NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	558.25
Volume:	560.021
LogP:	2.975
LogD:	1.993
LogS:	-4.107
# Rotatable Bonds:	11
TPSA:	142.5
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.214
Synthetic Accessibility Score:	6.474
Fsp3:	0.633
Lipinski Rule-of-5:	Accepted
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:	-5.125
MDCK Permeability:	5.604342368314974e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.361
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.736
Plasma Protein Binding (PPB):	45.54334259033203%
Volume Distribution (VD):	1.501
Pgp-substrate:	23.125591278076172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.33
CYP2C19-substrate:	0.163
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.183
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.844
CYP3A4-substrate:	0.558

ADMET: Excretion

Clearance (CL):	2.286
Half-life (T1/2):	0.207

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.532
AMES Toxicity:	0.536
Rat Oral Acute Toxicity:	0.55
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.84
Carcinogencity:	0.442
Eye Corrosion:	0.005
Eye Irritation:	0.072
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC477103

Natural Product ID:	NPC477103
*Common Name:**	[(1S,4S,5R,6R,9S,10R,12R)-6-acetyloxy-7,11-bis(acetyloxymethyl)-5-hydroxy-3,11-dimethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (Z)-2-methylbut-2-enoate
IUPAC Name:	[(1S,4S,5R,6R,9S,10R,12R)-6-acetyloxy-7,11-bis(acetyloxymethyl)-5-hydroxy-3,11-dimethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	RHLQGPBOQGFETH-HXFBSJHASA-N
Standard InCHI:	InChI=1S/C30H38O10/c1-8-15(2)27(35)40-25-16(3)12-29-10-9-22-23(28(22,7)14-38-18(5)32)21(24(29)34)11-20(13-37-17(4)31)26(30(25,29)36)39-19(6)33/h8,11-12,21-23,25-26,36H,9-10,13-14H2,1-7H3/b15-8-/t21-,22+,23-,25-,26+,28?,29+,30+/m0/s1
SMILES:	C/C=C(/C)\C(=O)O[C@H]1C(=C[C@@]23[C@@]1([C@@H](C(=C[C@H](C2=O)[C@H]4[C@H](C4(C)COC(=O)C)CC3)COC(=O)C)OC(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45271602
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	aerial parts	Yuanjiang, Yunnan Province, China	2008-APR	PMID[19438253]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[30730729]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	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
IC50	1
Others	3

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	=	0.92	ug/ml	PMID[19438253]
NPT2	Others	Unspecified	Inhibition	=	21.2	%	PMID[19438253]
NPT2	Others	Unspecified	Inhibition	=	62.8	%	PMID[19438253]
NPT2	Others	Unspecified	Inhibition	=	74.6	%	PMID[19438253]

☑ 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 NPC477103 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	265
0.1-0.2	1606
0.2-0.3	5249
0.3-0.4	9006
0.4-0.5	14459
0.5-0.6	7484
0.6-0.7	3557
0.7-0.8	1000
0.8-0.85	33
0.85-0.9	7
0.9-0.95	27
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9901	High Similarity	NPC477102
0.9612	High Similarity	NPC257240
0.934	High Similarity	NPC46269
0.934	High Similarity	NPC106395
0.9333	High Similarity	NPC287311
0.9252	High Similarity	NPC133677
0.9252	High Similarity	NPC67290
0.9252	High Similarity	NPC138303
0.9245	High Similarity	NPC138757
0.9245	High Similarity	NPC123855
0.9245	High Similarity	NPC76550
0.9231	High Similarity	NPC308191
0.9223	High Similarity	NPC179891
0.9135	High Similarity	NPC473911
0.8962	High Similarity	NPC47951
0.8679	High Similarity	NPC473488
0.8679	High Similarity	NPC475661
0.8598	High Similarity	NPC26617
0.8585	High Similarity	NPC203659
0.8505	High Similarity	NPC223450
0.8496	Intermediate Similarity	NPC475401
0.8491	Intermediate Similarity	NPC110989
0.8421	Intermediate Similarity	NPC477092
0.8411	Intermediate Similarity	NPC474741
0.8411	Intermediate Similarity	NPC100487
0.8407	Intermediate Similarity	NPC475305
0.8396	Intermediate Similarity	NPC225353
0.835	Intermediate Similarity	NPC261341
0.8333	Intermediate Similarity	NPC243998
0.8318	Intermediate Similarity	NPC475871
0.8318	Intermediate Similarity	NPC475945
0.8302	Intermediate Similarity	NPC474742
0.8291	Intermediate Similarity	NPC472399
0.8288	Intermediate Similarity	NPC475495
0.8224	Intermediate Similarity	NPC474747
0.8214	Intermediate Similarity	NPC475277
0.8214	Intermediate Similarity	NPC473522
0.8214	Intermediate Similarity	NPC475391
0.8214	Intermediate Similarity	NPC477093
0.8208	Intermediate Similarity	NPC280963
0.8205	Intermediate Similarity	NPC162009
0.8205	Intermediate Similarity	NPC257017
0.819	Intermediate Similarity	NPC108475
0.819	Intermediate Similarity	NPC157252
0.819	Intermediate Similarity	NPC213947
0.819	Intermediate Similarity	NPC471128
0.819	Intermediate Similarity	NPC471126
0.819	Intermediate Similarity	NPC145182
0.819	Intermediate Similarity	NPC170143
0.8174	Intermediate Similarity	NPC124676
0.8174	Intermediate Similarity	NPC288679
0.8174	Intermediate Similarity	NPC146280
0.8167	Intermediate Similarity	NPC236999
0.8158	Intermediate Similarity	NPC154363
0.8158	Intermediate Similarity	NPC471127
0.8158	Intermediate Similarity	NPC234858
0.8155	Intermediate Similarity	NPC476300
0.8148	Intermediate Similarity	NPC472755
0.8142	Intermediate Similarity	NPC474937
0.8131	Intermediate Similarity	NPC171759
0.8125	Intermediate Similarity	NPC174471
0.8125	Intermediate Similarity	NPC260786
0.8125	Intermediate Similarity	NPC96739
0.8125	Intermediate Similarity	NPC474871
0.812	Intermediate Similarity	NPC52839
0.812	Intermediate Similarity	NPC472401
0.8087	Intermediate Similarity	NPC10721
0.8087	Intermediate Similarity	NPC471145
0.8087	Intermediate Similarity	NPC471146
0.8077	Intermediate Similarity	NPC477131
0.8073	Intermediate Similarity	NPC472756
0.807	Intermediate Similarity	NPC472400
0.807	Intermediate Similarity	NPC474872
0.8067	Intermediate Similarity	NPC144625
0.8056	Intermediate Similarity	NPC472754
0.8056	Intermediate Similarity	NPC149371
0.8056	Intermediate Similarity	NPC86077
0.8053	Intermediate Similarity	NPC151216
0.8053	Intermediate Similarity	NPC221511
0.8053	Intermediate Similarity	NPC89227
0.8053	Intermediate Similarity	NPC170212
0.8053	Intermediate Similarity	NPC17138
0.8053	Intermediate Similarity	NPC101825
0.8053	Intermediate Similarity	NPC215643
0.8053	Intermediate Similarity	NPC265499
0.8051	Intermediate Similarity	NPC19464
0.8034	Intermediate Similarity	NPC475885
0.8019	Intermediate Similarity	NPC477949
0.8017	Intermediate Similarity	NPC472758
0.8017	Intermediate Similarity	NPC171905
0.8017	Intermediate Similarity	NPC471125
0.8017	Intermediate Similarity	NPC472397
0.8	Intermediate Similarity	NPC222307
0.8	Intermediate Similarity	NPC67584
0.8	Intermediate Similarity	NPC54737
0.8	Intermediate Similarity	NPC475900
0.8	Intermediate Similarity	NPC36954
0.7983	Intermediate Similarity	NPC473802
0.7982	Intermediate Similarity	NPC472757
0.7982	Intermediate Similarity	NPC475873
0.7982	Intermediate Similarity	NPC71889
0.7982	Intermediate Similarity	NPC209058
0.7966	Intermediate Similarity	NPC470829
0.7966	Intermediate Similarity	NPC473228
0.7963	Intermediate Similarity	NPC474339
0.7963	Intermediate Similarity	NPC47880
0.7963	Intermediate Similarity	NPC472753
0.7963	Intermediate Similarity	NPC150923
0.7963	Intermediate Similarity	NPC477950
0.7963	Intermediate Similarity	NPC164598
0.7961	Intermediate Similarity	NPC51004
0.7951	Intermediate Similarity	NPC13071
0.7949	Intermediate Similarity	NPC5991
0.7949	Intermediate Similarity	NPC236918
0.7949	Intermediate Similarity	NPC5989
0.7949	Intermediate Similarity	NPC255081
0.7949	Intermediate Similarity	NPC471108
0.7949	Intermediate Similarity	NPC22628
0.7949	Intermediate Similarity	NPC156745
0.7949	Intermediate Similarity	NPC275696
0.7946	Intermediate Similarity	NPC139838
0.7946	Intermediate Similarity	NPC273433
0.7946	Intermediate Similarity	NPC59489
0.7944	Intermediate Similarity	NPC141191
0.7931	Intermediate Similarity	NPC156252
0.7931	Intermediate Similarity	NPC475323
0.7931	Intermediate Similarity	NPC36754
0.7925	Intermediate Similarity	NPC476009
0.7925	Intermediate Similarity	NPC213078
0.7925	Intermediate Similarity	NPC476315
0.7917	Intermediate Similarity	NPC473709
0.7917	Intermediate Similarity	NPC473919
0.7917	Intermediate Similarity	NPC145238
0.7905	Intermediate Similarity	NPC470010
0.7905	Intermediate Similarity	NPC323008
0.7905	Intermediate Similarity	NPC470013
0.7905	Intermediate Similarity	NPC262133
0.7905	Intermediate Similarity	NPC167219
0.7905	Intermediate Similarity	NPC198853
0.7895	Intermediate Similarity	NPC95290
0.7895	Intermediate Similarity	NPC189338
0.789	Intermediate Similarity	NPC474709
0.789	Intermediate Similarity	NPC105725
0.789	Intermediate Similarity	NPC183571
0.7885	Intermediate Similarity	NPC30515
0.7885	Intermediate Similarity	NPC184463
0.7885	Intermediate Similarity	NPC221282
0.7885	Intermediate Similarity	NPC133698
0.7881	Intermediate Similarity	NPC329080
0.7881	Intermediate Similarity	NPC19336
0.7881	Intermediate Similarity	NPC185876
0.7881	Intermediate Similarity	NPC472759
0.7876	Intermediate Similarity	NPC50223
0.787	Intermediate Similarity	NPC288876
0.7869	Intermediate Similarity	NPC172823
0.7869	Intermediate Similarity	NPC270109
0.7864	Intermediate Similarity	NPC307411
0.7863	Intermediate Similarity	NPC13710
0.7863	Intermediate Similarity	NPC161060
0.7863	Intermediate Similarity	NPC475372
0.7851	Intermediate Similarity	NPC471939
0.785	Intermediate Similarity	NPC311904
0.785	Intermediate Similarity	NPC169205
0.785	Intermediate Similarity	NPC161493
0.785	Intermediate Similarity	NPC40812
0.7838	Intermediate Similarity	NPC291643
0.7838	Intermediate Similarity	NPC16313
0.7838	Intermediate Similarity	NPC9303
0.7833	Intermediate Similarity	NPC129992
0.7833	Intermediate Similarity	NPC42747
0.783	Intermediate Similarity	NPC275960
0.783	Intermediate Similarity	NPC52044
0.783	Intermediate Similarity	NPC14961
0.783	Intermediate Similarity	NPC193645
0.783	Intermediate Similarity	NPC304886
0.783	Intermediate Similarity	NPC90121
0.783	Intermediate Similarity	NPC475659
0.783	Intermediate Similarity	NPC48803
0.783	Intermediate Similarity	NPC270013
0.7818	Intermediate Similarity	NPC4620
0.7818	Intermediate Similarity	NPC124881
0.7818	Intermediate Similarity	NPC474165
0.7818	Intermediate Similarity	NPC69171
0.781	Intermediate Similarity	NPC212486
0.781	Intermediate Similarity	NPC308656
0.781	Intermediate Similarity	NPC135776
0.781	Intermediate Similarity	NPC473234
0.781	Intermediate Similarity	NPC473273
0.781	Intermediate Similarity	NPC60386
0.781	Intermediate Similarity	NPC473263
0.781	Intermediate Similarity	NPC475912
0.7807	Intermediate Similarity	NPC475937
0.7807	Intermediate Similarity	NPC158523
0.7797	Intermediate Similarity	NPC180640
0.7797	Intermediate Similarity	NPC472667
0.7797	Intermediate Similarity	NPC312536
0.7788	Intermediate Similarity	NPC475748
0.7787	Intermediate Similarity	NPC471940
0.7778	Intermediate Similarity	NPC471144
0.7778	Intermediate Similarity	NPC221615

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 NPC477103 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	2269
0.2-0.3	3624
0.3-0.4	1955
0.4-0.5	722
0.5-0.6	258
0.6-0.7	38
0.7-0.8	6
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9612	High Similarity	NPD6371	Approved
0.8598	High Similarity	NPD7899	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6698	Approved
0.7619	Intermediate Similarity	NPD46	Approved
0.7524	Intermediate Similarity	NPD1695	Approved
0.7453	Intermediate Similarity	NPD5785	Approved
0.729	Intermediate Similarity	NPD7838	Discovery
0.7241	Intermediate Similarity	NPD6686	Approved
0.7222	Intermediate Similarity	NPD7983	Approved
0.719	Intermediate Similarity	NPD7115	Discovery
0.7091	Intermediate Similarity	NPD5282	Discontinued
0.7019	Intermediate Similarity	NPD5209	Approved
0.7016	Intermediate Similarity	NPD6319	Approved
0.7	Intermediate Similarity	NPD6053	Discontinued
0.6991	Remote Similarity	NPD4225	Approved
0.6981	Remote Similarity	NPD5363	Approved
0.6981	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7319	Approved
0.6875	Remote Similarity	NPD7507	Approved
0.6762	Remote Similarity	NPD5369	Approved
0.6759	Remote Similarity	NPD5786	Approved
0.6724	Remote Similarity	NPD5344	Discontinued
0.6721	Remote Similarity	NPD8297	Approved
0.6698	Remote Similarity	NPD4269	Approved
0.6698	Remote Similarity	NPD4270	Approved
0.6696	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD7492	Approved
0.6639	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6649	Approved
0.6639	Remote Similarity	NPD6650	Approved
0.6639	Remote Similarity	NPD6008	Approved
0.6636	Remote Similarity	NPD5362	Discontinued
0.6615	Remote Similarity	NPD6616	Approved
0.6614	Remote Similarity	NPD6054	Approved
0.6612	Remote Similarity	NPD6372	Approved
0.6612	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6373	Approved
0.6589	Remote Similarity	NPD7642	Approved
0.6589	Remote Similarity	NPD7604	Phase 2
0.6583	Remote Similarity	NPD6412	Phase 2
0.6565	Remote Similarity	NPD7078	Approved
0.6562	Remote Similarity	NPD8513	Phase 3
0.6562	Remote Similarity	NPD8516	Approved
0.6562	Remote Similarity	NPD8517	Approved
0.6562	Remote Similarity	NPD8515	Approved
0.6552	Remote Similarity	NPD7638	Approved
0.6549	Remote Similarity	NPD5779	Approved
0.6549	Remote Similarity	NPD5778	Approved
0.6542	Remote Similarity	NPD6435	Approved
0.6529	Remote Similarity	NPD6899	Approved
0.6529	Remote Similarity	NPD6881	Approved
0.6529	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD7736	Approved
0.6514	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6370	Approved
0.6509	Remote Similarity	NPD4252	Approved
0.65	Remote Similarity	NPD5739	Approved
0.65	Remote Similarity	NPD6402	Approved
0.65	Remote Similarity	NPD7128	Approved
0.65	Remote Similarity	NPD6675	Approved
0.6496	Remote Similarity	NPD7639	Approved
0.6496	Remote Similarity	NPD7640	Approved
0.6496	Remote Similarity	NPD6648	Approved
0.6484	Remote Similarity	NPD6059	Approved
0.6481	Remote Similarity	NPD7154	Phase 3
0.6466	Remote Similarity	NPD6083	Phase 2
0.6466	Remote Similarity	NPD6084	Phase 2
0.6457	Remote Similarity	NPD7327	Approved
0.6457	Remote Similarity	NPD7328	Approved
0.6452	Remote Similarity	NPD6882	Approved
0.6446	Remote Similarity	NPD5697	Approved
0.6446	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD8293	Discontinued
0.6435	Remote Similarity	NPD5695	Phase 3
0.6434	Remote Similarity	NPD7503	Approved
0.6434	Remote Similarity	NPD6015	Approved
0.6434	Remote Similarity	NPD8033	Approved
0.6434	Remote Similarity	NPD6016	Approved
0.6423	Remote Similarity	NPD6883	Approved
0.6423	Remote Similarity	NPD7290	Approved
0.6423	Remote Similarity	NPD4634	Approved
0.6423	Remote Similarity	NPD7102	Approved
0.641	Remote Similarity	NPD5696	Approved
0.6406	Remote Similarity	NPD7516	Approved
0.6404	Remote Similarity	NPD6399	Phase 3
0.6396	Remote Similarity	NPD4250	Approved
0.6396	Remote Similarity	NPD4251	Approved
0.6393	Remote Similarity	NPD7320	Approved
0.6389	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD5988	Approved
0.6378	Remote Similarity	NPD6009	Approved
0.6371	Remote Similarity	NPD6869	Approved
0.6371	Remote Similarity	NPD6847	Approved
0.6371	Remote Similarity	NPD6617	Approved
0.6371	Remote Similarity	NPD8130	Phase 1
0.637	Remote Similarity	NPD7260	Phase 2
0.6364	Remote Similarity	NPD1694	Approved
0.6364	Remote Similarity	NPD8273	Phase 1
0.6357	Remote Similarity	NPD8377	Approved
0.6357	Remote Similarity	NPD8294	Approved
0.6355	Remote Similarity	NPD4820	Approved
0.6355	Remote Similarity	NPD4822	Approved
0.6355	Remote Similarity	NPD4819	Approved
0.6355	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4821	Approved
0.6355	Remote Similarity	NPD5368	Approved
0.6341	Remote Similarity	NPD6013	Approved
0.6341	Remote Similarity	NPD6014	Approved
0.6341	Remote Similarity	NPD6012	Approved
0.6336	Remote Similarity	NPD8328	Phase 3
0.6336	Remote Similarity	NPD7830	Approved
0.6336	Remote Similarity	NPD7829	Approved
0.6321	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8074	Phase 3
0.6316	Remote Similarity	NPD6411	Approved
0.6316	Remote Similarity	NPD7637	Suspended
0.6311	Remote Similarity	NPD5701	Approved
0.6308	Remote Similarity	NPD8296	Approved
0.6308	Remote Similarity	NPD8380	Approved
0.6308	Remote Similarity	NPD5983	Phase 2
0.6308	Remote Similarity	NPD8335	Approved
0.6308	Remote Similarity	NPD8379	Approved
0.6308	Remote Similarity	NPD8378	Approved
0.6306	Remote Similarity	NPD4249	Approved
0.6293	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.627	Remote Similarity	NPD8133	Approved
0.626	Remote Similarity	NPD6011	Approved
0.6259	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD6336	Discontinued
0.6239	Remote Similarity	NPD7839	Suspended
0.6174	Remote Similarity	NPD5693	Phase 1
0.6174	Remote Similarity	NPD5281	Approved
0.6174	Remote Similarity	NPD5284	Approved
0.6168	Remote Similarity	NPD4268	Approved
0.6168	Remote Similarity	NPD4271	Approved
0.6161	Remote Similarity	NPD7334	Approved
0.6161	Remote Similarity	NPD6684	Approved
0.6161	Remote Similarity	NPD5330	Approved
0.6161	Remote Similarity	NPD7146	Approved
0.6161	Remote Similarity	NPD7521	Approved
0.6161	Remote Similarity	NPD6409	Approved
0.614	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6101	Approved
0.6119	Remote Similarity	NPD8451	Approved
0.6116	Remote Similarity	NPD5211	Phase 2
0.6111	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6845	Suspended
0.6083	Remote Similarity	NPD4696	Approved
0.6083	Remote Similarity	NPD5285	Approved
0.6083	Remote Similarity	NPD5286	Approved
0.6077	Remote Similarity	NPD7641	Discontinued
0.6074	Remote Similarity	NPD8448	Approved
0.6061	Remote Similarity	NPD8444	Approved
0.6061	Remote Similarity	NPD6921	Approved
0.6053	Remote Similarity	NPD6903	Approved
0.6053	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7902	Approved
0.605	Remote Similarity	NPD4755	Approved
0.6047	Remote Similarity	NPD6274	Approved
0.6036	Remote Similarity	NPD5331	Approved
0.6036	Remote Similarity	NPD5332	Approved
0.6036	Remote Similarity	NPD6110	Phase 1
0.6031	Remote Similarity	NPD7101	Approved
0.6031	Remote Similarity	NPD7100	Approved
0.6029	Remote Similarity	NPD6033	Approved
0.6017	Remote Similarity	NPD4629	Approved
0.6017	Remote Similarity	NPD5210	Approved
0.6016	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD4790	Discontinued
0.6	Remote Similarity	NPD7500	Approved
0.6	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7632	Discontinued
0.5984	Remote Similarity	NPD4633	Approved
0.5984	Remote Similarity	NPD5224	Approved
0.5984	Remote Similarity	NPD5225	Approved
0.5984	Remote Similarity	NPD5226	Approved
0.5965	Remote Similarity	NPD7524	Approved
0.5954	Remote Similarity	NPD6335	Approved
0.5952	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.595	Remote Similarity	NPD4700	Approved
0.5942	Remote Similarity	NPD8390	Approved
0.5942	Remote Similarity	NPD8392	Approved
0.5942	Remote Similarity	NPD8391	Approved
0.5942	Remote Similarity	NPD5956	Approved
0.5935	Remote Similarity	NPD5174	Approved
0.5935	Remote Similarity	NPD5175	Approved
0.5932	Remote Similarity	NPD7748	Approved
0.5932	Remote Similarity	NPD6001	Approved
0.5926	Remote Similarity	NPD8299	Approved
0.5926	Remote Similarity	NPD8342	Approved
0.5926	Remote Similarity	NPD8340	Approved
0.5926	Remote Similarity	NPD8341	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