NPASS Compound

Structure

NPC130976 OpenBabel07101718192D 25 27 0 0 1 0 0 0 0 0999 V2000 -4.4709 -0.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5379 1.0582 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 0.0579 -0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -0.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7979 0.0176 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 -1.5731 -1.2071 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 -4.0226 1.2424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7657 0.8719 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3455 2.3824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7638 0.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6044 1.4165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9885 1.5012 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3469 2.4348 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 6 15 2 0 0 0 0 7 9 2 0 0 0 0 7 18 1 0 0 0 0 8 22 1 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 19 2 0 0 0 0 12 17 2 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 16 2 0 0 0 0 14 24 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 21 25 1 0 0 0 0 22 4 1 1 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.19
Volume:	371.314
LogP:	5.508
LogD:	4.673
LogS:	-5.71
# Rotatable Bonds:	5
TPSA:	42.6
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.707
Synthetic Accessibility Score:	3.799
Fsp3:	0.364
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:	-4.92
MDCK Permeability:	2.4366445359191857e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.63
30% Bioavailability (F30%):	0.285

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	100.13328552246094%
Volume Distribution (VD):	0.437
Pgp-substrate:	0.4657202959060669%

ADMET: Metabolism

CYP1A2-inhibitor:	0.772
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.84
CYP2C19-substrate:	0.644
CYP2C9-inhibitor:	0.786
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.947
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.927
CYP3A4-substrate:	0.571

ADMET: Excretion

Clearance (CL):	8.498
Half-life (T1/2):	0.522

ADMET: Toxicity

hERG Blockers:	0.148
Human Hepatotoxicity (H-HT):	0.78
Drug-inuced Liver Injury (DILI):	0.387
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.46
Carcinogencity:	0.185
Eye Corrosion:	0.003
Eye Irritation:	0.187
Respiratory Toxicity:	0.653

Download Data

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

Natural Product: NPC130976

Natural Product ID:	NPC130976
*Common Name:**	Capillobenzopyranol
IUPAC Name:	(2R)-2,7-dimethyl-2-[(E)-4-methyl-5-(4-methylfuran-2-yl)pent-3-enyl]chromen-6-ol
Synonyms:	Capillobenzopyranol
Standard InCHIKey:	VSUOGDPUZWQBKJ-KSBRZHAFSA-N
Standard InCHI:	InChI=1S/C22H26O3/c1-15(10-19-11-16(2)14-24-19)6-5-8-22(4)9-7-18-13-20(23)17(3)12-21(18)25-22/h6-7,9,11-14,23H,5,8,10H2,1-4H3/b15-6+/t22-/m1/s1
SMILES:	C/C(=CCC[C@]1(C)C=Cc2cc(c(C)cc2O1)O)/Cc1cc(C)co1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095581
PubChem CID:	46886865
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans

*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
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087604]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20155971]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964704]
NPO40348	Sinularia verruca	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27010413]
NPO22108	Sinularia capillosa	Species	Alcyoniidae	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
ED50	1
Others	2

Activity Type	# Activity
Cell Line	2
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	12.7	uM	PMID[537711]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	36.7	%	PMID[537711]
NPT21752	CELL-LINE	Peritoneal macrophage cells	n.a.	Inhibition	<	50.0	%	PMID[537712]

☑ 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 NPC130976 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	302
0.1-0.2	1631
0.2-0.3	4044
0.3-0.4	11399
0.4-0.5	7127
0.5-0.6	4288
0.6-0.7	9581
0.7-0.8	4242
0.8-0.85	72
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9618	High Similarity	NPC265793
0.9185	High Similarity	NPC278832
0.9185	High Similarity	NPC64157
0.9071	High Similarity	NPC469642
0.8769	High Similarity	NPC476165
0.8681	High Similarity	NPC308799
0.8621	High Similarity	NPC113428
0.8621	High Similarity	NPC61284
0.8523	High Similarity	NPC290927
0.8496	Intermediate Similarity	NPC118853
0.8478	Intermediate Similarity	NPC118253
0.8472	Intermediate Similarity	NPC158871
0.8467	Intermediate Similarity	NPC7569
0.8451	Intermediate Similarity	NPC112757
0.8433	Intermediate Similarity	NPC4012
0.8433	Intermediate Similarity	NPC147896
0.8403	Intermediate Similarity	NPC329493
0.838	Intermediate Similarity	NPC98395
0.8357	Intermediate Similarity	NPC209858
0.8345	Intermediate Similarity	NPC329427
0.8345	Intermediate Similarity	NPC317601
0.8333	Intermediate Similarity	NPC278787
0.8298	Intermediate Similarity	NPC204592
0.8296	Intermediate Similarity	NPC190086
0.8296	Intermediate Similarity	NPC276962
0.8278	Intermediate Similarity	NPC84721
0.8273	Intermediate Similarity	NPC141549
0.8252	Intermediate Similarity	NPC233707
0.8248	Intermediate Similarity	NPC142087
0.8248	Intermediate Similarity	NPC298884
0.8248	Intermediate Similarity	NPC95034
0.8243	Intermediate Similarity	NPC150215
0.8235	Intermediate Similarity	NPC224657
0.8227	Intermediate Similarity	NPC324117
0.8214	Intermediate Similarity	NPC474340
0.8201	Intermediate Similarity	NPC196621
0.82	Intermediate Similarity	NPC13282
0.8188	Intermediate Similarity	NPC201419
0.8182	Intermediate Similarity	NPC206007
0.8169	Intermediate Similarity	NPC281513
0.8169	Intermediate Similarity	NPC22222
0.8158	Intermediate Similarity	NPC72370
0.8156	Intermediate Similarity	NPC470871
0.8146	Intermediate Similarity	NPC149085
0.8143	Intermediate Similarity	NPC473982
0.8143	Intermediate Similarity	NPC324488
0.8125	Intermediate Similarity	NPC202260
0.8125	Intermediate Similarity	NPC62735
0.812	Intermediate Similarity	NPC137710
0.8117	Intermediate Similarity	NPC44199
0.8112	Intermediate Similarity	NPC163029
0.8112	Intermediate Similarity	NPC194847
0.8112	Intermediate Similarity	NPC21797
0.8099	Intermediate Similarity	NPC274876
0.8099	Intermediate Similarity	NPC477210
0.8092	Intermediate Similarity	NPC44606
0.8092	Intermediate Similarity	NPC205523
0.8082	Intermediate Similarity	NPC263337
0.8079	Intermediate Similarity	NPC167576
0.8077	Intermediate Similarity	NPC24761
0.8071	Intermediate Similarity	NPC245395
0.8065	Intermediate Similarity	NPC477692
0.8065	Intermediate Similarity	NPC226287
0.806	Intermediate Similarity	NPC14177
0.8058	Intermediate Similarity	NPC59502
0.8056	Intermediate Similarity	NPC477534
0.8054	Intermediate Similarity	NPC60389
0.8045	Intermediate Similarity	NPC21831
0.8045	Intermediate Similarity	NPC187547
0.8043	Intermediate Similarity	NPC474264
0.8041	Intermediate Similarity	NPC290038
0.803	Intermediate Similarity	NPC316062
0.8029	Intermediate Similarity	NPC56332
0.8028	Intermediate Similarity	NPC106247
0.8028	Intermediate Similarity	NPC472591
0.8015	Intermediate Similarity	NPC49441
0.8014	Intermediate Similarity	NPC477537
0.8014	Intermediate Similarity	NPC301717
0.8014	Intermediate Similarity	NPC474143
0.8014	Intermediate Similarity	NPC474246
0.8013	Intermediate Similarity	NPC474052
0.8	Intermediate Similarity	NPC271832
0.8	Intermediate Similarity	NPC238309
0.8	Intermediate Similarity	NPC474920
0.8	Intermediate Similarity	NPC59654
0.8	Intermediate Similarity	NPC939
0.7987	Intermediate Similarity	NPC98926
0.7986	Intermediate Similarity	NPC307401
0.7986	Intermediate Similarity	NPC279877
0.7986	Intermediate Similarity	NPC329707
0.7986	Intermediate Similarity	NPC472881
0.7985	Intermediate Similarity	NPC471449
0.7973	Intermediate Similarity	NPC1534
0.797	Intermediate Similarity	NPC312525
0.797	Intermediate Similarity	NPC217180
0.7959	Intermediate Similarity	NPC145673
0.7959	Intermediate Similarity	NPC124365
0.7958	Intermediate Similarity	NPC251549
0.7955	Intermediate Similarity	NPC473718
0.7949	Intermediate Similarity	NPC472877
0.7947	Intermediate Similarity	NPC95526
0.7945	Intermediate Similarity	NPC268691
0.7945	Intermediate Similarity	NPC475045
0.7945	Intermediate Similarity	NPC76312
0.7945	Intermediate Similarity	NPC475012
0.7943	Intermediate Similarity	NPC61788
0.7943	Intermediate Similarity	NPC475880
0.7933	Intermediate Similarity	NPC99454
0.7933	Intermediate Similarity	NPC130176
0.7933	Intermediate Similarity	NPC196114
0.7933	Intermediate Similarity	NPC211565
0.7933	Intermediate Similarity	NPC469758
0.7929	Intermediate Similarity	NPC50583
0.7926	Intermediate Similarity	NPC246214
0.7922	Intermediate Similarity	NPC470331
0.7922	Intermediate Similarity	NPC472462
0.7922	Intermediate Similarity	NPC477691
0.7919	Intermediate Similarity	NPC471451
0.7919	Intermediate Similarity	NPC89664
0.7919	Intermediate Similarity	NPC274085
0.7914	Intermediate Similarity	NPC290955
0.791	Intermediate Similarity	NPC171023
0.7908	Intermediate Similarity	NPC170169
0.7902	Intermediate Similarity	NPC477536
0.7899	Intermediate Similarity	NPC193805
0.7895	Intermediate Similarity	NPC59035
0.7895	Intermediate Similarity	NPC79202
0.7891	Intermediate Similarity	NPC477535
0.7891	Intermediate Similarity	NPC475044
0.7891	Intermediate Similarity	NPC475063
0.7887	Intermediate Similarity	NPC279596
0.7885	Intermediate Similarity	NPC212967
0.7885	Intermediate Similarity	NPC296957
0.7885	Intermediate Similarity	NPC164110
0.7885	Intermediate Similarity	NPC246647
0.7885	Intermediate Similarity	NPC123153
0.7885	Intermediate Similarity	NPC260902
0.7885	Intermediate Similarity	NPC96342
0.7881	Intermediate Similarity	NPC252208
0.7881	Intermediate Similarity	NPC14875
0.7881	Intermediate Similarity	NPC17816
0.7879	Intermediate Similarity	NPC114144
0.7877	Intermediate Similarity	NPC475005
0.7877	Intermediate Similarity	NPC474943
0.7871	Intermediate Similarity	NPC198490
0.7871	Intermediate Similarity	NPC99199
0.7867	Intermediate Similarity	NPC469764
0.7862	Intermediate Similarity	NPC473268
0.7862	Intermediate Similarity	NPC215109
0.7862	Intermediate Similarity	NPC308156
0.7862	Intermediate Similarity	NPC170604
0.7857	Intermediate Similarity	NPC131121
0.7857	Intermediate Similarity	NPC67654
0.7857	Intermediate Similarity	NPC71525
0.7857	Intermediate Similarity	NPC319422
0.7857	Intermediate Similarity	NPC477212
0.7857	Intermediate Similarity	NPC477214
0.7857	Intermediate Similarity	NPC477690
0.7857	Intermediate Similarity	NPC207624
0.7857	Intermediate Similarity	NPC477211
0.7848	Intermediate Similarity	NPC269117
0.7843	Intermediate Similarity	NPC37348
0.7843	Intermediate Similarity	NPC230713
0.7843	Intermediate Similarity	NPC78335
0.7842	Intermediate Similarity	NPC470858
0.7842	Intermediate Similarity	NPC23086
0.7836	Intermediate Similarity	NPC240664
0.7834	Intermediate Similarity	NPC472299
0.7829	Intermediate Similarity	NPC168085
0.7829	Intermediate Similarity	NPC272194
0.7829	Intermediate Similarity	NPC5537
0.7826	Intermediate Similarity	NPC141252
0.7826	Intermediate Similarity	NPC93730
0.7826	Intermediate Similarity	NPC11799
0.7823	Intermediate Similarity	NPC18457
0.7821	Intermediate Similarity	NPC160015
0.7821	Intermediate Similarity	NPC221992
0.7821	Intermediate Similarity	NPC469507
0.7821	Intermediate Similarity	NPC247677
0.7821	Intermediate Similarity	NPC180924
0.7817	Intermediate Similarity	NPC477645
0.7815	Intermediate Similarity	NPC300267
0.7815	Intermediate Similarity	NPC300540
0.7815	Intermediate Similarity	NPC51641
0.7812	Intermediate Similarity	NPC291110
0.7812	Intermediate Similarity	NPC136641
0.7806	Intermediate Similarity	NPC42458
0.7806	Intermediate Similarity	NPC158261
0.7806	Intermediate Similarity	NPC183874
0.7806	Intermediate Similarity	NPC122365
0.7806	Intermediate Similarity	NPC135522
0.7801	Intermediate Similarity	NPC81261
0.78	Intermediate Similarity	NPC471600
0.78	Intermediate Similarity	NPC302181
0.7799	Intermediate Similarity	NPC193998
0.7793	Intermediate Similarity	NPC475011
0.7793	Intermediate Similarity	NPC46896
0.7793	Intermediate Similarity	NPC217914
0.7792	Intermediate Similarity	NPC23668
0.7792	Intermediate Similarity	NPC115324

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 NPC130976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	994
0.2-0.3	1372
0.3-0.4	2616
0.4-0.5	1978
0.5-0.6	1283
0.6-0.7	521
0.7-0.8	94
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
0.8252	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2344	Approved
0.7931	Intermediate Similarity	NPD2935	Discontinued
0.7862	Intermediate Similarity	NPD4308	Phase 3
0.782	Intermediate Similarity	NPD6671	Approved
0.7808	Intermediate Similarity	NPD1551	Phase 2
0.7785	Intermediate Similarity	NPD2309	Approved
0.7755	Intermediate Similarity	NPD2346	Discontinued
0.7692	Intermediate Similarity	NPD2313	Discontinued
0.7681	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD2798	Approved
0.7643	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6559	Discontinued
0.7609	Intermediate Similarity	NPD3496	Discontinued
0.7589	Intermediate Similarity	NPD2797	Approved
0.7589	Intermediate Similarity	NPD1203	Approved
0.7586	Intermediate Similarity	NPD4307	Phase 2
0.7569	Intermediate Similarity	NPD411	Approved
0.7537	Intermediate Similarity	NPD1241	Discontinued
0.7536	Intermediate Similarity	NPD1778	Approved
0.7534	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6844	Discontinued
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD3972	Approved
0.7483	Intermediate Similarity	NPD1607	Approved
0.7483	Intermediate Similarity	NPD9494	Approved
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7468	Intermediate Similarity	NPD2801	Approved
0.745	Intermediate Similarity	NPD2796	Approved
0.7448	Intermediate Similarity	NPD3268	Approved
0.7436	Intermediate Similarity	NPD3226	Approved
0.7436	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6832	Phase 2
0.7419	Intermediate Similarity	NPD920	Approved
0.7415	Intermediate Similarity	NPD447	Suspended
0.7407	Intermediate Similarity	NPD1247	Approved
0.7405	Intermediate Similarity	NPD968	Approved
0.7403	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6696	Suspended
0.7386	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1510	Phase 2
0.7375	Intermediate Similarity	NPD3882	Suspended
0.7368	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3750	Approved
0.7361	Intermediate Similarity	NPD2861	Phase 2
0.7358	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6273	Approved
0.7351	Intermediate Similarity	NPD1549	Phase 2
0.7347	Intermediate Similarity	NPD1240	Approved
0.7333	Intermediate Similarity	NPD6100	Approved
0.7333	Intermediate Similarity	NPD6099	Approved
0.7312	Intermediate Similarity	NPD5402	Approved
0.7296	Intermediate Similarity	NPD1934	Approved
0.729	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1471	Phase 3
0.7285	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1876	Approved
0.7255	Intermediate Similarity	NPD7003	Approved
0.7254	Intermediate Similarity	NPD1481	Phase 2
0.7254	Intermediate Similarity	NPD1608	Approved
0.7246	Intermediate Similarity	NPD9493	Approved
0.7226	Intermediate Similarity	NPD1511	Approved
0.7214	Intermediate Similarity	NPD5585	Approved
0.7214	Intermediate Similarity	NPD1651	Approved
0.7205	Intermediate Similarity	NPD2296	Approved
0.7203	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3869	Phase 3
0.7197	Intermediate Similarity	NPD3873	Phase 3
0.719	Intermediate Similarity	NPD1243	Approved
0.7186	Intermediate Similarity	NPD3818	Discontinued
0.7183	Intermediate Similarity	NPD1535	Discovery
0.7181	Intermediate Similarity	NPD6355	Discontinued
0.7179	Intermediate Similarity	NPD2534	Approved
0.7179	Intermediate Similarity	NPD2533	Approved
0.7179	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2532	Approved
0.7178	Intermediate Similarity	NPD919	Approved
0.7172	Intermediate Similarity	NPD1019	Discontinued
0.717	Intermediate Similarity	NPD4380	Phase 2
0.7163	Intermediate Similarity	NPD4626	Approved
0.716	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1283	Approved
0.7153	Intermediate Similarity	NPD1398	Phase 1
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD9545	Approved
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7134	Intermediate Similarity	NPD5494	Approved
0.7134	Intermediate Similarity	NPD1512	Approved
0.7122	Intermediate Similarity	NPD7340	Approved
0.7117	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3749	Approved
0.711	Intermediate Similarity	NPD8434	Phase 2
0.7107	Intermediate Similarity	NPD7458	Discontinued
0.7103	Intermediate Similarity	NPD3266	Approved
0.7103	Intermediate Similarity	NPD3267	Approved
0.7095	Intermediate Similarity	NPD3764	Approved
0.7095	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6798	Discontinued
0.7092	Intermediate Similarity	NPD5691	Approved
0.7091	Intermediate Similarity	NPD6959	Discontinued
0.7083	Intermediate Similarity	NPD4749	Approved
0.7081	Intermediate Similarity	NPD6280	Approved
0.7081	Intermediate Similarity	NPD6279	Approved
0.707	Intermediate Similarity	NPD4662	Approved
0.707	Intermediate Similarity	NPD4661	Approved
0.7066	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1201	Approved
0.7063	Intermediate Similarity	NPD6599	Discontinued
0.7063	Intermediate Similarity	NPD1611	Approved
0.7059	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6233	Phase 2
0.7044	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD17	Approved
0.7039	Intermediate Similarity	NPD3748	Approved
0.7037	Intermediate Similarity	NPD5760	Phase 2
0.7037	Intermediate Similarity	NPD5761	Phase 2
0.7034	Intermediate Similarity	NPD3225	Approved
0.7027	Intermediate Similarity	NPD4625	Phase 3
0.7021	Intermediate Similarity	NPD1894	Discontinued
0.7019	Intermediate Similarity	NPD7411	Suspended
0.7013	Intermediate Similarity	NPD2424	Discontinued
0.7013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7075	Discontinued
0.7006	Intermediate Similarity	NPD6799	Approved
0.7	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3140	Approved
0.7	Intermediate Similarity	NPD2649	Approved
0.7	Intermediate Similarity	NPD3142	Approved
0.7	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD2651	Approved
0.6994	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3817	Phase 2
0.6993	Remote Similarity	NPD4477	Approved
0.6993	Remote Similarity	NPD4476	Approved
0.6986	Remote Similarity	NPD1470	Approved
0.6981	Remote Similarity	NPD5403	Approved
0.698	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2800	Approved
0.6966	Remote Similarity	NPD4359	Approved
0.6964	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6166	Phase 2
0.6964	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1933	Approved
0.6951	Remote Similarity	NPD7768	Phase 2
0.695	Remote Similarity	NPD5536	Phase 2
0.6948	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6004	Phase 3
0.6948	Remote Similarity	NPD6005	Phase 3
0.6948	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6002	Phase 3
0.6944	Remote Similarity	NPD1281	Approved
0.6943	Remote Similarity	NPD7440	Discontinued
0.694	Remote Similarity	NPD9697	Approved
0.6933	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5049	Phase 3
0.6909	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2237	Approved
0.6883	Remote Similarity	NPD6032	Approved
0.6882	Remote Similarity	NPD7177	Discontinued
0.6879	Remote Similarity	NPD3887	Approved
0.6879	Remote Similarity	NPD2354	Approved
0.6871	Remote Similarity	NPD7577	Discontinued
0.6871	Remote Similarity	NPD6801	Discontinued
0.6855	Remote Similarity	NPD5401	Approved
0.6848	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4618	Approved
0.6842	Remote Similarity	NPD4622	Approved
0.6842	Remote Similarity	NPD7054	Approved
0.6839	Remote Similarity	NPD8313	Approved
0.6839	Remote Similarity	NPD8312	Approved
0.6838	Remote Similarity	NPD290	Approved
0.6828	Remote Similarity	NPD422	Phase 1
0.6824	Remote Similarity	NPD6584	Phase 3
0.6821	Remote Similarity	NPD8032	Phase 2
0.6821	Remote Similarity	NPD6765	Approved
0.6821	Remote Similarity	NPD6764	Approved
0.6821	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4110	Phase 3
0.6815	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3926	Phase 2
0.6802	Remote Similarity	NPD7472	Approved
0.6802	Remote Similarity	NPD7074	Phase 3
0.68	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7095	Approved
0.6797	Remote Similarity	NPD6653	Approved
0.6788	Remote Similarity	NPD2684	Approved
0.6784	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD2163	Approved
0.6783	Remote Similarity	NPD1548	Phase 1
0.6782	Remote Similarity	NPD4338	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