NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	564.22
Volume:	539.726
LogP:	2.304
LogD:	1.495
LogS:	-4.426
# Rotatable Bonds:	8
TPSA:	164.26
# H-Bond Aceptor:	12
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.226
Synthetic Accessibility Score:	6.145
Fsp3:	0.75
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.327
MDCK Permeability:	0.0001366074720863253
Pgp-inhibitor:	0.996
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.812
20% Bioavailability (F20%):	0.185
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.28
Plasma Protein Binding (PPB):	27.143882751464844%
Volume Distribution (VD):	1.317
Pgp-substrate:	40.35663986206055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.221
CYP3A4-substrate:	0.321

ADMET: Excretion

Clearance (CL):	2.556
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.925
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.985
Rat Oral Acute Toxicity:	0.953
Maximum Recommended Daily Dose:	0.28
Skin Sensitization:	0.935
Carcinogencity:	0.983
Eye Corrosion:	0.14
Eye Irritation:	0.223
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC476711

Natural Product ID:	NPC476711
*Common Name:**	[(1S,2S,4S,7S,8Z,11S,12S,13R,14S,16S,17R,18S)-1,11,12-triacetyloxy-16-hydroxy-4,9,13,17-tetramethyl-5-oxo-3,6-dioxapentacyclo[10.6.0.02,4.02,7.013,18]octadec-8-en-14-yl] acetate
IUPAC Name:	[(1S,2S,4S,7S,8Z,11S,12S,13R,14S,16S,17R,18S)-1,11,12-triacetyloxy-16-hydroxy-4,9,13,17-tetramethyl-5-oxo-3,6-dioxapentacyclo[10.6.0.02,4.02,7.013,18]octadec-8-en-14-yl] acetate
Synonyms:	Excavatolide C
Standard InCHIKey:	AUEFUUCAYXEJJT-FBNOZLGZSA-N
Standard InCHI:	InChI=1S/C28H36O12/c1-12-9-20(36-15(4)30)26(38-16(5)31)24(7)19(35-14(3)29)11-18(33)13(2)22(24)28(26,39-17(6)32)27-21(10-12)37-23(34)25(27,8)40-27/h10,13,18-22,33H,9,11H2,1-8H3/b12-10-/t13-,18-,19-,20-,21-,22-,24-,25+,26+,27+,28-/m0/s1
SMILES:	C[C@H]1[C@H](C[C@@H]([C@]2([C@H]1[C@@]3([C@]2([C@H](C/C(=C\[C@H]4[C@@]35[C@](O5)(C(=O)O4)C)/C)OC(=O)C)OC(=O)C)OC(=O)C)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44575512
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096858]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10543904]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277747]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720523]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599257]
NPO4817	Briareum excavatum	Species	Briareidae	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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.3	ug/ml	PMID[9599257]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.9	ug/ml	PMID[9599257]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.9	ug/ml	PMID[9599257]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.9	ug/ml	PMID[9599257]

☑ 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 NPC476711 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	1552
0.2-0.3	4644
0.3-0.4	8123
0.4-0.5	13644
0.5-0.6	7931
0.6-0.7	5243
0.7-0.8	1232
0.8-0.85	57
0.85-0.9	16
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476710
0.9907	High Similarity	NPC476712
0.9907	High Similarity	NPC476713
0.9174	High Similarity	NPC473877
0.9115	High Similarity	NPC475003
0.8929	High Similarity	NPC474333
0.8899	High Similarity	NPC42662
0.8889	High Similarity	NPC475587
0.8889	High Similarity	NPC475510
0.885	High Similarity	NPC296822
0.8807	High Similarity	NPC473939
0.8807	High Similarity	NPC473595
0.8727	High Similarity	NPC475922
0.8649	High Similarity	NPC115257
0.8649	High Similarity	NPC161816
0.8649	High Similarity	NPC281624
0.8649	High Similarity	NPC474586
0.8649	High Similarity	NPC473843
0.8649	High Similarity	NPC473594
0.8649	High Similarity	NPC473975
0.8636	High Similarity	NPC94377
0.8571	High Similarity	NPC194619
0.8522	High Similarity	NPC473590
0.844	Intermediate Similarity	NPC474166
0.844	Intermediate Similarity	NPC19239
0.8435	Intermediate Similarity	NPC270478
0.8421	Intermediate Similarity	NPC477126
0.8403	Intermediate Similarity	NPC67251
0.8378	Intermediate Similarity	NPC72813
0.8378	Intermediate Similarity	NPC474421
0.8378	Intermediate Similarity	NPC194620
0.8378	Intermediate Similarity	NPC326994
0.8378	Intermediate Similarity	NPC324327
0.8376	Intermediate Similarity	NPC470186
0.8362	Intermediate Similarity	NPC469684
0.8348	Intermediate Similarity	NPC73314
0.8333	Intermediate Similarity	NPC317687
0.8304	Intermediate Similarity	NPC474664
0.8304	Intermediate Similarity	NPC169888
0.8304	Intermediate Similarity	NPC14862
0.8304	Intermediate Similarity	NPC55972
0.8304	Intermediate Similarity	NPC327286
0.8304	Intermediate Similarity	NPC233379
0.8291	Intermediate Similarity	NPC470776
0.8288	Intermediate Similarity	NPC475802
0.8288	Intermediate Similarity	NPC16313
0.8288	Intermediate Similarity	NPC9303
0.8276	Intermediate Similarity	NPC477509
0.8276	Intermediate Similarity	NPC474734
0.8273	Intermediate Similarity	NPC474165
0.8273	Intermediate Similarity	NPC69171
0.825	Intermediate Similarity	NPC18945
0.825	Intermediate Similarity	NPC472399
0.825	Intermediate Similarity	NPC105926
0.825	Intermediate Similarity	NPC265557
0.825	Intermediate Similarity	NPC91693
0.8246	Intermediate Similarity	NPC157476
0.8246	Intermediate Similarity	NPC474846
0.8246	Intermediate Similarity	NPC469655
0.8246	Intermediate Similarity	NPC469656
0.8246	Intermediate Similarity	NPC317107
0.8235	Intermediate Similarity	NPC470779
0.823	Intermediate Similarity	NPC15218
0.8205	Intermediate Similarity	NPC470775
0.8205	Intermediate Similarity	NPC98249
0.8205	Intermediate Similarity	NPC58662
0.8205	Intermediate Similarity	NPC53396
0.8205	Intermediate Similarity	NPC176513
0.8198	Intermediate Similarity	NPC258532
0.8182	Intermediate Similarity	NPC474709
0.8182	Intermediate Similarity	NPC24651
0.8182	Intermediate Similarity	NPC183571
0.8182	Intermediate Similarity	NPC476729
0.8167	Intermediate Similarity	NPC312833
0.8142	Intermediate Similarity	NPC322903
0.8136	Intermediate Similarity	NPC284707
0.8115	Intermediate Similarity	NPC181999
0.8108	Intermediate Similarity	NPC4620
0.8103	Intermediate Similarity	NPC94509
0.8099	Intermediate Similarity	NPC473802
0.8083	Intermediate Similarity	NPC472401
0.808	Intermediate Similarity	NPC470185
0.807	Intermediate Similarity	NPC273433
0.8065	Intermediate Similarity	NPC476851
0.8053	Intermediate Similarity	NPC112780
0.8053	Intermediate Similarity	NPC474716
0.8051	Intermediate Similarity	NPC478204
0.8049	Intermediate Similarity	NPC470780
0.8036	Intermediate Similarity	NPC220964
0.8036	Intermediate Similarity	NPC475676
0.8034	Intermediate Similarity	NPC473798
0.8033	Intermediate Similarity	NPC473919
0.8033	Intermediate Similarity	NPC473709
0.8033	Intermediate Similarity	NPC470922
0.8018	Intermediate Similarity	NPC472754
0.8017	Intermediate Similarity	NPC269530
0.8017	Intermediate Similarity	NPC471933
0.8017	Intermediate Similarity	NPC19464
0.8	Intermediate Similarity	NPC472214
0.8	Intermediate Similarity	NPC471128
0.8	Intermediate Similarity	NPC476852
0.8	Intermediate Similarity	NPC145182
0.8	Intermediate Similarity	NPC474718
0.8	Intermediate Similarity	NPC157252
0.8	Intermediate Similarity	NPC472215
0.8	Intermediate Similarity	NPC475134
0.8	Intermediate Similarity	NPC475563
0.8	Intermediate Similarity	NPC5103
0.8	Intermediate Similarity	NPC471126
0.7984	Intermediate Similarity	NPC476859
0.7984	Intermediate Similarity	NPC236999
0.7983	Intermediate Similarity	NPC478205
0.7983	Intermediate Similarity	NPC17772
0.7983	Intermediate Similarity	NPC478206
0.7983	Intermediate Similarity	NPC476714
0.7983	Intermediate Similarity	NPC108581
0.7982	Intermediate Similarity	NPC476479
0.7967	Intermediate Similarity	NPC471939
0.7966	Intermediate Similarity	NPC96312
0.7966	Intermediate Similarity	NPC40632
0.7966	Intermediate Similarity	NPC89929
0.7966	Intermediate Similarity	NPC213084
0.7966	Intermediate Similarity	NPC474046
0.7966	Intermediate Similarity	NPC470628
0.7966	Intermediate Similarity	NPC190185
0.7966	Intermediate Similarity	NPC179626
0.7966	Intermediate Similarity	NPC259306
0.7966	Intermediate Similarity	NPC251236
0.7966	Intermediate Similarity	NPC328374
0.7965	Intermediate Similarity	NPC123726
0.7965	Intermediate Similarity	NPC103088
0.7965	Intermediate Similarity	NPC470979
0.7965	Intermediate Similarity	NPC470975
0.7965	Intermediate Similarity	NPC284365
0.7949	Intermediate Similarity	NPC469496
0.7949	Intermediate Similarity	NPC469463
0.7949	Intermediate Similarity	NPC159333
0.7949	Intermediate Similarity	NPC469454
0.7946	Intermediate Similarity	NPC472755
0.7934	Intermediate Similarity	NPC52839
0.7934	Intermediate Similarity	NPC477046
0.7934	Intermediate Similarity	NPC102822
0.7931	Intermediate Similarity	NPC473921
0.7931	Intermediate Similarity	NPC475668
0.7931	Intermediate Similarity	NPC475480
0.7928	Intermediate Similarity	NPC98225
0.7928	Intermediate Similarity	NPC472753
0.792	Intermediate Similarity	NPC476854
0.7917	Intermediate Similarity	NPC472667
0.7913	Intermediate Similarity	NPC471934
0.7913	Intermediate Similarity	NPC474243
0.7913	Intermediate Similarity	NPC469370
0.7903	Intermediate Similarity	NPC471940
0.7903	Intermediate Similarity	NPC476008
0.7899	Intermediate Similarity	NPC97908
0.7899	Intermediate Similarity	NPC122033
0.7899	Intermediate Similarity	NPC13713
0.7899	Intermediate Similarity	NPC287343
0.7899	Intermediate Similarity	NPC474654
0.7899	Intermediate Similarity	NPC470854
0.7899	Intermediate Similarity	NPC146432
0.7899	Intermediate Similarity	NPC470778
0.7895	Intermediate Similarity	NPC67321
0.7895	Intermediate Similarity	NPC180744
0.7895	Intermediate Similarity	NPC187435
0.7895	Intermediate Similarity	NPC477513
0.7895	Intermediate Similarity	NPC143609
0.789	Intermediate Similarity	NPC476315
0.7881	Intermediate Similarity	NPC470919
0.7881	Intermediate Similarity	NPC117712
0.7881	Intermediate Similarity	NPC299849
0.7881	Intermediate Similarity	NPC469877
0.7876	Intermediate Similarity	NPC477127
0.7876	Intermediate Similarity	NPC472756
0.7869	Intermediate Similarity	NPC310035
0.7869	Intermediate Similarity	NPC162009
0.7869	Intermediate Similarity	NPC188222
0.7869	Intermediate Similarity	NPC282003
0.7869	Intermediate Similarity	NPC257017
0.7857	Intermediate Similarity	NPC475389
0.7857	Intermediate Similarity	NPC476855
0.7857	Intermediate Similarity	NPC476081
0.7857	Intermediate Similarity	NPC473838
0.7851	Intermediate Similarity	NPC317635
0.7851	Intermediate Similarity	NPC109607
0.7851	Intermediate Similarity	NPC329008
0.7851	Intermediate Similarity	NPC251226
0.7851	Intermediate Similarity	NPC472004
0.7851	Intermediate Similarity	NPC143755
0.7851	Intermediate Similarity	NPC107338
0.7845	Intermediate Similarity	NPC478209
0.7845	Intermediate Similarity	NPC253906
0.7838	Intermediate Similarity	NPC475949
0.7833	Intermediate Similarity	NPC251310
0.7833	Intermediate Similarity	NPC297179
0.7833	Intermediate Similarity	NPC171905
0.7833	Intermediate Similarity	NPC472758
0.7833	Intermediate Similarity	NPC240509
0.7833	Intermediate Similarity	NPC471125
0.7833	Intermediate Similarity	NPC472397

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 NPC476711 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	1933
0.2-0.3	3696
0.3-0.4	2194
0.4-0.5	663
0.5-0.6	305
0.6-0.7	140
0.7-0.8	6
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
0.7672	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4225	Approved
0.7395	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7115	Discovery
0.7311	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD6319	Approved
0.7273	Intermediate Similarity	NPD6698	Approved
0.7273	Intermediate Similarity	NPD46	Approved
0.7231	Intermediate Similarity	NPD7319	Approved
0.7188	Intermediate Similarity	NPD7492	Approved
0.7177	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6373	Approved
0.7167	Intermediate Similarity	NPD6372	Approved
0.7155	Intermediate Similarity	NPD5344	Discontinued
0.7143	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6059	Approved
0.7132	Intermediate Similarity	NPD6616	Approved
0.7131	Intermediate Similarity	NPD8297	Approved
0.7109	Intermediate Similarity	NPD8328	Phase 3
0.7107	Intermediate Similarity	NPD6371	Approved
0.7087	Intermediate Similarity	NPD8517	Approved
0.7087	Intermediate Similarity	NPD6921	Approved
0.7087	Intermediate Similarity	NPD8516	Approved
0.7087	Intermediate Similarity	NPD8513	Phase 3
0.7087	Intermediate Similarity	NPD8515	Approved
0.7083	Intermediate Similarity	NPD6686	Approved
0.7077	Intermediate Similarity	NPD8293	Discontinued
0.7077	Intermediate Similarity	NPD7078	Approved
0.7059	Intermediate Similarity	NPD6675	Approved
0.7059	Intermediate Similarity	NPD7128	Approved
0.7059	Intermediate Similarity	NPD5739	Approved
0.7059	Intermediate Similarity	NPD6402	Approved
0.7054	Intermediate Similarity	NPD7983	Approved
0.7049	Intermediate Similarity	NPD6649	Approved
0.7049	Intermediate Similarity	NPD6650	Approved
0.7031	Intermediate Similarity	NPD6370	Approved
0.7023	Intermediate Similarity	NPD7736	Approved
0.7	Intermediate Similarity	NPD7507	Approved
0.6991	Remote Similarity	NPD5778	Approved
0.6991	Remote Similarity	NPD5779	Approved
0.6983	Remote Similarity	NPD7638	Approved
0.6953	Remote Similarity	NPD6016	Approved
0.6953	Remote Similarity	NPD6015	Approved
0.6942	Remote Similarity	NPD6899	Approved
0.6942	Remote Similarity	NPD6881	Approved
0.6942	Remote Similarity	NPD7320	Approved
0.6923	Remote Similarity	NPD6648	Approved
0.6923	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD7639	Approved
0.6917	Remote Similarity	NPD6008	Approved
0.6911	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5988	Approved
0.687	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1700	Approved
0.686	Remote Similarity	NPD5701	Approved
0.686	Remote Similarity	NPD5697	Approved
0.6855	Remote Similarity	NPD6882	Approved
0.6846	Remote Similarity	NPD7604	Phase 2
0.6829	Remote Similarity	NPD7290	Approved
0.6829	Remote Similarity	NPD7102	Approved
0.6829	Remote Similarity	NPD6883	Approved
0.6818	Remote Similarity	NPD8074	Phase 3
0.6818	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4632	Approved
0.6783	Remote Similarity	NPD5282	Discontinued
0.6774	Remote Similarity	NPD8130	Phase 1
0.6774	Remote Similarity	NPD6869	Approved
0.6774	Remote Similarity	NPD6847	Approved
0.6774	Remote Similarity	NPD6617	Approved
0.6772	Remote Similarity	NPD6009	Approved
0.6754	Remote Similarity	NPD6411	Approved
0.6748	Remote Similarity	NPD6012	Approved
0.6748	Remote Similarity	NPD6013	Approved
0.6748	Remote Similarity	NPD6014	Approved
0.6692	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6642	Remote Similarity	NPD6033	Approved
0.664	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6336	Discontinued
0.6609	Remote Similarity	NPD7637	Suspended
0.6589	Remote Similarity	NPD7327	Approved
0.6589	Remote Similarity	NPD7328	Approved
0.6587	Remote Similarity	NPD6053	Discontinued
0.6579	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6101	Approved
0.656	Remote Similarity	NPD4634	Approved
0.6552	Remote Similarity	NPD6399	Phase 3
0.6538	Remote Similarity	NPD7516	Approved
0.6535	Remote Similarity	NPD8133	Approved
0.65	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD7260	Phase 2
0.648	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4755	Approved
0.6471	Remote Similarity	NPD6084	Phase 2
0.6471	Remote Similarity	NPD6083	Phase 2
0.6439	Remote Similarity	NPD8378	Approved
0.6439	Remote Similarity	NPD8033	Approved
0.6439	Remote Similarity	NPD8296	Approved
0.6439	Remote Similarity	NPD8379	Approved
0.6439	Remote Similarity	NPD8380	Approved
0.6439	Remote Similarity	NPD8335	Approved
0.6435	Remote Similarity	NPD1695	Approved
0.6434	Remote Similarity	NPD6274	Approved
0.6412	Remote Similarity	NPD7101	Approved
0.6412	Remote Similarity	NPD7100	Approved
0.6393	Remote Similarity	NPD7632	Discontinued
0.6393	Remote Similarity	NPD5211	Phase 2
0.6387	Remote Similarity	NPD7839	Suspended
0.6379	Remote Similarity	NPD5785	Approved
0.6364	Remote Similarity	NPD8294	Approved
0.6364	Remote Similarity	NPD4700	Approved
0.6364	Remote Similarity	NPD8377	Approved
0.6364	Remote Similarity	NPD5285	Approved
0.6364	Remote Similarity	NPD5286	Approved
0.6364	Remote Similarity	NPD4696	Approved
0.6336	Remote Similarity	NPD6335	Approved
0.6333	Remote Similarity	NPD7902	Approved
0.6331	Remote Similarity	NPD6845	Suspended
0.6316	Remote Similarity	NPD6909	Approved
0.6316	Remote Similarity	NPD6908	Approved
0.6316	Remote Similarity	NPD5786	Approved
0.6303	Remote Similarity	NPD5695	Phase 3
0.629	Remote Similarity	NPD5141	Approved
0.6281	Remote Similarity	NPD5696	Approved
0.6281	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5225	Approved
0.626	Remote Similarity	NPD5224	Approved
0.626	Remote Similarity	NPD6317	Approved
0.626	Remote Similarity	NPD5226	Approved
0.626	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.624	Remote Similarity	NPD4767	Approved
0.624	Remote Similarity	NPD4768	Approved
0.6228	Remote Similarity	NPD1694	Approved
0.6222	Remote Similarity	NPD7642	Approved
0.6218	Remote Similarity	NPD7748	Approved
0.6212	Remote Similarity	NPD6314	Approved
0.6212	Remote Similarity	NPD6313	Approved
0.621	Remote Similarity	NPD5174	Approved
0.621	Remote Similarity	NPD5175	Approved
0.6197	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD7503	Approved
0.6194	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6412	Phase 2
0.6186	Remote Similarity	NPD8035	Phase 2
0.6186	Remote Similarity	NPD8034	Phase 2
0.6186	Remote Similarity	NPD7515	Phase 2
0.6183	Remote Similarity	NPD6868	Approved
0.6179	Remote Similarity	NPD5223	Approved
0.6161	Remote Similarity	NPD5369	Approved
0.6154	Remote Similarity	NPD5328	Approved
0.6142	Remote Similarity	NPD4730	Approved
0.6142	Remote Similarity	NPD4729	Approved
0.614	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD8451	Approved
0.6131	Remote Similarity	NPD8273	Phase 1
0.6127	Remote Similarity	NPD8415	Approved
0.6121	Remote Similarity	NPD7524	Approved
0.6121	Remote Similarity	NPD4251	Approved
0.6121	Remote Similarity	NPD4250	Approved
0.6116	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD5222	Approved
0.6116	Remote Similarity	NPD5221	Approved
0.6106	Remote Similarity	NPD6435	Approved
0.6106	Remote Similarity	NPD4270	Approved
0.6106	Remote Similarity	NPD4269	Approved
0.6103	Remote Similarity	NPD7830	Approved
0.6103	Remote Similarity	NPD7829	Approved
0.6102	Remote Similarity	NPD3168	Discontinued
0.6087	Remote Similarity	NPD8448	Approved
0.6083	Remote Similarity	NPD7900	Approved
0.6083	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.608	Remote Similarity	NPD4754	Approved
0.6071	Remote Similarity	NPD8407	Phase 2
0.6068	Remote Similarity	NPD6672	Approved
0.6068	Remote Similarity	NPD5737	Approved
0.6066	Remote Similarity	NPD5173	Approved
0.6053	Remote Similarity	NPD6695	Phase 3
0.6053	Remote Similarity	NPD7154	Phase 3
0.605	Remote Similarity	NPD6079	Approved
0.605	Remote Similarity	NPD5693	Phase 1
0.6047	Remote Similarity	NPD5249	Phase 3
0.6047	Remote Similarity	NPD5247	Approved
0.6047	Remote Similarity	NPD5251	Approved
0.6047	Remote Similarity	NPD5250	Approved
0.6047	Remote Similarity	NPD5248	Approved
0.6034	Remote Similarity	NPD4249	Approved
0.6034	Remote Similarity	NPD3618	Phase 1
0.6033	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5128	Approved
0.6	Remote Similarity	NPD4786	Approved
0.5988	Remote Similarity	NPD8368	Discontinued
0.5965	Remote Similarity	NPD3667	Approved
0.5957	Remote Similarity	NPD5956	Approved
0.5957	Remote Similarity	NPD8390	Approved
0.5957	Remote Similarity	NPD8392	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