NPASS Compound

Structure

NPC475057 OpenBabel07101718192D 27 29 0 0 1 0 0 0 0 0999 V2000 3.7709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4049 -4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7788 -1.2399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7788 -4.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 -5.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3690 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5029 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6369 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 -4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -2.1910 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.0878 -3.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9049 -5.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6369 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7709 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.0388 -2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.0388 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4049 -6.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 -4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9049 -7.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4049 -6.5981 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 25 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 18 2 0 0 0 0 15 25 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 21 25 1 0 0 0 0 22 23 1 0 0 0 0 23 25 1 0 0 0 0 24 26 2 0 0 0 0 24 27 1 0 0 0 0 M CHG 1 27 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	365.25
Volume:	415.73
LogP:	4.4
LogD:	4.764
LogS:	-5.31
# Rotatable Bonds:	5
TPSA:	40.13
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	4.863
Fsp3:	0.56
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.674
MDCK Permeability:	2.8018932425766252e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.055
30% Bioavailability (F30%):	0.574

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	99.19363403320312%
Volume Distribution (VD):	0.759
Pgp-substrate:	2.472768545150757%

ADMET: Metabolism

CYP1A2-inhibitor:	0.289
CYP1A2-substrate:	0.428
CYP2C19-inhibitor:	0.647
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.9
CYP2C9-substrate:	0.499
CYP2D6-inhibitor:	0.25
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.883
CYP3A4-substrate:	0.595

ADMET: Excretion

Clearance (CL):	1.408
Half-life (T1/2):	0.495

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.579
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.029
Carcinogencity:	0.016
Eye Corrosion:	0.004
Eye Irritation:	0.08
Respiratory Toxicity:	0.14

Download Data

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

Natural Product: NPC475057

Natural Product ID:	NPC475057
*Common Name:**	Homo-Plakotenin Sodium Salt
IUPAC Name:	sodium;(E)-3-[(1R,3R,3aR,4S,5S,7aR)-4,7-diethyl-1,3-dimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoate
Synonyms:	Homo-Plakotenin Sodium Salt
Standard InCHIKey:	RUDLRKWXCVBQCI-YNFFRKDSSA-M
Standard InCHI:	InChI=1S/C25H34O2.Na/c1-6-19-14-21(20-11-9-8-10-12-20)25(7-2,15-18(5)24(26)27)23-17(4)13-16(3)22(19)23;/h8-12,14-17,21-23H,6-7,13H2,1-5H3,(H,26,27);/q;+1/p-1/b18-15+;/t16-,17-,21+,22+,23-,25+;/m1./s1
SMILES:	CCC1=CC(C(C2C1C(CC2C)C)(CC)C=C(C)C(=O)[O-])C3=CC=CC=C3.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494657
PubChem CID:	21775551
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001565] Iridoids 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
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	Palauan	n.a.	PMID[10479343]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11277756]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722494]
NPO4331	Plakortis lita	Species	Plakinidae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	27.8	%	PMID[553370]

☑ 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 NPC475057 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	202
0.1-0.2	1565
0.2-0.3	3158
0.3-0.4	15134
0.4-0.5	17681
0.5-0.6	4197
0.6-0.7	710
0.7-0.8	45
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9884	High Similarity	NPC475023
0.9884	High Similarity	NPC475059
0.9556	High Similarity	NPC133135
0.9556	High Similarity	NPC251579
0.828	Intermediate Similarity	NPC26224
0.8247	Intermediate Similarity	NPC120393
0.8144	Intermediate Similarity	NPC469891
0.8144	Intermediate Similarity	NPC469890
0.8144	Intermediate Similarity	NPC469892
0.8081	Intermediate Similarity	NPC264728
0.8041	Intermediate Similarity	NPC469893
0.7864	Intermediate Similarity	NPC85560
0.7864	Intermediate Similarity	NPC244933
0.7732	Intermediate Similarity	NPC188844
0.7732	Intermediate Similarity	NPC1682
0.7692	Intermediate Similarity	NPC472700
0.7692	Intermediate Similarity	NPC472699
0.7634	Intermediate Similarity	NPC267704
0.7629	Intermediate Similarity	NPC284475
0.7619	Intermediate Similarity	NPC472695
0.7619	Intermediate Similarity	NPC472683
0.7619	Intermediate Similarity	NPC472696
0.7619	Intermediate Similarity	NPC472701
0.76	Intermediate Similarity	NPC239185
0.7593	Intermediate Similarity	NPC287055
0.7593	Intermediate Similarity	NPC306977
0.7593	Intermediate Similarity	NPC206414
0.7593	Intermediate Similarity	NPC242957
0.7556	Intermediate Similarity	NPC50192
0.7551	Intermediate Similarity	NPC153885
0.7551	Intermediate Similarity	NPC59677
0.7525	Intermediate Similarity	NPC75724
0.7525	Intermediate Similarity	NPC134882
0.75	Intermediate Similarity	NPC303245
0.7475	Intermediate Similarity	NPC238219
0.7451	Intermediate Similarity	NPC7435
0.7449	Intermediate Similarity	NPC133461
0.7444	Intermediate Similarity	NPC3672
0.7444	Intermediate Similarity	NPC287790
0.7426	Intermediate Similarity	NPC226041
0.7426	Intermediate Similarity	NPC265220
0.7416	Intermediate Similarity	NPC32203
0.7416	Intermediate Similarity	NPC206800
0.74	Intermediate Similarity	NPC260233
0.7379	Intermediate Similarity	NPC109514
0.7379	Intermediate Similarity	NPC476993
0.7374	Intermediate Similarity	NPC155232
0.7374	Intermediate Similarity	NPC323420
0.7368	Intermediate Similarity	NPC53299
0.734	Intermediate Similarity	NPC208183
0.734	Intermediate Similarity	NPC243289
0.7333	Intermediate Similarity	NPC329282
0.7333	Intermediate Similarity	NPC472222
0.7333	Intermediate Similarity	NPC472221
0.7327	Intermediate Similarity	NPC219573
0.7327	Intermediate Similarity	NPC185208
0.732	Intermediate Similarity	NPC157778
0.729	Intermediate Similarity	NPC249811
0.7283	Intermediate Similarity	NPC167577
0.7283	Intermediate Similarity	NPC78517
0.7282	Intermediate Similarity	NPC221825
0.7245	Intermediate Similarity	NPC298115
0.7238	Intermediate Similarity	NPC475939
0.7238	Intermediate Similarity	NPC474866
0.7238	Intermediate Similarity	NPC472691
0.7238	Intermediate Similarity	NPC471829
0.7216	Intermediate Similarity	NPC43945
0.7212	Intermediate Similarity	NPC128248
0.7212	Intermediate Similarity	NPC133809
0.7212	Intermediate Similarity	NPC225079
0.7212	Intermediate Similarity	NPC136810
0.7204	Intermediate Similarity	NPC285716
0.7204	Intermediate Similarity	NPC17408
0.7184	Intermediate Similarity	NPC49994
0.7174	Intermediate Similarity	NPC176228
0.7172	Intermediate Similarity	NPC173413
0.7172	Intermediate Similarity	NPC58872
0.7168	Intermediate Similarity	NPC471936
0.7159	Intermediate Similarity	NPC95289
0.713	Intermediate Similarity	NPC470814
0.7128	Intermediate Similarity	NPC89950
0.7128	Intermediate Similarity	NPC71795
0.7128	Intermediate Similarity	NPC242628
0.7105	Intermediate Similarity	NPC152812
0.7105	Intermediate Similarity	NPC84129
0.71	Intermediate Similarity	NPC125226
0.708	Intermediate Similarity	NPC476476
0.708	Intermediate Similarity	NPC9274
0.7071	Intermediate Similarity	NPC113307
0.7069	Intermediate Similarity	NPC470585
0.7065	Intermediate Similarity	NPC249018
0.7065	Intermediate Similarity	NPC179726
0.7065	Intermediate Similarity	NPC3190
0.7054	Intermediate Similarity	NPC294458
0.7053	Intermediate Similarity	NPC230068
0.7053	Intermediate Similarity	NPC99240
0.7048	Intermediate Similarity	NPC472879
0.7045	Intermediate Similarity	NPC98880
0.7043	Intermediate Similarity	NPC89324
0.7041	Intermediate Similarity	NPC69057
0.7037	Intermediate Similarity	NPC191215
0.7037	Intermediate Similarity	NPC274089
0.7037	Intermediate Similarity	NPC37914
0.703	Intermediate Similarity	NPC77273
0.7027	Intermediate Similarity	NPC280789
0.7019	Intermediate Similarity	NPC179411
0.7018	Intermediate Similarity	NPC470820
0.7009	Intermediate Similarity	NPC50872
0.7	Intermediate Similarity	NPC110420
0.7	Intermediate Similarity	NPC84288
0.7	Intermediate Similarity	NPC54269
0.7	Intermediate Similarity	NPC240108
0.7	Intermediate Similarity	NPC67585
0.7	Intermediate Similarity	NPC213156
0.7	Intermediate Similarity	NPC303967
0.6989	Remote Similarity	NPC103488
0.6979	Remote Similarity	NPC308619
0.6979	Remote Similarity	NPC324835
0.6979	Remote Similarity	NPC127491
0.6972	Remote Similarity	NPC21929
0.6964	Remote Similarity	NPC93287
0.6957	Remote Similarity	NPC175393
0.6939	Remote Similarity	NPC160339
0.6939	Remote Similarity	NPC307
0.6937	Remote Similarity	NPC95126
0.6937	Remote Similarity	NPC133308
0.6937	Remote Similarity	NPC475002
0.6932	Remote Similarity	NPC311343
0.6931	Remote Similarity	NPC86987
0.6916	Remote Similarity	NPC247976
0.6915	Remote Similarity	NPC159661
0.6915	Remote Similarity	NPC151405
0.6915	Remote Similarity	NPC190211
0.6915	Remote Similarity	NPC139901
0.6911	Remote Similarity	NPC475138
0.6909	Remote Similarity	NPC470252
0.6907	Remote Similarity	NPC44546
0.6903	Remote Similarity	NPC471721
0.6897	Remote Similarity	NPC178527
0.6897	Remote Similarity	NPC472697
0.6897	Remote Similarity	NPC472698
0.6889	Remote Similarity	NPC155429
0.6889	Remote Similarity	NPC326200
0.6887	Remote Similarity	NPC245927
0.6887	Remote Similarity	NPC469481
0.6881	Remote Similarity	NPC94751
0.6881	Remote Similarity	NPC142326
0.6875	Remote Similarity	NPC218855
0.6875	Remote Similarity	NPC103387
0.6875	Remote Similarity	NPC66208
0.6869	Remote Similarity	NPC96625
0.6864	Remote Similarity	NPC37641
0.6864	Remote Similarity	NPC473439
0.6864	Remote Similarity	NPC311175
0.6864	Remote Similarity	NPC300827
0.6855	Remote Similarity	NPC470278
0.6847	Remote Similarity	NPC273837
0.6842	Remote Similarity	NPC246904
0.6842	Remote Similarity	NPC473869
0.6842	Remote Similarity	NPC476357
0.6842	Remote Similarity	NPC93181
0.6842	Remote Similarity	NPC157055
0.6842	Remote Similarity	NPC190567
0.6838	Remote Similarity	NPC204784
0.6837	Remote Similarity	NPC252067
0.6837	Remote Similarity	NPC123476
0.6837	Remote Similarity	NPC475710
0.6833	Remote Similarity	NPC470815
0.6832	Remote Similarity	NPC274455
0.6832	Remote Similarity	NPC86670
0.6832	Remote Similarity	NPC19256
0.6832	Remote Similarity	NPC70940
0.6832	Remote Similarity	NPC277277
0.6825	Remote Similarity	NPC203486
0.6822	Remote Similarity	NPC304873
0.6814	Remote Similarity	NPC477476
0.6814	Remote Similarity	NPC471481
0.6814	Remote Similarity	NPC477475
0.6813	Remote Similarity	NPC1901
0.6809	Remote Similarity	NPC137847
0.6809	Remote Similarity	NPC105197
0.6809	Remote Similarity	NPC76455
0.6807	Remote Similarity	NPC70973
0.6807	Remote Similarity	NPC473749
0.6807	Remote Similarity	NPC475328
0.6804	Remote Similarity	NPC270507
0.6804	Remote Similarity	NPC215008
0.6804	Remote Similarity	NPC44830
0.6803	Remote Similarity	NPC48992
0.68	Remote Similarity	NPC267262
0.68	Remote Similarity	NPC153308
0.6796	Remote Similarity	NPC23453
0.6796	Remote Similarity	NPC289883
0.6792	Remote Similarity	NPC80115
0.6782	Remote Similarity	NPC155172
0.6782	Remote Similarity	NPC32312
0.6782	Remote Similarity	NPC198023
0.6778	Remote Similarity	NPC263385
0.6777	Remote Similarity	NPC473083
0.6774	Remote Similarity	NPC474463

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 NPC475057 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	994
0.2-0.3	1453
0.3-0.4	3562
0.4-0.5	2172
0.5-0.6	676
0.6-0.7	89
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.8316	Intermediate Similarity	NPD6049	Phase 2
0.8316	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD3971	Phase 1
0.7732	Intermediate Similarity	NPD7631	Approved
0.7629	Intermediate Similarity	NPD7609	Phase 3
0.76	Intermediate Similarity	NPD3495	Discontinued
0.7593	Intermediate Similarity	NPD6858	Approved
0.7593	Intermediate Similarity	NPD7094	Approved
0.7416	Intermediate Similarity	NPD9716	Approved
0.7383	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD650	Approved
0.72	Intermediate Similarity	NPD1508	Approved
0.7115	Intermediate Similarity	NPD2066	Phase 3
0.7075	Intermediate Similarity	NPD6647	Phase 2
0.7041	Intermediate Similarity	NPD1087	Approved
0.703	Intermediate Similarity	NPD1088	Approved
0.7019	Intermediate Similarity	NPD5926	Approved
0.7009	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5951	Approved
0.699	Remote Similarity	NPD1843	Approved
0.6957	Remote Similarity	NPD7610	Discontinued
0.69	Remote Similarity	NPD5347	Phase 2
0.69	Remote Similarity	NPD5346	Phase 2
0.6897	Remote Similarity	NPD7009	Phase 2
0.6893	Remote Similarity	NPD1693	Approved
0.6852	Remote Similarity	NPD5909	Discontinued
0.6832	Remote Similarity	NPD3673	Approved
0.6832	Remote Similarity	NPD1090	Approved
0.6832	Remote Similarity	NPD1089	Approved
0.6832	Remote Similarity	NPD1086	Approved
0.6832	Remote Similarity	NPD3672	Approved
0.678	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1929	Approved
0.6759	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1930	Approved
0.6754	Remote Similarity	NPD7076	Approved
0.6754	Remote Similarity	NPD7077	Approved
0.6733	Remote Similarity	NPD800	Approved
0.67	Remote Similarity	NPD4793	Discontinued
0.67	Remote Similarity	NPD1282	Approved
0.6696	Remote Similarity	NPD4766	Approved
0.6667	Remote Similarity	NPD1989	Approved
0.6667	Remote Similarity	NPD1673	Approved
0.6639	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD1563	Approved
0.6632	Remote Similarity	NPD225	Approved
0.6632	Remote Similarity	NPD227	Approved
0.6609	Remote Similarity	NPD6010	Discontinued
0.6606	Remote Similarity	NPD5765	Approved
0.6598	Remote Similarity	NPD942	Approved
0.6577	Remote Similarity	NPD6685	Approved
0.656	Remote Similarity	NPD7055	Discontinued
0.6535	Remote Similarity	NPD7961	Discontinued
0.6514	Remote Similarity	NPD1932	Approved
0.65	Remote Similarity	NPD2932	Approved
0.6495	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5736	Approved
0.6476	Remote Similarity	NPD1202	Approved
0.646	Remote Similarity	NPD2329	Discontinued
0.646	Remote Similarity	NPD2182	Approved
0.6449	Remote Similarity	NPD1564	Approved
0.6449	Remote Similarity	NPD1565	Approved
0.6449	Remote Similarity	NPD1566	Phase 3
0.6442	Remote Similarity	NPD1239	Approved
0.6436	Remote Similarity	NPD9259	Approved
0.6436	Remote Similarity	NPD9257	Approved
0.6429	Remote Similarity	NPD226	Approved
0.6417	Remote Similarity	NPD3024	Approved
0.6417	Remote Similarity	NPD3025	Approved
0.6415	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD689	Discontinued
0.64	Remote Similarity	NPD4544	Approved
0.6396	Remote Similarity	NPD164	Approved
0.6392	Remote Similarity	NPD9490	Approved
0.6383	Remote Similarity	NPD5733	Approved
0.6383	Remote Similarity	NPD4687	Approved
0.6383	Remote Similarity	NPD4058	Approved
0.6364	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3019	Approved
0.6349	Remote Similarity	NPD7084	Phase 3
0.6324	Remote Similarity	NPD7236	Approved
0.6311	Remote Similarity	NPD3026	Approved
0.6311	Remote Similarity	NPD3023	Approved
0.63	Remote Similarity	NPD9491	Approved
0.6292	Remote Similarity	NPD675	Discontinued
0.6279	Remote Similarity	NPD6663	Approved
0.6279	Remote Similarity	NPD8032	Phase 2
0.6271	Remote Similarity	NPD2629	Approved
0.6262	Remote Similarity	NPD4094	Approved
0.6261	Remote Similarity	NPD5237	Approved
0.6261	Remote Similarity	NPD2067	Discontinued
0.6261	Remote Similarity	NPD4234	Approved
0.6261	Remote Similarity	NPD5240	Approved
0.6261	Remote Similarity	NPD5239	Approved
0.6261	Remote Similarity	NPD4233	Approved
0.6261	Remote Similarity	NPD5236	Approved
0.6261	Remote Similarity	NPD5235	Approved
0.626	Remote Similarity	NPD5618	Discontinued
0.625	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4198	Discontinued
0.6216	Remote Similarity	NPD2648	Phase 3
0.6216	Remote Similarity	NPD2196	Discontinued
0.6216	Remote Similarity	NPD2193	Phase 2
0.621	Remote Similarity	NPD6637	Approved
0.6207	Remote Similarity	NPD2201	Approved
0.6198	Remote Similarity	NPD7741	Discontinued
0.6198	Remote Similarity	NPD4479	Discontinued
0.6195	Remote Similarity	NPD5048	Discontinued
0.619	Remote Similarity	NPD9258	Approved
0.619	Remote Similarity	NPD9256	Approved
0.6182	Remote Similarity	NPD1238	Approved
0.617	Remote Similarity	NPD5276	Approved
0.6154	Remote Similarity	NPD6912	Phase 3
0.6154	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4657	Approved
0.6147	Remote Similarity	NPD4655	Approved
0.6142	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5705	Approved
0.614	Remote Similarity	NPD5706	Approved
0.614	Remote Similarity	NPD3134	Approved
0.614	Remote Similarity	NPD5704	Approved
0.6129	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6287	Discontinued
0.6124	Remote Similarity	NPD7008	Discontinued
0.6121	Remote Similarity	NPD1317	Discontinued
0.6117	Remote Similarity	NPD3099	Discontinued
0.6116	Remote Similarity	NPD6065	Approved
0.6102	Remote Similarity	NPD2607	Approved
0.6099	Remote Similarity	NPD7239	Suspended
0.6098	Remote Similarity	NPD4059	Approved
0.6091	Remote Similarity	NPD4813	Approved
0.6091	Remote Similarity	NPD4263	Approved
0.6077	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4803	Discontinued
0.6068	Remote Similarity	NPD3643	Approved
0.6068	Remote Similarity	NPD3644	Approved
0.6068	Remote Similarity	NPD3642	Approved
0.6067	Remote Similarity	NPD4193	Approved
0.6067	Remote Similarity	NPD4192	Approved
0.6067	Remote Similarity	NPD4194	Approved
0.6067	Remote Similarity	NPD4191	Approved
0.6066	Remote Similarity	NPD3091	Approved
0.6064	Remote Similarity	NPD4747	Approved
0.6064	Remote Similarity	NPD4691	Approved
0.6058	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD3093	Approved
0.6045	Remote Similarity	NPD7305	Phase 1
0.6038	Remote Similarity	NPD3344	Approved
0.6038	Remote Similarity	NPD3346	Approved
0.6036	Remote Similarity	NPD7798	Approved
0.6033	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3982	Approved
0.6019	Remote Similarity	NPD1066	Discontinued
0.6019	Remote Similarity	NPD3980	Approved
0.6019	Remote Similarity	NPD2878	Approved
0.6018	Remote Similarity	NPD3357	Discontinued
0.6018	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5691	Approved
0.6	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1101	Approved
0.6	Remote Similarity	NPD3904	Approved
0.6	Remote Similarity	NPD3903	Approved
0.6	Remote Similarity	NPD3979	Approved
0.6	Remote Similarity	NPD3981	Approved
0.5985	Remote Similarity	NPD4140	Approved
0.5984	Remote Similarity	NPD1876	Approved
0.5983	Remote Similarity	NPD5278	Discontinued
0.5983	Remote Similarity	NPD1752	Approved
0.5983	Remote Similarity	NPD1756	Approved
0.5983	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6354	Discontinued
0.598	Remote Similarity	NPD4635	Approved
0.5968	Remote Similarity	NPD3095	Discontinued
0.5968	Remote Similarity	NPD4199	Phase 3
0.5968	Remote Similarity	NPD4626	Approved
0.5963	Remote Similarity	NPD9260	Approved
0.5963	Remote Similarity	NPD4814	Discontinued
0.5962	Remote Similarity	NPD1697	Approved
0.5957	Remote Similarity	NPD4137	Phase 3
0.595	Remote Similarity	NPD3317	Approved
0.5946	Remote Similarity	NPD253	Approved
0.5942	Remote Similarity	NPD8166	Discontinued
0.5941	Remote Similarity	NPD3035	Approved
0.5932	Remote Similarity	NPD5927	Discontinued
0.5929	Remote Similarity	NPD6027	Approved
0.5929	Remote Similarity	NPD6024	Approved
0.5929	Remote Similarity	NPD7478	Approved
0.5929	Remote Similarity	NPD2171	Approved
0.5917	Remote Similarity	NPD3598	Phase 3
0.5917	Remote Similarity	NPD2652	Approved
0.5917	Remote Similarity	NPD2650	Approved
0.5913	Remote Similarity	NPD2192	Approved
0.5913	Remote Similarity	NPD1677	Discontinued
0.5913	Remote Similarity	NPD2197	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