NPASS Compound

Structure

NPC474820 OpenBabel07101718182D 31 32 0 0 1 0 0 0 0 0999 V2000 2.2617 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8605 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7258 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5918 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8597 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4578 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7879 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9937 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3238 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9219 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7879 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1277 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1899 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0559 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9219 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2617 3.0827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5296 3.0827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.0559 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0471 -1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 1 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 1.6349 -2.0316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0526 -1.3271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 14 22 1 0 0 0 0 15 24 1 0 0 0 0 16 24 2 0 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 27 1 0 0 0 0 25 28 2 0 0 0 0 25 29 1 0 0 0 0 26 3 1 1 0 0 0 26 30 1 0 0 0 0 27 4 1 1 0 0 0 27 31 1 0 0 0 0 30 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.32
Volume:	483.05
LogP:	6.878
LogD:	4.48
LogS:	-6.493
# Rotatable Bonds:	15
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	3.937
Fsp3:	0.741
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.834
MDCK Permeability:	2.0677720385720022e-05
Pgp-inhibitor:	0.113
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.244
Plasma Protein Binding (PPB):	98.99271392822266%
Volume Distribution (VD):	0.889
Pgp-substrate:	0.3742278218269348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.263
CYP2C19-inhibitor:	0.419
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.318
CYP2C9-substrate:	0.981
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.691
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	5.328
Half-life (T1/2):	0.551

ADMET: Toxicity

hERG Blockers:	0.18
Human Hepatotoxicity (H-HT):	0.273
Drug-inuced Liver Injury (DILI):	0.632
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.095
Skin Sensitization:	0.966
Carcinogencity:	0.069
Eye Corrosion:	0.312
Eye Irritation:	0.478
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC474820

Natural Product ID:	NPC474820
*Common Name:**	Epiplakinic Acid H
IUPAC Name:	2-[(3R,5R)-5-(2,4-dimethyl-12-phenyldodecyl)-3,5-dimethyldioxolan-3-yl]acetic acid
Synonyms:	Epiplakinic Acid H
Standard InCHIKey:	BXUWJKHPMWARGU-FADGCRCDSA-N
Standard InCHI:	InChI=1S/C27H44O4/c1-22(14-10-7-5-6-8-11-15-24-16-12-9-13-17-24)18-23(2)19-26(3)21-27(4,31-30-26)20-25(28)29/h9,12-13,16-17,22-23H,5-8,10-11,14-15,18-21H2,1-4H3,(H,28,29)/t22?,23?,26-,27+/m1/s1
SMILES:	CC(CC(C[C@@]1(C)OO[C@@](C1)(C)CC(=O)O)C)CCCCCCCCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484032
PubChem CID:	10342789
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted 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
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Palauan	n.a.	PMID[12350142]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[15387674]
NPO2117	Plakortis nigra	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
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	390.0	nM	PMID[507588]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	390.0	nM	PMID[507589]

☑ 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 NPC474820 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	178
0.1-0.2	760
0.2-0.3	2178
0.3-0.4	7680
0.4-0.5	16870
0.5-0.6	13175
0.6-0.7	1752
0.7-0.8	86
0.8-0.85	10
0.85-0.9	1
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475978
0.9894	High Similarity	NPC94487
0.9381	High Similarity	NPC474112
0.8969	High Similarity	NPC477767
0.8878	High Similarity	NPC271475
0.8351	Intermediate Similarity	NPC84288
0.8286	Intermediate Similarity	NPC474111
0.8286	Intermediate Similarity	NPC329705
0.8269	Intermediate Similarity	NPC19136
0.8191	Intermediate Similarity	NPC44830
0.7872	Intermediate Similarity	NPC127343
0.7857	Intermediate Similarity	NPC322387
0.781	Intermediate Similarity	NPC264728
0.781	Intermediate Similarity	NPC225079
0.78	Intermediate Similarity	NPC274455
0.78	Intermediate Similarity	NPC70940
0.78	Intermediate Similarity	NPC86670
0.7778	Intermediate Similarity	NPC244933
0.7778	Intermediate Similarity	NPC329064
0.7778	Intermediate Similarity	NPC85560
0.7768	Intermediate Similarity	NPC294458
0.7679	Intermediate Similarity	NPC477476
0.7679	Intermediate Similarity	NPC477475
0.7653	Intermediate Similarity	NPC95965
0.7632	Intermediate Similarity	NPC210531
0.7629	Intermediate Similarity	NPC477770
0.7629	Intermediate Similarity	NPC285773
0.7619	Intermediate Similarity	NPC120393
0.7553	Intermediate Similarity	NPC240170
0.7553	Intermediate Similarity	NPC120776
0.7549	Intermediate Similarity	NPC141607
0.7549	Intermediate Similarity	NPC187725
0.7549	Intermediate Similarity	NPC86987
0.7547	Intermediate Similarity	NPC54647
0.7524	Intermediate Similarity	NPC469892
0.7524	Intermediate Similarity	NPC469891
0.7524	Intermediate Similarity	NPC469890
0.7523	Intermediate Similarity	NPC321670
0.75	Intermediate Similarity	NPC138798
0.7477	Intermediate Similarity	NPC128248
0.7477	Intermediate Similarity	NPC133809
0.7477	Intermediate Similarity	NPC136810
0.7455	Intermediate Similarity	NPC25385
0.7455	Intermediate Similarity	NPC193640
0.7455	Intermediate Similarity	NPC475905
0.7431	Intermediate Similarity	NPC329282
0.7429	Intermediate Similarity	NPC469893
0.7429	Intermediate Similarity	NPC261947
0.7426	Intermediate Similarity	NPC477704
0.7426	Intermediate Similarity	NPC477693
0.7417	Intermediate Similarity	NPC108286
0.7387	Intermediate Similarity	NPC20485
0.7383	Intermediate Similarity	NPC7435
0.7364	Intermediate Similarity	NPC474307
0.7353	Intermediate Similarity	NPC231591
0.735	Intermediate Similarity	NPC94425
0.7339	Intermediate Similarity	NPC329556
0.7333	Intermediate Similarity	NPC206764
0.7321	Intermediate Similarity	NPC475006
0.7315	Intermediate Similarity	NPC158623
0.7281	Intermediate Similarity	NPC218855
0.7273	Intermediate Similarity	NPC288903
0.7273	Intermediate Similarity	NPC472703
0.7258	Intermediate Similarity	NPC268607
0.7236	Intermediate Similarity	NPC79608
0.7236	Intermediate Similarity	NPC476033
0.7213	Intermediate Similarity	NPC472704
0.7213	Intermediate Similarity	NPC236981
0.7212	Intermediate Similarity	NPC317645
0.7196	Intermediate Similarity	NPC226041
0.7193	Intermediate Similarity	NPC475002
0.7193	Intermediate Similarity	NPC95126
0.719	Intermediate Similarity	NPC369
0.719	Intermediate Similarity	NPC293831
0.7182	Intermediate Similarity	NPC247976
0.7179	Intermediate Similarity	NPC9274
0.7177	Intermediate Similarity	NPC146239
0.717	Intermediate Similarity	NPC172925
0.7167	Intermediate Similarity	NPC474223
0.7167	Intermediate Similarity	NPC475804
0.7167	Intermediate Similarity	NPC474222
0.7167	Intermediate Similarity	NPC475827
0.7155	Intermediate Similarity	NPC234637
0.7155	Intermediate Similarity	NPC130591
0.7154	Intermediate Similarity	NPC478108
0.7154	Intermediate Similarity	NPC317163
0.7143	Intermediate Similarity	NPC100767
0.7143	Intermediate Similarity	NPC94751
0.7143	Intermediate Similarity	NPC142326
0.7143	Intermediate Similarity	NPC317592
0.7143	Intermediate Similarity	NPC37914
0.7131	Intermediate Similarity	NPC469927
0.713	Intermediate Similarity	NPC179411
0.7129	Intermediate Similarity	NPC294134
0.71	Intermediate Similarity	NPC270507
0.7097	Intermediate Similarity	NPC477366
0.7091	Intermediate Similarity	NPC25458
0.7091	Intermediate Similarity	NPC304873
0.7087	Intermediate Similarity	NPC471334
0.7073	Intermediate Similarity	NPC477362
0.7069	Intermediate Similarity	NPC471481
0.7069	Intermediate Similarity	NPC93287
0.7064	Intermediate Similarity	NPC476042
0.7064	Intermediate Similarity	NPC221825
0.7064	Intermediate Similarity	NPC217621
0.7059	Intermediate Similarity	NPC471553
0.7048	Intermediate Similarity	NPC110704
0.704	Intermediate Similarity	NPC472706
0.704	Intermediate Similarity	NPC477365
0.704	Intermediate Similarity	NPC473751
0.704	Intermediate Similarity	NPC477357
0.7034	Intermediate Similarity	NPC188010
0.7031	Intermediate Similarity	NPC469499
0.7025	Intermediate Similarity	NPC133389
0.7025	Intermediate Similarity	NPC478015
0.7025	Intermediate Similarity	NPC478014
0.7025	Intermediate Similarity	NPC183339
0.7025	Intermediate Similarity	NPC234337
0.7025	Intermediate Similarity	NPC478016
0.7023	Intermediate Similarity	NPC474726
0.7023	Intermediate Similarity	NPC475955
0.7019	Intermediate Similarity	NPC9822
0.7018	Intermediate Similarity	NPC469511
0.7018	Intermediate Similarity	NPC40178
0.7016	Intermediate Similarity	NPC246166
0.701	Intermediate Similarity	NPC145898
0.7009	Intermediate Similarity	NPC87069
0.7009	Intermediate Similarity	NPC172525
0.7009	Intermediate Similarity	NPC62546
0.7009	Intermediate Similarity	NPC162113
0.7	Intermediate Similarity	NPC472697
0.7	Intermediate Similarity	NPC323103
0.7	Intermediate Similarity	NPC472698
0.7	Intermediate Similarity	NPC103387
0.6992	Remote Similarity	NPC474159
0.6992	Remote Similarity	NPC474254
0.6991	Remote Similarity	NPC477251
0.6984	Remote Similarity	NPC477370
0.6983	Remote Similarity	NPC292834
0.6981	Remote Similarity	NPC323164
0.6979	Remote Similarity	NPC189371
0.6977	Remote Similarity	NPC144257
0.6975	Remote Similarity	NPC212891
0.6972	Remote Similarity	NPC145052
0.6972	Remote Similarity	NPC317280
0.6972	Remote Similarity	NPC329387
0.6961	Remote Similarity	NPC475710
0.696	Remote Similarity	NPC470816
0.696	Remote Similarity	NPC477363
0.6953	Remote Similarity	NPC17840
0.6953	Remote Similarity	NPC247477
0.6949	Remote Similarity	NPC221870
0.6949	Remote Similarity	NPC29607
0.6949	Remote Similarity	NPC221275
0.6942	Remote Similarity	NPC202015
0.6939	Remote Similarity	NPC103488
0.6937	Remote Similarity	NPC284477
0.693	Remote Similarity	NPC47536
0.693	Remote Similarity	NPC249811
0.693	Remote Similarity	NPC21929
0.6929	Remote Similarity	NPC69496
0.6929	Remote Similarity	NPC37968
0.6923	Remote Similarity	NPC477245
0.6923	Remote Similarity	NPC306977
0.6923	Remote Similarity	NPC206414
0.6923	Remote Similarity	NPC287055
0.6923	Remote Similarity	NPC136994
0.6923	Remote Similarity	NPC242957
0.6923	Remote Similarity	NPC88255
0.6923	Remote Similarity	NPC477246
0.6917	Remote Similarity	NPC45794
0.6917	Remote Similarity	NPC325295
0.6917	Remote Similarity	NPC76308
0.6916	Remote Similarity	NPC34243
0.6911	Remote Similarity	NPC84281
0.6911	Remote Similarity	NPC291027
0.6911	Remote Similarity	NPC167323
0.6911	Remote Similarity	NPC169485
0.6911	Remote Similarity	NPC213126
0.6911	Remote Similarity	NPC317474
0.6911	Remote Similarity	NPC269923
0.6909	Remote Similarity	NPC228435
0.6905	Remote Similarity	NPC253681
0.6903	Remote Similarity	NPC471186
0.6891	Remote Similarity	NPC471616
0.6891	Remote Similarity	NPC260886
0.6885	Remote Similarity	NPC80150
0.6885	Remote Similarity	NPC243059
0.6885	Remote Similarity	NPC280827
0.6881	Remote Similarity	NPC240042
0.6881	Remote Similarity	NPC253423
0.6881	Remote Similarity	NPC324569
0.6875	Remote Similarity	NPC471317
0.687	Remote Similarity	NPC475282
0.687	Remote Similarity	NPC31274
0.6869	Remote Similarity	NPC272260
0.6866	Remote Similarity	NPC475413
0.6866	Remote Similarity	NPC473497
0.6866	Remote Similarity	NPC77493
0.6866	Remote Similarity	NPC474303

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 NPC474820 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	698
0.2-0.3	1511
0.3-0.4	3153
0.4-0.5	2489
0.5-0.6	903
0.6-0.7	204
0.7-0.8	27
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8247	Intermediate Similarity	NPD5347	Phase 2
0.8247	Intermediate Similarity	NPD5346	Phase 2
0.81	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD4793	Discontinued
0.8019	Intermediate Similarity	NPD5048	Discontinued
0.8	Intermediate Similarity	NPD5765	Approved
0.7979	Intermediate Similarity	NPD226	Approved
0.7944	Intermediate Similarity	NPD6685	Approved
0.7879	Intermediate Similarity	NPD800	Approved
0.7843	Intermediate Similarity	NPD1693	Approved
0.78	Intermediate Similarity	NPD1090	Approved
0.78	Intermediate Similarity	NPD1086	Approved
0.78	Intermediate Similarity	NPD1089	Approved
0.766	Intermediate Similarity	NPD227	Approved
0.766	Intermediate Similarity	NPD225	Approved
0.7647	Intermediate Similarity	NPD1088	Approved
0.7629	Intermediate Similarity	NPD9491	Approved
0.7547	Intermediate Similarity	NPD2066	Phase 3
0.75	Intermediate Similarity	NPD1087	Approved
0.7456	Intermediate Similarity	NPD2652	Approved
0.7456	Intermediate Similarity	NPD2650	Approved
0.7451	Intermediate Similarity	NPD3672	Approved
0.7451	Intermediate Similarity	NPD3673	Approved
0.7434	Intermediate Similarity	NPD6912	Phase 3
0.7381	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD1930	Approved
0.7339	Intermediate Similarity	NPD6647	Phase 2
0.7339	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD1929	Approved
0.7339	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7798	Approved
0.7216	Intermediate Similarity	NPD9490	Approved
0.7212	Intermediate Similarity	NPD1239	Approved
0.7196	Intermediate Similarity	NPD1566	Phase 3
0.7196	Intermediate Similarity	NPD1564	Approved
0.7196	Intermediate Similarity	NPD1565	Approved
0.717	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD467	Phase 1
0.7117	Intermediate Similarity	NPD5909	Discontinued
0.7105	Intermediate Similarity	NPD1317	Discontinued
0.7103	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1932	Approved
0.7064	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2329	Discontinued
0.7009	Intermediate Similarity	NPD6010	Discontinued
0.6972	Remote Similarity	NPD253	Approved
0.6957	Remote Similarity	NPD5278	Discontinued
0.6944	Remote Similarity	NPD1989	Approved
0.6929	Remote Similarity	NPD2613	Approved
0.6916	Remote Similarity	NPD1563	Approved
0.6911	Remote Similarity	NPD4216	Approved
0.6911	Remote Similarity	NPD3132	Approved
0.6911	Remote Similarity	NPD2609	Approved
0.6911	Remote Similarity	NPD2612	Approved
0.6911	Remote Similarity	NPD3131	Approved
0.6911	Remote Similarity	NPD2610	Approved
0.6911	Remote Similarity	NPD4217	Approved
0.6911	Remote Similarity	NPD2611	Approved
0.6911	Remote Similarity	NPD4215	Approved
0.6911	Remote Similarity	NPD2608	Approved
0.6911	Remote Similarity	NPD4218	Approved
0.6897	Remote Similarity	NPD3643	Approved
0.6897	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3642	Approved
0.6897	Remote Similarity	NPD3644	Approved
0.6818	Remote Similarity	NPD9495	Approved
0.6807	Remote Similarity	NPD2629	Approved
0.678	Remote Similarity	NPD6858	Approved
0.678	Remote Similarity	NPD7094	Approved
0.6772	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6085	Phase 2
0.6769	Remote Similarity	NPD2573	Approved
0.6769	Remote Similarity	NPD3616	Approved
0.6769	Remote Similarity	NPD3615	Approved
0.6769	Remote Similarity	NPD2566	Approved
0.6769	Remote Similarity	NPD3614	Approved
0.6769	Remote Similarity	NPD4746	Phase 3
0.6769	Remote Similarity	NPD2574	Discontinued
0.6769	Remote Similarity	NPD2570	Approved
0.6769	Remote Similarity	NPD2571	Approved
0.6769	Remote Similarity	NPD3088	Approved
0.6769	Remote Similarity	NPD3090	Approved
0.6769	Remote Similarity	NPD3089	Approved
0.6769	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4745	Approved
0.6769	Remote Similarity	NPD3087	Approved
0.6759	Remote Similarity	NPD1066	Discontinued
0.675	Remote Similarity	NPD3317	Approved
0.6727	Remote Similarity	NPD9566	Approved
0.6723	Remote Similarity	NPD3598	Phase 3
0.6667	Remote Similarity	NPD4685	Phase 3
0.6667	Remote Similarity	NPD4684	Phase 3
0.6667	Remote Similarity	NPD1246	Approved
0.6667	Remote Similarity	NPD2067	Discontinued
0.6667	Remote Similarity	NPD4686	Approved
0.6667	Remote Similarity	NPD1711	Phase 2
0.6641	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7610	Discontinued
0.6639	Remote Similarity	NPD6065	Approved
0.6636	Remote Similarity	NPD9256	Approved
0.6636	Remote Similarity	NPD9258	Approved
0.6635	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.661	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1202	Approved
0.6587	Remote Similarity	NPD1608	Approved
0.6587	Remote Similarity	NPD6637	Approved
0.6583	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5951	Approved
0.6519	Remote Similarity	NPD7033	Discontinued
0.6514	Remote Similarity	NPD7631	Approved
0.6508	Remote Similarity	NPD4806	Approved
0.6508	Remote Similarity	NPD4807	Approved
0.6496	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5306	Approved
0.648	Remote Similarity	NPD5305	Approved
0.6466	Remote Similarity	NPD1040	Phase 2
0.6466	Remote Similarity	NPD1018	Approved
0.646	Remote Similarity	NPD1067	Discontinued
0.6455	Remote Similarity	NPD3719	Approved
0.6455	Remote Similarity	NPD3718	Approved
0.6454	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7009	Phase 2
0.6452	Remote Similarity	NPD3798	Phase 3
0.6452	Remote Similarity	NPD4479	Discontinued
0.6442	Remote Similarity	NPD3971	Phase 1
0.6439	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD3797	Approved
0.6422	Remote Similarity	NPD7609	Phase 3
0.6415	Remote Similarity	NPD9259	Approved
0.6415	Remote Similarity	NPD9257	Approved
0.6404	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4105	Approved
0.64	Remote Similarity	NPD5981	Approved
0.64	Remote Similarity	NPD4102	Approved
0.64	Remote Similarity	NPD1245	Approved
0.6393	Remote Similarity	NPD4766	Approved
0.6393	Remote Similarity	NPD747	Discontinued
0.6391	Remote Similarity	NPD7961	Discontinued
0.6387	Remote Similarity	NPD4233	Approved
0.6387	Remote Similarity	NPD4234	Approved
0.6364	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD5779	Approved
0.6356	Remote Similarity	NPD9264	Approved
0.6356	Remote Similarity	NPD9263	Approved
0.6356	Remote Similarity	NPD9267	Approved
0.635	Remote Similarity	NPD7137	Phase 2
0.6349	Remote Similarity	NPD4199	Phase 3
0.6349	Remote Similarity	NPD17	Approved
0.6349	Remote Similarity	NPD2345	Approved
0.6341	Remote Similarity	NPD4198	Discontinued
0.6336	Remote Similarity	NPD3662	Phase 3
0.6336	Remote Similarity	NPD3664	Approved
0.6336	Remote Similarity	NPD5759	Approved
0.6336	Remote Similarity	NPD3661	Approved
0.6336	Remote Similarity	NPD3663	Approved
0.6333	Remote Similarity	NPD189	Phase 3
0.6333	Remote Similarity	NPD188	Approved
0.6328	Remote Similarity	NPD3071	Approved
0.6328	Remote Similarity	NPD3073	Approved
0.6328	Remote Similarity	NPD3072	Approved
0.632	Remote Similarity	NPD9545	Approved
0.632	Remote Similarity	NPD2217	Approved
0.632	Remote Similarity	NPD2218	Phase 2
0.6316	Remote Similarity	NPD3764	Approved
0.6311	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6004	Phase 3
0.6304	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6005	Phase 3
0.6304	Remote Similarity	NPD6002	Phase 3
0.6303	Remote Similarity	NPD9266	Approved
0.6303	Remote Similarity	NPD74	Approved
0.6303	Remote Similarity	NPD476	Approved
0.6303	Remote Similarity	NPD2182	Approved
0.63	Remote Similarity	NPD9716	Approved
0.6299	Remote Similarity	NPD4136	Approved
0.6299	Remote Similarity	NPD4135	Approved
0.6299	Remote Similarity	NPD4106	Approved
0.6296	Remote Similarity	NPD1101	Approved
0.6296	Remote Similarity	NPD531	Approved
0.629	Remote Similarity	NPD9493	Approved
0.6286	Remote Similarity	NPD2575	Approved
0.6277	Remote Similarity	NPD7305	Phase 1
0.6269	Remote Similarity	NPD7715	Approved
0.6269	Remote Similarity	NPD7714	Approved
0.625	Remote Similarity	NPD6049	Phase 2
0.625	Remote Similarity	NPD4814	Discontinued
0.625	Remote Similarity	NPD942	Approved
0.625	Remote Similarity	NPD4761	Approved
0.625	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3603	Phase 3
0.625	Remote Similarity	NPD4762	Approved
0.625	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5618	Discontinued
0.6241	Remote Similarity	NPD4738	Phase 2
0.6241	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.624	Remote Similarity	NPD2116	Approved
0.624	Remote Similarity	NPD2115	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