NPC473482
0.72	Intermediate Similarity	NPC277017
0.72	Intermediate Similarity	NPC189075
0.7197	Intermediate Similarity	NPC470779
0.719	Intermediate Similarity	NPC476299
0.719	Intermediate Similarity	NPC474012
0.7188	Intermediate Similarity	NPC56448
0.7188	Intermediate Similarity	NPC471204
0.7188	Intermediate Similarity	NPC51978
0.7188	Intermediate Similarity	NPC474271
0.7177	Intermediate Similarity	NPC477125
0.7177	Intermediate Similarity	NPC81630
0.7177	Intermediate Similarity	NPC472655
0.7177	Intermediate Similarity	NPC266570
0.7177	Intermediate Similarity	NPC471206
0.7176	Intermediate Similarity	NPC470777
0.7176	Intermediate Similarity	NPC211093
0.7176	Intermediate Similarity	NPC473636
0.7176	Intermediate Similarity	NPC268958
0.7176	Intermediate Similarity	NPC475775
0.7176	Intermediate Similarity	NPC473839
0.7176	Intermediate Similarity	NPC476529
0.7176	Intermediate Similarity	NPC77689
0.7165	Intermediate Similarity	NPC470467
0.7165	Intermediate Similarity	NPC170294
0.7165	Intermediate Similarity	NPC324683
0.7165	Intermediate Similarity	NPC474315

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 NPC478207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	877
0.2-0.3	1977
0.3-0.4	2729
0.4-0.5	2051
0.5-0.6	883
0.6-0.7	300
0.7-0.8	23
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7542	Intermediate Similarity	NPD4225	Approved
0.7154	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6336	Discontinued
0.6953	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6686	Approved
0.6911	Remote Similarity	NPD7639	Approved
0.6911	Remote Similarity	NPD7640	Approved
0.6829	Remote Similarity	NPD7638	Approved
0.6797	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7101	Approved
0.6791	Remote Similarity	NPD7100	Approved
0.6719	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6868	Approved
0.6691	Remote Similarity	NPD5983	Phase 2
0.6691	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD5956	Approved
0.6643	Remote Similarity	NPD6033	Approved
0.6596	Remote Similarity	NPD7319	Approved
0.6569	Remote Similarity	NPD8516	Approved
0.6569	Remote Similarity	NPD8515	Approved
0.6569	Remote Similarity	NPD8517	Approved
0.6569	Remote Similarity	NPD7503	Approved
0.6565	Remote Similarity	NPD6371	Approved
0.6544	Remote Similarity	NPD4522	Approved
0.6535	Remote Similarity	NPD7632	Discontinued
0.6515	Remote Similarity	NPD5217	Approved
0.6515	Remote Similarity	NPD5215	Approved
0.6515	Remote Similarity	NPD5216	Approved
0.65	Remote Similarity	NPD7507	Approved
0.6496	Remote Similarity	NPD6319	Approved
0.6493	Remote Similarity	NPD5167	Approved
0.6457	Remote Similarity	NPD5344	Discontinued
0.6423	Remote Similarity	NPD5779	Approved
0.6423	Remote Similarity	NPD5778	Approved
0.6412	Remote Similarity	NPD5168	Approved
0.6397	Remote Similarity	NPD6009	Approved
0.6393	Remote Similarity	NPD46	Approved
0.6393	Remote Similarity	NPD6698	Approved
0.6378	Remote Similarity	NPD6648	Approved
0.6364	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD8328	Phase 3
0.635	Remote Similarity	NPD6335	Approved
0.635	Remote Similarity	NPD6313	Approved
0.635	Remote Similarity	NPD6314	Approved
0.6343	Remote Similarity	NPD6053	Discontinued
0.6341	Remote Similarity	NPD7983	Approved
0.6341	Remote Similarity	NPD7637	Suspended
0.6338	Remote Similarity	NPD8074	Phase 3
0.6336	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD7492	Approved
0.6304	Remote Similarity	NPD7516	Approved
0.6277	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD6616	Approved
0.626	Remote Similarity	NPD6008	Approved
0.6259	Remote Similarity	NPD6054	Approved
0.6259	Remote Similarity	NPD6059	Approved
0.624	Remote Similarity	NPD5282	Discontinued
0.6232	Remote Similarity	NPD7327	Approved
0.6232	Remote Similarity	NPD7328	Approved
0.6224	Remote Similarity	NPD7078	Approved
0.6224	Remote Similarity	NPD8293	Discontinued
0.622	Remote Similarity	NPD7902	Approved
0.6214	Remote Similarity	NPD6921	Approved
0.6214	Remote Similarity	NPD6015	Approved
0.6214	Remote Similarity	NPD6016	Approved
0.6214	Remote Similarity	NPD8033	Approved
0.6212	Remote Similarity	NPD6412	Phase 2
0.621	Remote Similarity	NPD6411	Approved
0.619	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD7736	Approved
0.617	Remote Similarity	NPD5988	Approved
0.617	Remote Similarity	NPD6370	Approved
0.616	Remote Similarity	NPD6399	Phase 3
0.6143	Remote Similarity	NPD8294	Approved
0.6143	Remote Similarity	NPD8377	Approved
0.6136	Remote Similarity	NPD6675	Approved
0.6136	Remote Similarity	NPD7128	Approved
0.6136	Remote Similarity	NPD5739	Approved
0.6136	Remote Similarity	NPD6402	Approved
0.6134	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7838	Discovery
0.6119	Remote Similarity	NPD6372	Approved
0.6119	Remote Similarity	NPD6373	Approved
0.6116	Remote Similarity	NPD1694	Approved
0.6111	Remote Similarity	NPD7748	Approved
0.6103	Remote Similarity	NPD8297	Approved
0.6099	Remote Similarity	NPD8380	Approved
0.6099	Remote Similarity	NPD8296	Approved
0.6099	Remote Similarity	NPD8379	Approved
0.6099	Remote Similarity	NPD8335	Approved
0.6099	Remote Similarity	NPD8378	Approved
0.609	Remote Similarity	NPD5697	Approved
0.609	Remote Similarity	NPD5701	Approved
0.608	Remote Similarity	NPD7515	Phase 2
0.6074	Remote Similarity	NPD5169	Approved
0.6074	Remote Similarity	NPD4634	Approved
0.6066	Remote Similarity	NPD3618	Phase 1
0.6058	Remote Similarity	NPD8133	Approved
0.6057	Remote Similarity	NPD6785	Approved
0.6057	Remote Similarity	NPD6784	Approved
0.6054	Remote Similarity	NPD7260	Phase 2
0.6048	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6101	Approved
0.6047	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD7320	Approved
0.6045	Remote Similarity	NPD6881	Approved
0.6045	Remote Similarity	NPD6899	Approved
0.6029	Remote Similarity	NPD6650	Approved
0.6029	Remote Similarity	NPD6649	Approved
0.6029	Remote Similarity	NPD5127	Approved
0.6016	Remote Similarity	NPD7524	Approved
0.6014	Remote Similarity	NPD6845	Suspended
0.6	Remote Similarity	NPD5785	Approved
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD6012	Approved
0.6	Remote Similarity	NPD6013	Approved
0.5984	Remote Similarity	NPD7900	Approved
0.5984	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD7102	Approved
0.5956	Remote Similarity	NPD7290	Approved
0.5956	Remote Similarity	NPD6883	Approved
0.5926	Remote Similarity	NPD6011	Approved
0.5926	Remote Similarity	NPD5128	Approved
0.5912	Remote Similarity	NPD6869	Approved
0.5912	Remote Similarity	NPD6617	Approved
0.5912	Remote Similarity	NPD8130	Phase 1
0.5912	Remote Similarity	NPD6847	Approved
0.5909	Remote Similarity	NPD5211	Phase 2
0.5903	Remote Similarity	NPD7604	Phase 2
0.5891	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6882	Approved
0.5846	Remote Similarity	NPD4755	Approved
0.5846	Remote Similarity	NPD6084	Phase 2
0.5846	Remote Similarity	NPD6083	Phase 2
0.5827	Remote Similarity	NPD8035	Phase 2
0.5827	Remote Similarity	NPD8034	Phase 2
0.5821	Remote Similarity	NPD5141	Approved
0.5814	Remote Similarity	NPD5654	Approved
0.5806	Remote Similarity	NPD8384	Approved
0.5806	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4249	Approved
0.5802	Remote Similarity	NPD5696	Approved
0.5797	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5328	Approved
0.5793	Remote Similarity	NPD6067	Discontinued
0.5781	Remote Similarity	NPD4202	Approved
0.5772	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD4697	Phase 3
0.576	Remote Similarity	NPD4250	Approved
0.576	Remote Similarity	NPD4251	Approved
0.5758	Remote Similarity	NPD5285	Approved
0.5758	Remote Similarity	NPD4700	Approved
0.5758	Remote Similarity	NPD5286	Approved
0.5758	Remote Similarity	NPD4696	Approved
0.5752	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD6274	Approved
0.5738	Remote Similarity	NPD3667	Approved
0.5725	Remote Similarity	NPD5959	Approved
0.5703	Remote Similarity	NPD5281	Approved
0.5703	Remote Similarity	NPD5284	Approved
0.5703	Remote Similarity	NPD6079	Approved
0.5692	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD5695	Phase 3
0.5691	Remote Similarity	NPD7154	Phase 3
0.5691	Remote Similarity	NPD6695	Phase 3
0.568	Remote Similarity	NPD5330	Approved
0.568	Remote Similarity	NPD7521	Approved
0.568	Remote Similarity	NPD7146	Approved
0.568	Remote Similarity	NPD7334	Approved
0.568	Remote Similarity	NPD5279	Phase 3
0.568	Remote Similarity	NPD6684	Approved
0.568	Remote Similarity	NPD6409	Approved
0.5672	Remote Similarity	NPD5224	Approved
0.5672	Remote Similarity	NPD4633	Approved
0.5672	Remote Similarity	NPD5225	Approved
0.5672	Remote Similarity	NPD5226	Approved
0.5672	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD8434	Phase 2
0.5655	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD7839	Suspended
0.5649	Remote Similarity	NPD5221	Approved
0.5649	Remote Similarity	NPD5222	Approved
0.5645	Remote Similarity	NPD3666	Approved
0.5645	Remote Similarity	NPD3133	Approved
0.5645	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD4786	Approved
0.5645	Remote Similarity	NPD3665	Phase 1
0.563	Remote Similarity	NPD5175	Approved
0.563	Remote Similarity	NPD5174	Approved
0.5629	Remote Similarity	NPD37	Approved
0.5621	Remote Similarity	NPD4966	Approved
0.5621	Remote Similarity	NPD4965	Approved
0.5621	Remote Similarity	NPD4967	Phase 2
0.562	Remote Similarity	NPD6614	Approved
0.5606	Remote Similarity	NPD5173	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