NPASS Compound

Structure

NPC264728 OpenBabel07101718292D 28 30 0 0 1 0 0 0 0 0999 V2000 3.9703 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6340 -1.3660 0.0000 O 0 0 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 8 1 0 0 0 0 5 25 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 19 2 0 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 26 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 21 2 0 0 0 0 17 26 1 0 0 0 0 18 4 1 6 0 0 0 18 22 1 0 0 0 0 20 23 1 0 0 0 0 22 21 1 1 0 0 0 22 23 1 0 0 0 0 23 25 1 6 0 0 0 24 25 1 0 0 0 0 24 27 2 0 0 0 0 24 28 1 0 0 0 0 25 26 1 6 0 0 0 26 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.26
Volume:	431.708
LogP:	6.238
LogD:	4.962
LogS:	-4.811
# Rotatable Bonds:	6
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.556
Synthetic Accessibility Score:	4.661
Fsp3:	0.5
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:	-4.671
MDCK Permeability:	2.8836200726800598e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.429
Plasma Protein Binding (PPB):	97.78386688232422%
Volume Distribution (VD):	0.465
Pgp-substrate:	2.439300060272217%

ADMET: Metabolism

CYP1A2-inhibitor:	0.27
CYP1A2-substrate:	0.683
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.778
CYP2C9-inhibitor:	0.803
CYP2C9-substrate:	0.448
CYP2D6-inhibitor:	0.183
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.869
CYP3A4-substrate:	0.517

ADMET: Excretion

Clearance (CL):	0.771
Half-life (T1/2):	0.088

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.132
Drug-inuced Liver Injury (DILI):	0.873
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.267
Maximum Recommended Daily Dose:	0.676
Skin Sensitization:	0.085
Carcinogencity:	0.672
Eye Corrosion:	0.005
Eye Irritation:	0.049
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC264728

Natural Product ID:	NPC264728
*Common Name:**	Spiculoic Acid B
IUPAC Name:	(1R,3aR,4R,5S,7aS)-3,5,7-triethyl-1,4-dimethyl-5-[(E)-2-phenylethenyl]-3a,7a-dihydro-1H-indene-4-carboxylic acid
Synonyms:
Standard InCHIKey:	LCASYKMXJWDKDE-HBSACRNXSA-N
Standard InCHI:	InChI=1S/C26H34O2/c1-6-20-16-18(4)22-21(7-2)17-26(8-3,25(5,23(20)22)24(27)28)15-14-19-12-10-9-11-13-19/h9-18,22-23H,6-8H2,1-5H3,(H,27,28)/b15-14+/t18-,22-,23+,25+,26+/m1/s1
SMILES:	CCC1=C[C@@H](C)[C@@H]2C(=C[C@](CC)(/C=C/c3ccccc3)[C@@](C)([C@@H]12)C(=O)O)CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224893
PubChem CID:	49866365
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277739]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[12762801]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14703354]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800643]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	Brazil	n.a.	PMID[18177008]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	caribbean	n.a.	PMID[20738102]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	caribbean	n.a.	PMID[20738102]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	Puerto Rican	n.a.	PMID[20923180]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277322]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882424]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22559	Plakortis halichondrioides	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
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	27200.0	nM	PMID[549975]

☑ 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 NPC264728 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	172
0.1-0.2	917
0.2-0.3	2119
0.3-0.4	8149
0.4-0.5	19230
0.5-0.6	10155
0.6-0.7	1697
0.7-0.8	223
0.8-0.85	19
0.85-0.9	9
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9785	High Similarity	NPC120393
0.9677	High Similarity	NPC469891
0.9677	High Similarity	NPC469890
0.9677	High Similarity	NPC469892
0.957	High Similarity	NPC469893
0.9293	High Similarity	NPC85560
0.9293	High Similarity	NPC244933
0.8788	High Similarity	NPC136810
0.8788	High Similarity	NPC128248
0.8788	High Similarity	NPC225079
0.8788	High Similarity	NPC133809
0.8485	Intermediate Similarity	NPC226041
0.8365	Intermediate Similarity	NPC94751
0.8365	Intermediate Similarity	NPC142326
0.8351	Intermediate Similarity	NPC86987
0.8349	Intermediate Similarity	NPC9274
0.8317	Intermediate Similarity	NPC7435
0.8317	Intermediate Similarity	NPC221825
0.83	Intermediate Similarity	NPC251579
0.83	Intermediate Similarity	NPC133135
0.828	Intermediate Similarity	NPC44830
0.8247	Intermediate Similarity	NPC70940
0.8247	Intermediate Similarity	NPC274455
0.8247	Intermediate Similarity	NPC86670
0.8173	Intermediate Similarity	NPC329282
0.8165	Intermediate Similarity	NPC294458
0.8125	Intermediate Similarity	NPC322387
0.8081	Intermediate Similarity	NPC475057
0.8073	Intermediate Similarity	NPC306977
0.8073	Intermediate Similarity	NPC287055
0.8073	Intermediate Similarity	NPC477475
0.8073	Intermediate Similarity	NPC242957
0.8073	Intermediate Similarity	NPC206414
0.8073	Intermediate Similarity	NPC477476
0.8056	Intermediate Similarity	NPC475002
0.8056	Intermediate Similarity	NPC95126
0.8041	Intermediate Similarity	NPC329064
0.802	Intermediate Similarity	NPC261947
0.8019	Intermediate Similarity	NPC37914
0.798	Intermediate Similarity	NPC475023
0.798	Intermediate Similarity	NPC475059
0.7957	Intermediate Similarity	NPC127343
0.7944	Intermediate Similarity	NPC21929
0.7941	Intermediate Similarity	NPC477767
0.7925	Intermediate Similarity	NPC471186
0.7921	Intermediate Similarity	NPC172925
0.7909	Intermediate Similarity	NPC93287
0.7905	Intermediate Similarity	NPC247976
0.7879	Intermediate Similarity	NPC84288
0.7864	Intermediate Similarity	NPC271475
0.7818	Intermediate Similarity	NPC218855
0.781	Intermediate Similarity	NPC474820
0.781	Intermediate Similarity	NPC475978
0.7778	Intermediate Similarity	NPC249811
0.7768	Intermediate Similarity	NPC221275
0.7736	Intermediate Similarity	NPC329556
0.7719	Intermediate Similarity	NPC45794
0.7714	Intermediate Similarity	NPC94487
0.7708	Intermediate Similarity	NPC285773
0.7685	Intermediate Similarity	NPC100767
0.7679	Intermediate Similarity	NPC234637
0.7679	Intermediate Similarity	NPC130591
0.7679	Intermediate Similarity	NPC471721
0.7652	Intermediate Similarity	NPC472698
0.7652	Intermediate Similarity	NPC472697
0.7632	Intermediate Similarity	NPC212891
0.7629	Intermediate Similarity	NPC267704
0.7619	Intermediate Similarity	NPC54647
0.7615	Intermediate Similarity	NPC112903
0.7589	Intermediate Similarity	NPC471481
0.7589	Intermediate Similarity	NPC470253
0.7589	Intermediate Similarity	NPC469547
0.7586	Intermediate Similarity	NPC202015
0.7568	Intermediate Similarity	NPC265513
0.7551	Intermediate Similarity	NPC95965
0.7545	Intermediate Similarity	NPC475006
0.7523	Intermediate Similarity	NPC185763
0.7523	Intermediate Similarity	NPC83409
0.7521	Intermediate Similarity	NPC470585
0.75	Intermediate Similarity	NPC471189
0.75	Intermediate Similarity	NPC477693
0.75	Intermediate Similarity	NPC280789
0.75	Intermediate Similarity	NPC19136
0.75	Intermediate Similarity	NPC471188
0.75	Intermediate Similarity	NPC66208
0.75	Intermediate Similarity	NPC477704
0.7477	Intermediate Similarity	NPC304873
0.7451	Intermediate Similarity	NPC220596
0.7438	Intermediate Similarity	NPC470816
0.7436	Intermediate Similarity	NPC473974
0.7436	Intermediate Similarity	NPC258366
0.7436	Intermediate Similarity	NPC42657
0.7436	Intermediate Similarity	NPC79933
0.7436	Intermediate Similarity	NPC31296
0.7434	Intermediate Similarity	NPC143768
0.7426	Intermediate Similarity	NPC298115
0.7417	Intermediate Similarity	NPC328107
0.7417	Intermediate Similarity	NPC473938
0.7414	Intermediate Similarity	NPC471926
0.7379	Intermediate Similarity	NPC1682
0.7379	Intermediate Similarity	NPC188844
0.7373	Intermediate Similarity	NPC234337
0.7373	Intermediate Similarity	NPC183339
0.7373	Intermediate Similarity	NPC133389
0.7358	Intermediate Similarity	NPC317280
0.7358	Intermediate Similarity	NPC329387
0.7347	Intermediate Similarity	NPC477770
0.7347	Intermediate Similarity	NPC83569
0.7347	Intermediate Similarity	NPC69279
0.7347	Intermediate Similarity	NPC288903
0.7345	Intermediate Similarity	NPC292834
0.7339	Intermediate Similarity	NPC56168
0.7339	Intermediate Similarity	NPC475138
0.7339	Intermediate Similarity	NPC472222
0.7339	Intermediate Similarity	NPC472221
0.7328	Intermediate Similarity	NPC471925
0.7328	Intermediate Similarity	NPC471928
0.7328	Intermediate Similarity	NPC105141
0.7328	Intermediate Similarity	NPC242764
0.7328	Intermediate Similarity	NPC471924
0.7323	Intermediate Similarity	NPC471864
0.7315	Intermediate Similarity	NPC474112
0.7311	Intermediate Similarity	NPC241001
0.7304	Intermediate Similarity	NPC215419
0.7304	Intermediate Similarity	NPC93181
0.7304	Intermediate Similarity	NPC217111
0.7304	Intermediate Similarity	NPC476357
0.7304	Intermediate Similarity	NPC186933
0.73	Intermediate Similarity	NPC243166
0.7295	Intermediate Similarity	NPC9180
0.7295	Intermediate Similarity	NPC100402
0.7292	Intermediate Similarity	NPC477371
0.7292	Intermediate Similarity	NPC196827
0.7292	Intermediate Similarity	NPC274996
0.729	Intermediate Similarity	NPC217621
0.7288	Intermediate Similarity	NPC204784
0.7282	Intermediate Similarity	NPC125226
0.7282	Intermediate Similarity	NPC284475
0.7282	Intermediate Similarity	NPC187725
0.7282	Intermediate Similarity	NPC141607
0.7273	Intermediate Similarity	NPC105899
0.7273	Intermediate Similarity	NPC12881
0.7273	Intermediate Similarity	NPC140118
0.7273	Intermediate Similarity	NPC321670
0.7265	Intermediate Similarity	NPC152812
0.7264	Intermediate Similarity	NPC239185
0.7257	Intermediate Similarity	NPC474057
0.7255	Intermediate Similarity	NPC9822
0.725	Intermediate Similarity	NPC269923
0.725	Intermediate Similarity	NPC369
0.725	Intermediate Similarity	NPC167323
0.725	Intermediate Similarity	NPC293831
0.7248	Intermediate Similarity	NPC274443
0.7248	Intermediate Similarity	NPC255676
0.7245	Intermediate Similarity	NPC230068
0.7244	Intermediate Similarity	NPC203486
0.7236	Intermediate Similarity	NPC190849
0.7236	Intermediate Similarity	NPC171007
0.7234	Intermediate Similarity	NPC476844
0.7232	Intermediate Similarity	NPC318327
0.7227	Intermediate Similarity	NPC474222
0.7227	Intermediate Similarity	NPC190501
0.7227	Intermediate Similarity	NPC318552
0.7227	Intermediate Similarity	NPC475804
0.7227	Intermediate Similarity	NPC475827
0.7227	Intermediate Similarity	NPC474223
0.7222	Intermediate Similarity	NPC469481
0.7212	Intermediate Similarity	NPC153885
0.7212	Intermediate Similarity	NPC314690
0.7212	Intermediate Similarity	NPC59677
0.7207	Intermediate Similarity	NPC274089
0.7207	Intermediate Similarity	NPC329705
0.7207	Intermediate Similarity	NPC191215
0.7207	Intermediate Similarity	NPC472699
0.7207	Intermediate Similarity	NPC472700
0.7207	Intermediate Similarity	NPC474111
0.7203	Intermediate Similarity	NPC254233
0.72	Intermediate Similarity	NPC294134
0.7196	Intermediate Similarity	NPC75724
0.7196	Intermediate Similarity	NPC145052
0.7196	Intermediate Similarity	NPC229242
0.7196	Intermediate Similarity	NPC134882
0.719	Intermediate Similarity	NPC121168
0.7188	Intermediate Similarity	NPC103488
0.7184	Intermediate Similarity	NPC26224
0.7179	Intermediate Similarity	NPC469843
0.7172	Intermediate Similarity	NPC270507
0.7172	Intermediate Similarity	NPC167103
0.7167	Intermediate Similarity	NPC164852
0.7167	Intermediate Similarity	NPC50872
0.7165	Intermediate Similarity	NPC159811
0.7158	Intermediate Similarity	NPC309399
0.7156	Intermediate Similarity	NPC244427
0.7156	Intermediate Similarity	NPC25458
0.7156	Intermediate Similarity	NPC222390
0.7154	Intermediate Similarity	NPC470765
0.7154	Intermediate Similarity	NPC478107
0.7154	Intermediate Similarity	NPC470649
0.7143	Intermediate Similarity	NPC477372
0.7143	Intermediate Similarity	NPC472695

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 NPC264728 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	805
0.2-0.3	1337
0.3-0.4	3000
0.4-0.5	2429
0.5-0.6	1075
0.6-0.7	267
0.7-0.8	53
0.8-0.85	12
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8454	Intermediate Similarity	NPD1088	Approved
0.8367	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5347	Phase 2
0.8333	Intermediate Similarity	NPD5346	Phase 2
0.8247	Intermediate Similarity	NPD1089	Approved
0.8247	Intermediate Similarity	NPD1090	Approved
0.8247	Intermediate Similarity	NPD1086	Approved
0.8144	Intermediate Similarity	NPD800	Approved
0.8125	Intermediate Similarity	NPD4793	Discontinued
0.81	Intermediate Similarity	NPD1693	Approved
0.8073	Intermediate Similarity	NPD7094	Approved
0.8073	Intermediate Similarity	NPD6858	Approved
0.8065	Intermediate Similarity	NPD226	Approved
0.7961	Intermediate Similarity	NPD2066	Phase 3
0.7938	Intermediate Similarity	NPD1087	Approved
0.7921	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1239	Approved
0.7767	Intermediate Similarity	NPD1565	Approved
0.7767	Intermediate Similarity	NPD1564	Approved
0.7767	Intermediate Similarity	NPD1566	Phase 3
0.7742	Intermediate Similarity	NPD225	Approved
0.7742	Intermediate Similarity	NPD227	Approved
0.7736	Intermediate Similarity	NPD1930	Approved
0.7736	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1929	Approved
0.7719	Intermediate Similarity	NPD7610	Discontinued
0.7708	Intermediate Similarity	NPD9491	Approved
0.77	Intermediate Similarity	NPD3672	Approved
0.77	Intermediate Similarity	NPD3673	Approved
0.7652	Intermediate Similarity	NPD7009	Phase 2
0.7611	Intermediate Similarity	NPD5951	Approved
0.757	Intermediate Similarity	NPD5765	Approved
0.7523	Intermediate Similarity	NPD6685	Approved
0.75	Intermediate Similarity	NPD1989	Approved
0.7477	Intermediate Similarity	NPD1932	Approved
0.7476	Intermediate Similarity	NPD1563	Approved
0.7456	Intermediate Similarity	NPD4766	Approved
0.7411	Intermediate Similarity	NPD3642	Approved
0.7411	Intermediate Similarity	NPD3643	Approved
0.7411	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD3644	Approved
0.7407	Intermediate Similarity	NPD6647	Phase 2
0.7404	Intermediate Similarity	NPD6049	Phase 2
0.7404	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD2329	Discontinued
0.7379	Intermediate Similarity	NPD7631	Approved
0.7374	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD2932	Approved
0.7339	Intermediate Similarity	NPD5909	Discontinued
0.7333	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD3797	Approved
0.7304	Intermediate Similarity	NPD2629	Approved
0.7292	Intermediate Similarity	NPD9490	Approved
0.7282	Intermediate Similarity	NPD7609	Phase 3
0.7264	Intermediate Similarity	NPD3495	Discontinued
0.7248	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD3019	Approved
0.7227	Intermediate Similarity	NPD4199	Phase 3
0.7222	Intermediate Similarity	NPD7961	Discontinued
0.7217	Intermediate Similarity	NPD6010	Discontinued
0.7203	Intermediate Similarity	NPD3798	Phase 3
0.7196	Intermediate Similarity	NPD253	Approved
0.7168	Intermediate Similarity	NPD5278	Discontinued
0.7167	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5618	Discontinued
0.7087	Intermediate Similarity	NPD6663	Approved
0.7069	Intermediate Similarity	NPD3598	Phase 3
0.7059	Intermediate Similarity	NPD4479	Discontinued
0.7043	Intermediate Similarity	NPD6912	Phase 3
0.704	Intermediate Similarity	NPD5736	Approved
0.7018	Intermediate Similarity	NPD1317	Discontinued
0.7	Intermediate Similarity	NPD3971	Phase 1
0.6975	Remote Similarity	NPD6065	Approved
0.6972	Remote Similarity	NPD7798	Approved
0.6964	Remote Similarity	NPD1018	Approved
0.6923	Remote Similarity	NPD2652	Approved
0.6923	Remote Similarity	NPD2650	Approved
0.6905	Remote Similarity	NPD7084	Phase 3
0.6893	Remote Similarity	NPD650	Approved
0.6885	Remote Similarity	NPD3023	Approved
0.6885	Remote Similarity	NPD3026	Approved
0.6875	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.687	Remote Similarity	NPD4234	Approved
0.687	Remote Similarity	NPD4233	Approved
0.686	Remote Similarity	NPD3024	Approved
0.686	Remote Similarity	NPD3025	Approved
0.6838	Remote Similarity	NPD2607	Approved
0.6822	Remote Similarity	NPD1066	Discontinued
0.6818	Remote Similarity	NPD7305	Phase 1
0.6814	Remote Similarity	NPD5048	Discontinued
0.6797	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5284	Approved
0.6792	Remote Similarity	NPD5281	Approved
0.6789	Remote Similarity	NPD9566	Approved
0.678	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD1508	Approved
0.6727	Remote Similarity	NPD9495	Approved
0.6724	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1756	Approved
0.6724	Remote Similarity	NPD1752	Approved
0.6721	Remote Similarity	NPD5981	Approved
0.6719	Remote Similarity	NPD7055	Discontinued
0.6715	Remote Similarity	NPD7236	Approved
0.6698	Remote Similarity	NPD9256	Approved
0.6698	Remote Similarity	NPD9258	Approved
0.6693	Remote Similarity	NPD6085	Phase 2
0.6693	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD2345	Approved
0.6667	Remote Similarity	NPD1101	Approved
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5162	Approved
0.6609	Remote Similarity	NPD467	Phase 1
0.6606	Remote Similarity	NPD4814	Discontinued
0.6585	Remote Similarity	NPD1855	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6993	Approved
0.6585	Remote Similarity	NPD6994	Approved
0.6565	Remote Similarity	NPD7715	Approved
0.6565	Remote Similarity	NPD7714	Approved
0.656	Remote Similarity	NPD3132	Approved
0.656	Remote Similarity	NPD2611	Approved
0.656	Remote Similarity	NPD4217	Approved
0.656	Remote Similarity	NPD4218	Approved
0.656	Remote Similarity	NPD4807	Approved
0.656	Remote Similarity	NPD4216	Approved
0.656	Remote Similarity	NPD4215	Approved
0.656	Remote Similarity	NPD4806	Approved
0.656	Remote Similarity	NPD3131	Approved
0.656	Remote Similarity	NPD2610	Approved
0.656	Remote Similarity	NPD2612	Approved
0.656	Remote Similarity	NPD2608	Approved
0.656	Remote Similarity	NPD2609	Approved
0.6545	Remote Similarity	NPD1843	Approved
0.6535	Remote Similarity	NPD1283	Approved
0.6532	Remote Similarity	NPD5306	Approved
0.6532	Remote Similarity	NPD5305	Approved
0.6529	Remote Similarity	NPD3317	Approved
0.6525	Remote Similarity	NPD188	Approved
0.6525	Remote Similarity	NPD5927	Discontinued
0.6525	Remote Similarity	NPD189	Phase 3
0.6518	Remote Similarity	NPD1067	Discontinued
0.6514	Remote Similarity	NPD720	Approved
0.6514	Remote Similarity	NPD3718	Approved
0.6514	Remote Similarity	NPD3719	Approved
0.6514	Remote Similarity	NPD719	Approved
0.6514	Remote Similarity	NPD1202	Approved
0.6508	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD7741	Discontinued
0.6504	Remote Similarity	NPD2617	Discontinued
0.65	Remote Similarity	NPD7077	Approved
0.65	Remote Similarity	NPD7076	Approved
0.6496	Remote Similarity	NPD2182	Approved
0.6496	Remote Similarity	NPD7082	Approved
0.6491	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6563	Approved
0.6484	Remote Similarity	NPD6565	Approved
0.6484	Remote Similarity	NPD6564	Approved
0.648	Remote Similarity	NPD3881	Discontinued
0.648	Remote Similarity	NPD4879	Approved
0.6479	Remote Similarity	NPD7239	Suspended
0.6476	Remote Similarity	NPD4694	Approved
0.6476	Remote Similarity	NPD5280	Approved
0.6476	Remote Similarity	NPD9259	Approved
0.6476	Remote Similarity	NPD9257	Approved
0.646	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4094	Approved
0.6452	Remote Similarity	NPD4102	Approved
0.6452	Remote Similarity	NPD1245	Approved
0.6452	Remote Similarity	NPD4105	Approved
0.6449	Remote Similarity	NPD7259	Approved
0.6449	Remote Similarity	NPD8166	Discontinued
0.6446	Remote Similarity	NPD1246	Approved
0.6442	Remote Similarity	NPD4786	Approved
0.6441	Remote Similarity	NPD2067	Discontinued
0.6435	Remote Similarity	NPD164	Approved
0.6434	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5926	Approved
0.6423	Remote Similarity	NPD2116	Approved
0.6423	Remote Similarity	NPD2117	Pre-registration
0.6423	Remote Similarity	NPD2115	Approved
0.6422	Remote Similarity	NPD6399	Phase 3
0.6422	Remote Similarity	NPD752	Approved
0.6417	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4223	Phase 3
0.6408	Remote Similarity	NPD4221	Approved
0.6403	Remote Similarity	NPD7295	Approved
0.64	Remote Similarity	NPD4059	Approved
0.6389	Remote Similarity	NPD5207	Approved
0.6385	Remote Similarity	NPD5759	Approved
0.6381	Remote Similarity	NPD5329	Approved
0.6378	Remote Similarity	NPD6637	Approved
0.6373	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD3020	Approved
0.6372	Remote Similarity	NPD6404	Discontinued

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