NPASS Compound

Structure

NPC27615 OpenBabel07101718292D 43 48 0 0 0 0 0 0 0 0999 V2000 -0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 4.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 3.1691 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 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 4.3301 1.5000 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 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6665 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1665 4.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 35 1 0 0 0 0 4 35 1 0 0 0 0 5 36 1 0 0 0 0 6 36 1 0 0 0 0 7 40 1 0 0 0 0 8 41 1 0 0 0 0 9 42 1 0 0 0 0 10 17 2 0 0 0 0 10 22 1 0 0 0 0 11 18 2 0 0 0 0 11 24 1 0 0 0 0 12 19 1 0 0 0 0 12 26 2 0 0 0 0 13 20 1 0 0 0 0 13 27 2 0 0 0 0 14 21 1 0 0 0 0 14 29 2 0 0 0 0 15 23 2 0 0 0 0 15 30 1 0 0 0 0 16 25 2 0 0 0 0 16 28 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 20 24 2 0 0 0 0 21 25 1 0 0 0 0 22 28 2 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 35 1 0 0 0 0 26 40 1 0 0 0 0 27 41 1 0 0 0 0 28 43 1 0 0 0 0 29 34 1 0 0 0 0 29 42 1 0 0 0 0 30 36 1 0 0 0 0 30 37 2 0 0 0 0 31 33 2 0 0 0 0 31 36 1 0 0 0 0 32 33 1 0 0 0 0 32 38 2 0 0 0 0 33 43 1 0 0 0 0 34 35 1 0 0 0 0 34 39 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.23
Volume:	604.494
LogP:	6.72
LogD:	3.659
LogS:	-7.538
# Rotatable Bonds:	5
TPSA:	88.13
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	3.644
Fsp3:	0.306
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.8
MDCK Permeability:	1.085198346117977e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.085
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	95.99445343017578%
Volume Distribution (VD):	0.296
Pgp-substrate:	4.883296489715576%

ADMET: Metabolism

CYP1A2-inhibitor:	0.157
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.892
CYP2C19-substrate:	0.709
CYP2C9-inhibitor:	0.849
CYP2C9-substrate:	0.849
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.288
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	1.589
Half-life (T1/2):	0.02

ADMET: Toxicity

hERG Blockers:	0.241
Human Hepatotoxicity (H-HT):	0.359
Drug-inuced Liver Injury (DILI):	0.892
AMES Toxicity:	0.112
Rat Oral Acute Toxicity:	0.732
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.457
Carcinogencity:	0.797
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.442

Download Data

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

Natural Product: NPC27615

Natural Product ID:	NPC27615
*Common Name:**	Fimbricalyx A
IUPAC Name:	4-(3,6-dimethoxy-1,1,7-trimethyl-2-oxophenanthren-9-yl)oxy-8-methoxy-3,3,7-trimethylcyclopenta[a]naphthalene-2,5-dione
Synonyms:
Standard InCHIKey:	GOAXONQUIUAYOC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C36H34O7/c1-17-10-22-19(12-26(17)40-7)21-14-29(42-9)34(39)35(3,4)25(21)16-28(22)43-33-31-23(15-30(37)36(31,5)6)20-13-27(41-8)18(2)11-24(20)32(33)38/h10-16H,1-9H3
SMILES:	Cc1cc2c(cc1OC)c1C=C(C(=O)C(C)(C)c1cc2OC1=C2C(=CC(=O)C2(C)C)c2cc(c(C)cc2C1=O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409524
PubChem CID:	71623988
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0003007] Phenanthrols

*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
NPO6431	Strophioblachia fimbricalyx	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[19778068]
NPO6431	Strophioblachia fimbricalyx	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23806014]
NPO6431	Strophioblachia fimbricalyx	Species	Euphorbiaceae	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	5

Activity Type	# Activity
Cell Line	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	8300.0	nM	PMID[459999]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	10000.0	nM	PMID[459999]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[459999]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[459999]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	2900.0	nM	PMID[459999]

☑ 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 NPC27615 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	516
0.1-0.2	1727
0.2-0.3	3729
0.3-0.4	9539
0.4-0.5	9273
0.5-0.6	4352
0.6-0.7	8025
0.7-0.8	5370
0.8-0.85	152
0.85-0.9	9
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8966	High Similarity	NPC290601
0.8836	High Similarity	NPC186647
0.8693	High Similarity	NPC472839
0.8667	High Similarity	NPC201297
0.8662	High Similarity	NPC276231
0.8571	High Similarity	NPC472841
0.8553	High Similarity	NPC472836
0.8487	Intermediate Similarity	NPC472840
0.8481	Intermediate Similarity	NPC478159
0.8481	Intermediate Similarity	NPC478161
0.8446	Intermediate Similarity	NPC22644
0.8431	Intermediate Similarity	NPC308006
0.8425	Intermediate Similarity	NPC239134
0.8425	Intermediate Similarity	NPC164295
0.8408	Intermediate Similarity	NPC189773
0.8389	Intermediate Similarity	NPC471670
0.8387	Intermediate Similarity	NPC478163
0.8367	Intermediate Similarity	NPC183103
0.8354	Intermediate Similarity	NPC10429
0.8313	Intermediate Similarity	NPC288353
0.8312	Intermediate Similarity	NPC114513
0.8312	Intermediate Similarity	NPC245522
0.8312	Intermediate Similarity	NPC189650
0.8311	Intermediate Similarity	NPC470406
0.8258	Intermediate Similarity	NPC478166
0.8224	Intermediate Similarity	NPC470407
0.8221	Intermediate Similarity	NPC103816
0.8221	Intermediate Similarity	NPC61382
0.821	Intermediate Similarity	NPC228654
0.8194	Intermediate Similarity	NPC260152
0.8182	Intermediate Similarity	NPC314653
0.8182	Intermediate Similarity	NPC41689
0.8182	Intermediate Similarity	NPC316262
0.8176	Intermediate Similarity	NPC279596
0.8176	Intermediate Similarity	NPC230848
0.8176	Intermediate Similarity	NPC474414
0.8176	Intermediate Similarity	NPC472838
0.8176	Intermediate Similarity	NPC306011
0.8171	Intermediate Similarity	NPC475144
0.8165	Intermediate Similarity	NPC80370
0.8151	Intermediate Similarity	NPC428300
0.8148	Intermediate Similarity	NPC123153
0.8133	Intermediate Similarity	NPC85047
0.8133	Intermediate Similarity	NPC120857
0.8133	Intermediate Similarity	NPC17274
0.8129	Intermediate Similarity	NPC167663
0.8121	Intermediate Similarity	NPC469395
0.8113	Intermediate Similarity	NPC140133
0.8113	Intermediate Similarity	NPC477914
0.8113	Intermediate Similarity	NPC474660
0.811	Intermediate Similarity	NPC273467
0.811	Intermediate Similarity	NPC189552
0.811	Intermediate Similarity	NPC219686
0.8101	Intermediate Similarity	NPC475848
0.8101	Intermediate Similarity	NPC474306
0.8101	Intermediate Similarity	NPC474107
0.8098	Intermediate Similarity	NPC472299
0.8095	Intermediate Similarity	NPC181675
0.8089	Intermediate Similarity	NPC473927
0.8082	Intermediate Similarity	NPC474737
0.8077	Intermediate Similarity	NPC290038
0.8075	Intermediate Similarity	NPC329844
0.8075	Intermediate Similarity	NPC473664
0.8063	Intermediate Similarity	NPC149526
0.8063	Intermediate Similarity	NPC474417
0.8063	Intermediate Similarity	NPC48671
0.8063	Intermediate Similarity	NPC258249
0.8063	Intermediate Similarity	NPC478148
0.8061	Intermediate Similarity	NPC475106
0.805	Intermediate Similarity	NPC97028
0.805	Intermediate Similarity	NPC100985
0.805	Intermediate Similarity	NPC65589
0.805	Intermediate Similarity	NPC474305
0.805	Intermediate Similarity	NPC288036
0.805	Intermediate Similarity	NPC97029
0.805	Intermediate Similarity	NPC158338
0.805	Intermediate Similarity	NPC300983
0.8049	Intermediate Similarity	NPC313368
0.8049	Intermediate Similarity	NPC312993
0.8049	Intermediate Similarity	NPC65784
0.8049	Intermediate Similarity	NPC186325
0.8037	Intermediate Similarity	NPC201127
0.8036	Intermediate Similarity	NPC20734
0.8036	Intermediate Similarity	NPC286074
0.8036	Intermediate Similarity	NPC54903
0.8025	Intermediate Similarity	NPC478160
0.8025	Intermediate Similarity	NPC49282
0.8013	Intermediate Similarity	NPC1249
0.8012	Intermediate Similarity	NPC40356
0.8012	Intermediate Similarity	NPC154683
0.8	Intermediate Similarity	NPC470333
0.8	Intermediate Similarity	NPC295977
0.8	Intermediate Similarity	NPC472261
0.8	Intermediate Similarity	NPC473466
0.8	Intermediate Similarity	NPC58310
0.7988	Intermediate Similarity	NPC193698
0.7988	Intermediate Similarity	NPC55443
0.7988	Intermediate Similarity	NPC313717
0.7988	Intermediate Similarity	NPC265563
0.7988	Intermediate Similarity	NPC304125
0.7988	Intermediate Similarity	NPC315306
0.7988	Intermediate Similarity	NPC177650
0.7988	Intermediate Similarity	NPC18699
0.7987	Intermediate Similarity	NPC27221
0.7987	Intermediate Similarity	NPC256672
0.7987	Intermediate Similarity	NPC7025
0.7987	Intermediate Similarity	NPC95526
0.7976	Intermediate Similarity	NPC286230
0.7976	Intermediate Similarity	NPC253730
0.7975	Intermediate Similarity	NPC474360
0.7975	Intermediate Similarity	NPC180924
0.7975	Intermediate Similarity	NPC192587
0.7974	Intermediate Similarity	NPC36868
0.7965	Intermediate Similarity	NPC47191
0.7964	Intermediate Similarity	NPC469664
0.7963	Intermediate Similarity	NPC169990
0.7963	Intermediate Similarity	NPC210942
0.7962	Intermediate Similarity	NPC477913
0.7962	Intermediate Similarity	NPC471305
0.795	Intermediate Similarity	NPC232645
0.795	Intermediate Similarity	NPC72958
0.7941	Intermediate Similarity	NPC478002
0.7939	Intermediate Similarity	NPC471003
0.7939	Intermediate Similarity	NPC470342
0.7939	Intermediate Similarity	NPC472052
0.7939	Intermediate Similarity	NPC472060
0.7939	Intermediate Similarity	NPC472618
0.7937	Intermediate Similarity	NPC472837
0.7937	Intermediate Similarity	NPC472298
0.7933	Intermediate Similarity	NPC301717
0.7927	Intermediate Similarity	NPC272196
0.7927	Intermediate Similarity	NPC164110
0.7927	Intermediate Similarity	NPC96342
0.7927	Intermediate Similarity	NPC474637
0.7927	Intermediate Similarity	NPC246647
0.7927	Intermediate Similarity	NPC212967
0.7925	Intermediate Similarity	NPC123202
0.7925	Intermediate Similarity	NPC7943
0.7925	Intermediate Similarity	NPC22005
0.7925	Intermediate Similarity	NPC34802
0.7922	Intermediate Similarity	NPC62735
0.7922	Intermediate Similarity	NPC233707
0.7919	Intermediate Similarity	NPC70318
0.7917	Intermediate Similarity	NPC291742
0.7917	Intermediate Similarity	NPC475109
0.7914	Intermediate Similarity	NPC226656
0.7914	Intermediate Similarity	NPC3898
0.7914	Intermediate Similarity	NPC66508
0.7904	Intermediate Similarity	NPC308156
0.7904	Intermediate Similarity	NPC290160
0.7901	Intermediate Similarity	NPC87708
0.7901	Intermediate Similarity	NPC60211
0.7898	Intermediate Similarity	NPC478164
0.7895	Intermediate Similarity	NPC469393
0.7895	Intermediate Similarity	NPC131862
0.7895	Intermediate Similarity	NPC209858
0.7895	Intermediate Similarity	NPC324117
0.7895	Intermediate Similarity	NPC213122
0.7892	Intermediate Similarity	NPC18380
0.7891	Intermediate Similarity	NPC232387
0.7888	Intermediate Similarity	NPC13282
0.7885	Intermediate Similarity	NPC171094
0.7879	Intermediate Similarity	NPC195167
0.7879	Intermediate Similarity	NPC474373
0.7879	Intermediate Similarity	NPC472617
0.7875	Intermediate Similarity	NPC474556
0.7875	Intermediate Similarity	NPC192069
0.7871	Intermediate Similarity	NPC476191
0.787	Intermediate Similarity	NPC105414
0.787	Intermediate Similarity	NPC302392
0.787	Intermediate Similarity	NPC470341
0.787	Intermediate Similarity	NPC193222
0.787	Intermediate Similarity	NPC324522
0.787	Intermediate Similarity	NPC472058
0.787	Intermediate Similarity	NPC76647
0.787	Intermediate Similarity	NPC234497
0.7866	Intermediate Similarity	NPC56049
0.7866	Intermediate Similarity	NPC54830
0.7861	Intermediate Similarity	NPC478000
0.7857	Intermediate Similarity	NPC169471
0.7857	Intermediate Similarity	NPC301341
0.7857	Intermediate Similarity	NPC119542
0.7853	Intermediate Similarity	NPC214632
0.7853	Intermediate Similarity	NPC25351
0.7848	Intermediate Similarity	NPC471451
0.7844	Intermediate Similarity	NPC15374
0.784	Intermediate Similarity	NPC118332
0.784	Intermediate Similarity	NPC305965
0.7838	Intermediate Similarity	NPC177925
0.7836	Intermediate Similarity	NPC472639
0.7836	Intermediate Similarity	NPC477529
0.7836	Intermediate Similarity	NPC472638
0.7834	Intermediate Similarity	NPC308572
0.7834	Intermediate Similarity	NPC69755
0.7831	Intermediate Similarity	NPC292863
0.7831	Intermediate Similarity	NPC184326
0.7831	Intermediate Similarity	NPC195136
0.7829	Intermediate Similarity	NPC470332
0.7826	Intermediate Similarity	NPC329933
0.7826	Intermediate Similarity	NPC269420

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 NPC27615 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	433
0.1-0.2	1023
0.2-0.3	1461
0.3-0.4	2601
0.4-0.5	2057
0.5-0.6	1002
0.6-0.7	454
0.7-0.8	118
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7892	Intermediate Similarity	NPD6959	Discontinued
0.7885	Intermediate Similarity	NPD7003	Approved
0.7853	Intermediate Similarity	NPD7819	Suspended
0.7821	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD3972	Approved
0.7677	Intermediate Similarity	NPD3748	Approved
0.7669	Intermediate Similarity	NPD6599	Discontinued
0.7616	Intermediate Similarity	NPD5844	Phase 1
0.7607	Intermediate Similarity	NPD7458	Discontinued
0.7607	Intermediate Similarity	NPD3226	Approved
0.759	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8032	Phase 2
0.758	Intermediate Similarity	NPD1471	Phase 3
0.7578	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7534	Intermediate Similarity	NPD1651	Approved
0.7531	Intermediate Similarity	NPD6273	Approved
0.753	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7457	Intermediate Similarity	NPD7177	Discontinued
0.7442	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7768	Phase 2
0.7438	Intermediate Similarity	NPD3750	Approved
0.7412	Intermediate Similarity	NPD5494	Approved
0.741	Intermediate Similarity	NPD7411	Suspended
0.7405	Intermediate Similarity	NPD6099	Approved
0.7405	Intermediate Similarity	NPD6100	Approved
0.7399	Intermediate Similarity	NPD7473	Discontinued
0.7396	Intermediate Similarity	NPD7075	Discontinued
0.7356	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1876	Approved
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6232	Discontinued
0.7308	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6799	Approved
0.7301	Intermediate Similarity	NPD7390	Discontinued
0.7294	Intermediate Similarity	NPD3749	Approved
0.7283	Intermediate Similarity	NPD3926	Phase 2
0.7278	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1243	Approved
0.7267	Intermediate Similarity	NPD1281	Approved
0.7262	Intermediate Similarity	NPD6801	Discontinued
0.7251	Intermediate Similarity	NPD919	Approved
0.725	Intermediate Similarity	NPD2344	Approved
0.7241	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6166	Phase 2
0.7241	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3882	Suspended
0.7233	Intermediate Similarity	NPD2799	Discontinued
0.7219	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD8312	Approved
0.7197	Intermediate Similarity	NPD2979	Phase 3
0.7176	Intermediate Similarity	NPD3817	Phase 2
0.7169	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1247	Approved
0.7168	Intermediate Similarity	NPD8127	Discontinued
0.716	Intermediate Similarity	NPD2800	Approved
0.7152	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD2532	Approved
0.7152	Intermediate Similarity	NPD2533	Approved
0.7135	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD17	Approved
0.7133	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7125	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1283	Approved
0.7115	Intermediate Similarity	NPD7095	Approved
0.7107	Intermediate Similarity	NPD1607	Approved
0.7099	Intermediate Similarity	NPD1549	Phase 2
0.7088	Intermediate Similarity	NPD8434	Phase 2
0.7088	Intermediate Similarity	NPD8150	Discontinued
0.7086	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5405	Approved
0.7081	Intermediate Similarity	NPD5404	Approved
0.7081	Intermediate Similarity	NPD5408	Approved
0.7081	Intermediate Similarity	NPD5406	Approved
0.7073	Intermediate Similarity	NPD2309	Approved
0.707	Intermediate Similarity	NPD3764	Approved
0.707	Intermediate Similarity	NPD6798	Discontinued
0.7067	Intermediate Similarity	NPD5691	Approved
0.7066	Intermediate Similarity	NPD920	Approved
0.7062	Intermediate Similarity	NPD3751	Discontinued
0.7059	Intermediate Similarity	NPD5327	Phase 3
0.7044	Intermediate Similarity	NPD6355	Discontinued
0.7041	Intermediate Similarity	NPD4380	Phase 2
0.7039	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4107	Approved
0.703	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7236	Approved
0.7019	Intermediate Similarity	NPD1510	Phase 2
0.7018	Intermediate Similarity	NPD8455	Phase 2
0.7013	Intermediate Similarity	NPD8651	Approved
0.7012	Intermediate Similarity	NPD8166	Discontinued
0.7007	Intermediate Similarity	NPD1241	Discontinued
0.7006	Intermediate Similarity	NPD1512	Approved
0.7	Intermediate Similarity	NPD6559	Discontinued
0.6994	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1608	Approved
0.6988	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1240	Approved
0.6981	Remote Similarity	NPD4060	Phase 1
0.6981	Remote Similarity	NPD4307	Phase 2
0.6975	Remote Similarity	NPD2438	Suspended
0.6975	Remote Similarity	NPD2935	Discontinued
0.6975	Remote Similarity	NPD2531	Phase 2
0.697	Remote Similarity	NPD3887	Approved
0.6962	Remote Similarity	NPD2313	Discontinued
0.6962	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7808	Phase 3
0.6959	Remote Similarity	NPD1934	Approved
0.6954	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6832	Phase 2
0.6933	Remote Similarity	NPD2353	Approved
0.6933	Remote Similarity	NPD5763	Approved
0.6933	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5762	Approved
0.6932	Remote Similarity	NPD3787	Discontinued
0.6928	Remote Similarity	NPD1611	Approved
0.6923	Remote Similarity	NPD2971	Approved
0.6923	Remote Similarity	NPD2968	Approved
0.6923	Remote Similarity	NPD7239	Suspended
0.6923	Remote Similarity	NPD2798	Approved
0.6919	Remote Similarity	NPD1465	Phase 2
0.6919	Remote Similarity	NPD5760	Phase 2
0.6919	Remote Similarity	NPD2801	Approved
0.6919	Remote Similarity	NPD5761	Phase 2
0.6911	Remote Similarity	NPD4482	Phase 3
0.6908	Remote Similarity	NPD4626	Approved
0.6906	Remote Similarity	NPD6764	Approved
0.6906	Remote Similarity	NPD7251	Discontinued
0.6906	Remote Similarity	NPD6765	Approved
0.6903	Remote Similarity	NPD6696	Suspended
0.6899	Remote Similarity	NPD4625	Phase 3
0.6894	Remote Similarity	NPD6651	Approved
0.6891	Remote Similarity	NPD7870	Phase 2
0.6891	Remote Similarity	NPD7871	Phase 2
0.6886	Remote Similarity	NPD1511	Approved
0.6879	Remote Similarity	NPD5402	Approved
0.6875	Remote Similarity	NPD7199	Phase 2
0.6875	Remote Similarity	NPD3057	Approved
0.6865	Remote Similarity	NPD7693	Approved
0.6864	Remote Similarity	NPD5403	Approved
0.686	Remote Similarity	NPD6280	Approved
0.686	Remote Similarity	NPD6279	Approved
0.6859	Remote Similarity	NPD1470	Approved
0.6859	Remote Similarity	NPD3267	Approved
0.6859	Remote Similarity	NPD3266	Approved
0.6855	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6797	Phase 2
0.6845	Remote Similarity	NPD5401	Approved
0.6845	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3025	Approved
0.6842	Remote Similarity	NPD7028	Phase 2
0.6842	Remote Similarity	NPD3024	Approved
0.6839	Remote Similarity	NPD7698	Approved
0.6839	Remote Similarity	NPD7697	Approved
0.6839	Remote Similarity	NPD7696	Phase 3
0.6839	Remote Similarity	NPD7435	Discontinued
0.6818	Remote Similarity	NPD1201	Approved
0.681	Remote Similarity	NPD4308	Phase 3
0.6806	Remote Similarity	NPD8285	Discontinued
0.6805	Remote Similarity	NPD5049	Phase 3
0.68	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1778	Approved
0.6796	Remote Similarity	NPD7074	Phase 3
0.6788	Remote Similarity	NPD2897	Discontinued
0.6788	Remote Similarity	NPD2972	Approved
0.6788	Remote Similarity	NPD3533	Approved
0.6782	Remote Similarity	NPD4288	Approved
0.6771	Remote Similarity	NPD6782	Approved
0.6771	Remote Similarity	NPD6779	Approved
0.6771	Remote Similarity	NPD6776	Approved
0.6771	Remote Similarity	NPD6778	Approved
0.6771	Remote Similarity	NPD6777	Approved
0.6771	Remote Similarity	NPD6781	Approved
0.6771	Remote Similarity	NPD6780	Approved
0.677	Remote Similarity	NPD4140	Approved
0.6768	Remote Similarity	NPD4476	Approved
0.6768	Remote Similarity	NPD4477	Approved
0.6766	Remote Similarity	NPD2354	Approved
0.6763	Remote Similarity	NPD7577	Discontinued
0.6757	Remote Similarity	NPD6785	Approved
0.6757	Remote Similarity	NPD6784	Approved
0.6753	Remote Similarity	NPD3026	Approved
0.6753	Remote Similarity	NPD3023	Approved
0.6751	Remote Similarity	NPD8151	Discontinued
0.675	Remote Similarity	NPD6410	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data