NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	486.23
Volume:	487.269
LogP:	2.486
LogD:	1.412
LogS:	-4.047
# Rotatable Bonds:	4
TPSA:	112.27
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.391
Synthetic Accessibility Score:	6.507
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.294
MDCK Permeability:	5.0088005082216114e-05
Pgp-inhibitor:	0.237
Pgp-substrate:	0.915
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.058

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.76
Plasma Protein Binding (PPB):	65.6400146484375%
Volume Distribution (VD):	1.694
Pgp-substrate:	39.137176513671875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.665
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.737
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.477
CYP3A4-substrate:	0.611

ADMET: Excretion

Clearance (CL):	8.45
Half-life (T1/2):	0.173

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.45
Drug-inuced Liver Injury (DILI):	0.823
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.994
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.137
Carcinogencity:	0.598
Eye Corrosion:	0.037
Eye Irritation:	0.036
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC477405

Natural Product ID:	NPC477405
*Common Name:**	6-Hydroxyangolensic acid methyl ester
IUPAC Name:	methyl 2-[(1S,3S,7R,8R,12S,13S)-13-(furan-3-yl)-6,6,8,12-tetramethyl-17-methylidene-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.01,12.03,8]heptadecan-7-yl]-2-hydroxyacetate
Synonyms:
Standard InCHIKey:	GOYZKWCPWBKPIG-RNKBQGBYSA-N
Standard InCHI:	InChI=1S/C27H34O8/c1-14-16-7-9-25(4)22(15-8-10-33-13-15)34-19(29)12-27(14,25)35-18-11-17(28)24(2,3)21(26(16,18)5)20(30)23(31)32-6/h8,10,13,16,18,20-22,30H,1,7,9,11-12H2,2-6H3/t16?,18-,20?,21-,22-,25-,26-,27-/m0/s1
SMILES:	C[C@@]12CCC3C(=C)[C@]1(CC(=O)O[C@H]2C4=COC=C4)O[C@@H]5[C@]3([C@H](C(C(=O)C5)(C)C)C(C(=O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	6708540
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	exocarp	n.a.	DOI[10.1021/jo00172a004]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444710]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[19299148]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Mengla County, Yunnan Province, China	2005-AUG	PMID[21401117]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21401117]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[30335380]
NPO20633	Lansium domesticum	Species	Meliaceae	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	2

Activity Type	# Activity
Individual Protein	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	20	ug/ml	PMID[19299148]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	23.65	%	PMID[23571415]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	61.1	%	PMID[23571415]

☑ 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 NPC477405 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	359
0.1-0.2	1384
0.2-0.3	3188
0.3-0.4	5291
0.4-0.5	9894
0.5-0.6	10285
0.6-0.7	8911
0.7-0.8	2889
0.8-0.85	283
0.85-0.9	122
0.9-0.95	81
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC276551
0.9804	High Similarity	NPC69028
0.9742	High Similarity	NPC470875
0.974	High Similarity	NPC469338
0.974	High Similarity	NPC292389
0.9679	High Similarity	NPC472282
0.9677	High Similarity	NPC469849
0.9677	High Similarity	NPC470940
0.9675	High Similarity	NPC263432
0.9618	High Similarity	NPC471397
0.961	High Similarity	NPC477402
0.9554	High Similarity	NPC472774
0.9554	High Similarity	NPC472775
0.9554	High Similarity	NPC173516
0.9551	High Similarity	NPC476857
0.9551	High Similarity	NPC476856
0.9551	High Similarity	NPC476858
0.9548	High Similarity	NPC329938
0.9548	High Similarity	NPC82851
0.9494	High Similarity	NPC160651
0.9487	High Similarity	NPC472773
0.9484	High Similarity	NPC25255
0.9481	High Similarity	NPC45101
0.9481	High Similarity	NPC249021
0.9477	High Similarity	NPC469336
0.943	High Similarity	NPC476850
0.943	High Similarity	NPC476861
0.943	High Similarity	NPC476853
0.9427	High Similarity	NPC123088
0.9423	High Similarity	NPC5079
0.9423	High Similarity	NPC472771
0.9423	High Similarity	NPC200782
0.9423	High Similarity	NPC193798
0.9419	High Similarity	NPC477403
0.9412	High Similarity	NPC178932
0.9367	High Similarity	NPC23387
0.9363	High Similarity	NPC39986
0.9363	High Similarity	NPC134254
0.9363	High Similarity	NPC302369
0.9363	High Similarity	NPC51568
0.9363	High Similarity	NPC234660
0.9359	High Similarity	NPC335761
0.9355	High Similarity	NPC472772
0.9355	High Similarity	NPC472283
0.9351	High Similarity	NPC281258
0.9351	High Similarity	NPC264943
0.9342	High Similarity	NPC477404
0.9342	High Similarity	NPC196864
0.9313	High Similarity	NPC82602
0.9304	High Similarity	NPC271657
0.9304	High Similarity	NPC476860
0.9299	High Similarity	NPC207978
0.9299	High Similarity	NPC470939
0.9299	High Similarity	NPC117986
0.9295	High Similarity	NPC475967
0.929	High Similarity	NPC469485
0.9286	High Similarity	NPC282445
0.925	High Similarity	NPC271235
0.9245	High Similarity	NPC475779
0.9236	High Similarity	NPC472653
0.9236	High Similarity	NPC305016
0.9231	High Similarity	NPC173544
0.9231	High Similarity	NPC286722
0.9226	High Similarity	NPC44675
0.9226	High Similarity	NPC214541
0.9221	High Similarity	NPC476201
0.9221	High Similarity	NPC469503
0.9216	High Similarity	NPC469335
0.9216	High Similarity	NPC159927
0.9187	High Similarity	NPC472651
0.9182	High Similarity	NPC470182
0.9177	High Similarity	NPC211777
0.9177	High Similarity	NPC290400
0.9177	High Similarity	NPC18347
0.9177	High Similarity	NPC149896
0.9177	High Similarity	NPC96443
0.9172	High Similarity	NPC307383
0.9172	High Similarity	NPC475295
0.9172	High Similarity	NPC473473
0.9172	High Similarity	NPC237155
0.9167	High Similarity	NPC60973
0.9167	High Similarity	NPC107646
0.9167	High Similarity	NPC209364
0.9136	High Similarity	NPC169299
0.9136	High Similarity	NPC160818
0.913	High Similarity	NPC472652
0.9125	High Similarity	NPC97574
0.9125	High Similarity	NPC93172
0.9119	High Similarity	NPC198047
0.9119	High Similarity	NPC419
0.9114	High Similarity	NPC475381
0.9108	High Similarity	NPC36655
0.9108	High Similarity	NPC167142
0.9108	High Similarity	NPC261597
0.9103	High Similarity	NPC469850
0.9103	High Similarity	NPC476262
0.9097	High Similarity	NPC44577
0.9091	High Similarity	NPC476122
0.9068	High Similarity	NPC473753
0.9068	High Similarity	NPC473766
0.9051	High Similarity	NPC262872
0.9045	High Similarity	NPC263265
0.9045	High Similarity	NPC126723
0.9024	High Similarity	NPC471437
0.9006	High Similarity	NPC121995
0.9	High Similarity	NPC476197
0.9	High Similarity	NPC663
0.9	High Similarity	NPC224394
0.8994	High Similarity	NPC470789
0.8994	High Similarity	NPC191828
0.8987	High Similarity	NPC299038
0.8987	High Similarity	NPC187149
0.8981	High Similarity	NPC35000
0.8974	High Similarity	NPC75906
0.8968	High Similarity	NPC46551
0.8954	High Similarity	NPC262198
0.8951	High Similarity	NPC100333
0.8938	High Similarity	NPC188649
0.8938	High Similarity	NPC18986
0.8917	High Similarity	NPC30222
0.8916	High Similarity	NPC478177
0.8903	High Similarity	NPC69647
0.8903	High Similarity	NPC125182
0.8902	High Similarity	NPC285227
0.8896	High Similarity	NPC472765
0.8896	High Similarity	NPC470941
0.8896	High Similarity	NPC472766
0.8882	High Similarity	NPC469846
0.8882	High Similarity	NPC288602
0.8882	High Similarity	NPC88841
0.8875	High Similarity	NPC287559
0.8868	High Similarity	NPC472778
0.8868	High Similarity	NPC472777
0.8868	High Similarity	NPC472776
0.8861	High Similarity	NPC92979
0.8855	High Similarity	NPC262386
0.8841	High Similarity	NPC470995
0.8834	High Similarity	NPC472764
0.8827	High Similarity	NPC146991
0.8824	High Similarity	NPC476944
0.882	High Similarity	NPC68848
0.882	High Similarity	NPC472767
0.8812	High Similarity	NPC474611
0.8802	High Similarity	NPC472665
0.8797	High Similarity	NPC57998
0.8795	High Similarity	NPC236004
0.8795	High Similarity	NPC94763
0.879	High Similarity	NPC18135
0.8782	High Similarity	NPC472654
0.8782	High Similarity	NPC195325
0.878	High Similarity	NPC296558
0.8774	High Similarity	NPC255414
0.8773	High Similarity	NPC478178
0.8773	High Similarity	NPC149945
0.8773	High Similarity	NPC472141
0.8766	High Similarity	NPC41182
0.8765	High Similarity	NPC472139
0.8758	High Similarity	NPC243577
0.875	High Similarity	NPC194499
0.875	High Similarity	NPC197137
0.875	High Similarity	NPC88007
0.8742	High Similarity	NPC75310
0.8734	High Similarity	NPC147168
0.872	High Similarity	NPC270312
0.8701	High Similarity	NPC137295
0.8701	High Similarity	NPC142113
0.8698	High Similarity	NPC470938
0.8696	High Similarity	NPC475226
0.8696	High Similarity	NPC473368
0.8693	High Similarity	NPC121158
0.8688	High Similarity	NPC41880
0.8683	High Similarity	NPC471632
0.8675	High Similarity	NPC159232
0.8671	High Similarity	NPC272590
0.8659	High Similarity	NPC214600
0.8655	High Similarity	NPC242068
0.8655	High Similarity	NPC247563
0.8655	High Similarity	NPC105395
0.8654	High Similarity	NPC250228
0.8654	High Similarity	NPC221809
0.865	High Similarity	NPC285567
0.865	High Similarity	NPC165218
0.865	High Similarity	NPC283209
0.8645	High Similarity	NPC5676
0.8636	High Similarity	NPC476946
0.8634	High Similarity	NPC195954
0.8625	High Similarity	NPC141538
0.8625	High Similarity	NPC296807
0.8625	High Similarity	NPC155939
0.8616	High Similarity	NPC33938
0.8616	High Similarity	NPC121615
0.8616	High Similarity	NPC268905
0.8616	High Similarity	NPC475777
0.8616	High Similarity	NPC294511
0.8614	High Similarity	NPC302392
0.8608	High Similarity	NPC470997
0.8608	High Similarity	NPC156189
0.8606	High Similarity	NPC476224
0.8606	High Similarity	NPC478179
0.8598	High Similarity	NPC56358

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 NPC477405 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	1005
0.2-0.3	2176
0.3-0.4	2594
0.4-0.5	1854
0.5-0.6	886
0.6-0.7	286
0.7-0.8	41
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8596	High Similarity	NPD8434	Phase 2
0.8509	High Similarity	NPD5761	Phase 2
0.8509	High Similarity	NPD5760	Phase 2
0.8193	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD6764	Approved
0.7886	Intermediate Similarity	NPD6765	Approved
0.7738	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD6784	Approved
0.7709	Intermediate Similarity	NPD6785	Approved
0.7706	Intermediate Similarity	NPD7075	Discontinued
0.7584	Intermediate Similarity	NPD6559	Discontinued
0.756	Intermediate Similarity	NPD6599	Discontinued
0.7546	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6801	Discontinued
0.7418	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5494	Approved
0.7412	Intermediate Similarity	NPD7411	Suspended
0.7403	Intermediate Similarity	NPD8312	Approved
0.7403	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD5402	Approved
0.7384	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8404	Phase 2
0.7353	Intermediate Similarity	NPD4380	Phase 2
0.7345	Intermediate Similarity	NPD6166	Phase 2
0.7345	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6799	Approved
0.7299	Intermediate Similarity	NPD3749	Approved
0.7299	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3226	Approved
0.7283	Intermediate Similarity	NPD3817	Phase 2
0.7283	Intermediate Similarity	NPD8150	Discontinued
0.7278	Intermediate Similarity	NPD5403	Approved
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5401	Approved
0.7256	Intermediate Similarity	NPD1471	Phase 3
0.7241	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5844	Phase 1
0.7198	Intermediate Similarity	NPD7251	Discontinued
0.7182	Intermediate Similarity	NPD7074	Phase 3
0.7176	Intermediate Similarity	NPD920	Approved
0.7175	Intermediate Similarity	NPD1247	Approved
0.7175	Intermediate Similarity	NPD8127	Discontinued
0.7169	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7799	Discontinued
0.7167	Intermediate Similarity	NPD3818	Discontinued
0.7159	Intermediate Similarity	NPD919	Approved
0.7158	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7808	Phase 3
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7236	Approved
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD3882	Suspended
0.7127	Intermediate Similarity	NPD7054	Approved
0.7126	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6273	Approved
0.7113	Intermediate Similarity	NPD7435	Discontinued
0.7111	Intermediate Similarity	NPD7473	Discontinued
0.7088	Intermediate Similarity	NPD7472	Approved
0.7079	Intermediate Similarity	NPD6959	Discontinued
0.7072	Intermediate Similarity	NPD3751	Discontinued
0.7069	Intermediate Similarity	NPD1934	Approved
0.7059	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2346	Discontinued
0.7039	Intermediate Similarity	NPD3787	Discontinued
0.7035	Intermediate Similarity	NPD7239	Suspended
0.7024	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7458	Discontinued
0.6994	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8407	Phase 2
0.6978	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7228	Approved
0.6959	Remote Similarity	NPD6782	Approved
0.6959	Remote Similarity	NPD6780	Approved
0.6959	Remote Similarity	NPD6777	Approved
0.6959	Remote Similarity	NPD6781	Approved
0.6959	Remote Similarity	NPD2533	Approved
0.6959	Remote Similarity	NPD2532	Approved
0.6959	Remote Similarity	NPD6779	Approved
0.6959	Remote Similarity	NPD6778	Approved
0.6959	Remote Similarity	NPD2534	Approved
0.6959	Remote Similarity	NPD6776	Approved
0.6951	Remote Similarity	NPD6355	Discontinued
0.6944	Remote Similarity	NPD6232	Discontinued
0.6941	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7697	Approved
0.6939	Remote Similarity	NPD7698	Approved
0.6939	Remote Similarity	NPD7696	Phase 3
0.6932	Remote Similarity	NPD8455	Phase 2
0.6932	Remote Similarity	NPD1465	Phase 2
0.6928	Remote Similarity	NPD2799	Discontinued
0.6919	Remote Similarity	NPD8368	Discontinued
0.6919	Remote Similarity	NPD7685	Pre-registration
0.6908	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3926	Phase 2
0.6905	Remote Similarity	NPD1549	Phase 2
0.6904	Remote Similarity	NPD8319	Approved
0.6904	Remote Similarity	NPD8320	Phase 1
0.69	Remote Similarity	NPD7874	Approved
0.69	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6100	Approved
0.6886	Remote Similarity	NPD2796	Approved
0.6886	Remote Similarity	NPD6099	Approved
0.6884	Remote Similarity	NPD7701	Phase 2
0.6875	Remote Similarity	NPD37	Approved
0.686	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4967	Phase 2
0.6854	Remote Similarity	NPD4966	Approved
0.6854	Remote Similarity	NPD7768	Phase 2
0.6854	Remote Similarity	NPD4965	Approved
0.6845	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5763	Approved
0.6845	Remote Similarity	NPD5762	Approved
0.6842	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD2801	Approved
0.6828	Remote Similarity	NPD7240	Approved
0.6826	Remote Similarity	NPD7033	Discontinued
0.6824	Remote Similarity	NPD3750	Approved
0.6821	Remote Similarity	NPD8285	Discontinued
0.6818	Remote Similarity	NPD7870	Phase 2
0.6818	Remote Similarity	NPD7871	Phase 2
0.6813	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7907	Approved
0.6796	Remote Similarity	NPD7199	Phase 2
0.6796	Remote Similarity	NPD4111	Phase 1
0.6796	Remote Similarity	NPD4665	Approved
0.6786	Remote Similarity	NPD1551	Phase 2
0.6782	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7801	Approved
0.6782	Remote Similarity	NPD7783	Phase 2
0.6778	Remote Similarity	NPD6234	Discontinued
0.6769	Remote Similarity	NPD7699	Phase 2
0.6769	Remote Similarity	NPD7700	Phase 2
0.6768	Remote Similarity	NPD2313	Discontinued
0.6768	Remote Similarity	NPD3268	Approved
0.6766	Remote Similarity	NPD7097	Phase 1
0.6765	Remote Similarity	NPD1243	Approved
0.6765	Remote Similarity	NPD2800	Approved
0.6754	Remote Similarity	NPD8361	Approved
0.6754	Remote Similarity	NPD8360	Approved
0.6754	Remote Similarity	NPD8435	Approved
0.6748	Remote Similarity	NPD6832	Phase 2
0.6746	Remote Similarity	NPD2344	Approved
0.6726	Remote Similarity	NPD3748	Approved
0.6724	Remote Similarity	NPD1512	Approved
0.6718	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD3057	Approved
0.6707	Remote Similarity	NPD7095	Approved
0.6706	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6534	Approved
0.6701	Remote Similarity	NPD4107	Approved
0.6701	Remote Similarity	NPD6535	Approved
0.6686	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6190	Approved
0.6686	Remote Similarity	NPD2935	Discontinued
0.6683	Remote Similarity	NPD8151	Discontinued
0.6683	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD7057	Phase 3
0.6667	Remote Similarity	NPD6808	Phase 2
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD7058	Phase 2
0.6667	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7229	Phase 3
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6823	Phase 2
0.6633	Remote Similarity	NPD3533	Approved
0.6633	Remote Similarity	NPD2972	Approved
0.6628	Remote Similarity	NPD7003	Approved
0.6627	Remote Similarity	NPD1510	Phase 2
0.6627	Remote Similarity	NPD6233	Phase 2
0.6609	Remote Similarity	NPD1511	Approved
0.6608	Remote Similarity	NPD2424	Discontinued
0.6595	Remote Similarity	NPD2403	Approved
0.6595	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.659	Remote Similarity	NPD2309	Approved
0.659	Remote Similarity	NPD2354	Approved
0.659	Remote Similarity	NPD3887	Approved
0.6584	Remote Similarity	NPD1608	Approved
0.6583	Remote Similarity	NPD4482	Phase 3
0.6576	Remote Similarity	NPD5711	Approved
0.6576	Remote Similarity	NPD5710	Approved
0.6571	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3764	Approved
0.6564	Remote Similarity	NPD3267	Approved
0.6564	Remote Similarity	NPD3266	Approved
0.655	Remote Similarity	NPD6004	Phase 3
0.655	Remote Similarity	NPD6002	Phase 3
0.655	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2491	Approved
0.655	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6005	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