NPASS Compound

Structure

NPC85560 OpenBabel07101718232D 30 32 0 0 1 0 0 0 0 0999 V2000 -2.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1723 -1.0182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4612 1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2213 -1.3272 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6691 0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4781 -0.6581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5827 0.3364 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 0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4487 0.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 4 9 1 0 0 0 0 6 20 1 0 0 0 0 8 26 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 19 2 0 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 26 1 0 0 0 0 17 20 2 0 0 0 0 17 26 1 0 0 0 0 18 5 1 6 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 21 7 1 1 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 22 20 1 6 0 0 0 22 23 1 0 0 0 0 23 27 1 1 0 0 0 24 28 2 0 0 0 0 25 27 1 0 0 0 0 25 29 2 0 0 0 0 25 30 1 0 0 0 0 26 27 1 1 0 0 0 27 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.27
Volume:	457.794
LogP:	4.71
LogD:	3.001
LogS:	-3.472
# Rotatable Bonds:	7
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	4.776
Fsp3:	0.556
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:	-4.692
MDCK Permeability:	3.40760889230296e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.858
Plasma Protein Binding (PPB):	97.93408966064453%
Volume Distribution (VD):	0.477
Pgp-substrate:	1.8801957368850708%

ADMET: Metabolism

CYP1A2-inhibitor:	0.237
CYP1A2-substrate:	0.723
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.809
CYP2C9-substrate:	0.565
CYP2D6-inhibitor:	0.11
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.827
CYP3A4-substrate:	0.602

ADMET: Excretion

Clearance (CL):	1.452
Half-life (T1/2):	0.202

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.907
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.072
Carcinogencity:	0.44
Eye Corrosion:	0.507
Eye Irritation:	0.173
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC85560

Natural Product ID:	NPC85560
*Common Name:**	Isospiculoic Acid A
IUPAC Name:	(1R,3R,3aS,4S,5R,7aS)-1,4,5,7-tetraethyl-3-methyl-2-oxo-5-[(E)-2-phenylethenyl]-1,3,3a,7a-tetrahydroindene-4-carboxylic acid
Synonyms:
Standard InCHIKey:	IJBZGABOCOJLTC-DLBIIVFHSA-N
Standard InCHI:	InChI=1S/C27H36O3/c1-6-20-17-26(8-3,16-15-19-13-11-10-12-14-19)27(9-4,25(29)30)23-18(5)24(28)21(7-2)22(20)23/h10-18,21-23H,6-9H2,1-5H3,(H,29,30)/b16-15+/t18-,21-,22-,23-,26-,27-/m1/s1
SMILES:	CCC1=C[C@@](CC)(/C=C/c2ccccc2)[C@](CC)([C@@H]2[C@@H](C)C(=O)[C@H](CC)[C@@H]12)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518609
PubChem CID:	11452571
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
NPO28817	Plakortis zyggompha	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844945]
NPO28817	Plakortis zyggompha	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26859086]
NPO28817	Plakortis zyggompha	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
GI50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	GI50	=	15000.0	nM	PMID[575439]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	15000.0	nM	PMID[575439]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	>	25000.0	nM	PMID[575439]

☑ 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 NPC85560 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	191
0.1-0.2	932
0.2-0.3	1952
0.3-0.4	7364
0.4-0.5	19145
0.5-0.6	11241
0.6-0.7	1682
0.7-0.8	169
0.8-0.85	13
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC244933
0.9293	High Similarity	NPC264728
0.9091	High Similarity	NPC120393
0.899	High Similarity	NPC469891
0.899	High Similarity	NPC469892
0.899	High Similarity	NPC469890
0.8889	High Similarity	NPC469893
0.8624	High Similarity	NPC294458
0.8544	High Similarity	NPC225079
0.8468	Intermediate Similarity	NPC9274
0.8365	Intermediate Similarity	NPC128248
0.8365	Intermediate Similarity	NPC133809
0.8365	Intermediate Similarity	NPC136810
0.8364	Intermediate Similarity	NPC93287
0.8246	Intermediate Similarity	NPC472697
0.8246	Intermediate Similarity	NPC472698
0.8198	Intermediate Similarity	NPC477475
0.8198	Intermediate Similarity	NPC477476
0.8148	Intermediate Similarity	NPC37914
0.8131	Intermediate Similarity	NPC329282
0.8125	Intermediate Similarity	NPC471721
0.8125	Intermediate Similarity	NPC130591
0.8125	Intermediate Similarity	NPC234637
0.8095	Intermediate Similarity	NPC7435
0.8095	Intermediate Similarity	NPC54647
0.8077	Intermediate Similarity	NPC251579
0.8077	Intermediate Similarity	NPC226041
0.8077	Intermediate Similarity	NPC133135
0.8036	Intermediate Similarity	NPC471481
0.8036	Intermediate Similarity	NPC242957
0.8036	Intermediate Similarity	NPC287055
0.8036	Intermediate Similarity	NPC206414
0.8036	Intermediate Similarity	NPC306977
0.7982	Intermediate Similarity	NPC94751
0.7982	Intermediate Similarity	NPC142326
0.7946	Intermediate Similarity	NPC280789
0.7946	Intermediate Similarity	NPC218855
0.7941	Intermediate Similarity	NPC86987
0.7925	Intermediate Similarity	NPC221825
0.7895	Intermediate Similarity	NPC476357
0.789	Intermediate Similarity	NPC471186
0.787	Intermediate Similarity	NPC247976
0.7864	Intermediate Similarity	NPC475057
0.7857	Intermediate Similarity	NPC475002
0.7857	Intermediate Similarity	NPC95126
0.7857	Intermediate Similarity	NPC44830
0.7843	Intermediate Similarity	NPC86670
0.7843	Intermediate Similarity	NPC70940
0.7843	Intermediate Similarity	NPC274455
0.783	Intermediate Similarity	NPC271475
0.781	Intermediate Similarity	NPC261947
0.7778	Intermediate Similarity	NPC474820
0.7778	Intermediate Similarity	NPC475978
0.7767	Intermediate Similarity	NPC475023
0.7767	Intermediate Similarity	NPC475059
0.7748	Intermediate Similarity	NPC112903
0.7739	Intermediate Similarity	NPC215419
0.7736	Intermediate Similarity	NPC477767
0.7723	Intermediate Similarity	NPC322387
0.7719	Intermediate Similarity	NPC469547
0.7712	Intermediate Similarity	NPC202015
0.7706	Intermediate Similarity	NPC329556
0.7705	Intermediate Similarity	NPC470649
0.7705	Intermediate Similarity	NPC478107
0.7699	Intermediate Similarity	NPC265513
0.7685	Intermediate Similarity	NPC94487
0.767	Intermediate Similarity	NPC84288
0.7667	Intermediate Similarity	NPC269923
0.7667	Intermediate Similarity	NPC167323
0.7658	Intermediate Similarity	NPC100767
0.7658	Intermediate Similarity	NPC83409
0.7658	Intermediate Similarity	NPC472699
0.7658	Intermediate Similarity	NPC185763
0.7658	Intermediate Similarity	NPC472700
0.7647	Intermediate Similarity	NPC475804
0.7647	Intermediate Similarity	NPC474222
0.7647	Intermediate Similarity	NPC474223
0.7647	Intermediate Similarity	NPC475827
0.7647	Intermediate Similarity	NPC477693
0.7647	Intermediate Similarity	NPC329064
0.7647	Intermediate Similarity	NPC477704
0.7642	Intermediate Similarity	NPC48992
0.7642	Intermediate Similarity	NPC470648
0.7589	Intermediate Similarity	NPC21929
0.7589	Intermediate Similarity	NPC249811
0.7589	Intermediate Similarity	NPC472695
0.7589	Intermediate Similarity	NPC472683
0.7589	Intermediate Similarity	NPC472701
0.7589	Intermediate Similarity	NPC472696
0.7586	Intermediate Similarity	NPC221275
0.7581	Intermediate Similarity	NPC472678
0.7565	Intermediate Similarity	NPC470253
0.7565	Intermediate Similarity	NPC143768
0.7563	Intermediate Similarity	NPC258366
0.7563	Intermediate Similarity	NPC473974
0.7563	Intermediate Similarity	NPC79933
0.7563	Intermediate Similarity	NPC31296
0.7551	Intermediate Similarity	NPC127343
0.7547	Intermediate Similarity	NPC172925
0.7542	Intermediate Similarity	NPC45794
0.7541	Intermediate Similarity	NPC85511
0.7541	Intermediate Similarity	NPC328107
0.7525	Intermediate Similarity	NPC95965
0.75	Intermediate Similarity	NPC470585
0.75	Intermediate Similarity	NPC83569
0.75	Intermediate Similarity	NPC179411
0.75	Intermediate Similarity	NPC69279
0.7478	Intermediate Similarity	NPC292834
0.7478	Intermediate Similarity	NPC471189
0.7478	Intermediate Similarity	NPC471188
0.7459	Intermediate Similarity	NPC474254
0.7459	Intermediate Similarity	NPC474159
0.7458	Intermediate Similarity	NPC469843
0.7458	Intermediate Similarity	NPC212891
0.7451	Intermediate Similarity	NPC6247
0.7449	Intermediate Similarity	NPC477371
0.7438	Intermediate Similarity	NPC476234
0.7417	Intermediate Similarity	NPC204784
0.7411	Intermediate Similarity	NPC321670
0.7404	Intermediate Similarity	NPC298115
0.7395	Intermediate Similarity	NPC268930
0.7395	Intermediate Similarity	NPC471926
0.7387	Intermediate Similarity	NPC274443
0.7368	Intermediate Similarity	NPC475006
0.7364	Intermediate Similarity	NPC203486
0.7364	Intermediate Similarity	NPC109514
0.7358	Intermediate Similarity	NPC1682
0.7358	Intermediate Similarity	NPC188844
0.7355	Intermediate Similarity	NPC472679
0.7355	Intermediate Similarity	NPC183339
0.7355	Intermediate Similarity	NPC190501
0.7355	Intermediate Similarity	NPC133389
0.7355	Intermediate Similarity	NPC234337
0.7355	Intermediate Similarity	NPC472680
0.7355	Intermediate Similarity	NPC318552
0.7339	Intermediate Similarity	NPC329387
0.7339	Intermediate Similarity	NPC317280
0.7327	Intermediate Similarity	NPC285773
0.7323	Intermediate Similarity	NPC475138
0.7321	Intermediate Similarity	NPC56168
0.7321	Intermediate Similarity	NPC19136
0.7311	Intermediate Similarity	NPC471928
0.7311	Intermediate Similarity	NPC471924
0.7311	Intermediate Similarity	NPC471925
0.7302	Intermediate Similarity	NPC316553
0.73	Intermediate Similarity	NPC38350
0.73	Intermediate Similarity	NPC477372
0.73	Intermediate Similarity	NPC147066
0.73	Intermediate Similarity	NPC201912
0.7297	Intermediate Similarity	NPC474112
0.7297	Intermediate Similarity	NPC222390
0.7297	Intermediate Similarity	NPC244427
0.7288	Intermediate Similarity	NPC274839
0.7288	Intermediate Similarity	NPC93181
0.7288	Intermediate Similarity	NPC217111
0.7287	Intermediate Similarity	NPC159811
0.7282	Intermediate Similarity	NPC243166
0.728	Intermediate Similarity	NPC470816
0.728	Intermediate Similarity	NPC477366
0.7273	Intermediate Similarity	NPC472708
0.7273	Intermediate Similarity	NPC42657
0.7264	Intermediate Similarity	NPC141607
0.7264	Intermediate Similarity	NPC284475
0.7264	Intermediate Similarity	NPC187725
0.7258	Intermediate Similarity	NPC140118
0.7258	Intermediate Similarity	NPC472681
0.7258	Intermediate Similarity	NPC318067
0.7258	Intermediate Similarity	NPC12881
0.7258	Intermediate Similarity	NPC477362
0.7257	Intermediate Similarity	NPC172483
0.7255	Intermediate Similarity	NPC267704
0.7252	Intermediate Similarity	NPC477596
0.725	Intermediate Similarity	NPC323440
0.725	Intermediate Similarity	NPC61651
0.725	Intermediate Similarity	NPC152812
0.725	Intermediate Similarity	NPC80605
0.725	Intermediate Similarity	NPC222968
0.725	Intermediate Similarity	NPC94425
0.7248	Intermediate Similarity	NPC239185
0.7241	Intermediate Similarity	NPC474057
0.7236	Intermediate Similarity	NPC369
0.7236	Intermediate Similarity	NPC293831
0.7232	Intermediate Similarity	NPC475939
0.7232	Intermediate Similarity	NPC471829
0.7232	Intermediate Similarity	NPC472691
0.7232	Intermediate Similarity	NPC474866
0.7231	Intermediate Similarity	NPC329913
0.7231	Intermediate Similarity	NPC126516
0.7228	Intermediate Similarity	NPC133391
0.7228	Intermediate Similarity	NPC260956
0.7227	Intermediate Similarity	NPC260886
0.7222	Intermediate Similarity	NPC269598
0.7222	Intermediate Similarity	NPC477365
0.7222	Intermediate Similarity	NPC477357
0.7217	Intermediate Similarity	NPC475282
0.72	Intermediate Similarity	NPC477703
0.7196	Intermediate Similarity	NPC153885
0.7196	Intermediate Similarity	NPC59677
0.7193	Intermediate Similarity	NPC475905
0.7193	Intermediate Similarity	NPC25385

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 NPC85560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	776
0.2-0.3	1387
0.3-0.4	3103
0.4-0.5	2398
0.5-0.6	1024
0.6-0.7	245
0.7-0.8	40
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8317	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1693	Approved
0.8198	Intermediate Similarity	NPD7094	Approved
0.8198	Intermediate Similarity	NPD6858	Approved
0.8039	Intermediate Similarity	NPD1088	Approved
0.7925	Intermediate Similarity	NPD2066	Phase 3
0.7921	Intermediate Similarity	NPD5347	Phase 2
0.7921	Intermediate Similarity	NPD5346	Phase 2
0.7845	Intermediate Similarity	NPD7610	Discontinued
0.7843	Intermediate Similarity	NPD1089	Approved
0.7843	Intermediate Similarity	NPD1086	Approved
0.7843	Intermediate Similarity	NPD1090	Approved
0.7778	Intermediate Similarity	NPD7009	Phase 2
0.7745	Intermediate Similarity	NPD800	Approved
0.7723	Intermediate Similarity	NPD4793	Discontinued
0.7706	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD1930	Approved
0.7706	Intermediate Similarity	NPD1929	Approved
0.7653	Intermediate Similarity	NPD226	Approved
0.7549	Intermediate Similarity	NPD1087	Approved
0.7547	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5765	Approved
0.7522	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6685	Approved
0.75	Intermediate Similarity	NPD2932	Approved
0.7455	Intermediate Similarity	NPD1932	Approved
0.7429	Intermediate Similarity	NPD1239	Approved
0.7407	Intermediate Similarity	NPD1565	Approved
0.7407	Intermediate Similarity	NPD1564	Approved
0.7407	Intermediate Similarity	NPD1566	Phase 3
0.7391	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2329	Discontinued
0.7358	Intermediate Similarity	NPD7631	Approved
0.7355	Intermediate Similarity	NPD3019	Approved
0.7347	Intermediate Similarity	NPD225	Approved
0.7347	Intermediate Similarity	NPD227	Approved
0.7344	Intermediate Similarity	NPD7961	Discontinued
0.7333	Intermediate Similarity	NPD3672	Approved
0.7333	Intermediate Similarity	NPD3673	Approved
0.7327	Intermediate Similarity	NPD9491	Approved
0.7295	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4766	Approved
0.7288	Intermediate Similarity	NPD5951	Approved
0.7264	Intermediate Similarity	NPD7609	Phase 3
0.7248	Intermediate Similarity	NPD3495	Discontinued
0.7232	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6647	Phase 2
0.7203	Intermediate Similarity	NPD6010	Discontinued
0.7168	Intermediate Similarity	NPD5909	Discontinued
0.7156	Intermediate Similarity	NPD1989	Approved
0.7143	Intermediate Similarity	NPD2629	Approved
0.713	Intermediate Similarity	NPD1563	Approved
0.7094	Intermediate Similarity	NPD3643	Approved
0.7094	Intermediate Similarity	NPD3642	Approved
0.7094	Intermediate Similarity	NPD3644	Approved
0.7077	Intermediate Similarity	NPD6663	Approved
0.7073	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7305	Phase 1
0.7064	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6049	Phase 2
0.7034	Intermediate Similarity	NPD6912	Phase 3
0.7031	Intermediate Similarity	NPD5736	Approved
0.7031	Intermediate Similarity	NPD7084	Phase 3
0.7019	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3026	Approved
0.7016	Intermediate Similarity	NPD3023	Approved
0.7009	Intermediate Similarity	NPD1317	Discontinued
0.7	Intermediate Similarity	NPD6766	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3025	Approved
0.6992	Remote Similarity	NPD3024	Approved
0.696	Remote Similarity	NPD5618	Discontinued
0.6957	Remote Similarity	NPD7236	Approved
0.6944	Remote Similarity	NPD5281	Approved
0.6944	Remote Similarity	NPD5284	Approved
0.6935	Remote Similarity	NPD4199	Phase 3
0.6931	Remote Similarity	NPD9490	Approved
0.6917	Remote Similarity	NPD2652	Approved
0.6917	Remote Similarity	NPD2650	Approved
0.6911	Remote Similarity	NPD4479	Discontinued
0.6887	Remote Similarity	NPD650	Approved
0.6885	Remote Similarity	NPD3797	Approved
0.6881	Remote Similarity	NPD1508	Approved
0.6875	Remote Similarity	NPD253	Approved
0.6864	Remote Similarity	NPD5278	Discontinued
0.6846	Remote Similarity	NPD7055	Discontinued
0.6829	Remote Similarity	NPD6065	Approved
0.6822	Remote Similarity	NPD6085	Phase 2
0.6822	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8032	Phase 2
0.6814	Remote Similarity	NPD7798	Approved
0.6814	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5048	Discontinued
0.681	Remote Similarity	NPD1018	Approved
0.68	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD3598	Phase 3
0.6774	Remote Similarity	NPD3798	Phase 3
0.6723	Remote Similarity	NPD4234	Approved
0.6723	Remote Similarity	NPD4233	Approved
0.6713	Remote Similarity	NPD7239	Suspended
0.6696	Remote Similarity	NPD1843	Approved
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3971	Phase 1
0.6667	Remote Similarity	NPD3317	Approved
0.6667	Remote Similarity	NPD2345	Approved
0.6639	Remote Similarity	NPD7077	Approved
0.6639	Remote Similarity	NPD7076	Approved
0.6636	Remote Similarity	NPD5280	Approved
0.6636	Remote Similarity	NPD4694	Approved
0.6619	Remote Similarity	NPD7082	Approved
0.6614	Remote Similarity	NPD4879	Approved
0.6604	Remote Similarity	NPD4786	Approved
0.6579	Remote Similarity	NPD9495	Approved
0.6577	Remote Similarity	NPD6399	Phase 3
0.6571	Remote Similarity	NPD4223	Phase 3
0.6571	Remote Similarity	NPD7259	Approved
0.6571	Remote Similarity	NPD4221	Approved
0.6557	Remote Similarity	NPD2607	Approved
0.6545	Remote Similarity	NPD5207	Approved
0.6542	Remote Similarity	NPD5329	Approved
0.6541	Remote Similarity	NPD7008	Discontinued
0.6532	Remote Similarity	NPD4198	Discontinued
0.6529	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7295	Approved
0.6518	Remote Similarity	NPD1066	Discontinued
0.6512	Remote Similarity	NPD6637	Approved
0.6508	Remote Similarity	NPD7741	Discontinued
0.6504	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD9566	Approved
0.6486	Remote Similarity	NPD6050	Approved
0.6486	Remote Similarity	NPD5694	Approved
0.6486	Remote Similarity	NPD6079	Approved
0.6481	Remote Similarity	NPD5690	Phase 2
0.6481	Remote Similarity	NPD6098	Approved
0.6481	Remote Similarity	NPD5279	Phase 3
0.6471	Remote Similarity	NPD467	Phase 1
0.6466	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4094	Approved
0.6457	Remote Similarity	NPD1245	Approved
0.6457	Remote Similarity	NPD5981	Approved
0.6455	Remote Similarity	NPD5328	Approved
0.6454	Remote Similarity	NPD8166	Discontinued
0.6452	Remote Similarity	NPD1246	Approved
0.6449	Remote Similarity	NPD4197	Approved
0.6446	Remote Similarity	NPD1752	Approved
0.6446	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD1756	Approved
0.6444	Remote Similarity	NPD7714	Approved
0.6444	Remote Similarity	NPD7715	Approved
0.6439	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5696	Approved
0.6434	Remote Similarity	NPD4216	Approved
0.6434	Remote Similarity	NPD3132	Approved
0.6434	Remote Similarity	NPD2610	Approved
0.6434	Remote Similarity	NPD7478	Approved
0.6434	Remote Similarity	NPD2611	Approved
0.6434	Remote Similarity	NPD4215	Approved
0.6434	Remote Similarity	NPD2608	Approved
0.6434	Remote Similarity	NPD4806	Approved
0.6434	Remote Similarity	NPD4218	Approved
0.6434	Remote Similarity	NPD4217	Approved
0.6434	Remote Similarity	NPD4807	Approved
0.6434	Remote Similarity	NPD3131	Approved
0.6434	Remote Similarity	NPD2609	Approved
0.6434	Remote Similarity	NPD2612	Approved
0.6415	Remote Similarity	NPD3667	Approved
0.6412	Remote Similarity	NPD1283	Approved
0.6412	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD4059	Approved
0.6406	Remote Similarity	NPD5305	Approved
0.6406	Remote Similarity	NPD5306	Approved
0.6397	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD9256	Approved
0.6396	Remote Similarity	NPD5692	Phase 3
0.6396	Remote Similarity	NPD9258	Approved
0.6385	Remote Similarity	NPD4878	Approved
0.6381	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD3091	Approved
0.637	Remote Similarity	NPD3268	Approved
0.6364	Remote Similarity	NPD1101	Approved
0.6364	Remote Similarity	NPD6672	Approved
0.6364	Remote Similarity	NPD5737	Approved
0.6356	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5162	Approved
0.6348	Remote Similarity	NPD6083	Phase 2
0.6348	Remote Similarity	NPD4655	Approved
0.6348	Remote Similarity	NPD4657	Approved
0.6348	Remote Similarity	NPD6084	Phase 2
0.6341	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6684	Approved
0.633	Remote Similarity	NPD7146	Approved
0.633	Remote Similarity	NPD4688	Approved
0.633	Remote Similarity	NPD4138	Approved
0.633	Remote Similarity	NPD7334	Approved
0.633	Remote Similarity	NPD6409	Approved
0.633	Remote Similarity	NPD4689	Approved
0.633	Remote Similarity	NPD5330	Approved
0.633	Remote Similarity	NPD4693	Phase 3
0.633	Remote Similarity	NPD7521	Approved
0.633	Remote Similarity	NPD4690	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