NPASS Compound

Structure

NPC120393 OpenBabel07101718192D 27 29 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 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 -0.8660 -2.5000 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 0.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 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 -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 4 18 1 0 0 0 0 5 24 1 0 0 0 0 6 20 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 19 2 0 0 0 0 12 19 1 0 0 0 0 13 14 2 0 0 0 0 13 19 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 18 2 0 0 0 0 16 25 1 0 0 0 0 17 3 1 6 0 0 0 17 21 1 0 0 0 0 20 22 1 0 0 0 0 21 18 1 1 0 0 0 21 22 1 0 0 0 0 22 24 1 6 0 0 0 23 24 1 0 0 0 0 23 26 2 0 0 0 0 23 27 1 0 0 0 0 24 25 1 6 0 0 0 25 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.24
Volume:	414.412
LogP:	6.063
LogD:	4.726
LogS:	-4.602
# Rotatable Bonds:	5
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.617
Synthetic Accessibility Score:	4.59
Fsp3:	0.48
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:	-4.665
MDCK Permeability:	2.8644375561270863e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.902
30% Bioavailability (F30%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.466
Plasma Protein Binding (PPB):	96.95255279541016%
Volume Distribution (VD):	0.486
Pgp-substrate:	3.082515001296997%

ADMET: Metabolism

CYP1A2-inhibitor:	0.254
CYP1A2-substrate:	0.681
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.66
CYP2C9-substrate:	0.276
CYP2D6-inhibitor:	0.095
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.829
CYP3A4-substrate:	0.488

ADMET: Excretion

Clearance (CL):	0.908
Half-life (T1/2):	0.129

ADMET: Toxicity

hERG Blockers:	0.304
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.758
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.209
Maximum Recommended Daily Dose:	0.199
Skin Sensitization:	0.286
Carcinogencity:	0.522
Eye Corrosion:	0.029
Eye Irritation:	0.135
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC120393

Natural Product ID:	NPC120393
*Common Name:**	24-Nor-Spiculoic Acid B
IUPAC Name:	(1R,3aR,4R,5S,7aS)-3,5-diethyl-1,4,7-trimethyl-5-[(E)-2-phenylethenyl]-3a,7a-dihydro-1H-indene-4-carboxylic acid
Synonyms:
Standard InCHIKey:	DGVIYEMUVWSVTP-OXAAXFJDSA-N
Standard InCHI:	InChI=1S/C25H32O2/c1-6-20-15-17(3)21-18(4)16-25(7-2,24(5,22(20)21)23(26)27)14-13-19-11-9-8-10-12-19/h8-17,21-22H,6-7H2,1-5H3,(H,26,27)/b14-13+/t17-,21-,22+,24+,25+/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)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224892
PubChem CID:	46938441
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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	470.0	nM	PMID[502812]
NPT2	Others	Unspecified		IC50	=	54900.0	nM	PMID[502812]

☑ 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 NPC120393 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	167
0.1-0.2	891
0.2-0.3	2247
0.3-0.4	9260
0.4-0.5	20067
0.5-0.6	8489
0.6-0.7	1372
0.7-0.8	179
0.8-0.85	16
0.85-0.9	2
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC469892
0.989	High Similarity	NPC469890
0.989	High Similarity	NPC469891
0.9785	High Similarity	NPC264728
0.978	High Similarity	NPC469893
0.9091	High Similarity	NPC244933
0.9091	High Similarity	NPC85560
0.8586	High Similarity	NPC133809
0.8586	High Similarity	NPC128248
0.8586	High Similarity	NPC225079
0.8586	High Similarity	NPC136810
0.8469	Intermediate Similarity	NPC251579
0.8469	Intermediate Similarity	NPC133135
0.8283	Intermediate Similarity	NPC226041
0.8247	Intermediate Similarity	NPC475057
0.8173	Intermediate Similarity	NPC94751
0.8173	Intermediate Similarity	NPC142326
0.8165	Intermediate Similarity	NPC9274
0.8144	Intermediate Similarity	NPC86987
0.8144	Intermediate Similarity	NPC475059
0.8144	Intermediate Similarity	NPC475023
0.8119	Intermediate Similarity	NPC221825
0.8119	Intermediate Similarity	NPC7435
0.8065	Intermediate Similarity	NPC44830
0.8041	Intermediate Similarity	NPC86670
0.8041	Intermediate Similarity	NPC70940
0.8041	Intermediate Similarity	NPC274455
0.7982	Intermediate Similarity	NPC294458
0.7981	Intermediate Similarity	NPC329282
0.7925	Intermediate Similarity	NPC21929
0.7917	Intermediate Similarity	NPC322387
0.789	Intermediate Similarity	NPC287055
0.789	Intermediate Similarity	NPC206414
0.789	Intermediate Similarity	NPC477475
0.789	Intermediate Similarity	NPC242957
0.789	Intermediate Similarity	NPC477476
0.789	Intermediate Similarity	NPC306977
0.787	Intermediate Similarity	NPC95126
0.787	Intermediate Similarity	NPC475002
0.7835	Intermediate Similarity	NPC329064
0.783	Intermediate Similarity	NPC37914
0.7822	Intermediate Similarity	NPC261947
0.7789	Intermediate Similarity	NPC267704
0.7745	Intermediate Similarity	NPC477767
0.7742	Intermediate Similarity	NPC127343
0.7736	Intermediate Similarity	NPC471186
0.7727	Intermediate Similarity	NPC93287
0.7723	Intermediate Similarity	NPC172925
0.7714	Intermediate Similarity	NPC247976
0.7677	Intermediate Similarity	NPC84288
0.767	Intermediate Similarity	NPC271475
0.7636	Intermediate Similarity	NPC218855
0.7619	Intermediate Similarity	NPC475978
0.7619	Intermediate Similarity	NPC474820
0.7593	Intermediate Similarity	NPC249811
0.7589	Intermediate Similarity	NPC221275
0.7547	Intermediate Similarity	NPC329556
0.7544	Intermediate Similarity	NPC45794
0.7524	Intermediate Similarity	NPC94487
0.7523	Intermediate Similarity	NPC475006
0.75	Intermediate Similarity	NPC471721
0.75	Intermediate Similarity	NPC234637
0.75	Intermediate Similarity	NPC100767
0.75	Intermediate Similarity	NPC130591
0.75	Intermediate Similarity	NPC285773
0.7478	Intermediate Similarity	NPC472698
0.7478	Intermediate Similarity	NPC472697
0.7456	Intermediate Similarity	NPC212891
0.7431	Intermediate Similarity	NPC112903
0.7429	Intermediate Similarity	NPC54647
0.7426	Intermediate Similarity	NPC220596
0.7414	Intermediate Similarity	NPC202015
0.7411	Intermediate Similarity	NPC470253
0.7411	Intermediate Similarity	NPC471481
0.7411	Intermediate Similarity	NPC469547
0.74	Intermediate Similarity	NPC298115
0.7387	Intermediate Similarity	NPC265513
0.7353	Intermediate Similarity	NPC1682
0.7353	Intermediate Similarity	NPC188844
0.735	Intermediate Similarity	NPC470585
0.7347	Intermediate Similarity	NPC95965
0.7339	Intermediate Similarity	NPC83409
0.7339	Intermediate Similarity	NPC191215
0.7339	Intermediate Similarity	NPC274089
0.7339	Intermediate Similarity	NPC185763
0.7327	Intermediate Similarity	NPC26224
0.7321	Intermediate Similarity	NPC471188
0.7321	Intermediate Similarity	NPC280789
0.7321	Intermediate Similarity	NPC471189
0.7321	Intermediate Similarity	NPC66208
0.732	Intermediate Similarity	NPC477770
0.7315	Intermediate Similarity	NPC19136
0.7315	Intermediate Similarity	NPC472221
0.7315	Intermediate Similarity	NPC472222
0.7315	Intermediate Similarity	NPC56168
0.7304	Intermediate Similarity	NPC105141
0.7304	Intermediate Similarity	NPC242764
0.73	Intermediate Similarity	NPC477693
0.73	Intermediate Similarity	NPC477704
0.729	Intermediate Similarity	NPC304873
0.7281	Intermediate Similarity	NPC217111
0.7273	Intermediate Similarity	NPC470816
0.7273	Intermediate Similarity	NPC243166
0.7265	Intermediate Similarity	NPC258366
0.7265	Intermediate Similarity	NPC31296
0.7265	Intermediate Similarity	NPC42657
0.7265	Intermediate Similarity	NPC79933
0.7265	Intermediate Similarity	NPC473974
0.7257	Intermediate Similarity	NPC143768
0.7255	Intermediate Similarity	NPC284475
0.7255	Intermediate Similarity	NPC125226
0.725	Intermediate Similarity	NPC473938
0.725	Intermediate Similarity	NPC328107
0.7241	Intermediate Similarity	NPC471926
0.7238	Intermediate Similarity	NPC239185
0.7216	Intermediate Similarity	NPC230068
0.7203	Intermediate Similarity	NPC133389
0.7203	Intermediate Similarity	NPC234337
0.7203	Intermediate Similarity	NPC183339
0.7196	Intermediate Similarity	NPC469481
0.7184	Intermediate Similarity	NPC153885
0.7184	Intermediate Similarity	NPC314690
0.7184	Intermediate Similarity	NPC59677
0.7182	Intermediate Similarity	NPC472699
0.7182	Intermediate Similarity	NPC472700
0.7179	Intermediate Similarity	NPC254233
0.7177	Intermediate Similarity	NPC475138
0.717	Intermediate Similarity	NPC329387
0.717	Intermediate Similarity	NPC179411
0.717	Intermediate Similarity	NPC317280
0.717	Intermediate Similarity	NPC134882
0.717	Intermediate Similarity	NPC75724
0.7168	Intermediate Similarity	NPC292834
0.7165	Intermediate Similarity	NPC471864
0.7158	Intermediate Similarity	NPC103488
0.7155	Intermediate Similarity	NPC471928
0.7155	Intermediate Similarity	NPC471925
0.7155	Intermediate Similarity	NPC471924
0.7143	Intermediate Similarity	NPC288903
0.7143	Intermediate Similarity	NPC270507
0.7143	Intermediate Similarity	NPC83569
0.7143	Intermediate Similarity	NPC69279
0.7143	Intermediate Similarity	NPC241001
0.7131	Intermediate Similarity	NPC100402
0.7131	Intermediate Similarity	NPC9180
0.713	Intermediate Similarity	NPC215419
0.713	Intermediate Similarity	NPC474112
0.713	Intermediate Similarity	NPC93181
0.713	Intermediate Similarity	NPC476357
0.713	Intermediate Similarity	NPC186933
0.7119	Intermediate Similarity	NPC204784
0.7117	Intermediate Similarity	NPC472696
0.7117	Intermediate Similarity	NPC472695
0.7117	Intermediate Similarity	NPC472683
0.7117	Intermediate Similarity	NPC472701
0.7115	Intermediate Similarity	NPC238219
0.7107	Intermediate Similarity	NPC140118
0.7107	Intermediate Similarity	NPC12881
0.7103	Intermediate Similarity	NPC217621
0.7094	Intermediate Similarity	NPC152812
0.7091	Intermediate Similarity	NPC321670
0.7091	Intermediate Similarity	NPC105899
0.7087	Intermediate Similarity	NPC203486
0.7087	Intermediate Similarity	NPC79917
0.7087	Intermediate Similarity	NPC187725
0.7087	Intermediate Similarity	NPC133461
0.7087	Intermediate Similarity	NPC141607
0.7083	Intermediate Similarity	NPC196827
0.7083	Intermediate Similarity	NPC369
0.7083	Intermediate Similarity	NPC167323
0.7083	Intermediate Similarity	NPC269923
0.7083	Intermediate Similarity	NPC477371
0.7083	Intermediate Similarity	NPC274996
0.7083	Intermediate Similarity	NPC293831
0.708	Intermediate Similarity	NPC474057
0.7075	Intermediate Similarity	NPC265220
0.7075	Intermediate Similarity	NPC324602
0.7075	Intermediate Similarity	NPC240042
0.7073	Intermediate Similarity	NPC190849
0.7073	Intermediate Similarity	NPC171007
0.7065	Intermediate Similarity	NPC155429
0.7064	Intermediate Similarity	NPC274443
0.7064	Intermediate Similarity	NPC255676
0.7059	Intermediate Similarity	NPC190501
0.7059	Intermediate Similarity	NPC474223
0.7059	Intermediate Similarity	NPC475804
0.7059	Intermediate Similarity	NPC318552
0.7059	Intermediate Similarity	NPC475827
0.7059	Intermediate Similarity	NPC474222
0.7059	Intermediate Similarity	NPC9822
0.7054	Intermediate Similarity	NPC318327
0.7048	Intermediate Similarity	NPC260233
0.7041	Intermediate Similarity	NPC103387
0.7041	Intermediate Similarity	NPC323103
0.7037	Intermediate Similarity	NPC109514
0.7037	Intermediate Similarity	NPC476993
0.7037	Intermediate Similarity	NPC289117
0.7027	Intermediate Similarity	NPC474111
0.7027	Intermediate Similarity	NPC329705
0.7025	Intermediate Similarity	NPC121168

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 NPC120393 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	784
0.2-0.3	1380
0.3-0.4	3095
0.4-0.5	2393
0.5-0.6	1054
0.6-0.7	223
0.7-0.8	49
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8247	Intermediate Similarity	NPD1088	Approved
0.8163	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5346	Phase 2
0.8125	Intermediate Similarity	NPD5347	Phase 2
0.8041	Intermediate Similarity	NPD1090	Approved
0.8041	Intermediate Similarity	NPD1089	Approved
0.8041	Intermediate Similarity	NPD1086	Approved
0.7938	Intermediate Similarity	NPD800	Approved
0.7917	Intermediate Similarity	NPD4793	Discontinued
0.79	Intermediate Similarity	NPD1693	Approved
0.789	Intermediate Similarity	NPD7094	Approved
0.789	Intermediate Similarity	NPD6858	Approved
0.7849	Intermediate Similarity	NPD226	Approved
0.7767	Intermediate Similarity	NPD2066	Phase 3
0.7732	Intermediate Similarity	NPD1087	Approved
0.7723	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1239	Approved
0.7573	Intermediate Similarity	NPD1565	Approved
0.7573	Intermediate Similarity	NPD1564	Approved
0.7573	Intermediate Similarity	NPD1566	Phase 3
0.7549	Intermediate Similarity	NPD6049	Phase 2
0.7549	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1929	Approved
0.7547	Intermediate Similarity	NPD5765	Approved
0.7547	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1930	Approved
0.7544	Intermediate Similarity	NPD7610	Discontinued
0.7527	Intermediate Similarity	NPD227	Approved
0.7527	Intermediate Similarity	NPD225	Approved
0.7526	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9491	Approved
0.75	Intermediate Similarity	NPD3672	Approved
0.75	Intermediate Similarity	NPD6685	Approved
0.75	Intermediate Similarity	NPD3673	Approved
0.7478	Intermediate Similarity	NPD7009	Phase 2
0.7434	Intermediate Similarity	NPD5951	Approved
0.7383	Intermediate Similarity	NPD6647	Phase 2
0.7353	Intermediate Similarity	NPD7631	Approved
0.7345	Intermediate Similarity	NPD6010	Discontinued
0.7308	Intermediate Similarity	NPD1989	Approved
0.729	Intermediate Similarity	NPD1932	Approved
0.7282	Intermediate Similarity	NPD1563	Approved
0.7281	Intermediate Similarity	NPD4766	Approved
0.7255	Intermediate Similarity	NPD7609	Phase 3
0.7238	Intermediate Similarity	NPD3495	Discontinued
0.7232	Intermediate Similarity	NPD3644	Approved
0.7232	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD3643	Approved
0.7232	Intermediate Similarity	NPD3642	Approved
0.7222	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD2329	Discontinued
0.7203	Intermediate Similarity	NPD2932	Approved
0.7203	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5909	Discontinued
0.7155	Intermediate Similarity	NPD3797	Approved
0.7143	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3971	Phase 1
0.713	Intermediate Similarity	NPD2629	Approved
0.7083	Intermediate Similarity	NPD5618	Discontinued
0.7083	Intermediate Similarity	NPD9490	Approved
0.7063	Intermediate Similarity	NPD7961	Discontinued
0.7059	Intermediate Similarity	NPD4199	Phase 3
0.7059	Intermediate Similarity	NPD3019	Approved
0.7034	Intermediate Similarity	NPD4479	Discontinued
0.7034	Intermediate Similarity	NPD3798	Phase 3
0.7018	Intermediate Similarity	NPD6912	Phase 3
0.7016	Intermediate Similarity	NPD5736	Approved
0.7009	Intermediate Similarity	NPD253	Approved
0.7	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5278	Discontinued
0.6944	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5048	Discontinued
0.6929	Remote Similarity	NPD6663	Approved
0.6897	Remote Similarity	NPD3598	Phase 3
0.6863	Remote Similarity	NPD650	Approved
0.6842	Remote Similarity	NPD1317	Discontinued
0.6807	Remote Similarity	NPD6065	Approved
0.6792	Remote Similarity	NPD1066	Discontinued
0.6789	Remote Similarity	NPD7798	Approved
0.6786	Remote Similarity	NPD1018	Approved
0.6752	Remote Similarity	NPD2652	Approved
0.6752	Remote Similarity	NPD2650	Approved
0.6746	Remote Similarity	NPD7084	Phase 3
0.6721	Remote Similarity	NPD3026	Approved
0.6721	Remote Similarity	NPD3023	Approved
0.6719	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD1508	Approved
0.6696	Remote Similarity	NPD4233	Approved
0.6696	Remote Similarity	NPD4234	Approved
0.6694	Remote Similarity	NPD3024	Approved
0.6694	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD7305	Phase 1
0.6667	Remote Similarity	NPD2607	Approved
0.6641	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4198	Discontinued
0.6638	Remote Similarity	NPD5927	Discontinued
0.6635	Remote Similarity	NPD1101	Approved
0.661	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD9566	Approved
0.6604	Remote Similarity	NPD5284	Approved
0.6604	Remote Similarity	NPD5281	Approved
0.6574	Remote Similarity	NPD4814	Discontinued
0.6569	Remote Similarity	NPD7236	Approved
0.6562	Remote Similarity	NPD7055	Discontinued
0.6557	Remote Similarity	NPD5981	Approved
0.6552	Remote Similarity	NPD1756	Approved
0.6552	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1752	Approved
0.6545	Remote Similarity	NPD9495	Approved
0.6545	Remote Similarity	NPD5926	Approved
0.6538	Remote Similarity	NPD8032	Phase 2
0.6535	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6085	Phase 2
0.6514	Remote Similarity	NPD1843	Approved
0.6512	Remote Similarity	NPD7008	Discontinued
0.6509	Remote Similarity	NPD9256	Approved
0.6509	Remote Similarity	NPD9258	Approved
0.6504	Remote Similarity	NPD2345	Approved
0.6504	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD9716	Approved
0.6486	Remote Similarity	NPD1067	Discontinued
0.6481	Remote Similarity	NPD720	Approved
0.6481	Remote Similarity	NPD3718	Approved
0.6481	Remote Similarity	NPD719	Approved
0.6481	Remote Similarity	NPD3719	Approved
0.6475	Remote Similarity	NPD7741	Discontinued
0.6471	Remote Similarity	NPD7077	Approved
0.6471	Remote Similarity	NPD7076	Approved
0.646	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD5162	Approved
0.6435	Remote Similarity	NPD467	Phase 1
0.6423	Remote Similarity	NPD6994	Approved
0.6423	Remote Similarity	NPD6993	Approved
0.6423	Remote Similarity	NPD1855	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4094	Approved
0.6412	Remote Similarity	NPD7715	Approved
0.6412	Remote Similarity	NPD7714	Approved
0.64	Remote Similarity	NPD4807	Approved
0.64	Remote Similarity	NPD2610	Approved
0.64	Remote Similarity	NPD4217	Approved
0.64	Remote Similarity	NPD2609	Approved
0.64	Remote Similarity	NPD4216	Approved
0.64	Remote Similarity	NPD4218	Approved
0.64	Remote Similarity	NPD3132	Approved
0.64	Remote Similarity	NPD2611	Approved
0.64	Remote Similarity	NPD4806	Approved
0.64	Remote Similarity	NPD2608	Approved
0.64	Remote Similarity	NPD2612	Approved
0.64	Remote Similarity	NPD3131	Approved
0.64	Remote Similarity	NPD4215	Approved
0.6389	Remote Similarity	NPD752	Approved
0.6378	Remote Similarity	NPD1283	Approved
0.6371	Remote Similarity	NPD5306	Approved
0.6371	Remote Similarity	NPD4059	Approved
0.6371	Remote Similarity	NPD5305	Approved
0.6364	Remote Similarity	NPD3317	Approved
0.6356	Remote Similarity	NPD188	Approved
0.6356	Remote Similarity	NPD189	Phase 3
0.635	Remote Similarity	NPD7082	Approved
0.6349	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2617	Discontinued
0.6341	Remote Similarity	NPD3091	Approved
0.6339	Remote Similarity	NPD3020	Approved
0.6338	Remote Similarity	NPD7239	Suspended
0.6337	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.633	Remote Similarity	NPD1409	Phase 3
0.633	Remote Similarity	NPD1202	Approved
0.6328	Remote Similarity	NPD6565	Approved
0.6328	Remote Similarity	NPD6563	Approved
0.6328	Remote Similarity	NPD6564	Approved
0.6325	Remote Similarity	NPD2182	Approved
0.632	Remote Similarity	NPD4879	Approved
0.632	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.632	Remote Similarity	NPD3881	Discontinued
0.6306	Remote Similarity	NPD1875	Phase 1
0.6306	Remote Similarity	NPD4655	Approved
0.6306	Remote Similarity	NPD4657	Approved
0.6304	Remote Similarity	NPD8166	Discontinued
0.6304	Remote Similarity	NPD7259	Approved
0.6293	Remote Similarity	NPD5706	Approved
0.6293	Remote Similarity	NPD5704	Approved
0.6293	Remote Similarity	NPD5705	Approved
0.629	Remote Similarity	NPD1245	Approved
0.629	Remote Similarity	NPD4102	Approved
0.629	Remote Similarity	NPD4105	Approved
0.629	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4163	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5280	Approved
0.6286	Remote Similarity	NPD9259	Approved
0.6286	Remote Similarity	NPD9257	Approved
0.6286	Remote Similarity	NPD4694	Approved
0.6283	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD1246	Approved
0.6279	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD942	Approved
0.6273	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD2067	Discontinued
0.6261	Remote Similarity	NPD164	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