NPASS Compound

Structure

NPC155849 OpenBabel07101719252D 23 23 0 0 0 0 0 0 0 0999 V2000 4.4143 -0.6328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0601 -1.7127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6235 4.2954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3264 3.1656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2358 -1.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9010 3.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9010 3.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8019 3.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6235 2.7317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6235 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6479 1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4254 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9010 -0.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9010 -0.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4254 -0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4254 2.7317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8019 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6235 -0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2581 -1.7127 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6123 -0.6328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 23 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 17 2 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 16 19 1 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.24
Volume:	367.614
LogP:	5.619
LogD:	5.001
LogS:	-5.989
# Rotatable Bonds:	3
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.467
Synthetic Accessibility Score:	3.594
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.836
MDCK Permeability:	1.6267253158730455e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.867
30% Bioavailability (F30%):	0.564

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	97.62682342529297%
Volume Distribution (VD):	0.826
Pgp-substrate:	0.7287605404853821%

ADMET: Metabolism

CYP1A2-inhibitor:	0.484
CYP1A2-substrate:	0.598
CYP2C19-inhibitor:	0.466
CYP2C19-substrate:	0.83
CYP2C9-inhibitor:	0.589
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.867
CYP2D6-substrate:	0.582
CYP3A4-inhibitor:	0.354
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	1.67
Half-life (T1/2):	0.431

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.221
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.625
Skin Sensitization:	0.97
Carcinogencity:	0.065
Eye Corrosion:	0.152
Eye Irritation:	0.78
Respiratory Toxicity:	0.46

Download Data

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

Natural Product: NPC155849

Natural Product ID:	NPC155849
*Common Name:**	Sarcophytonolide N
IUPAC Name:	methyl (1Z,3E,7E,11E)-7,11-dimethyl-4-propan-2-ylcyclotetradeca-1,3,7,11-tetraene-1-carboxylate
Synonyms:
Standard InCHIKey:	JAXCRQBPGSFOHJ-ZPASOVNYSA-N
Standard InCHI:	InChI=1S/C21H32O2/c1-16(2)19-13-12-18(4)9-6-8-17(3)10-7-11-20(15-14-19)21(22)23-5/h9-10,14-16H,6-8,11-13H2,1-5H3/b17-10+,18-9+,19-14+,20-15-
SMILES:	CC(C)/C/1=C/C=C(/CC/C=C(C)/CC/C=C(C)/CC1)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2414197
PubChem CID:	71770297
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000008] Cembrane diterpenoids

*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
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10923847]
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23859780]
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	5950.0	nM	PMID[489690]

☑ 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 NPC155849 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	198
0.1-0.2	1777
0.2-0.3	10099
0.3-0.4	17990
0.4-0.5	7671
0.5-0.6	3832
0.6-0.7	994
0.7-0.8	131
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8281	Intermediate Similarity	NPC34883
0.803	Intermediate Similarity	NPC142423
0.803	Intermediate Similarity	NPC308294
0.8	Intermediate Similarity	NPC474758
0.7971	Intermediate Similarity	NPC257618
0.791	Intermediate Similarity	NPC21998
0.7887	Intermediate Similarity	NPC68624
0.7887	Intermediate Similarity	NPC244166
0.7879	Intermediate Similarity	NPC470688
0.7857	Intermediate Similarity	NPC287878
0.7857	Intermediate Similarity	NPC276336
0.7826	Intermediate Similarity	NPC37929
0.7826	Intermediate Similarity	NPC64234
0.7794	Intermediate Similarity	NPC470256
0.7761	Intermediate Similarity	NPC191233
0.7746	Intermediate Similarity	NPC294434
0.7746	Intermediate Similarity	NPC259599
0.7746	Intermediate Similarity	NPC15499
0.7746	Intermediate Similarity	NPC117746
0.7742	Intermediate Similarity	NPC96663
0.7705	Intermediate Similarity	NPC478120
0.7681	Intermediate Similarity	NPC265574
0.7681	Intermediate Similarity	NPC470693
0.7681	Intermediate Similarity	NPC232812
0.7671	Intermediate Similarity	NPC180290
0.7647	Intermediate Similarity	NPC194871
0.7647	Intermediate Similarity	NPC472266
0.7639	Intermediate Similarity	NPC329852
0.7612	Intermediate Similarity	NPC220766
0.76	Intermediate Similarity	NPC474510
0.7576	Intermediate Similarity	NPC217940
0.7571	Intermediate Similarity	NPC469660
0.7571	Intermediate Similarity	NPC67183
0.7538	Intermediate Similarity	NPC79756
0.7536	Intermediate Similarity	NPC313444
0.7534	Intermediate Similarity	NPC27205
0.7532	Intermediate Similarity	NPC16488
0.7532	Intermediate Similarity	NPC170377
0.75	Intermediate Similarity	NPC248125
0.75	Intermediate Similarity	NPC140287
0.75	Intermediate Similarity	NPC476355
0.75	Intermediate Similarity	NPC42470
0.7465	Intermediate Similarity	NPC316185
0.7465	Intermediate Similarity	NPC163003
0.7432	Intermediate Similarity	NPC57744
0.7429	Intermediate Similarity	NPC151481
0.7424	Intermediate Similarity	NPC151648
0.7414	Intermediate Similarity	NPC128280
0.7403	Intermediate Similarity	NPC221231
0.7403	Intermediate Similarity	NPC471326
0.7397	Intermediate Similarity	NPC469414
0.7397	Intermediate Similarity	NPC228978
0.7397	Intermediate Similarity	NPC329826
0.7391	Intermediate Similarity	NPC203335
0.7377	Intermediate Similarity	NPC216407
0.7342	Intermediate Similarity	NPC197903
0.7342	Intermediate Similarity	NPC474424
0.7342	Intermediate Similarity	NPC99395
0.7333	Intermediate Similarity	NPC236338
0.7333	Intermediate Similarity	NPC128276
0.7324	Intermediate Similarity	NPC316029
0.7324	Intermediate Similarity	NPC473361
0.7324	Intermediate Similarity	NPC315285
0.7324	Intermediate Similarity	NPC329904
0.7313	Intermediate Similarity	NPC322457
0.7313	Intermediate Similarity	NPC68110
0.7313	Intermediate Similarity	NPC210303
0.7313	Intermediate Similarity	NPC474658
0.7313	Intermediate Similarity	NPC44343
0.7313	Intermediate Similarity	NPC179087
0.7302	Intermediate Similarity	NPC188789
0.7302	Intermediate Similarity	NPC478117
0.7297	Intermediate Similarity	NPC40353
0.7297	Intermediate Similarity	NPC473223
0.7297	Intermediate Similarity	NPC123360
0.7286	Intermediate Similarity	NPC218477
0.7286	Intermediate Similarity	NPC276290
0.7273	Intermediate Similarity	NPC471325
0.726	Intermediate Similarity	NPC20025
0.726	Intermediate Similarity	NPC315843
0.726	Intermediate Similarity	NPC107654
0.725	Intermediate Similarity	NPC315395
0.725	Intermediate Similarity	NPC316426
0.725	Intermediate Similarity	NPC164393
0.7246	Intermediate Similarity	NPC315115
0.7246	Intermediate Similarity	NPC185587
0.7241	Intermediate Similarity	NPC270706
0.7237	Intermediate Similarity	NPC178277
0.7237	Intermediate Similarity	NPC264227
0.7237	Intermediate Similarity	NPC63649
0.7237	Intermediate Similarity	NPC472965
0.7222	Intermediate Similarity	NPC84038
0.7215	Intermediate Similarity	NPC14575
0.7215	Intermediate Similarity	NPC196487
0.7206	Intermediate Similarity	NPC226066
0.72	Intermediate Similarity	NPC97516
0.72	Intermediate Similarity	NPC41780
0.72	Intermediate Similarity	NPC187568
0.72	Intermediate Similarity	NPC68156
0.72	Intermediate Similarity	NPC316324
0.7183	Intermediate Similarity	NPC476591
0.7183	Intermediate Similarity	NPC473603
0.7183	Intermediate Similarity	NPC88877
0.7183	Intermediate Similarity	NPC476059
0.7167	Intermediate Similarity	NPC135698
0.7162	Intermediate Similarity	NPC65650
0.7123	Intermediate Similarity	NPC238948
0.7123	Intermediate Similarity	NPC269206
0.7123	Intermediate Similarity	NPC215745
0.7123	Intermediate Similarity	NPC58956
0.7123	Intermediate Similarity	NPC295633
0.7123	Intermediate Similarity	NPC135703
0.7123	Intermediate Similarity	NPC474705
0.7123	Intermediate Similarity	NPC12815
0.7105	Intermediate Similarity	NPC471220
0.7105	Intermediate Similarity	NPC93763
0.7105	Intermediate Similarity	NPC108816
0.7101	Intermediate Similarity	NPC182794
0.7101	Intermediate Similarity	NPC471556
0.7101	Intermediate Similarity	NPC133904
0.7097	Intermediate Similarity	NPC151919
0.7097	Intermediate Similarity	NPC170167
0.7089	Intermediate Similarity	NPC474790
0.7089	Intermediate Similarity	NPC475947
0.7089	Intermediate Similarity	NPC474976
0.7083	Intermediate Similarity	NPC475310
0.7083	Intermediate Similarity	NPC315597
0.7077	Intermediate Similarity	NPC293437
0.7077	Intermediate Similarity	NPC249850
0.7067	Intermediate Similarity	NPC4509
0.7067	Intermediate Similarity	NPC235906
0.7051	Intermediate Similarity	NPC325031
0.7051	Intermediate Similarity	NPC40228
0.7037	Intermediate Similarity	NPC122502
0.7037	Intermediate Similarity	NPC234038
0.7031	Intermediate Similarity	NPC173157
0.7031	Intermediate Similarity	NPC228473
0.7031	Intermediate Similarity	NPC477984
0.7027	Intermediate Similarity	NPC470686
0.7015	Intermediate Similarity	NPC19241
0.7013	Intermediate Similarity	NPC469690
0.7013	Intermediate Similarity	NPC469617
0.7013	Intermediate Similarity	NPC471299
0.7013	Intermediate Similarity	NPC270126
0.6986	Remote Similarity	NPC288667
0.6986	Remote Similarity	NPC129665
0.6986	Remote Similarity	NPC186531
0.6986	Remote Similarity	NPC181587
0.6984	Remote Similarity	NPC45283
0.6974	Remote Similarity	NPC476794
0.6974	Remote Similarity	NPC171204
0.6974	Remote Similarity	NPC141789
0.6974	Remote Similarity	NPC7563
0.6974	Remote Similarity	NPC470240
0.6974	Remote Similarity	NPC116177
0.6974	Remote Similarity	NPC320630
0.6974	Remote Similarity	NPC476028
0.6974	Remote Similarity	NPC65603
0.6974	Remote Similarity	NPC315394
0.697	Remote Similarity	NPC21946
0.697	Remote Similarity	NPC254095
0.6962	Remote Similarity	NPC173609
0.6962	Remote Similarity	NPC94200
0.6962	Remote Similarity	NPC200513
0.6962	Remote Similarity	NPC474291
0.6962	Remote Similarity	NPC85772
0.6962	Remote Similarity	NPC35556
0.6962	Remote Similarity	NPC474028
0.6962	Remote Similarity	NPC474439
0.6957	Remote Similarity	NPC329698
0.6951	Remote Similarity	NPC477228
0.6944	Remote Similarity	NPC101622
0.6944	Remote Similarity	NPC269841
0.6935	Remote Similarity	NPC48162
0.6935	Remote Similarity	NPC244452
0.6935	Remote Similarity	NPC148056
0.6933	Remote Similarity	NPC193351
0.6933	Remote Similarity	NPC260396
0.6933	Remote Similarity	NPC138408
0.6933	Remote Similarity	NPC155587
0.6933	Remote Similarity	NPC226669
0.6923	Remote Similarity	NPC160582
0.6923	Remote Similarity	NPC281132
0.6923	Remote Similarity	NPC325977
0.6901	Remote Similarity	NPC225272
0.6901	Remote Similarity	NPC254886
0.6892	Remote Similarity	NPC222244
0.6892	Remote Similarity	NPC16349
0.6892	Remote Similarity	NPC474543
0.6892	Remote Similarity	NPC476490
0.6892	Remote Similarity	NPC238425
0.6892	Remote Similarity	NPC472018
0.6892	Remote Similarity	NPC476489
0.6883	Remote Similarity	NPC299235
0.6883	Remote Similarity	NPC253749
0.6883	Remote Similarity	NPC315765
0.6883	Remote Similarity	NPC267231
0.6875	Remote Similarity	NPC118423
0.6875	Remote Similarity	NPC475989
0.6875	Remote Similarity	NPC322461

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 NPC155849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	2161
0.2-0.3	4369
0.3-0.4	1837
0.4-0.5	450
0.5-0.6	130
0.6-0.7	18
0.7-0.8	4
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
0.75	Intermediate Similarity	NPD6927	Phase 3
0.7397	Intermediate Similarity	NPD8039	Approved
0.7353	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5209	Approved
0.6962	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5343	Approved
0.6667	Remote Similarity	NPD4194	Approved
0.6667	Remote Similarity	NPD4192	Approved
0.6667	Remote Similarity	NPD4193	Approved
0.6667	Remote Similarity	NPD4191	Approved
0.6613	Remote Similarity	NPD4220	Pre-registration
0.6538	Remote Similarity	NPD4756	Discovery
0.6512	Remote Similarity	NPD7838	Discovery
0.6406	Remote Similarity	NPD28	Approved
0.6406	Remote Similarity	NPD29	Approved
0.6393	Remote Similarity	NPD3174	Discontinued
0.6322	Remote Similarity	NPD5785	Approved
0.6322	Remote Similarity	NPD6698	Approved
0.6322	Remote Similarity	NPD46	Approved
0.631	Remote Similarity	NPD1694	Approved
0.623	Remote Similarity	NPD6096	Approved
0.623	Remote Similarity	NPD6097	Approved
0.6196	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4222	Approved
0.6129	Remote Similarity	NPD39	Approved
0.6119	Remote Similarity	NPD3196	Approved
0.6119	Remote Similarity	NPD3194	Approved
0.6119	Remote Similarity	NPD3195	Phase 2
0.6119	Remote Similarity	NPD4266	Approved
0.6118	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD5363	Approved
0.6118	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD3173	Approved
0.6081	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD7331	Phase 2
0.6076	Remote Similarity	NPD1452	Discontinued
0.6071	Remote Similarity	NPD7154	Phase 3
0.6071	Remote Similarity	NPD5362	Discontinued
0.6049	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.597	Remote Similarity	NPD3172	Approved
0.5904	Remote Similarity	NPD4820	Approved
0.5904	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD4819	Approved
0.5904	Remote Similarity	NPD4822	Approved
0.5904	Remote Similarity	NPD4821	Approved
0.5889	Remote Similarity	NPD7983	Approved
0.5882	Remote Similarity	NPD5332	Approved
0.5882	Remote Similarity	NPD5331	Approved
0.5862	Remote Similarity	NPD5330	Approved
0.5862	Remote Similarity	NPD6684	Approved
0.5862	Remote Similarity	NPD7334	Approved
0.5862	Remote Similarity	NPD7146	Approved
0.5862	Remote Similarity	NPD7521	Approved
0.5862	Remote Similarity	NPD6409	Approved
0.5857	Remote Similarity	NPD8779	Phase 3
0.5854	Remote Similarity	NPD4271	Approved
0.5854	Remote Similarity	NPD4268	Approved
0.5851	Remote Similarity	NPD7638	Approved
0.5843	Remote Similarity	NPD1695	Approved
0.5833	Remote Similarity	NPD4790	Discontinued
0.5824	Remote Similarity	NPD5778	Approved
0.5824	Remote Similarity	NPD5779	Approved
0.5806	Remote Similarity	NPD5326	Phase 3
0.5789	Remote Similarity	NPD7639	Approved
0.5789	Remote Similarity	NPD7640	Approved
0.5789	Remote Similarity	NPD6648	Approved
0.5765	Remote Similarity	NPD4270	Approved
0.5765	Remote Similarity	NPD4269	Approved
0.575	Remote Similarity	NPD5733	Approved
0.575	Remote Similarity	NPD4058	Approved
0.5733	Remote Similarity	NPD7341	Phase 2
0.573	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.573	Remote Similarity	NPD6672	Approved
0.573	Remote Similarity	NPD5737	Approved
0.573	Remote Similarity	NPD6903	Approved
0.5714	Remote Similarity	NPD6050	Approved
0.5714	Remote Similarity	NPD4252	Approved
0.5714	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7637	Suspended
0.5714	Remote Similarity	NPD5693	Phase 1
0.5699	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD5276	Approved
0.5684	Remote Similarity	NPD4225	Approved
0.5684	Remote Similarity	NPD5926	Approved
0.5682	Remote Similarity	NPD5786	Approved
0.5667	Remote Similarity	NPD6101	Approved
0.5667	Remote Similarity	NPD5783	Phase 3
0.5667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD5369	Approved
0.5638	Remote Similarity	NPD7839	Suspended
0.5625	Remote Similarity	NPD6404	Discontinued
0.5625	Remote Similarity	NPD4265	Approved
0.5618	Remote Similarity	NPD3573	Approved
0.5612	Remote Similarity	NPD6647	Phase 2
0.5604	Remote Similarity	NPD5207	Approved
0.5604	Remote Similarity	NPD5692	Phase 3
0.56	Remote Similarity	NPD3197	Phase 1
0.56	Remote Similarity	NPD7899	Clinical (unspecified phase)

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